58:
560:
537:
49:
1062:
1672:. C7' shows only C1 labeling of acetate, while C8' and C9' show a reversed pattern of 13C labeled acetate. It is speculated that C7-C9 arises from a 3-hydroxypropionate starter unit, which is extended three times with malonyl-CoA and fully reduced to yield 9-HN. It has also been suggested that 9-HN is initiated by 3-hydroxy-3-methylglutaric acid (HMG). This latter theory was not supported by feeding of or -HMG.
1051:
795:
1085:
1012:
4141:
1108:
1598:
region. Module 2 adds another two carbons by the malonyl-CoA extender unit, followed by ketoreduction (KR) and dehydration. Module three adds a malonyl-CoA extender unit, followed by SAM-dependent methylation at C8, ketoreduction, and dehydration. Module 4 extends the molecule with a malonyl-CoA unit
1675:
It is proposed that MmpB to catalyze the synthesis of 9-HN (Figure 5). MmpB contains a KS, KR, DH, 3 ACPs, and a thioesterase (TE) domain. It does not contain an enoyl reductase (ER) domain, which would be required for the complete reduction to the nine-carbon fatty acid. MupE is a single-domain
1629:
experiments of mupO, mupU, mupV, and macpE have eliminated PA-A production. PA-B production is not removed by these knockouts, demonstrating that PA-B is not created by hydroxylating PA-A. A knockout of mupW eliminated the pyran ring, identifying MupW as being involved in ring formation.
1181:(AT) organization, in that there are only two AT domains, and both are found on the same protein, MmpC. These AT domains are the only domains present on MmpC, while the other three type I PKS proteins contain no AT domains. The mupirocin pathway also contains several tandem
623:
1018:. The domain structure of MmpA, MmpC, and MmpD for the synthesis of monic acid. The biosynthesis of monic acid is not colinear but has been rearranged in this diagram. The protein name is displayed inside of the arrow with module and domain structure listed below. ACP=
1586:
Biosynthesis of the 17C monic acid unit begins on MmpD (Figure 1). One of the AT domains from MmpC may transfer an activated acetyl group from acetyl-Coenzyme A (CoA) to the first ACP domain. The chain is extended by malonyl-CoA, followed by a SAM-dependent
1177:(PKS) proteins are encoded, as well as several single function enzymes with sequence similarity to type II PKSs. Therefore, it is believed that mupirocin is constructed by a mixed type I and type II PKS system. The mupirocin cluster exhibits an atypical
1114:. MmpB is proposed to synthesize 9-HN with a 3-hydroxy-propionate starter unit and three malonyl-CoA extender units. The domain structure of MmpB is shown below alongside MupE, the proposed enoyl reductase required for complete saturation of 9-HN. ACP=
1003:(Ile-AMS). The unique 9-hydroxynonanoic acid "tail" wraps around the enzyme and further stabilizes the complex, keeping the catalytic part stuck. Mupirocin is able to bind to bacterial and archaeal versions of the enzyme, but not eukaryotic versions.
2949:
675:
InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1
2942:
2318:"Relationship of protein structure of isoleucyl-tRNA synthetase with pseudomonic acid resistance of Escherichia coli. A proposed mode of action of pseudomonic acid as an inhibitor of isoleucyl-tRNA synthetase"
2935:
1134:
Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional
248:
1591:
at C12 (see Figure 2 for PA-A numbering) and reduction of the B-keto group to an alcohol. The dehydration (DH) domain in module 1 is predicted to be non-functional due to a mutation in the
2294:
4186:
1724:
193:
988:, which in turn inhibits RNA synthesis. The combined inhibition of protein synthesis and RNA synthesis results in bacteriostasis. This mechanism of action is shared with
691:
832:
and preventative intranasal or catheter-site treatment is effective for reducing the risk of catheter site infection in persons treated with chronic peritoneal dialysis.
2491:"Synthesis of guanosine tetra- and pentaphosphate requires the presence of a codon-specific, uncharged transfer ribonucleic acid in the acceptor site of ribosomes"
3811:
1618:
of the resulting acetyl-ACP is linked to C3 of the polyketide chain by MupH. This intermediate is dehydrated and decarboxylated by MupJ and MupK, respectively.
91:
3308:
1788:
647:
2410:
2086:
1310:
961:
819:
1812:"Effects of sub-lethal concentrations of mupirocin on global transcription in Staphylococcus aureus 8325-4 and a model for the escape from inhibition"
1758:
745:
Common side effects include itchiness and rash at the site of application, headache, and nausea. Long term use may result in increased growth of
2908:
Martin FM, Simpson TJ (1989). "Biosynthetic studies on pseudomonic acid (mupirocin), a novel antibiotic metabolite of
Pseudomonas fluorescens".
2286:
860:= 8–256 mg/L), and another possessed high-level resistance (MuH: MIC > 256 mg/L). Resistance in the MuL strains is probably due to
3755:
1207:
into the carbon backbone has been ruled out because C1 of monic acid and C9' of 9-hydroxy-nonanoic acid are both derived from C1 of acetate.
775:
884:, a single amino acid mutation was shown to alter mupirocin resistance. MuH is linked to the acquisition of a separate Ile synthetase gene,
999:
Inhibition of the tRNA ligase/synthase is brought by the structural similarity between the molecule's monic acid "head" part and isoleucyl-
2754:"Shift to Pseudomonic acid B production in P. fluorescens NCIMB10586 by mutation of mupirocin tailoring genes mupO, mupU, mupV, and macpE"
2250:
Cookson BD (January 1998). "The emergence of mupirocin resistance: a challenge to infection control and antibiotic prescribing practice".
1977:
1946:
4181:
2851:
O'Hanlon PJ, Rogers NH, Tyler JW (1983). "The chemistry of pseudomonic acid. Part 6. Structure and preparation of pseudomonic acid D".
3804:
3728:
2167:
1379:
1073:
1625:
ring requires many enzyme-mediated steps (Figure 4). The double bond between C8 and C9 is proposed to migrate to between C8 and C16.
1971:
1940:
1913:
1704:
1306:
667:
1710:
3301:
857:
1185:
doublets or triplets. This may be an adaptation to increase the throughput rate or to bind multiple substrates simultaneously.
1031:
732:
334:
233:
123:
2027:
1641:
such as MupO. A gene knockout of mupO abolished PA-A production but PA-B, which also contains the C10-C11 epoxide, remained.
825:(MRSA) infections. Mupirocin is inactive for most anaerobic bacteria, mycobacteria, mycoplasma, chlamydia, yeast, and fungi.
1868:
3797:
3720:
993:
3732:
3612:
2585:"Structural basis for the recognition of isoleucyl-adenylate and an antibiotic, mupirocin, by isoleucyl-tRNA synthetase"
2080:
436:
1146:
of PA-A, and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin.
4166:
3772:
3294:
981:
516:
973:
142:
984:. The uncharged form of the tRNA binds to the aminoacyl-tRNA binding site of ribosomes, triggering the formation of
4131:
3736:
3724:
3530:
2877:
Feline TC, Jones RB, Mellows G, Phillips L (1977). "Pseudomonic acid. Part 2. Biosynthesis of pseudomonic acid A".
1780:
3716:
2927:
2406:
1991:
1893:
1554:
1550:
868:
2359:"High-level mupirocin resistance in Staphylococcus aureus: evidence for two distinct isoleucyl-tRNA synthetases"
2074:
3740:
1653:
1196:
9-hydroxy-nonanoic acid. The possibility that the entire molecule is assembled as a single polyketide with a
3837:
3760:
3591:
2548:
Tanaka K, Tamaki M, Watanabe S (November 1969). "Effect of furanomycin on the synthesis of isoleucyl-tRNA".
1477:
1426:
1099:
of mupO, mupU, mupV and macpE abolish PA-A production but not PA-B production, demonstrating that PA-B is a
770:
179:
742:, use for greater than ten days is not recommended. It is used as a cream or ointment applied to the skin.
555:
4093:
3673:
3565:
3134:
1750:
303:
186:
1610:
The keto group at C3 is replaced with a methyl group in a multi-step reaction (Figure 3). MupG begins by
1227:
1100:
739:
260:
2752:
Cooper SM, Laosripaiboon W, Rahman AS, Hothersall J, El-Sayed AK, Winfield C, et al. (July 2005).
1467:
828:
Intranasal mupirocin before surgery is effective for prevention of post-operative wound infection with
2704:"Characterization of the mupirocin biosynthesis gene cluster from Pseudomonas fluorescens NCIMB 10586"
2113:"Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Escherichia coli by pseudomonic acid"
778:. In 2021, it was the 203rd most commonly prescribed medication in the United States, with more than 2
505:
4176:
4161:
3486:
3462:
3330:
3060:
2502:
1669:
1337:
1245:
1182:
1115:
1019:
313:
2824:
Clayton JP, O'Hanlon PJ, Rogers NH (1980). "The structure and configuration of pseudomonic acid C".
941:
with other antibacterial resistance genes. This has been observed already with resistance genes for
3707:
3637:
3561:
3378:
3286:
3142:
1436:
1389:
1249:
1174:
1077:
909:
897:
532:
351:
924:
are also resistant to mupirocin as they produce the antibiotic and it's possible other species of
3571:
2663:
2471:
1592:
783:
153:
1657:
4171:
3657:
3002:
2962:
2890:
2806:
2775:
2725:
2655:
2606:
2565:
2530:
2463:
2388:
2339:
2267:
2223:
2142:
1967:
1961:
1936:
1930:
1909:
1833:
1725:"Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017"
1700:
1295:
1035:
285:
272:
73:
888:. Mupirocin is not a viable antibiotic against MuH strains. Other antibiotic agents, such as
485:
3841:
3261:
2913:
2882:
2856:
2833:
2798:
2765:
2715:
2645:
2637:
2596:
2557:
2520:
2510:
2453:
2445:
2378:
2370:
2329:
2259:
2213:
2205:
2132:
2124:
1999:
1901:
1823:
1661:
938:
934:
572:
425:
295:
2160:
1061:
445:
360:
4145:
3712:
3689:
3408:
3383:
3339:
3215:
3032:
3007:
2194:"Antimicrobial approaches in the prevention of Staphylococcus aureus infections: a review"
1676:
protein that shows sequence similarity to known ER domains and may complete the reaction.
1638:
1611:
1447:
1283:
1197:
1178:
1023:
976:
in bacteria, leading to depletion of isoleucyl-tRNA and accumulation of the corresponding
852:
clearance rates of less than 30% success. Two distinct populations of mupirocin-resistant
845:
758:
720:
2793:
Chain EB, Mellows G (1977). "Pseudomonic acid. Part 3. Structure of pseudomonic acid B".
2626:"Structural Basis for the Antibiotic Resistance of Eukaryotic Isoleucyl-tRNA Synthetase"
2506:
1602:
Assembly of monic acid is continued by the transfer of the 12C product of MmpD to MmpA.
933:
The mechanism of action of mupirocin differs from other clinical antibiotics, rendering
559:
536:
57:
4032:
3789:
3766:
3617:
3522:
3454:
3433:
3423:
3353:
3177:
3157:
3039:
2997:
2966:
2650:
2625:
2458:
2433:
2218:
2193:
2137:
2112:
1530:
1189:
1163:
977:
2837:
2720:
2703:
2525:
2490:
2383:
2358:
2334:
2317:
1668:
feeding has shown that C1-C6 are constructed with acetate in the canonical fashion of
761:. It works by blocking a bacteria's ability to make protein, which usually results in
4155:
4108:
4088:
4037:
3965:
3945:
3702:
3586:
3550:
3535:
3467:
3403:
3398:
3266:
3167:
3162:
3147:
3075:
3071:
2667:
2561:
1626:
1135:
1096:
914:
893:
802:
Mupirocin is used as a topical treatment for bacterial skin infections (for example,
754:
634:
548:
115:
2702:
El-Sayed AK, Hothersall J, Cooper SM, Stephens E, Simpson TJ, Thomas CM (May 2003).
2475:
1050:
4017:
4012:
3926:
3828:
3824:
3576:
3491:
3477:
3368:
3321:
3317:
3271:
3225:
3125:
3096:
3064:
3012:
2988:
2970:
2770:
2753:
2432:
Seah C, Alexander DC, Louie L, Simor A, Low DE, Longtin J, Melano RG (April 2012).
1615:
1273:
1242:
1159:
1127:
1123:
1069:
1043:
1039:
956:
A second type of high-level resistant synthetase was discovered in 2012 and termed
950:
946:
889:
762:
728:
385:
216:
211:
206:
201:
48:
2019:
2049:
1864:
1694:
101:
4098:
4073:
4022:
3983:
3907:
3874:
3864:
3859:
3820:
3555:
3545:
3506:
3418:
3413:
3393:
3373:
3363:
3348:
3240:
3195:
3190:
3106:
2641:
2434:"MupB, a new high-level mupirocin resistance mechanism in Staphylococcus aureus"
1595:
1588:
1540:
1269:
1139:
1119:
1027:
989:
926:
794:
738:(MRSA) when present in the nose without symptoms. Due to concerns of developing
109:
2495:
Proceedings of the
National Academy of Sciences of the United States of America
1084:
4103:
4068:
4063:
4053:
4003:
3993:
3955:
3950:
3884:
3879:
3869:
3854:
3652:
3632:
3627:
3622:
3581:
3540:
3511:
3501:
3496:
3472:
3428:
3388:
3210:
3101:
3048:
3028:
2979:
2958:
1650:
1511:
1193:
901:
716:
599:
416:
4113:
4083:
4078:
4058:
4027:
3978:
3936:
3894:
3849:
3697:
3607:
3358:
3220:
3205:
3200:
3185:
3086:
3082:
1408:
1200:
1072:
of monic acid is attached to C3 by the following reaction scheme. MupH is a
1000:
942:
865:
750:
95:
2779:
2729:
2659:
2610:
2601:
2584:
2515:
2467:
2227:
1996:
World Health
Organization model list of essential medicines: 21st list 2019
1837:
2569:
2534:
2392:
2343:
2271:
2263:
1781:"Bactroban (mupirocin) cream, for topical use Initial U.S. Approval: 1997"
40:
4118:
3988:
3973:
3902:
3443:
3235:
3152:
3053:
3043:
2917:
2894:
2886:
2860:
2810:
2802:
2550:
Biochimica et
Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis
2449:
2209:
2146:
1828:
1811:
1155:
985:
861:
807:
724:
396:
137:
31:
17:
2374:
2004:
1637:
of PA-A at C10-11 is believed to be inserted after pyran formation by a
1011:
405:
3917:
3647:
3230:
1963:
Quantitative
Bacteriology: Its Role in the Armamentarium of the Surgeon
1905:
1665:
1634:
1564:
1170:
1166:
1143:
877:
371:
2128:
3245:
1204:
1057:. The structure of pseudomonic acid A–D, labeled A to D, respectively
964:
isolate "MUP87" and is probably located on a nonconjugative plasmid.
496:
1935:(3rd ed.). Springer Science & Business Media. p. 421.
1095:
ring of mupirocin is generated in this proposed multistep reaction.
342:
9-oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
465:
1622:
1106:
1092:
1083:
1060:
1049:
1010:
953:. It may also result in overgrowth of non-susceptible organisms.
849:
793:
746:
622:
613:
476:
1656:(9-HN) is derived as a separate compound and later esterified to
1107:
803:
456:
266:
3793:
3290:
2931:
856:
were isolated. One strain possessed low-level resistance (MuL:
279:
132:
62:
Pseudomonic acid A (PA-A), the principal component of mupirocin
840:
Shortly after the clinical use of mupirocin began, strains of
521:
2287:"Topical MRSA Decolonization Is Warranted During Outbreaks"
810:, or open wounds), which are typically due to infection by
242:
164:
2316:
Yanagisawa T, Lee JT, Wu HC, Kawakami M (September 1994).
937:
to other antibiotics unlikely. However, the MupA gene may
2008:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
255:
776:
698:
2910:
Journal of the
Chemical Society, Perkin Transactions 1
2879:
Journal of the
Chemical Society, Perkin Transactions 1
2853:
Journal of the
Chemical Society, Perkin Transactions 1
2795:
Journal of the
Chemical Society, Perkin Transactions 1
2624:
Chung S, Kim S, Ryu SH, Hwang KY, Cho Y (April 2020).
2407:"Antibiotic Susceptibility of Propionibacterium acnes"
2192:
Troeman DP, Van Hout D, Kluytmans JA (February 2019).
4129:
1867:. The American Society of Health-System Pharmacists.
904:
have been shown to be effective against MuH strains.
1211:
Table 1: The biosynthetic gene cluster of mupirocin
818:. It is also useful in the treatment of superficial
4046:
4002:
3964:
3935:
3916:
3893:
3836:
3686:
3666:
3600:
3521:
3487:
mast cell stabilizer (some are also antihistamines)
3442:
3338:
3329:
3254:
3176:
3133:
3124:
3021:
2987:
2978:
633:
611:
598:
571:
566:
547:
515:
495:
475:
455:
435:
415:
395:
370:
350:
325:
312:
302:
294:
232:
227:
192:
178:
152:
122:
108:
90:
82:
72:
67:
655:O=C(O)CCCCCCCCOC(=O)\C=C(/C)C2OC(C1O1(C)(O)C)(O)2O
1932:Nolph and Gokal's Textbook of Peritoneal Dialysis
1192:between the 17C polyketide monic acid and the 9C
2697:
2583:Nakama T, Nureki O, Yokoyama S (December 2001).
2357:Gilbart J, Perry CR, Slocombe B (January 1993).
384:
2747:
2745:
2743:
2741:
2739:
2695:
2693:
2691:
2689:
2687:
2685:
2683:
2681:
2679:
2677:
1896:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).
359:
2245:
2243:
2241:
2239:
2237:
1696:Emergency Dermatology: A Rapid Treatment Guide
768:Mupirocin was initially isolated in 1971 from
757:appears to be safe. Mupirocin is chemically a
4187:World Health Organization essential medicines
3805:
3302:
2943:
2872:
2870:
2106:
2104:
8:
1298:ACP KS DH KR ACP KS DH KR MeT ACP KS KR ACP
782:million prescriptions. It is available as a
141:
39:
1960:Heggers JP, Robson MC, Phillips LG (1990).
1122:, ER=enoyl reductase, KR=ketoreductase, KS=
3812:
3798:
3790:
3335:
3309:
3295:
3287:
3130:
2984:
2950:
2936:
2928:
1900:. World Health Organization. p. 298.
1859:
1857:
1855:
1853:
1851:
1849:
1847:
1173:(Table 1). Four large multi-domain type I
980:. Depletion of isoleucyl-tRNA results in
558:
535:
424:
2769:
2719:
2649:
2600:
2524:
2514:
2457:
2382:
2333:
2252:The Journal of Antimicrobial Chemotherapy
2217:
2198:The Journal of Antimicrobial Chemotherapy
2136:
2003:
1888:
1886:
1827:
1699:. McGraw Hill Professional. p. 173.
1074:Hydroxymethylglutaryl-Coenzyme A synthase
444:
2291:American College of Emergency Physicians
1209:
1188:Pseudomonic acid A is the product of an
917:, are naturally resistant to mupirocin.
913:, a causative agent in the skin disease
4136:
2075:"Competitive Generic Therapy Approvals"
1980:from the original on 10 September 2017.
1949:from the original on 10 September 2017.
1713:from the original on 10 September 2017.
1685:
672:
652:
531:
404:
339:
114:
2173:from the original on 24 September 2015
1810:AlHoufie ST, Foster HA (August 2016).
1729:Therapeutic Goods Administration (TGA)
549:
38:
2438:Antimicrobial Agents and Chemotherapy
2363:Antimicrobial Agents and Chemotherapy
1998:. Geneva: World Health Organization.
1871:from the original on 21 December 2016
1791:from the original on 26 February 2023
1761:from the original on 26 February 2023
639:77 to 78 °C (171 to 172 °F)
504:
484:
100:
7:
2111:Hughes J, Mellows G (October 1978).
2030:from the original on 15 January 2024
1645:9-Hydroxy-nonanoic acid biosynthesis
1142:between C10 and C11, instead of the
731:. It may also be used to get rid of
215:
205:
2589:The Journal of Biological Chemistry
2409:. ScienceOfAcne.com. 11 June 2011.
2322:The Journal of Biological Chemistry
2050:"Mupirocin - Drug Usage Statistics"
464:
375:
2489:Haseltine WA, Block R (May 1973).
1150:Biosynthesis of pseudomonic acid A
25:
2413:from the original on 29 July 2012
2089:from the original on 29 June 2023
1138:at C8, pseudomonic acid C with a
4139:
2297:from the original on 18 May 2014
2293:. Elsevier Global Medical News.
583:
56:
47:
1816:Journal of Medical Microbiology
1751:"Bactroban Product information"
1032:3-hydroxy-3-methylglutaric acid
982:inhibition of protein synthesis
680:Key:MINDHVHHQZYEEK-HBBNESRFSA-N
3320:and other nasal preparations (
2771:10.1016/j.chembiol.2005.05.015
589:
577:
1:
2838:10.1016/S0040-4039(00)71533-4
2721:10.1016/S1074-5521(03)00091-7
2335:10.1016/S0021-9258(19)51082-1
2161:"Product Monograph Bactroban"
1929:Khanna R, Krediet RT (2009).
960:. It was found in a Canadian
3613:Calcium hexamine thiocyanate
2562:10.1016/0005-2787(69)90621-2
2081:Food and Drug Administration
711:, sold under the brand name
2642:10.14348/molcells.2020.2287
1599:followed by ketoreduction.
930:may be resistant as well.
848:to mupirocin emerged, with
719:useful against superficial
715:among others, is a topical
4203:
4182:Drugs developed by GSK plc
3531:Beclometasone dipropionate
2285:Worcester S (March 2008).
1966:. CRC Press. p. 118.
1030:, ER=enoyl reductase, HMG=
972:Pseudomonic acid inhibits
567:Chemical and physical data
29:
3750:
3448:excluding corticosteroids
1992:World Health Organization
1894:World Health Organization
1555:transcriptional activator
1371:3-oxoacyl-ACP synthase I
869:isoleucyl-tRNA synthetase
688:
663:
643:
330:
55:
46:
3601:Other nasal preparations
1898:WHO Model Formulary 2008
1329:3-oxoacyl-ACP reductase
30:Not to be confused with
3592:Triamcinolone acetonide
2758:Chemistry & Biology
2708:Chemistry & Biology
2117:The Biochemical Journal
1654:9-hydroxy-nonanoic acid
1582:Monic acid biosynthesis
1478:3-oxoacyl-ACP reductase
1427:isoleucyl-tRNA synthase
1260:3-oxoacyl-ACP synthase
1038:, KR=ketoreductase, KS=
922:Pseudomonas fluorescens
771:Pseudomonas fluorescens
3674:Olopatadine/mometasone
3566:Fluticasone propionate
2602:10.1074/jbc.M109089200
2516:10.1073/pnas.70.5.1564
1131:
1104:
1081:
1058:
1047:
974:isoleucine—tRNA ligase
820:methicillin-resistant
816:Streptococcus pyogenes
799:
733:methicillin-resistant
3463:histamine antagonists
2020:"The Top 300 of 2021"
1693:Fleischer AB (2002).
1621:The formation of the
1169:and twenty-six other
1110:
1087:
1064:
1053:
1014:
842:Staphylococcus aureus
822:Staphylococcus aureus
812:Staphylococcus aureus
797:
4047:Other antibacterials
3667:Combination products
2918:10.1039/P19890000207
2887:10.1039/p19770000309
2861:10.1039/P19830002655
2803:10.1039/p19770000318
2450:10.1128/AAC.05325-11
1829:10.1099/jmm.0.000270
1670:fatty acid synthesis
1399:enoyl-CoA hydratase
1234:dependent oxygenase
1183:acyl carrier protein
1116:acyl carrier protein
1078:Enoyl-CoA hydratases
1076:, MupJ and MupK are
1020:acyl carrier protein
830:Staphylcoccus aureus
3729:+dexbrompheniramine
3708:Phenylpropanolamine
3638:Ipratropium bromide
3562:Fluticasone furoate
3143:Silver sulfadiazine
2826:Tetrahedron Letters
2630:Molecules and Cells
2595:(50): 47387–47393.
2507:1973PNAS...70.1564H
2375:10.1128/aac.37.1.32
2328:(39): 24304–24309.
2264:10.1093/jac/41.1.11
1757:. 22 October 2009.
1614:a malonyl-ACP. The
1437:phosphopantetheinyl
1418:putative hydrolase
1390:enoyl-CoA hydratase
1212:
1175:polyketide synthase
968:Mechanism of action
910:Cutibacterium acnes
898:silver sulfadiazine
798:A tube of Bactroban
275:(Prescription only)
251:(Prescription only)
43:
4167:Carboxylate esters
3777:Never to phase III
3572:Mometasone furoate
2210:10.1093/jac/dky421
1606:Post-PKS tailoring
1522:acyl-CoA synthase
1210:
1132:
1105:
1082:
1059:
1048:
1036:methyl transferase
864:in the organism's
800:
784:generic medication
4127:
4126:
3842:Lipoglycopeptides
3787:
3786:
3682:
3681:
3284:
3283:
3280:
3279:
3126:Chemotherapeutics
3120:
3119:
3003:Chlortetracycline
2963:chemotherapeutics
2129:10.1042/bj1760305
1579:
1578:
1468:acyl-CoA synthase
706:
705:
624:Interactive image
517:CompTox Dashboard
283:
270:
258:
246:
168:
135:
78:Bactroban, others
27:Chemical compound
16:(Redirected from
4194:
4144:
4143:
4142:
4135:
3814:
3807:
3800:
3791:
3690:Sympathomimetics
3492:Cromoglicic acid
3379:Levmetamfetamine
3340:Sympathomimetics
3336:
3311:
3304:
3297:
3288:
3262:Ingenol mebutate
3131:
2985:
2952:
2945:
2938:
2929:
2922:
2921:
2905:
2899:
2898:
2874:
2865:
2864:
2848:
2842:
2841:
2821:
2815:
2814:
2790:
2784:
2783:
2773:
2749:
2734:
2733:
2723:
2699:
2672:
2671:
2653:
2621:
2615:
2614:
2604:
2580:
2574:
2573:
2545:
2539:
2538:
2528:
2518:
2501:(5): 1564–1568.
2486:
2480:
2479:
2461:
2444:(4): 1916–1920.
2429:
2423:
2422:
2420:
2418:
2403:
2397:
2396:
2386:
2354:
2348:
2347:
2337:
2313:
2307:
2306:
2304:
2302:
2282:
2276:
2275:
2247:
2232:
2231:
2221:
2189:
2183:
2182:
2180:
2178:
2172:
2165:
2157:
2151:
2150:
2140:
2108:
2099:
2098:
2096:
2094:
2085:. 29 June 2023.
2071:
2065:
2064:
2062:
2060:
2046:
2040:
2039:
2037:
2035:
2016:
2010:
2009:
2007:
1988:
1982:
1981:
1957:
1951:
1950:
1926:
1920:
1919:
1890:
1881:
1880:
1878:
1876:
1861:
1842:
1841:
1831:
1807:
1801:
1800:
1798:
1796:
1777:
1771:
1770:
1768:
1766:
1747:
1741:
1740:
1738:
1736:
1721:
1715:
1714:
1690:
1662:pseudomonic acid
1649:The nine-carbon
1380:HMG-CoA synthase
1213:
1024:acyl transferase
935:cross-resistance
920:Most strains of
907:Most strains of
781:
702:
701:
694:
626:
606:
591:
585:
579:
562:
551:
540:
539:
525:
523:
508:
488:
468:
448:
428:
408:
388:
378:
377:
363:
321:20 to 40 minutes
317:
281:
278:
268:
265:
257:
254:
244:
241:
219:
209:
166:
163:
145:
134:
131:
118:
104:
60:
51:
44:
42:
21:
4202:
4201:
4197:
4196:
4195:
4193:
4192:
4191:
4152:
4151:
4150:
4140:
4138:
4130:
4128:
4123:
4042:
3998:
3960:
3931:
3912:
3889:
3840:
3832:
3818:
3788:
3783:
3782:
3767:Clinical trials
3746:
3713:Pseudoephedrine
3688:
3678:
3662:
3596:
3523:Corticosteroids
3517:
3447:
3438:
3409:Propylhexedrine
3384:Methylephedrine
3325:
3315:
3285:
3276:
3250:
3216:Podophyllotoxin
3172:
3116:
3040:Aminoglycosides
3033:Chloramphenicol
3017:
3008:Oxytetracycline
2991:and derivatives
2974:
2956:
2926:
2925:
2907:
2906:
2902:
2876:
2875:
2868:
2850:
2849:
2845:
2823:
2822:
2818:
2792:
2791:
2787:
2751:
2750:
2737:
2701:
2700:
2675:
2623:
2622:
2618:
2582:
2581:
2577:
2547:
2546:
2542:
2488:
2487:
2483:
2431:
2430:
2426:
2416:
2414:
2405:
2404:
2400:
2356:
2355:
2351:
2315:
2314:
2310:
2300:
2298:
2284:
2283:
2279:
2249:
2248:
2235:
2191:
2190:
2186:
2176:
2174:
2170:
2163:
2159:
2158:
2154:
2110:
2109:
2102:
2092:
2090:
2073:
2072:
2068:
2058:
2056:
2048:
2047:
2043:
2033:
2031:
2018:
2017:
2013:
1990:
1989:
1985:
1974:
1959:
1958:
1954:
1943:
1928:
1927:
1923:
1916:
1892:
1891:
1884:
1874:
1872:
1863:
1862:
1845:
1809:
1808:
1804:
1794:
1792:
1779:
1778:
1774:
1764:
1762:
1749:
1748:
1744:
1734:
1732:
1723:
1722:
1718:
1707:
1692:
1691:
1687:
1682:
1647:
1639:cytochrome P450
1612:decarboxylating
1608:
1584:
1575:N-AHL synthase
1448:cytochrome P450
1338:enoyl reductase
1313:oxidoreductase
1272:KR ACP ACP ACP
1252:ACP KS ACP ACP
1233:
1198:Baeyer-Villiger
1179:acyltransferase
1152:
1009:
996:of isoleucine.
970:
838:
792:
779:
774:. It is on the
763:bacterial death
759:carboxylic acid
721:skin infections
697:
695:
692:(what is this?)
689:
684:
681:
676:
671:
670:
659:
656:
651:
650:
629:
604:
594:
588:
582:
543:
519:
511:
491:
471:
451:
431:
411:
391:
374:
366:
346:
343:
338:
337:
315:
304:Protein binding
296:Pharmacokinetic
290:
223:
181:
174:
155:
148:
63:
35:
28:
23:
22:
15:
12:
11:
5:
4200:
4198:
4190:
4189:
4184:
4179:
4174:
4169:
4164:
4154:
4153:
4149:
4148:
4125:
4124:
4122:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4050:
4048:
4044:
4043:
4041:
4040:
4035:
4033:Nitrofurantoin
4030:
4025:
4020:
4015:
4009:
4007:
4000:
3999:
3997:
3996:
3991:
3986:
3981:
3976:
3970:
3968:
3966:Pleuromutilins
3962:
3961:
3959:
3958:
3953:
3948:
3942:
3940:
3933:
3932:
3930:
3929:
3923:
3921:
3920:antibacterials
3914:
3913:
3911:
3910:
3905:
3899:
3897:
3891:
3890:
3888:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3852:
3846:
3844:
3834:
3833:
3821:Antibacterials
3819:
3817:
3816:
3809:
3802:
3794:
3785:
3784:
3781:
3780:
3779:
3778:
3775:
3764:
3758:
3752:
3751:
3748:
3747:
3745:
3744:
3721:+carbinoxamine
3710:
3705:
3700:
3694:
3692:
3684:
3683:
3680:
3679:
3677:
3676:
3670:
3668:
3664:
3663:
3661:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3618:Eucalyptus oil
3615:
3610:
3604:
3602:
3598:
3597:
3595:
3594:
3589:
3584:
3579:
3574:
3569:
3558:
3553:
3548:
3543:
3538:
3533:
3527:
3525:
3519:
3518:
3516:
3515:
3509:
3504:
3499:
3494:
3482:
3481:
3475:
3470:
3458:
3457:
3455:Spaglumic acid
3451:
3449:
3440:
3439:
3437:
3436:
3434:Xylometazoline
3431:
3426:
3424:Tuaminoheptane
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3354:Cyclopentamine
3351:
3345:
3343:
3333:
3327:
3326:
3316:
3314:
3313:
3306:
3299:
3291:
3282:
3281:
3278:
3277:
3275:
3274:
3269:
3264:
3258:
3256:
3252:
3251:
3249:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3198:
3193:
3188:
3182:
3180:
3174:
3173:
3171:
3170:
3165:
3160:
3158:Sulfamethizole
3155:
3150:
3145:
3139:
3137:
3128:
3122:
3121:
3118:
3117:
3115:
3114:
3109:
3104:
3099:
3090:
3089:
3079:
3078:
3068:
3067:
3057:
3056:
3051:
3046:
3036:
3035:
3025:
3023:
3019:
3018:
3016:
3015:
3010:
3005:
3000:
2998:Demeclocycline
2994:
2992:
2982:
2976:
2975:
2967:dermatological
2957:
2955:
2954:
2947:
2940:
2932:
2924:
2923:
2912:(1): 207–209.
2900:
2881:(3): 309–318.
2866:
2843:
2832:(9): 881–884.
2816:
2797:(3): 318–324.
2785:
2764:(7): 825–833.
2735:
2714:(5): 419–430.
2673:
2636:(4): 350–359.
2616:
2575:
2556:(1): 244–245.
2540:
2481:
2424:
2398:
2349:
2308:
2277:
2233:
2204:(2): 281–294.
2184:
2152:
2123:(1): 305–318.
2100:
2066:
2041:
2011:
1983:
1972:
1952:
1941:
1921:
1914:
1882:
1843:
1822:(8): 858–866.
1802:
1772:
1742:
1731:. 21 June 2022
1716:
1705:
1684:
1683:
1681:
1678:
1646:
1643:
1607:
1604:
1583:
1580:
1577:
1576:
1573:
1569:
1568:
1562:
1558:
1557:
1548:
1544:
1543:
1538:
1534:
1533:
1531:oxidoreductase
1528:
1524:
1523:
1520:
1516:
1515:
1509:
1505:
1504:
1501:
1497:
1496:
1493:
1489:
1488:
1485:
1481:
1480:
1475:
1471:
1470:
1465:
1461:
1460:
1455:
1451:
1450:
1445:
1441:
1440:
1434:
1430:
1429:
1424:
1420:
1419:
1416:
1412:
1411:
1405:
1401:
1400:
1397:
1393:
1392:
1387:
1383:
1382:
1377:
1373:
1372:
1369:
1365:
1364:
1361:
1357:
1356:
1353:
1349:
1348:
1345:
1341:
1340:
1335:
1331:
1330:
1327:
1323:
1322:
1319:
1315:
1314:
1304:
1300:
1299:
1292:
1288:
1287:
1281:
1277:
1276:
1266:
1262:
1261:
1258:
1254:
1253:
1240:
1236:
1235:
1231:
1225:
1221:
1220:
1217:
1190:esterification
1151:
1148:
1136:hydroxyl group
1097:Gene knockouts
1008:
1005:
978:uncharged tRNA
969:
966:
837:
834:
791:
788:
704:
703:
686:
685:
683:
682:
679:
677:
674:
666:
665:
664:
661:
660:
658:
657:
654:
646:
645:
644:
641:
640:
637:
631:
630:
628:
627:
619:
617:
609:
608:
602:
596:
595:
592:
586:
580:
575:
569:
568:
564:
563:
553:
545:
544:
542:
541:
528:
526:
513:
512:
510:
509:
501:
499:
493:
492:
490:
489:
481:
479:
473:
472:
470:
469:
461:
459:
453:
452:
450:
449:
441:
439:
433:
432:
430:
429:
421:
419:
413:
412:
410:
409:
401:
399:
393:
392:
390:
389:
381:
379:
368:
367:
365:
364:
356:
354:
348:
347:
345:
344:
341:
333:
332:
331:
328:
327:
323:
322:
319:
310:
309:
306:
300:
299:
292:
291:
289:
288:
276:
263:
252:
238:
236:
230:
229:
225:
224:
222:
221:
198:
196:
190:
189:
184:
182:administration
176:
175:
173:
172:
170:
160:
158:
150:
149:
147:
146:
128:
126:
120:
119:
112:
106:
105:
98:
88:
87:
84:
80:
79:
76:
70:
69:
65:
64:
61:
53:
52:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4199:
4188:
4185:
4183:
4180:
4178:
4175:
4173:
4170:
4168:
4165:
4163:
4160:
4159:
4157:
4147:
4137:
4133:
4120:
4117:
4115:
4112:
4110:
4109:Spectinomycin
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4089:Mandelic acid
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4051:
4049:
4045:
4039:
4038:Nitrofurazone
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4010:
4008:
4005:
4001:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3971:
3969:
3967:
3963:
3957:
3954:
3952:
3949:
3947:
3946:Metronidazole
3944:
3943:
3941:
3938:
3934:
3928:
3925:
3924:
3922:
3919:
3915:
3909:
3906:
3904:
3901:
3900:
3898:
3896:
3892:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3847:
3845:
3843:
3839:
3838:Glycopeptides
3835:
3830:
3826:
3822:
3815:
3810:
3808:
3803:
3801:
3796:
3795:
3792:
3776:
3774:
3771:
3770:
3768:
3765:
3762:
3759:
3757:
3754:
3753:
3749:
3742:
3738:
3734:
3733:+fexofenadine
3730:
3726:
3722:
3718:
3714:
3711:
3709:
3706:
3704:
3703:Phenylephrine
3701:
3699:
3696:
3695:
3693:
3691:
3687:Systemic use:
3685:
3675:
3672:
3671:
3669:
3665:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3605:
3603:
3599:
3593:
3590:
3588:
3587:Triamcinolone
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3567:
3563:
3560:Fluticasone (
3559:
3557:
3554:
3552:
3551:Dexamethasone
3549:
3547:
3544:
3542:
3539:
3537:
3536:Betamethasone
3534:
3532:
3529:
3528:
3526:
3524:
3520:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3489:
3488:
3484:
3483:
3479:
3476:
3474:
3471:
3469:
3468:Levocabastine
3465:
3464:
3460:
3459:
3456:
3453:
3452:
3450:
3445:
3441:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3404:Phenylephrine
3402:
3400:
3399:Oxymetazoline
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3346:
3344:
3341:
3337:
3334:
3332:
3328:
3323:
3319:
3318:Decongestants
3312:
3307:
3305:
3300:
3298:
3293:
3292:
3289:
3273:
3270:
3268:
3267:Metronidazole
3265:
3263:
3260:
3259:
3257:
3253:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3183:
3181:
3179:
3175:
3169:
3168:Sulfamerazine
3166:
3164:
3163:Sulfanilamide
3161:
3159:
3156:
3154:
3151:
3149:
3148:Sulfathiazole
3146:
3144:
3141:
3140:
3138:
3136:
3132:
3129:
3127:
3123:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3092:
3091:
3088:
3084:
3081:
3080:
3077:
3076:Virginiamycin
3073:
3072:Streptogramin
3070:
3069:
3066:
3062:
3059:
3058:
3055:
3052:
3050:
3047:
3045:
3041:
3038:
3037:
3034:
3030:
3027:
3026:
3024:
3020:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2995:
2993:
2990:
2986:
2983:
2981:
2977:
2972:
2968:
2964:
2960:
2953:
2948:
2946:
2941:
2939:
2934:
2933:
2930:
2919:
2915:
2911:
2904:
2901:
2896:
2892:
2888:
2884:
2880:
2873:
2871:
2867:
2862:
2858:
2855:: 2655–2657.
2854:
2847:
2844:
2839:
2835:
2831:
2827:
2820:
2817:
2812:
2808:
2804:
2800:
2796:
2789:
2786:
2781:
2777:
2772:
2767:
2763:
2759:
2755:
2748:
2746:
2744:
2742:
2740:
2736:
2731:
2727:
2722:
2717:
2713:
2709:
2705:
2698:
2696:
2694:
2692:
2690:
2688:
2686:
2684:
2682:
2680:
2678:
2674:
2669:
2665:
2661:
2657:
2652:
2647:
2643:
2639:
2635:
2631:
2627:
2620:
2617:
2612:
2608:
2603:
2598:
2594:
2590:
2586:
2579:
2576:
2571:
2567:
2563:
2559:
2555:
2551:
2544:
2541:
2536:
2532:
2527:
2522:
2517:
2512:
2508:
2504:
2500:
2496:
2492:
2485:
2482:
2477:
2473:
2469:
2465:
2460:
2455:
2451:
2447:
2443:
2439:
2435:
2428:
2425:
2412:
2408:
2402:
2399:
2394:
2390:
2385:
2380:
2376:
2372:
2368:
2364:
2360:
2353:
2350:
2345:
2341:
2336:
2331:
2327:
2323:
2319:
2312:
2309:
2296:
2292:
2288:
2281:
2278:
2273:
2269:
2265:
2261:
2257:
2253:
2246:
2244:
2242:
2240:
2238:
2234:
2229:
2225:
2220:
2215:
2211:
2207:
2203:
2199:
2195:
2188:
2185:
2169:
2162:
2156:
2153:
2148:
2144:
2139:
2134:
2130:
2126:
2122:
2118:
2114:
2107:
2105:
2101:
2088:
2084:
2082:
2076:
2070:
2067:
2055:
2051:
2045:
2042:
2029:
2025:
2021:
2015:
2012:
2006:
2001:
1997:
1993:
1987:
1984:
1979:
1975:
1973:9780849351297
1969:
1965:
1964:
1956:
1953:
1948:
1944:
1942:9780387789408
1938:
1934:
1933:
1925:
1922:
1917:
1915:9789241547659
1911:
1907:
1903:
1899:
1895:
1889:
1887:
1883:
1870:
1866:
1860:
1858:
1856:
1854:
1852:
1850:
1848:
1844:
1839:
1835:
1830:
1825:
1821:
1817:
1813:
1806:
1803:
1790:
1786:
1782:
1776:
1773:
1760:
1756:
1755:Health Canada
1752:
1746:
1743:
1730:
1726:
1720:
1717:
1712:
1708:
1706:9780071379953
1702:
1698:
1697:
1689:
1686:
1679:
1677:
1673:
1671:
1667:
1663:
1659:
1655:
1652:
1644:
1642:
1640:
1636:
1631:
1628:
1627:Gene knockout
1624:
1619:
1617:
1613:
1605:
1603:
1600:
1597:
1594:
1590:
1581:
1574:
1571:
1570:
1566:
1563:
1560:
1559:
1556:
1552:
1549:
1546:
1545:
1542:
1539:
1536:
1535:
1532:
1529:
1526:
1525:
1521:
1518:
1517:
1513:
1510:
1507:
1506:
1502:
1499:
1498:
1494:
1491:
1490:
1486:
1483:
1482:
1479:
1476:
1473:
1472:
1469:
1466:
1463:
1462:
1459:
1456:
1453:
1452:
1449:
1446:
1443:
1442:
1438:
1435:
1432:
1431:
1428:
1425:
1422:
1421:
1417:
1414:
1413:
1410:
1406:
1403:
1402:
1398:
1395:
1394:
1391:
1388:
1385:
1384:
1381:
1378:
1375:
1374:
1370:
1367:
1366:
1362:
1359:
1358:
1354:
1351:
1350:
1346:
1343:
1342:
1339:
1336:
1333:
1332:
1328:
1325:
1324:
1320:
1317:
1316:
1312:
1308:
1305:
1302:
1301:
1297:
1293:
1290:
1289:
1285:
1282:
1279:
1278:
1275:
1271:
1267:
1264:
1263:
1259:
1256:
1255:
1251:
1247:
1244:
1241:
1238:
1237:
1229:
1226:
1223:
1222:
1218:
1215:
1214:
1208:
1206:
1203:inserting an
1202:
1199:
1195:
1191:
1186:
1184:
1180:
1176:
1172:
1168:
1165:
1162:contains six
1161:
1157:
1149:
1147:
1145:
1141:
1137:
1129:
1125:
1121:
1117:
1113:
1109:
1102:
1098:
1094:
1090:
1086:
1079:
1075:
1071:
1067:
1063:
1056:
1052:
1045:
1041:
1037:
1033:
1029:
1025:
1021:
1017:
1013:
1006:
1004:
1002:
997:
995:
991:
987:
983:
979:
975:
967:
965:
963:
959:
954:
952:
948:
944:
940:
936:
931:
929:
928:
923:
918:
916:
915:acne vulgaris
912:
911:
905:
903:
899:
895:
894:nitrofurazone
891:
887:
883:
880:
879:
874:
870:
867:
863:
859:
855:
851:
847:
843:
835:
833:
831:
826:
824:
823:
817:
813:
809:
805:
796:
789:
787:
785:
777:
773:
772:
766:
764:
760:
756:
755:breastfeeding
752:
749:. Use during
748:
743:
741:
737:
736:
730:
726:
722:
718:
714:
710:
700:
693:
687:
678:
673:
669:
662:
653:
649:
642:
638:
636:
635:Melting point
632:
625:
621:
620:
618:
615:
610:
603:
601:
597:
576:
574:
570:
565:
561:
557:
554:
552:
550:ECHA InfoCard
546:
538:
534:
533:DTXSID0046438
530:
529:
527:
518:
514:
507:
503:
502:
500:
498:
494:
487:
483:
482:
480:
478:
474:
467:
463:
462:
460:
458:
454:
447:
443:
442:
440:
438:
434:
427:
423:
422:
420:
418:
414:
407:
403:
402:
400:
398:
394:
387:
383:
382:
380:
373:
369:
362:
358:
357:
355:
353:
349:
340:
336:
329:
324:
320:
318:
311:
307:
305:
301:
297:
293:
287:
277:
274:
264:
262:
253:
250:
240:
239:
237:
235:
231:
226:
218:
213:
208:
203:
200:
199:
197:
195:
191:
188:
185:
183:
177:
171:
162:
161:
159:
157:
151:
144:
139:
130:
129:
127:
125:
121:
117:
113:
111:
107:
103:
99:
97:
93:
89:
85:
81:
77:
75:
71:
68:Clinical data
66:
59:
54:
50:
45:
37:
33:
19:
4018:Nifuroxazide
4013:Furazolidone
3927:Fusidic acid
3658:Saline water
3642:
3577:Prednisolone
3485:
3478:Thonzylamine
3461:
3444:Antiallergic
3369:Fenoxazoline
3272:Tirbanibulin
3226:Tromantadine
3135:Sulfonamides
3111:
3097:Fusidic acid
3093:
3065:Nadifloxacin
3013:Tetracycline
2989:Tetracycline
2909:
2903:
2878:
2852:
2846:
2829:
2825:
2819:
2794:
2788:
2761:
2757:
2711:
2707:
2633:
2629:
2619:
2592:
2588:
2578:
2553:
2549:
2543:
2498:
2494:
2484:
2441:
2437:
2427:
2415:. Retrieved
2401:
2369:(1): 32–38.
2366:
2362:
2352:
2325:
2321:
2311:
2299:. Retrieved
2290:
2280:
2258:(1): 11–18.
2255:
2251:
2201:
2197:
2187:
2175:. Retrieved
2155:
2120:
2116:
2091:. Retrieved
2078:
2069:
2057:. Retrieved
2053:
2044:
2032:. Retrieved
2023:
2014:
2005:10665/325771
1995:
1986:
1962:
1955:
1931:
1924:
1897:
1873:. Retrieved
1819:
1815:
1805:
1793:. Retrieved
1784:
1775:
1763:. Retrieved
1754:
1745:
1733:. Retrieved
1728:
1719:
1695:
1688:
1674:
1664:. C labeled
1648:
1632:
1620:
1616:alpha carbon
1609:
1601:
1585:
1553:-responsive
1514:dioxygenase
1457:
1439:transferase
1187:
1164:multi-domain
1160:gene cluster
1153:
1133:
1128:thioesterase
1124:ketosynthase
1111:
1088:
1070:methyl group
1065:
1054:
1044:thioesterase
1040:ketosynthase
1015:
1007:Biosynthesis
998:
971:
957:
955:
951:trimethoprim
947:tetracycline
932:
925:
921:
919:
908:
906:
890:azelaic acid
885:
881:
876:
872:
853:
841:
839:
829:
827:
821:
815:
811:
801:
790:Medical uses
769:
767:
744:
734:
729:folliculitis
712:
708:
707:
696:
690:
314:Elimination
234:Legal status
228:Legal status
124:License data
36:
4177:Fatty acids
4162:Antibiotics
4099:Nitroxoline
4094:Methenamine
4074:Furaltadone
4023:Nifurtoinol
4006:derivatives
3984:Retapamulin
3939:derivatives
3908:Polymyxin B
3875:Teicoplanin
3865:Oritavancin
3860:Dalbavancin
3763:from market
3737:+loratadine
3725:+cetirizine
3556:Flunisolide
3546:Ciclesonide
3507:Olopatadine
3419:Tramazoline
3414:Tetryzoline
3394:Naphazoline
3374:Iproheptine
3364:Epinephrine
3349:Amidephrine
3241:Ibacitabine
3196:Idoxuridine
3191:Penciclovir
3107:Tyrothricin
2980:Antibiotics
2959:Antibiotics
2301:18 November
2177:8 September
1906:10665/44053
1865:"Mupirocin"
1795:26 February
1765:26 February
1596:active site
1589:methylation
1567:/hydrolase
1541:dioxygenase
1140:double bond
1120:dehydratase
1028:dehydratase
990:furanomycin
939:co-transfer
927:Pseudomonas
607: g·mol
556:100.106.215
326:Identifiers
110:MedlinePlus
83:Other names
74:Trade names
4156:Categories
4104:Novobiocin
4069:Fosfomycin
4064:Daptomycin
4054:Bacitracin
4004:Nitrofuran
3994:Valnemulin
3956:Tinidazole
3951:Ornidazole
3895:Polymyxins
3885:Vancomycin
3880:Telavancin
3870:Ristocetin
3855:Corbomycin
3823:: others (
3717:+azatadine
3653:Ritiometan
3633:Hyaluronan
3628:Hexamidine
3623:Framycetin
3582:Tixocortol
3541:Budesonide
3512:Lodoxamide
3502:Azelastine
3497:Nedocromil
3473:Antazoline
3429:Tymazoline
3389:Metizoline
3211:Resiquimod
3178:Antivirals
3102:Bacitracin
3061:Quinolones
3049:Gentamicin
3029:Amphenicol
2059:14 January
2034:14 January
1875:8 December
1680:References
1658:monic acid
1651:fatty acid
1512:ferredoxin
1194:fatty acid
1158:mupirocin
1068:. The C15
902:ramoplanin
844:that were
836:Resistance
740:resistance
717:antibiotic
612:3D model (
600:Molar mass
486:CHEBI:7025
446:D0GX863OA5
417:ChemSpider
361:12650-69-0
352:CAS Number
335:IUPAC name
86:muciprocin
4114:Tedizolid
4084:Linezolid
4079:Lefamulin
4059:Clofoctol
4028:Nifurzide
3979:Lefamulin
3937:Imidazole
3850:Avoparcin
3773:Phase III
3761:Withdrawn
3741:+naproxen
3698:Ephedrine
3643:Mupirocin
3608:Cafaminol
3359:Ephedrine
3221:Docosanol
3206:Imiquimod
3201:Edoxudine
3186:Aciclovir
3112:Mupirocin
3087:Rifaximin
3083:Rifamycin
2668:211263261
2417:27 August
1593:conserved
1409:hydrolase
1294:KS DH KR
1219:Function
1201:oxidation
1101:precursor
1001:adenylate
943:triclosan
866:wild-type
862:mutations
854:S. aureus
846:resistant
751:pregnancy
735:S. aureus
713:Bactroban
709:Mupirocin
506:ChEMBL719
316:half-life
180:Routes of
154:Pregnancy
143:Mupirocin
102:Monograph
96:Drugs.com
41:Mupirocin
18:Bactroban
4172:Epoxides
4146:Medicine
4119:Xibornol
3989:Tiamulin
3974:Azamulin
3903:Colistin
3236:Lysozyme
3153:Mafenide
3054:Amikacin
3044:Neomycin
2780:16039529
2730:12770824
2660:32088946
2611:11584022
2476:21526116
2468:22252810
2411:Archived
2295:Archived
2228:30376041
2168:Archived
2087:Archived
2054:ClinCalc
2028:Archived
2024:ClinCalc
1994:(2019).
1978:Archived
1947:Archived
1869:Archived
1838:27184545
1789:Archived
1785:DailyMed
1759:Archived
1735:30 March
1711:Archived
1660:to form
1171:peptides
1112:Figure 5
1103:to PA-A.
1089:Figure 4
1066:Figure 3
1055:Figure 2
1016:Figure 1
986:(p)ppGpp
808:impetigo
725:impetigo
723:such as
699:(verify)
397:DrugBank
194:ATC code
169: B1
156:category
138:DailyMed
32:Miprocin
3918:Steroid
3648:Retinol
3446:agents,
3342:, plain
3331:Topical
3231:Inosine
2651:7191050
2570:4982424
2535:4576025
2503:Bibcode
2459:3318397
2393:8431015
2344:7929087
2272:9511032
2219:6337897
2138:1186229
2093:29 June
1666:acetate
1635:epoxide
1565:amidase
1458:unknown
1167:enzymes
1154:The 74
1144:epoxide
878:E. coli
605:500.629
573:Formula
406:DB00410
372:PubChem
259::
214: (
212:R01AX06
210:)
204: (
202:D06AX09
187:Topical
140::
116:a688004
4132:Portal
3756:WHO-EM
3246:Lysine
3094:other:
3022:Others
2895:402372
2893:
2811:402373
2809:
2778:
2728:
2666:
2658:
2648:
2609:
2568:
2533:
2526:433543
2523:
2474:
2466:
2456:
2391:
2384:187600
2381:
2342:
2270:
2226:
2216:
2147:365175
2145:
2135:
1970:
1939:
1912:
1836:
1703:
1500:macpE
1484:macpD
1360:macpC
1344:macpB
1318:macpA
1205:oxygen
1091:. The
1034:, MeT=
994:analog
949:, and
900:, and
875:). In
780:
648:SMILES
497:ChEMBL
466:D01076
426:393914
386:446596
286:℞-only
284:
271:
247:
136:
3829:D06AX
3255:Other
2969:use (
2664:S2CID
2472:S2CID
2171:(PDF)
2164:(PDF)
2083:(FDA)
2079:U.S.
1623:pyran
1572:mupI
1561:mupX
1551:N-AHL
1547:mupR
1537:mupW
1527:mupV
1519:mupU
1508:mupT
1492:mmpF
1474:mupS
1464:mupQ
1454:mupP
1444:mupO
1433:mupN
1423:mupM
1415:mupL
1404:mmpE
1396:mupK
1386:mupJ
1376:mupH
1368:mupG
1352:mupF
1334:mupE
1326:mupD
1311:NADPH
1303:mupC
1291:mmpD
1280:mmpC
1265:mmpB
1257:mupB
1239:mmpA
1224:mupA
1216:Gene
1126:, TE=
1118:, DH=
1093:pyran
1042:, TE=
1026:, DH=
1022:, AT=
992:, an
850:nares
804:boils
747:fungi
668:InChI
614:JSmol
477:ChEBI
3825:J01X
2965:for
2961:and
2891:PMID
2807:PMID
2776:PMID
2726:PMID
2656:PMID
2607:PMID
2566:PMID
2531:PMID
2464:PMID
2419:2012
2389:PMID
2340:PMID
2303:2013
2268:PMID
2224:PMID
2179:2014
2143:PMID
2095:2023
2061:2024
2036:2024
1968:ISBN
1937:ISBN
1910:ISBN
1877:2016
1834:PMID
1797:2023
1767:2023
1737:2024
1701:ISBN
1633:The
1503:ACP
1487:ACP
1363:ACP
1347:ACP
1321:ACP
1307:NADH
962:MRSA
958:MupB
886:MupA
882:IleS
873:IleS
753:and
457:KEGG
437:UNII
298:data
92:AHFS
3322:R01
2971:D06
2914:doi
2883:doi
2857:doi
2834:doi
2799:doi
2766:doi
2716:doi
2646:PMC
2638:doi
2597:doi
2593:276
2558:doi
2554:195
2521:PMC
2511:doi
2454:PMC
2446:doi
2379:PMC
2371:doi
2330:doi
2326:269
2260:doi
2214:PMC
2206:doi
2133:PMC
2125:doi
2121:176
2000:hdl
1902:hdl
1824:doi
1495:KS
1407:KS
1355:KR
1296:MeT
1286:AT
1268:KS
1248:KS
1246:ACP
1228:FMN
858:MIC
814:or
727:or
522:EPA
376:CID
308:97%
273:POM
261:OTC
217:WHO
207:WHO
4158::
3827:,
3769::
3739:,
3735:,
3731:,
3727:,
3723:,
3719:,
3564:,
3085::
3074::
3063::
3042::
3031::
2889:.
2869:^
2830:21
2828:.
2805:.
2774:.
2762:12
2760:.
2756:.
2738:^
2724:.
2712:10
2710:.
2706:.
2676:^
2662:.
2654:.
2644:.
2634:43
2632:.
2628:.
2605:.
2591:.
2587:.
2564:.
2552:.
2529:.
2519:.
2509:.
2499:70
2497:.
2493:.
2470:.
2462:.
2452:.
2442:56
2440:.
2436:.
2387:.
2377:.
2367:37
2365:.
2361:.
2338:.
2324:.
2320:.
2289:.
2266:.
2256:41
2254:.
2236:^
2222:.
2212:.
2202:74
2200:.
2196:.
2166:.
2141:.
2131:.
2119:.
2115:.
2103:^
2077:.
2052:.
2026:.
2022:.
1976:.
1945:.
1908:.
1885:^
1846:^
1832:.
1820:65
1818:.
1814:.
1787:.
1783:.
1753:.
1727:.
1709:.
1284:AT
1274:TE
1270:DH
1250:KR
1243:KS
1156:kb
945:,
896:,
892:,
806:,
786:.
765:.
587:44
581:26
280:US
267:UK
256:CA
249:S4
243:AU
165:AU
133:US
4134::
3831:)
3813:e
3806:t
3799:v
3743:)
3715:(
3568:)
3514:)
3490:(
3480:)
3466:(
3324:)
3310:e
3303:t
3296:v
2973:)
2951:e
2944:t
2937:v
2920:.
2916::
2897:.
2885::
2863:.
2859::
2840:.
2836::
2813:.
2801::
2782:.
2768::
2732:.
2718::
2670:.
2640::
2613:.
2599::
2572:.
2560::
2537:.
2513::
2505::
2478:.
2448::
2421:.
2395:.
2373::
2346:.
2332::
2305:.
2274:.
2262::
2230:.
2208::
2181:.
2149:.
2127::
2097:.
2063:.
2038:.
2002::
1918:.
1904::
1879:.
1840:.
1826::
1799:.
1769:.
1739:.
1309:/
1232:2
1230:H
1130:.
1080:.
1046:.
871:(
616:)
593:9
590:O
584:H
578:C
524:)
520:(
282::
269::
245::
220:)
167::
94:/
34:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
