1303:
49:
1295:
1167:. The normal function of these sodium channels is halted temporarily, as the drug interferes with their opening, thereby inhibiting the conduction of action potentials in nerves involved in sympathetic, sensory, and motor activity. This interruption results in decreased muscle control, and overall analgesic effects which allow for levobupivacaine to act as a local anaesthetic.
40:
1310:
A 5-step process to synthesise levobupivacaine from N-CBZ (S)-lysine, published in 1996, is depicted in Scheme 1. The key steps in this process include oxidative de-animation and stereospecific ring closure to form the pipecolamide core structure. This method is claimed to be efficient, but showed to
1181:
When compared to the racemic bupivacaine mixture, levobupivacaine generally has been shown to have similar effects. As an anaesthetic, it is similar in nerve-blocking potency compared to its R(+)-enantiomer and racemic mixture, although its effects are affected by the route of administration and the
1213:, specifically CYP1A2 and CYP3A isoforms as part of phase one biotransformation, thereby producing inactive metabolites. The major metabolite produced is 3-hydroxy-levobupivacaine and the minor one is desbutyl-levobupivacaine. Subsequently, levobupivacaine metabolites are further converted into
854:
Levobupivacaine was designed, in the late 1970s, to be a safer and more effective alternative to bupivacaine, which had been associated with a higher risk of cardiotoxicity. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is
2177:
1035:
Levobupivacaine has become a more favourable alternative for regional anaesthesia than bupivacaine due to its reduced toxicity. A plethora of non-human studies have established levobupivacaine’s lower risk of cardiac and neurotoxic adverse effects. Most animal studies show that the
1156:. Indeed, it has been found in certain studies that, as a surgical anaesthetic, it has a sensory ad motor blocking activity for over 90% of adult patients who received appropriate doses for their bodily composition, and duration of the surgery, with an onset time of 15 minutes.
911:
or lower body surgery, as it does not diverge dramatically in terms of sensory and/or motor block duration in comparison to bupivacaine. Deserving of consideration is the fact that its enhanced motor blocking can be a downside for patients receiving an epidural injection during
1044:) of levobupivacaine is approximately 50% higher than that of bupivacaine. In general, laevorotatory isomers tend to cause significantly fewer adverse effects and are thus a safer pharmacological alternative. Levobupivacaine has a 97%
1010:
activity, thereby increasing the duration of sensory blockage with a relatively low risk of central nervous system toxicity on one hand, and on the other, it can have the same effect on uteroplacental blood flow, which can harm the
1217:
and sulphate ester conjugates as a part of phase two. Metabolic inversion of levobupivacaine is not observed. The extensive metabolism of levobupivacaine by the liver ensures that no unchanged drug is excreted via
1786:
Gomez de Segura IA, Menafro A, García-Fernández P, Murillo S, Parodi EM (September 2009). "Analgesic and motor-blocking action of epidurally administered levobupivacaine or bupivacaine in the conscious dog".
998:
may be a result of indirect effects of the drug, such as the blockade of myocardial sympathetic nerves, thus leading to contractile delay, or by direct effects, such as the blockade of potassium channels.
1051:
In human volunteer studies, levobupivacaine consistently proved to have a safety advantage over bupivacaine. Risk factors for local anaesthetic toxicity depend on the administration of levobupivacaine to
851:
and therefore similar in pharmacological effects. The drug typically starts taking effect within 15 minutes and can last up to 16 hours depending on factors such as site of administration and dosage.
1075:, which contribute to the slower absorption rate and plasma concentrations below the toxic level compared to younger patients. On the other hand, homeostatic disbalance can exacerbate toxic effects.
246:
1186:
indicate that among the three, levobupivacaine shows an increased duration of anaesthesia and/or greater potency, and there is evidence that in humans it is as potent as bupivacaine.
201:
799:
1082:
patients due to their underdeveloped metabolic processing to prevent reaching toxic levels. The dosage of local anaesthetics is calculated based on the patient’s weight and
1601:
1859:
Huang YF, Pryor ME, Mather LE, Veering BT (April 1998). "Cardiovascular and central nervous system effects of intravenous levobupivacaine and bupivacaine in sheep".
1145:
quality (97%) is characteristic of levobupivacaine, which strengthens its binding to cell surface proteins, thereby lengthening the binding, and thus action time.
143:
755:
2209:
1137:
of cells. This, however, is counteracted by the high lipid solubility of levobupivacaine, which increases the ease with which it can diffuse through the
1302:
1063:
Age is a relevant factor in vulnerability to levobupivacaine toxicity. Elderly patients are more likely to have pre-existing conditions impacting the
887:
Levobupivacaine, the S(-)-enantiomer of bupivacaine has been developed as an alternative to the racemic mixture, as it has been shown to have a lower
741:
1015:. Ultimately, levobupivacaine has been shown to have a lower risk of cardiovascular and central nervous system toxicity compared to bupivacaine in
1202:
depends on the vascularity of the tissue. Maximum plasma concentration of 1.2 μg/mL is reached approximately 30 minutes post epidural injection.
1953:"A comparison of the cardiovascular effects of levobupivacaine and rac-bupivacaine following intravenous administration to healthy volunteers"
2536:
2502:
1130:, such as that of levobupivacaine, tend to be their ionised form under physiological state, meaning that they would not easily cross the
1107:, motor blocking, and sensory blocking effects on the human body, whose properties are dictated by its chemical characteristics, such as
1577:
1048:
which is 2% higher than what is observed in bupivacaine. The faster protein binding rate contributes to its reduced toxicity level.
820:
775:
783:
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
2202:
967:
387:
231:
1372:
Heppolette CA, Brunnen D, Bampoe S, Odor PM (June 2020). "Clinical
Pharmacokinetics and Pharmacodynamics of Levobupivacaine".
1178:
are targeted and more easily blocked than unmyelinated neurons, and small nerves are more easily blocked than large nerves.
1170:
Levobupivacaine varies slightly in its effects depending on the characteristics of the neuron in question. For example, in
994:, which may be due to the blockade of sodium, potassium and calcium channels in tissues that were not intended as targets.
2411:
1331:
2175:, 장사정; 이재목 & 공준수, "New synthetic method of levobupivacaine and its hydrochloride", issued 2008-07-07
1697:
Sanford M, Keating GM (April 2010). "Levobupivacaine: a review of its use in regional anaesthesia and pain management".
543:
2553:
1086:, however, the association power is stronger in children than in adults. Moreover, symptoms of systemic toxicity like
856:
647:
1002:
Effects of this nature lead to lowered contractile function and arrhythmogenic effects, which can potentially cause
2585:
2580:
2195:
1647:
Foster RH, Markham A (March 2000). "Levobupivacaine: a review of its pharmacology and use as a local anaesthetic".
1108:
1199:
919:
Other than childbirth, possible applications of levobupivacaine include upper and lower limb surgery, as well as
636:
2187:
1246:
1270:
anaesthetic that is similar in structure to bupivacaine, namely the S-enantiomer of bupivacaine. A lipophilic
927:, highly efficient and convenient for patients undergoing vitreoretinal anterior segment or cataract surgery.
484:
954:
in obstetrics is also contraindicated. Levobupivacaine is furthermore contraindicated in patients with known
2541:
1195:
1123:
1024:
187:
1286:
and exert its local anaesthetic effect by causing a reversible blockade of open neuronal sodium channels.
2223:
2005:
Gristwood RW, Greaves JL (June 1999). "Levobupivacaine: a new safer long acting local anaesthetic agent".
1149:
1142:
1045:
1020:
979:
859:
onset time. Ropivacaine is, next to levobupivacaine, another less cardiotoxic alternative to bupivacaine.
628:
297:
1904:"Pharmacokinetics of the enantiomers of bupivacaine following intravenous administration of the racemate"
1318:
from 2008, consists of a 3-step process (see Scheme 2) to synthesise levobupivacaine hydrochloride of an
1311:
be dangerous for mass production due to the high risk of explosion of the diazonium salt intermediates.
2507:
1294:
475:
2590:
2512:
339:
1159:
More specifically, levobupivacaine achieves its effects by acting on the neuronal voltage-sensitive
2248:
1327:
1319:
1238:
1003:
924:
896:
828:
414:
48:
1884:
1722:
1672:
1548:
1502:
1397:
1275:
951:
161:
2405:
2595:
2154:
2115:
2061:
2022:
1982:
1933:
1876:
1804:
1714:
1664:
1583:
1573:
1540:
1494:
1453:
1389:
1230:
1206:
963:
908:
871:
855:
approximately 13 per cent less potent (by molarity) than racemic bupivacaine and has a longer
259:
121:
671:
663:
608:
2218:
2146:
2105:
2095:
2053:
2014:
1972:
1964:
1923:
1915:
1868:
1838:
1796:
1706:
1656:
1532:
1484:
1443:
1433:
1381:
1323:
1164:
1007:
955:
943:
839:-type local anaesthetic that blocks nerve impulses by inhibiting sodium ion influx into the
824:
687:
352:
279:
66:
1827:"Enantiomeric Local Anesthetics: Can Ropivacaine and Levobupivacaine Improve Our Practice?"
1306:
Scheme 2 | Process to synthesise levobupivacaine and its hydrochloride by 장사정, 이재목 and 공준수.
560:
552:
532:
431:
423:
2364:
2301:
2296:
1745:
1214:
1210:
1175:
1153:
1083:
983:
900:
832:
329:
307:
287:
1338:, can lead to an optical purity of at least 98% levobupivacaine. Lastly, the addition of
1060:, as well as the predisposition of these tissues to levobupivacaine’s negative effects.
1473:"Intrathecal bupivacaine or levobupivacaine: which should be used for elderly patients?"
2547:
2326:
2276:
2110:
2083:
1977:
1952:
1928:
1919:
1903:
1448:
1421:
1283:
1223:
1183:
1160:
1053:
1016:
995:
904:
892:
888:
2134:
2574:
2451:
2369:
2172:
2150:
2057:
1968:
1872:
1800:
1710:
1676:
1660:
1552:
1506:
1401:
1339:
1279:
1194:
The plasma concentration of levobupivacaine is influenced by both the dosage and the
1138:
1134:
1888:
1726:
2346:
2316:
2281:
2229:
958:
to levobupivacaine or other amide-type local anaesthetics, in patients with severe
464:
214:
209:
1322:
of at least 99%. (S)-2,6-pipecocholxylide (I) is reacted with 1-bromobutane and a
456:
153:
2084:"Clinical profile of levobupivacaine in regional anesthesia: A systematic review"
2040:
Rosen MA, Thigpen JW, Shnider SM, Foutz SE, Levinson G, Koike M (November 1985).
2517:
2476:
2461:
2446:
2438:
2389:
2291:
2261:
1335:
1271:
1233:
levobupivacaine showed that 71% was recovered in urine and 24% was recovered in
1087:
1037:
959:
920:
848:
31:
1842:
1536:
1385:
2522:
2486:
2481:
2466:
2384:
2379:
2354:
2336:
2311:
2306:
2256:
1587:
1131:
1119:
1079:
991:
947:
913:
867:
844:
717:
523:
319:
194:
39:
2158:
2100:
2018:
1902:
Burm AG, van der Meer AD, van Kleef JW, Zeijlmans PW, Groen K (August 1994).
1544:
1489:
1472:
512:
2471:
2456:
2433:
2331:
2266:
1242:
1104:
903:. Particularly, it has been found suitable for multiple procedures, such as
362:
147:
2119:
2026:
1826:
1808:
1718:
1668:
1567:
1498:
1457:
1393:
1182:
concentration, however, they were ultimately similar among the three. Some
2065:
2041:
1986:
1937:
1880:
17:
2321:
2271:
1057:
987:
495:
1226:, only the inactive metabolites accumulate instead of the drug itself.
504:
2374:
2359:
2286:
1572:(7th ed.). Adelaide, S.A.: Australian Medicines Handbook Pty Ltd.
1438:
942:
Using 0.75% (7.5 mg/mL) of levobupivacaine, similar to bupivacaine, is
442:
1951:
Bardsley H, Gristwood R, Baker H, Watson N, Nimmo W (September 1998).
1315:
1171:
1068:
931:
863:
840:
619:
367:
1602:"Levobupivacaine - List of nationally authorised medicinal products"
1330:, to obtain a solution of (S)-bupivacaine (II) and its enantiomers.
588:
580:
2425:
2238:
2042:"Bupivacaine-induced cardiotoxicity in hypoxic and acidotic sheep"
1267:
1263:
1234:
1219:
1072:
1064:
1012:
836:
740:
731:
599:
371:
312:
930:
Levobupivacaine can be combined with other analgesics, including
1766:
Chirocaine (levobupivacaine injection) prescribing information.
1523:
Cada DJ, Baker DE, Levien T (December 1999). "Levobupivacaine".
1471:
Gulec D, Karsli B, Ertugrul F, Bigat Z, Kayacan N (April 2014).
1298:
Scheme 1 | Process to synthesise levobupivacaine by Adger et al.
571:
266:
253:
2191:
72:
2135:"Stereospecific synthesis of the anaesthetic levobupivacaine"
1118:
of a drug can be informative information that indicates its
652:
84:
1078:
It is important to adjust the dosage of levobupivacaine in
874:– in concentrations ranging from 0.625 mg/mL to 7.5 mg/mL.
240:
172:
105:
99:
78:
1746:"Chirocaine 2.5 mg/mL: summary of product characteristics"
907:. It is effective for human patients who receive elective
93:
1027:, and should be therefore considered as an alternative.
916:, as a certain level of movement may still be required.
1422:"Update on local anesthetics: focus on levobupivacaine"
806:
862:
Levobupivacaine hydrochloride is commonly marketed by
108:
102:
96:
90:
81:
75:
69:
2495:
2424:
2398:
2345:
2247:
2237:
729:
716:
686:
681:
646:
618:
598:
570:
542:
522:
494:
483:
474:
441:
413:
378:
361:
351:
338:
328:
318:
306:
296:
286:
278:
230:
225:
200:
186:
160:
142:
130:
120:
87:
60:
55:
324:3-hydroxy-levobupivacaine desbutyl-levobupivacaine
2133:Adger B, Dyer U, Hutton G, Woods M (1996-08-26).
1152:, long-acting anaesthetic with a relatively slow
1148:The S(-)-enantiomer of levobupivacaine is a high-
870:Chirocaine. In Europe, Chirocaine is available –
2088:Journal of Anaesthesiology Clinical Pharmacology
1334:of this solution with a solvent (b), preferably
1282:components of levobupivacaine allow it to cross
1006:and death. It is to note that the drug also has
463:
455:
430:
422:
895:advice, it can be applied for minor and major
2203:
1477:The Journal of International Medical Research
1245:was approximately 80 minutes and the rate of
8:
30:
2244:
2210:
2196:
2188:
531:
47:
38:
2109:
2099:
1976:
1927:
1488:
1447:
1437:
1426:Therapeutics and Clinical Risk Management
559:
551:
1957:British Journal of Clinical Pharmacology
1908:British Journal of Clinical Pharmacology
1301:
1293:
1163:, where it prevents the transmission of
154:Micromedex Detailed Consumer Information
2007:Expert Opinion on Investigational Drugs
1351:
780:
760:
670:
662:
511:
503:
392:
2077:
2075:
2000:
1998:
1996:
934:, for postoperative pain management.
29:
1854:
1852:
1820:
1818:
1781:
1779:
1777:
1761:
1759:
1642:
1640:
1638:
635:
627:
607:
152:
7:
1789:Veterinary Anaesthesia and Analgesia
1740:
1738:
1736:
1692:
1690:
1688:
1686:
1636:
1634:
1632:
1630:
1628:
1626:
1624:
1622:
1620:
1618:
1518:
1516:
1415:
1413:
1411:
1367:
1365:
1363:
1361:
1359:
1357:
1355:
982:caused by levobupivacaine usage are
213:
1420:Burlacu CL, Buggy DJ (April 2008).
1126:. For example, drugs with a high pK
1103:Levobupivacaine is a drug that has
827:drug indicated for minor and major
587:
579:
446:
1920:10.1111/j.1365-2125.1994.tb04335.x
1114:, which has a value of 8.1. The pK
1090:are harder to notice in children.
763:O=C(1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
25:
2082:Bajwa SJ, Kaur J (October 2013).
1241:of 40 mg of levobupivacaine, the
2058:10.1213/00000539-198511000-00010
1969:10.1046/j.1365-2125.1998.00775.x
1873:10.1213/00000539-199804000-00023
1801:10.1111/j.1467-2995.2009.00469.x
1711:10.2165/11203250-000000000-00000
1661:10.2165/00003495-200059030-00013
1222:. As a result, in patients with
978:Possible adverse effects in the
968:intravenous regional anaesthesia
704:
698:
65:
1825:Casati A, Baciarello M (2006).
788:Key:LEBVLXFERQHONN-INIZCTEOSA-N
899:, as well as (post-operative)
710:
692:
1:
2412:3-(p-Fluorobenzoyloxy)tropane
2399:ArCO2- (not para-amino or Ph)
2151:10.1016/0040-4039(96)01357-3
843:. Levobupivacaine is the S-
2612:
2503:Anesthetic/vasoconstrictor
1843:10.2174/157488506775268506
1537:10.1177/194512539903401211
1386:10.1007/s40262-020-00868-0
1239:intravenous administration
1205:Levobupivacaine undergoes
682:Chemical and physical data
2531:
2408:(3,4,5-Trimethoxybenzoyl)
1609:European Medicines Agency
1374:Clinical Pharmacokinetics
796:
771:
751:
383:
46:
37:
2101:10.4103/0970-9185.119172
2046:Anesthesia and Analgesia
2019:10.1517/13543784.8.6.861
1861:Anesthesia and Analgesia
1490:10.1177/0300060513496737
1249:was 651 ± 221.5 mL/min.
1196:method of administration
1124:physiological conditions
1019:, not at the expense of
891:than bupivacaine. Under
405:piperidine-2-carboxamide
2462:Cinchocaine (Dibucaine)
2224:sodium channel blockers
1004:cardiovascular collapse
1307:
1299:
1278:by an amide bond. The
1262:Levobupivacaine is an
1211:cytochrome P450 enzyme
990:, tongue numbness and
980:central nervous system
923:, where it blocks the
835:. It is a long-acting
2508:Bupivacaine/meloxicam
1305:
1297:
403:-(2,6-dimethylphenyl)
2513:Lidocaine/prilocaine
2322:Procaine (Novocaine)
1831:Current Drug Therapy
1209:in the liver by the
1143:high-protein binding
1139:phospholipid bilayer
1046:protein binding rate
897:surgical anaesthesia
829:surgical anaesthesia
2139:Tetrahedron Letters
1328:potassium carbonate
952:paracervical blocks
637:ChEMBLChEMBL1201177
262:(Prescription only)
249:(Prescription only)
34:
2558:Never to phase III
1768:Purdue Pharma L.P.
1750:Abbot Laboratories
1439:10.2147/TCRM.S1433
1308:
1300:
925:extraocular muscle
353:Duration of action
2586:Enantiopure drugs
2581:Local anesthetics
2568:
2567:
2420:
2419:
2219:Local anesthetics
2145:(35): 6399–6402.
2052:(11): 1089–1096.
1531:(12): 1441–1453.
1525:Hospital Pharmacy
1332:Recrystallisation
1276:hydrocarbon chain
1229:Research tracing
1224:renal dysfunction
1207:biotransformation
966:) and for use in
964:hypovolemic shock
962:(e.g. cardiac or
950:patients. Use in
938:Contraindications
909:Caesarean section
872:prescription only
825:local anaesthetic
814:
813:
742:Interactive image
648:CompTox Dashboard
334:Within 15 minutes
270:
257:
244:
176:
27:Chemical compound
16:(Redirected from
2603:
2245:
2227:
2212:
2205:
2198:
2189:
2182:
2181:
2180:
2176:
2169:
2163:
2162:
2130:
2124:
2123:
2113:
2103:
2079:
2070:
2069:
2037:
2031:
2030:
2002:
1991:
1990:
1980:
1948:
1942:
1941:
1931:
1899:
1893:
1892:
1856:
1847:
1846:
1822:
1813:
1812:
1783:
1772:
1771:
1763:
1754:
1753:
1742:
1731:
1730:
1694:
1681:
1680:
1644:
1613:
1612:
1606:
1598:
1592:
1591:
1566:Rossi S (2006).
1563:
1557:
1556:
1520:
1511:
1510:
1492:
1468:
1462:
1461:
1451:
1441:
1417:
1406:
1405:
1369:
1342:(c) is possible.
1198:. Additionally,
1190:Pharmacokinetics
1176:nodes of Ranvier
1141:. Additionally,
1099:Pharmacodynamics
1008:vasoconstrictive
984:light-headedness
970:(Bier’s block).
956:hypersensitivity
810:
809:
802:
744:
724:
712:
706:
700:
694:
674:
666:
656:
654:
639:
631:
611:
591:
583:
563:
555:
535:
515:
507:
487:
467:
459:
449:
448:
434:
426:
343:
268:
265:
255:
252:
242:
239:
217:
174:
171:
156:
138:L(-)-bupivacaine
136:(-)-bupivacaine
134:(S)-bupivacaine
115:
114:
111:
110:
107:
104:
101:
98:
95:
92:
89:
86:
83:
80:
77:
74:
71:
51:
42:
35:
33:
21:
2611:
2610:
2606:
2605:
2604:
2602:
2601:
2600:
2571:
2570:
2569:
2564:
2563:
2548:Clinical trials
2527:
2491:
2443:Levobupivacaine
2416:
2394:
2365:Cyclomethycaine
2341:
2302:Metabutoxycaine
2297:Metabutethamine
2233:
2221:
2216:
2186:
2185:
2178:
2171:
2170:
2166:
2132:
2131:
2127:
2081:
2080:
2073:
2039:
2038:
2034:
2004:
2003:
1994:
1950:
1949:
1945:
1901:
1900:
1896:
1858:
1857:
1850:
1824:
1823:
1816:
1785:
1784:
1775:
1770:(Report). 1999.
1765:
1764:
1757:
1744:
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1522:
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1514:
1470:
1469:
1465:
1419:
1418:
1409:
1371:
1370:
1353:
1348:
1292:
1284:cell membraness
1274:is linked to a
1260:
1255:
1215:glucuronic acid
1192:
1161:sodium channels
1154:onset of action
1135:plasma membrane
1129:
1117:
1112:
1101:
1096:
1084:body mass index
1073:hepatic systems
1058:cerebral tissue
1043:
1033:
976:
974:Adverse effects
944:contraindicated
940:
901:pain management
885:
880:
833:pain management
817:Levobupivacaine
805:
803:
800:(what is this?)
797:
792:
789:
784:
779:
778:
767:
764:
759:
758:
747:
722:
709:
703:
697:
677:
650:
642:
614:
594:
566:
538:
518:
490:
470:
445:
437:
409:
406:
404:
391:
390:
341:
330:Onset of action
298:Protein binding
288:Bioavailability
280:Pharmacokinetic
274:
221:
189:
182:
163:
68:
64:
32:Levobupivacaine
28:
23:
22:
15:
12:
11:
5:
2609:
2607:
2599:
2598:
2593:
2588:
2583:
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2367:
2362:
2357:
2351:
2349:
2343:
2342:
2340:
2339:
2334:
2329:
2327:Proxymetacaine
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2277:Chloroprocaine
2274:
2269:
2264:
2259:
2253:
2251:
2242:
2235:
2234:
2217:
2215:
2214:
2207:
2200:
2192:
2184:
2183:
2164:
2125:
2094:(4): 530–539.
2071:
2032:
2013:(6): 861–876.
1992:
1963:(3): 245–249.
1943:
1914:(2): 125–129.
1894:
1867:(4): 797–804.
1848:
1814:
1795:(5): 485–494.
1773:
1755:
1732:
1705:(6): 761–791.
1682:
1655:(3): 551–579.
1614:
1593:
1578:
1558:
1512:
1483:(2): 376–385.
1463:
1432:(2): 381–392.
1407:
1380:(6): 715–745.
1350:
1349:
1347:
1344:
1320:optical purity
1314:A more recent
1291:
1288:
1259:
1256:
1254:
1251:
1191:
1188:
1184:animal studies
1165:nerve impulses
1127:
1115:
1110:
1100:
1097:
1095:
1092:
1041:
1032:
1029:
1017:animal studies
996:Cardiotoxicity
975:
972:
939:
936:
905:epidural block
893:European Union
889:cardiotoxicity
884:
881:
879:
876:
812:
811:
794:
793:
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790:
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394:
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365:
359:
358:
357:Up to 16 hours
355:
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2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2452:Butanilicaine
2450:
2448:
2444:
2440:
2437:
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2173:KR100844336B1
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1611:. 2018-09-06.
1610:
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1579:0-9757919-2-3
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1356:
1352:
1345:
1343:
1341:
1340:hydrochloride
1337:
1333:
1329:
1326:(a), such as
1325:
1321:
1317:
1312:
1304:
1296:
1289:
1287:
1285:
1281:
1277:
1273:
1272:aromatic ring
1269:
1265:
1257:
1252:
1250:
1248:
1244:
1240:
1236:
1232:
1231:radiolabelled
1227:
1225:
1221:
1216:
1212:
1208:
1203:
1201:
1197:
1189:
1187:
1185:
1179:
1177:
1174:neurons, the
1173:
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1157:
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834:
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826:
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795:
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770:
761:
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750:
743:
739:
738:
736:
733:
728:
721:
719:
715:
691:
689:
685:
680:
673:
668:
665:
661:
660:
658:
649:
645:
638:
633:
630:
629:ChEMBL1201193
626:
625:
623:
621:
617:
610:
606:
605:
603:
601:
597:
590:
585:
582:
578:
577:
575:
573:
569:
562:
557:
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550:
549:
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541:
534:
530:
529:
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321:
317:
314:
311:
309:
305:
301:
299:
295:
291:
289:
285:
281:
277:
271: Rx-only
264:
261:
251:
248:
238:
237:
235:
233:
229:
224:
216:
211:
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205:
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185:
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145:
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137:
133:
129:
125:
123:
119:
113:
63:
61:Pronunciation
59:
56:Clinical data
54:
50:
45:
41:
36:
19:
2496:Combinations
2442:
2317:Propoxycaine
2282:Dimethocaine
2249:Aminobenzoic
2167:
2142:
2138:
2128:
2091:
2087:
2049:
2045:
2035:
2010:
2006:
1960:
1956:
1946:
1911:
1907:
1897:
1864:
1860:
1837:(1): 85–89.
1834:
1830:
1792:
1788:
1767:
1749:
1702:
1698:
1652:
1648:
1608:
1596:
1568:
1561:
1528:
1524:
1480:
1476:
1466:
1429:
1425:
1377:
1373:
1313:
1309:
1261:
1228:
1204:
1193:
1180:
1169:
1158:
1147:
1102:
1094:Pharmacology
1088:paraesthesia
1077:
1062:
1050:
1034:
1001:
977:
941:
929:
918:
886:
878:Clinical use
861:
853:
816:
815:
804:
798:
513:DBSALT000834
400:
396:
340:Elimination
232:Legal status
226:Legal status
135:
2591:Piperidines
2544:from market
2477:Mepivacaine
2447:Ropivacaine
2439:Bupivacaine
2390:Piperocaine
2292:Meprylcaine
2262:Benzonatate
2222:(primarily
1336:cyclohexane
1132:hydrophobic
1038:lethal dose
992:convulsions
960:hypotension
921:eye surgery
883:Indications
857:motor block
849:bupivacaine
847:of racemic
841:nerve cells
725: g·mol
379:Identifiers
320:Metabolites
131:Other names
122:Trade names
2575:Categories
2523:Iontocaine
2487:Trimecaine
2482:Prilocaine
2467:Etidocaine
2457:Carticaine
2385:Isobucaine
2380:Hexylcaine
2355:Amylocaine
2337:Tetracaine
2312:Orthocaine
2307:Nitracaine
2257:Benzocaine
1588:1322357781
1346:References
1280:lipophilic
1237:After the
1200:absorption
1172:myelinated
1120:ionisation
1080:paediatric
1054:myocardial
914:childbirth
868:trade name
866:under the
845:enantiomer
730:3D model (
718:Molar mass
669:HCl:
634:HCl:
609:CHEBI:6149
586:HCl:
561:J998RDZ51I
558:HCl:
553:A5H73K9U3W
524:ChemSpider
510:HCl:
476:IUPHAR/BPS
462:HCl:
432:27262-48-2
429:HCl:
424:27262-47-1
415:CAS Number
399:)-1-butyl-
388:IUPAC name
347:80 minutes
308:Metabolism
195:Parenteral
126:Chirocaine
18:Chirocaine
2554:Phase III
2542:Withdrawn
2472:Lidocaine
2434:Articaine
2406:Amoproxan
2375:β-Eucaine
2370:α-Eucaine
2332:Risocaine
2267:Butacaine
2159:0040-4039
1677:195691108
1553:261109078
1545:0018-5787
1507:206506181
1402:211061840
1290:Synthesis
1258:Structure
1253:Chemistry
1247:clearance
1243:half-life
1105:analgesic
948:obstetric
363:Excretion
342:half-life
188:Routes of
162:Pregnancy
148:Drugs.com
2596:Anilides
2272:Butamben
2120:24249993
2027:15992136
1889:19156695
1809:19508452
1727:70725624
1719:20394458
1669:10776835
1569:AMH 2006
1499:24595149
1458:18728849
1394:32034727
1031:Toxicity
1025:efficacy
988:tinnitus
807:(verify)
496:DrugBank
202:ATC code
177: B3
164:category
2360:Cocaine
2347:Benzoic
2287:Lucaine
2241:by acid
2111:3819850
2066:4051206
1987:9764965
1978:1873676
1938:7981012
1929:1364857
1881:9539605
1752:. 1999.
1449:2504073
1235:faecesl
1150:potency
1065:cardiac
1021:potency
932:opioids
823:) is a
723:288.435
688:Formula
672:9046071
664:8048496
505:DB01002
443:PubChem
313:Hepatic
218:)
212: (
210:N01BB10
2537:WHO-EM
2426:Amides
2239:Esters
2179:
2157:
2118:
2108:
2064:
2025:
1985:
1975:
1936:
1926:
1887:
1879:
1807:
1725:
1717:
1675:
1667:
1586:
1576:
1551:
1543:
1505:
1497:
1456:
1446:
1400:
1392:
1316:patent
1122:under
1013:foetus
864:AbbVie
756:SMILES
620:ChEMBL
589:D01287
581:D08116
465:117965
372:faecal
258:
245:
116:
1885:S2CID
1723:S2CID
1699:Drugs
1673:S2CID
1649:Drugs
1605:(PDF)
1549:S2CID
1503:S2CID
1398:S2CID
1268:amide
1264:amino
1220:urine
1069:renal
837:amide
776:InChI
732:JSmol
600:ChEBI
533:83289
457:92253
370:71%,
368:Renal
2230:N01B
2155:ISSN
2116:PMID
2062:PMID
2023:PMID
1983:PMID
1934:PMID
1877:PMID
1805:PMID
1715:PMID
1665:PMID
1584:OCLC
1574:ISBN
1541:ISSN
1495:PMID
1454:PMID
1390:PMID
1324:base
1071:and
1056:and
1023:and
831:and
821:rINN
572:KEGG
544:UNII
485:7211
282:data
144:AHFS
2518:TAC
2147:doi
2106:PMC
2096:doi
2054:doi
2015:doi
1973:PMC
1965:doi
1924:PMC
1916:doi
1869:doi
1839:doi
1797:doi
1707:doi
1657:doi
1533:doi
1485:doi
1444:PMC
1434:doi
1382:doi
1040:(LD
946:in
653:EPA
447:CID
374:24%
302:97%
292:n/a
260:POM
215:WHO
85:juː
2577::
2550::
2153:.
2143:37
2141:.
2137:.
2114:.
2104:.
2092:29
2090:.
2086:.
2074:^
2060:.
2050:64
2048:.
2044:.
2021:.
2009:.
1995:^
1981:.
1971:.
1961:46
1959:.
1955:.
1932:.
1922:.
1912:38
1910:.
1906:.
1883:.
1875:.
1865:86
1863:.
1851:^
1833:.
1829:.
1817:^
1803:.
1793:36
1791:.
1776:^
1758:^
1748:.
1735:^
1721:.
1713:.
1703:70
1701:.
1685:^
1671:.
1663:.
1653:59
1651:.
1617:^
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