817:—tolerance to agents such as glyceryl trinitrate— may develop in a patient, reducing its effectiveness. Tolerance is defined as the loss of symptomatic and hemodynamic effects of glyceryl trinitrate and/or the need for higher doses of the drug to achieve the same effects, and was first described soon after the introduction of glyceryl trinitrate in cardiovascular therapy. Studies have shown that nitrate tolerance is associated with vascular abnormalities which have the potential to worsen patients' prognosis. These include endothelial and autonomic dysfunction.
47:
1287:"Il faut toutefois être sur ses gardes en faissant cet essai, car il suffit d'en tenir une très-petite quantité (ce qu'on peut en prendre en y mouillant légèrement le bout du petit doigt) sur la langue pour en éprouver une migraine assez forte pendant pleusieurs heures. Cette action sur le corps humain a été constatée par plusieurs personnes dans mon laboratoire, et je l'ai éprouvée plusieurs fois sur moi-même avant que je fusse certain qu'elle a des propriétés toxiques."
1318:" … basta il tenere una gocciolina di Piroglicerina sulla lingua, senza inghiottirla, perchè si provi tosto un violento dolore di capo, quale è quello di una forte emicrania, accompagnato da pulsazioni interne assai penose: nello stesso tempo provasi debolezza alle estremità inferiori. Questo effetto sentii io più volte, ed il provarono il signor prof. Valerico Cauda prepartore della mia scuola, ed altre persone ehe tentarono l'esperimento."
1289:(It is always necessary to be on one's guard when making this test, for it suffices to take a very small quantity of it (which one can take by lightly wetting, in it, the tip of the little finger) on tongue in order to feel a quite strong headache for several hours. This action on the human body has been confirmed by several persons in my laboratory, and I tested it several times on myself before I was certain that it has toxic properties.)
38:
4158:
1995:(Sobrero, 1849), pp. 198–199. On pages 198–199, Sobrero describes the results of administering nitroglycerin to a puppy, a mouse, and a guinea pig. After giving (orally) several centigrams of nitroglycerin to a puppy, the animal vomited, and within 7-8 minutes, it ceased to breath. Sobrero managed to revive it, but it convulsed.
708:
1999:(The opening of its body did not reveal any deterioration of the ventricle. The vessels of the brain were full of blood; similarly swollen with blood were the right auricle of the heart and especially the superior vena cava.) Administering nitroglycerin to a mouse and a guinea pig produced similar results.
1324:
on tongue, without swallowing it, because one soon feels a violent pain in the head, which is a strong headache, accompanied by very painful internal throbbings; at the same time one would feel weakness in the lower extremities. This effect I felt many times, and it was felt by Prof. Valerico Cauda,
755:
within 2–3 weeks of sustained use. Continuous administration and absorption (such as provided by daily pills and especially skin patches) accelerate onset of tolerance and limit the usefulness of the agent. Thus, glyceryl trinitrate works best when used only in short-term, pulse dosing. Glyceryl
940:
are the primary source of glyceryl trinitrate bioactivation. In recent years, a great deal of evidence has been produced that supports the conclusion that glyceryl trinitrate's clinically relevant denitration and reduction produce 1,2-glyceryl dinitrate (GDN) and NO, and that this reaction is
764:, again working best if used quickly, within a few minutes of symptom onset, as a pulse dose. It may also be given as a sublingual or buccal dose in the form of a tablet placed under the tongue or a spray into the mouth for the treatment of an angina attack.
1012:
developed a form of nitroglycerin in 1847 and advocated for its dosing as a treatment of a number of diseases; however, its use as a specific treatment for blood pressure and chest pain was not among these. This is primarily due to his deep rooted focus in
751:, before the structure of NO as the responsible agent was known. This led to the development of transdermal patches of glyceryl trinitrate, providing 24-hour release. However, the effectiveness of glyceryl trinitrate is limited by development of tolerance/
2642:
1997:"L'apertura del suo corpo non diede a scorgere alterazione veruna al ventricolo. I vasi de cervello erano pieni di sangue, come rigonfii di sangue erano l'orocchietta destra de cuore e specialmente la vena cava superiore."
1781:
Gambito ED, Gonzalez-Suarez CB, Oquiñena TI, Agbayani RB (August 2010). "Evidence on the effectiveness of topical nitroglycerin in the treatment of tendinopathies: a systematic review and meta-analysis".
2358:
924:, and the denitration and reduction occur via a variety of mechanisms. The mechanism by which such nitrates produce NO is widely disputed. Some believe that organic nitrates produce NO by reacting with
2635:
182:
1939:
2846:
2628:
521:
4198:
127:
579:
4203:
2351:
1049:
The medical establishment used the name "glyceryl trinitrate" or "trinitrin" to avoid alarming patients, because of a general awareness that nitroglycerin was explosive.
691:
Nitroglycerin was written about as early as 1846 and came into medical use in 1878. The drug nitroglycerin is a dilute form of the same chemical used as the explosive,
2839:
2344:
69:
820:
The mechanisms of nitrate tolerance have been investigated over the last 30 years, and several hypotheses to explain tolerance have been offered, including:
884:
due to the risk of explosion and/or burns, but investigations have concluded that glyceryl trinitrate patch explosions during defibrillation were due to the
535:
3979:
1040:. Murrell began treating patients with small doses of glyceryl trinitrate in 1878, and the substance was widely adopted after he published his results in
2832:
850:, and severe headaches that necessitate analgesic intervention for pain relief, the painful nature of which can have a marked negative effect on patient
4188:
2106:
Kaplan KJ, Taber M, Teagarden JR, Parker M, Davison R (January 1985). "Association of methemoglobinemia and intravenous nitroglycerin administration".
1935:
1587:
2586:
1936:
Recommendation From the
Scientific Committee on Occupational Exposure Limits for Glycerol Trinitrate (Nitroglycerin) [SCOEL/SUM/147]
3608:
1440:
1404:
748:
695:. Dilution makes it non-explosive. In 2021, it was the 174th most commonly prescribed medication in the United States, with more than 2
4183:
4034:
2086:
4193:
3293:
1885:
Such activation is suggested to cause sympathetic activation, and release of vasoconstrictors such as endothelin and angiotensin II.
1434:
1398:
555:
3459:
3646:
2972:
2262:
Lundberg JO, Weitzberg E, Gladwin MT (February 2008). "The nitrate-nitrite-nitric oxide pathway in physiology and therapeutics".
1273:"Sur plusieur composés détonants produits avec l'acide nitrique et le sucre, la dextrine, la lactine, la mannite et la glycérine"
1113:
3263:
277:
167:
3368:
4048:
1462:
973:
969:
957:
2092:
1304:"Sopra alcuni nuovi composti fulminanti ottenuti col mezzo dell'azione dell'acido nitrico sulle sostante organiche vegetali"
1221:"Role of voltage-gated sodium, potassium and calcium channels in the development of cocaine-associated cardiac arrhythmias"
3730:
3598:
1275:[On several detonating compounds produced with nitric acid and sugar, dextrin, lactose, mannitol, and glycerine].
1138:
Fenton C, Wellington K, Easthope SE (2006). "0.4% nitroglycerin ointment: in the treatment of chronic anal fissure pain".
965:
4148:
4136:
3298:
3122:
2724:
2429:
2392:
1912:
399:
3984:
3795:
3268:
3008:
2603:
1565:
1029:
747:
attacks, perhaps more so than reversing angina once started, by supplementing blood concentrations of NO, also called
716:
1306:[On some new explosive products obtained by the action of nitric acid on some vegetable organic substances].
2299:
Marsh N, Marsh A (April 2000). "A short history of nitroglycerine and nitric oxide in pharmacology and physiology".
3867:
3753:
3686:
3553:
3132:
1605:
Goldin M, Malanga GA (September 2013). "Tendinopathy: a review of the pathophysiology and evidence for treatment".
3018:
2906:
929:
728:
644:
3825:
3699:
3616:
3258:
2803:
3513:
1510:
348:
46:
3805:
3636:
3503:
2010:
1303:
1272:
857:
Glyceryl trinitrate also can cause severe hypotension, circulatory collapse, and death if used together with
4065:
3676:
3593:
3325:
3137:
3013:
2591:
937:
101:
3965:
3872:
3621:
3353:
4062:
3766:
3712:
3575:
3562:
3320:
3023:
2404:
961:
942:
676:
3681:
3283:
3253:
1961:
Liddle R, Richmond W (June 1998). "Investigation into voltage breakdown in glyceryl trinitrate patches".
1339:
4178:
3989:
3671:
3486:
3273:
2742:
2620:
851:
802:
757:
720:
636:
339:
3626:
3330:
3278:
3102:
3097:
3911:
3508:
3248:
3117:
3107:
448:
3523:
3518:
3348:
3335:
3288:
3112:
3038:
3028:
2777:
2729:
2398:
1184:
Morgan PJ, Kung R, Tarshis J (May 2002). "Nitroglycerin as a uterine relaxant: a systematic review".
862:
246:
3999:
3929:
2808:
2656:
972:. Thus, production of NO from exogenous sources such as glyceryl trinitrate increases the level of
724:
711:
Three different forms of nitroglycerin: intravenous, sublingual spray, and the nitroglycerin patch.
640:
294:
2947:
679:
family of medications. While it is not entirely clear how it works, it is believed to function by
3666:
3651:
3429:
3409:
3378:
3230:
3187:
2952:
2932:
2927:
2922:
2861:
2324:
2287:
1630:
1163:
1009:
847:
195:
3934:
3725:
3656:
3404:
3383:
3810:
3543:
2937:
2917:
2336:
3845:
3840:
3454:
3449:
3373:
3207:
3068:
3063:
3058:
3053:
2897:
2752:
2747:
2316:
2279:
2250:
2123:
2082:
2056:
1978:
1850:
1799:
1763:
1728:
1679:
1622:
1532:
1430:
1424:
1394:
1388:
1325:
who prepares lecture demonstrations at my school, and other people who tried the experiment.)
1250:
1201:
1155:
1053:
977:
921:
885:
814:
428:
208:
59:
3835:
3830:
3820:
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3533:
3048:
3881:
3475:
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3358:
3309:
3202:
3153:
3033:
2706:
2701:
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2409:
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2232:
2141:
2115:
2046:
1970:
1840:
1830:
1791:
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1669:
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1614:
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1359:
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1240:
1232:
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949:
464:
218:
3631:
3243:
2163:
408:
4162:
4069:
3740:
3528:
3363:
3127:
2678:
2434:
2371:
993:
933:
761:
388:
236:
226:
772:
Tentative evidence indicates efficacy of glyceryl trinitrate in the treatment of various
1699:"Glyceryl trinitrate patches-An alternative treatment for shoulder impingement syndrome"
303:
4089:
3748:
3641:
3538:
3238:
3225:
3212:
2858:
2597:
2245:
2220:
1845:
1818:
1723:
1698:
1674:
1649:
1372:
1245:
1220:
1033:
1021:
881:
668:
1974:
1746:
Bokhari AR, Murrell GA (February 2012). "The role of nitric oxide in tendon healing".
1355:
1197:
663:
and low blood pressure. The low blood pressure can be severe. It is unclear if use in
4172:
4030:
3779:
3588:
3217:
3197:
3192:
3177:
2312:
2119:
1484:
1236:
1151:
1109:
997:
752:
692:
620:
612:
93:
79:
20:
2824:
2328:
1634:
1167:
783:, though usually at a much lower concentration than that used for angina treatment.
4107:
4083:
3414:
3182:
2882:
2869:
2855:
2660:
2532:
2477:
2375:
2291:
1025:
1005:
992:
It was known almost from the time of the first synthesis of glyceryl trinitrate by
913:
858:
798:
794:
787:
780:
773:
732:
680:
627:, and to treat and prevent chest pain caused by decreased blood flow to the heart (
624:
616:
150:
145:
140:
135:
1650:"Treatment of tendinopathy: what works, what does not, and what is on the horizon"
1511:"Coronary artery spasm--clinical features, diagnosis, pathogenesis, and treatment"
1454:
667:
is safe for the fetus. It should not be used together with medications within the
2076:
1904:
328:
4120:
3891:
3815:
3424:
3419:
3304:
3145:
3043:
2887:
2737:
2693:
2669:
2557:
2522:
2482:
2461:
2442:
2419:
2414:
2367:
901:
843:
648:
608:
120:
112:
87:
1795:
1527:
4093:
4073:
4007:
3661:
3078:
3073:
2962:
2942:
2772:
2767:
2762:
2688:
2572:
2552:
2547:
2542:
2537:
2517:
2512:
2492:
2424:
1759:
1714:
1665:
1042:
1014:
925:
874:
866:
672:
497:
379:
108:
29:
2236:
2188:
1618:
1363:
830:
counteraction of glyceryl trinitrate vasodilation by neurohormonal activation
4079:
4038:
3901:
3896:
2957:
2787:
2782:
2757:
2711:
2562:
2527:
2507:
2487:
2452:
981:
870:
793:
Glyceryl trinitrate was once researched for the prevention and treatment of
664:
285:
1,3-dinitrooxypropan-2-yl nitrate; propyl] nitrate; 1,2,3-trinitroxy propane
259:
73:
2320:
2283:
2254:
2051:
2034:
1854:
1803:
1767:
1732:
1683:
1626:
1557:
1536:
1426:
The
Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs
1254:
1205:
1159:
37:
4113:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
2127:
2060:
1982:
1835:
1032:
experimented with the use of nitroglycerin to alleviate angina and reduce
4100:
4056:
4042:
3957:
3859:
3548:
3439:
2986:
2877:
2567:
2502:
1037:
1001:
917:
827:
impaired transformation of glyceryl trinitrate into NO or related species
660:
359:
116:
2142:"Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan"
368:
4020:
3886:
3399:
3394:
3343:
3162:
3157:
3083:
3003:
2992:
2813:
2719:
2497:
1070:
905:
897:
632:
314:
984:, which initiates relaxation of smooth muscle cells in blood vessels.
801:
was found to have falsified the findings, sparking one of the largest
4116:
4012:
3906:
3469:
1036:, and showed that the accompanying headaches occurred as a result of
744:
628:
439:
2275:
786:
Glyceryl trinitrate has been used to decrease pain associated with
2652:
909:
776:, both in pain management and acceleration of soft tissue repair.
706:
520:
511:
419:
1934:
Scientific
Committee on Occupational Exposure Limits (May 2008).
1509:
Yasue H, Nakagawa H, Itoh T, Harada E, Mizuno Y (February 2008).
880:
Glyceryl trinitrate transdermal patches should be removed before
3994:
3921:
3495:
1558:"Nitro-Dur - FDA prescribing information, side effects and uses"
953:
707:
563:
InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
189:
2828:
2624:
2340:
956:-dependent mechanisms; this activation results in formation of
675:
due to the risk of low blood pressure. Nitroglycerin is in the
202:
964:(GTP). Among other roles, cGMP serves as a substrate for a
176:
948:
The NO produced by this process is a potent activator of
920:
that undergo these two steps within the body are called
2301:
586:
2878:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
4146:
2221:"Nitroglycerin use in myocardial infarction patients"
1308:
Memorie della Reale
Accademia delle Scienze di Torino
1112:. The American Society of Health-System Pharmacists.
779:
Glyceryl trinitrate is also used in the treatment of
2081:. New York, NY: John Wiley & Sons. p. 433.
1938:(Report). The Hague, NDL: Sociaal-Economische Raad.
3947:
3920:
3858:
3788:
3739:
3607:
3494:
3485:
3468:
3369:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
2985:
2905:
2896:
2868:
2796:
2668:
2470:
2451:
2383:
715:Nitroglycerin is used for the treatment of angina,
509:
496:
463:
458:
438:
418:
398:
378:
358:
347:
338:
313:
293:
268:
258:
245:
235:
225:
217:
166:
161:
126:
100:
86:
68:
58:
53:
928:groups, while others believe that enzymes such as
3183:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
1340:"Nitro-glycerine as a remedy for angina pectoris"
19:For the undiluted form used as an explosive, see
1784:Archives of Physical Medicine and Rehabilitation
327:
3044:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
2023:Note: Hering renamed nitroglycerine "glonoine".
2011:"Glonoine, a new medicine for headache, &c"
1588:"Nitroclycerin Oral Route and Sublingual Route"
302:
4199:World Health Organization essential medicines
3460:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
3019:Ethylene glycol dinitrate (EGDN; nitroglycol)
2840:
2636:
2352:
241:liver (rapid), red blood cells, vascular wall
8:
1186:Journal of Obstetrics and Gynaecology Canada
813:After long-term use for chronic conditions,
743:Glyceryl trinitrate is useful in decreasing
28:
4204:Chemical substances for emergency medicine
3491:
3482:
2902:
2847:
2833:
2825:
2643:
2629:
2621:
2359:
2345:
2337:
1654:Clinical Orthopaedics and Related Research
1350:(2894): 80–81, 113–115, 151–152, 225–227.
1104:
1102:
1100:
1098:
1096:
1094:
1092:
1090:
1088:
1086:
387:
45:
36:
3203:Isobutyl nitrite (2-methylpropyl nitrite)
3113:Nitroglycerin (glyceryl trinitrate (GTN))
2244:
2050:
1844:
1834:
1819:"Misconduct saga rattles bone scientists"
1722:
1673:
1526:
1418:
1416:
1414:
1371:
1244:
1179:
1177:
1133:
1131:
407:
1333:
1331:
1297:
1295:
1266:
1264:
1225:British Journal of Clinical Pharmacology
4153:
3279:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
3269:S-Nitroso-N-valerylpenicillamine (SNVP)
1485:"Nitroglycerin - Drug Usage Statistics"
1082:
1073:after Upjohn was spun off from Pfizer.
560:
540:
367:
282:
92:
3264:S-Nitroso-N-acetylpenicillamine (SNAP)
3138:Sodium trioxodinitrate (Angeli's salt)
2778:Sodium chlorite (tetrachlorodecaoxide)
2095:from the original on 8 September 2017.
1443:from the original on 20 December 2016.
1429:. John Wiley & Sons. p. 153.
1407:from the original on 20 December 2016.
1393:. John Wiley & Sons. p. 454.
27:
2035:"Nitroglycerin: a homeopathic remedy"
1748:Journal of Shoulder and Elbow Surgery
1320:( … it suffices to hold a droplet of
1116:from the original on 21 December 2016
996:in 1846 that handling and tasting of
842:Glyceryl trinitrate can cause severe
447:
427:
78:
7:
4099:non-selective PDE inhibitors (e.g.,
2883:Nitric oxide (NO; nitrogen monoxide)
2219:Ferreira JC, Mochly-Rosen D (2012).
1823:Canadian Medical Association Journal
1465:from the original on 15 January 2024
1069:In the US, Nitrostat is marketed by
631:) or due to the recreational use of
149:
139:
3123:Pentaerithrityl tetranitrate (PETN)
3009:Diethylene glycol dinitrate (DEGDN)
1894:Hypothesis of Munzel et al. (1995).
1648:Andres BM, Murrell GA (July 2008).
1028:could be used to treat chest pain,
908:anion or a related species further
888:of the metal mesh in some patches.
749:endothelium-derived relaxing factor
318:
4189:Drugs developed by Merck & Co.
4028:Indirect/downstream NO modulators:
3796:Asymmetric dimethylarginine (ADMA)
2108:The American Journal of Cardiology
1703:Journal of Orthopaedic Translation
1219:O'Leary ME, Hancox JC (May 2010).
1008:effect (as suggested by Sobrero).
635:. This includes chest pain from a
14:
3826:Nitroarginine methyl ester (NAME)
3289:S-Nitrosoglutathione (GSNO, SNOG)
3259:S-Nitroso-N-acetylcysteine (SNAC)
3133:Propylene glycol dinitrate (PGDN)
2888:Nitrosonium (NO; nitrosyl cation)
1942:from the original on 3 March 2016
1915:from the original on 13 June 2017
1697:Assem Y, Arora M (January 2015).
1568:from the original on 1 April 2017
912:to produce the active metabolite
719:, severe hypertension, and acute
4156:
2313:10.1046/j.1440-1681.2000.03240.x
1817:Shuchman M (20 September 2016).
1607:The Physician and Sportsmedicine
1237:10.1111/j.1365-2125.2010.03629.x
1152:10.2165/00003495-200666030-00006
976:within the cell, and stimulates
481:
475:
3354:Diethylenetriamine/NO (DETA/NO)
2015:American Journal of Homoeopathy
1387:Fischer J, Ganellin CR (2006).
568:Key:SNIOPGDIGTZGOP-UHFFFAOYSA-N
3554:N-(1-Iminoethyl)-L-ornithine (
2651:Preparations for treatment of
2264:Nature Reviews. Drug Discovery
1905:"Phosphodiesterase Inhibitors"
970:myosin light chain phosphatase
958:cyclic guanosine monophosphate
487:
469:
1:
4137:Receptor/signaling modulators
3806:Guanidinoethyldisulfide (GED)
3024:Isosorbide mononitrate (ISMN)
3014:Erythritol tetranitrate (ETN)
1975:10.1016/S0300-9572(98)00059-8
1390:Analogue-based Drug Discovery
1356:10.1016/s0140-6736(02)42404-x
1198:10.1016/S1701-2163(16)30403-0
966:cGMP-dependent protein kinase
647:, applied to the skin, or by
3274:S-Nitrosocaptopril (SNO-Cap)
3103:Nitroflurbiprofen (HCT-1026)
3098:Nitroatorvastatin (NCX-6560)
2430:Pentaerythritol tetranitrate
2120:10.1016/0002-9149(85)90324-8
687:History, society and culture
659:Common side effects include
3749:Aminoguanidine (pimagedine)
3642:Aminoguanidine (pimagedine)
3539:Aminoguanidine (pimagedine)
3303:N-Nitroso compounds (e.g.,
3118:Nitropravastatin (NCX-6550)
3029:Isosorbide dinitrate (ISDN)
1310:. 2nd series (in Italian).
1000:could cause sudden intense
941:catalysed by mitochondrial
717:acute myocardial infarction
4222:
4035:AT-II receptor antagonists
3780:Nitroarginine (NNA, NOARG)
3617:1-Amino-2-hydroxyguanidine
3589:Nitroarginine (NNA, NOARG)
3336:Sodium nitroprusside (SNP)
2152:– via Business Wire.
2144:. Pfizer. 16 November 2020
1796:10.1016/j.apmr.2010.02.008
1528:10.1016/j.jjcc.2008.01.001
930:glutathione S-transferases
797:; however, the researcher
655:Side effects and mechanism
459:Chemical and physical data
18:
4184:Drugs developed by AbbVie
4130:
2581:
2078:Drug Discovery: A History
1760:10.1016/j.jse.2011.11.001
1715:10.1016/j.jot.2014.11.001
1666:10.1007/s11999-008-0260-1
896:Glyceryl trinitrate is a
756:trinitrate is useful for
733:patch applied to the skin
723:. It may be administered
576:
551:
531:
273:
44:
35:
4194:Drugs developed by Merck
3514:3-Chloro-5-nitroindazole
3349:Diethylamine/NO (DEA/NO)
3321:Metal nitrosyl complexes
3249:S-Nitrosoalbumin (SNALB)
2943:Cinaciguat (BAY 58-2667)
2237:10.1253/circj.cj-11-1133
1619:10.3810/psm.2013.09.2019
861:drugs that are used for
4106:PDE9 inhibitors (e.g.,
3594:Pentamidine isethionate
3504:3-Bromo-7-nitroindazole
3391:Heterocyclic compounds:
2915:Activators/stimulators:
2753:Centella asiatica herba
2033:Fye WB (January 1986).
1052:Overdoses may generate
938:xanthine oxidoreductase
824:plasma volume expansion
699:million prescriptions.
615:, high blood pressure (
4063:L-Type calcium channel
2804:Bromelain (anacaulase)
2405:Isosorbide mononitrate
2052:10.1161/01.cir.73.1.21
962:guanosine triphosphate
943:aldehyde dehydrogenase
721:coronary artery spasms
712:
681:dilating blood vessels
543:C(C(CO(=O))O(=O))O(=O)
3667:Cindunistat (SD-6010)
3622:2-Ethylaminoguanidine
3379:Spermine/NO (SPER/NO)
3176:O-Nitroso compounds (
2743:Beremagene geperpavec
1836:10.1503/cmaj.109-5314
1515:Journal of Cardiology
1455:"The Top 300 of 2021"
803:scientific misconduct
758:myocardial infarction
710:
649:injection into a vein
4053:receptor antagonists
3726:Ronopterin (VAS-203)
3425:Molsidomine (SIN-10)
3346:(diazeniumdiolates):
3326:Roussin's black salt
3039:Mannitol hexanitrate
2730:Isosorbide dinitrate
2707:Calcium pantothenate
2399:Isosorbide dinitrate
1004:, which suggested a
863:erectile dysfunction
3420:Linsidomine (SIN-1)
3317:Nitrosyl compounds:
3284:S-Nitrosodiclofenac
3254:S-Nitrosated AR545C
3239:S-Nitroso compounds
2809:Clostridiopeptidase
2797:Proteolytic enzymes
2225:Circulation Journal
1060:Society and culture
945:(ALDH2 or mtALDH).
892:Mechanism of action
760:(heart attack) and
601:glyceryl trinitrate
32:
3331:Roussin's red salt
3188:Cyclohexyl nitrite
3079:Nipradilol (K-351)
2608:Never to phase III
2195:. 16 November 2020
2075:Sneader W (2005).
1592:www.mayoclinic.org
1338:Murrell W (1879).
1302:Sobrero A (1849).
1271:Sobrero A (1847).
1024:'s discovery that
1010:Constantine Hering
848:reflex tachycardia
713:
196:Pharmacy medicines
4144:
4143:
3969:
3960:
3943:
3942:
3876:
3854:
3853:
3774:
3770:
3761:
3757:
3754:N-(1-Iminoethyl)-
3720:
3716:
3707:
3703:
3700:N-(1-Iminoethyl)-
3694:
3690:
3687:N-(1-Iminoethyl)-
3627:2-Iminopiperidine
3583:
3579:
3570:
3566:
3557:
3479:
3208:Isopropyl nitrite
3154:Nitroso compounds
2996:
2981:
2980:
2822:
2821:
2618:
2617:
2385:Nitrovasodilators
2009:Hering C (1849).
1423:Ravina E (2011).
1364:2027/uc1.b5295238
1054:methemoglobinemia
978:dephosphorylation
922:nitrovasodilators
886:breakdown voltage
815:nitrate tolerance
805:cases in Canada.
594:
593:
522:Interactive image
264:In urine, in bile
206:
193:
185:(Pharmacist only)
180:
4211:
4161:
4160:
4159:
4152:
4070:dihydropyridines
3970:-arginine (NOHA)
3967:
3958:
3912:alpha aminoacids
3882:chlorogenic acid
3877:-arginine (NOHA)
3874:
3772:
3768:
3759:
3755:
3718:
3714:
3705:
3701:
3692:
3688:
3581:
3577:
3568:
3564:
3555:
3509:3-Chloroindazole
3492:
3483:
3473:
3171:
3170:
3108:Nitrofluvastatin
3092:
3091:
3034:Itramin tosilate
2990:
2903:
2849:
2842:
2835:
2826:
2684:Cadexomer iodine
2645:
2638:
2631:
2622:
2410:Itramin tosilate
2372:cardiac diseases
2361:
2354:
2347:
2338:
2332:
2295:
2258:
2248:
2205:
2204:
2202:
2200:
2185:
2179:
2178:
2176:
2174:
2160:
2154:
2153:
2151:
2149:
2138:
2132:
2131:
2103:
2097:
2096:
2072:
2066:
2064:
2054:
2030:
2024:
2022:
2006:
2000:
1993:
1987:
1986:
1958:
1952:
1951:
1949:
1947:
1931:
1925:
1924:
1922:
1920:
1901:
1895:
1892:
1886:
1883:
1877:
1874:
1868:
1865:
1859:
1858:
1848:
1838:
1814:
1808:
1807:
1778:
1772:
1771:
1743:
1737:
1736:
1726:
1694:
1688:
1687:
1677:
1645:
1639:
1638:
1602:
1596:
1595:
1584:
1578:
1577:
1575:
1573:
1554:
1548:
1547:
1545:
1543:
1530:
1506:
1500:
1499:
1497:
1495:
1481:
1475:
1474:
1472:
1470:
1451:
1445:
1444:
1420:
1409:
1408:
1384:
1378:
1377:
1375:
1335:
1326:
1315:
1299:
1290:
1284:
1268:
1259:
1258:
1248:
1216:
1210:
1209:
1181:
1172:
1171:
1135:
1126:
1125:
1123:
1121:
1106:
950:guanylyl cyclase
833:oxidative stress
729:sublingual spray
698:
645:under the tongue
599:, also known as
590:
589:
582:
524:
504:
489:
483:
477:
471:
451:
431:
411:
391:
371:
351:
331:
321:
320:
306:
250:
204:
201:
191:
188:
178:
175:
153:
143:
96:
82:
49:
40:
33:
31:
4221:
4220:
4214:
4213:
4212:
4210:
4209:
4208:
4169:
4168:
4167:
4157:
4155:
4147:
4145:
4140:
4126:
4090:PDE5 inhibitors
4052:
4016:
4003:
3939:
3916:
3850:
3784:
3735:
3603:
3529:7-Nitroindazole
3524:6-Nitroindazole
3519:5-Nitroindazole
3472:
3464:
3241:(thionitrites):
3169:
3166:
3165:
3164:
3128:Propatylnitrate
3090:
3087:
3086:
3085:
2989:
2977:
2892:
2864:
2853:
2823:
2818:
2792:
2763:Hyaluronic acid
2679:epichlorohydrin
2664:
2649:
2619:
2614:
2613:
2598:Clinical trials
2577:
2466:
2447:
2435:Propatylnitrate
2379:
2365:
2335:
2298:
2276:10.1038/nrd2466
2261:
2218:
2214:
2212:Further reading
2209:
2208:
2198:
2196:
2187:
2186:
2182:
2172:
2170:
2162:
2161:
2157:
2147:
2145:
2140:
2139:
2135:
2105:
2104:
2100:
2089:
2074:
2073:
2069:
2032:
2031:
2027:
2008:
2007:
2003:
1994:
1990:
1960:
1959:
1955:
1945:
1943:
1933:
1932:
1928:
1918:
1916:
1909:CV Pharmacology
1903:
1902:
1898:
1893:
1889:
1884:
1880:
1875:
1871:
1867:Nakamura et al.
1866:
1862:
1829:(13): 938–939.
1816:
1815:
1811:
1790:(8): 1291–305.
1780:
1779:
1775:
1745:
1744:
1740:
1696:
1695:
1691:
1647:
1646:
1642:
1604:
1603:
1599:
1586:
1585:
1581:
1571:
1569:
1556:
1555:
1551:
1541:
1539:
1508:
1507:
1503:
1493:
1491:
1483:
1482:
1478:
1468:
1466:
1453:
1452:
1448:
1437:
1422:
1421:
1412:
1401:
1386:
1385:
1381:
1337:
1336:
1329:
1301:
1300:
1293:
1270:
1269:
1262:
1218:
1217:
1213:
1183:
1182:
1175:
1137:
1136:
1129:
1119:
1117:
1110:"Nitroglycerin"
1108:
1107:
1084:
1079:
1067:
1062:
1030:William Murrell
994:Ascanio Sobrero
990:
968:that activates
934:cytochrome P450
894:
840:
811:
770:
762:pulmonary edema
741:
705:
696:
689:
671:family such as
657:
625:painful periods
585:
583:
580:(what is this?)
577:
572:
569:
564:
559:
558:
547:
544:
539:
538:
527:
502:
492:
486:
480:
474:
454:
434:
414:
394:
374:
354:
334:
317:
309:
289:
286:
281:
280:
248:
227:Bioavailability
219:Pharmacokinetic
213:
157:
103:
24:
17:
12:
11:
5:
4219:
4218:
4215:
4207:
4206:
4201:
4196:
4191:
4186:
4181:
4171:
4170:
4166:
4165:
4142:
4141:
4131:
4128:
4127:
4125:
4124:
4114:
4111:
4104:
4097:
4087:
4077:
4060:
4050:
4046:
4031:ACE inhibitors
4024:
4023:
4018:
4014:
4010:
4005:
4001:
3997:
3992:
3987:
3982:
3973:
3972:
3963:
3951:
3949:
3945:
3944:
3941:
3940:
3938:
3937:
3932:
3926:
3924:
3918:
3917:
3915:
3914:
3909:
3904:
3899:
3894:
3889:
3884:
3879:
3870:
3864:
3862:
3856:
3855:
3852:
3851:
3849:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3792:
3790:
3786:
3785:
3783:
3782:
3777:
3764:
3751:
3745:
3743:
3737:
3736:
3734:
3733:
3728:
3723:
3710:
3697:
3684:
3679:
3674:
3669:
3664:
3659:
3654:
3649:
3644:
3639:
3634:
3629:
3624:
3619:
3613:
3611:
3605:
3604:
3602:
3601:
3596:
3591:
3586:
3573:
3560:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3500:
3498:
3489:
3480:
3466:
3465:
3463:
3462:
3457:
3452:
3447:
3442:
3433:
3432:
3427:
3422:
3417:
3402:
3387:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3339:
3338:
3333:
3328:
3313:
3312:
3296:
3291:
3286:
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3234:-Butyl nitrite
3228:
3226:Pentyl nitrite
3223:
3221:-Butyl nitrite
3215:
3213:Methyl nitrite
3210:
3205:
3200:
3195:
3190:
3185:
3178:alkyl nitrites
3167:
3149:
3148:
3143:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3088:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
2999:
2997:
2983:
2982:
2979:
2978:
2976:
2975:
2966:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2911:
2909:
2900:
2894:
2893:
2891:
2890:
2885:
2880:
2874:
2872:
2866:
2865:
2854:
2852:
2851:
2844:
2837:
2829:
2820:
2819:
2817:
2816:
2811:
2806:
2800:
2798:
2794:
2793:
2791:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2748:Betulae cortex
2745:
2740:
2733:
2732:
2727:
2715:
2714:
2709:
2697:
2696:
2691:
2686:
2674:
2672:
2666:
2665:
2650:
2648:
2647:
2640:
2633:
2625:
2616:
2615:
2612:
2611:
2610:
2609:
2606:
2595:
2589:
2583:
2582:
2579:
2578:
2576:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2474:
2472:
2468:
2467:
2465:
2464:
2458:
2456:
2449:
2448:
2446:
2445:
2440:
2437:
2432:
2427:
2422:
2417:
2412:
2407:
2402:
2396:
2389:
2387:
2381:
2380:
2366:
2364:
2363:
2356:
2349:
2341:
2334:
2333:
2296:
2259:
2215:
2213:
2210:
2207:
2206:
2180:
2155:
2133:
2098:
2088:978-0471899808
2087:
2067:
2065:See pp. 22–23.
2025:
2001:
1988:
1953:
1926:
1896:
1887:
1878:
1869:
1860:
1809:
1773:
1738:
1689:
1660:(7): 1539–54.
1640:
1597:
1579:
1549:
1501:
1476:
1446:
1435:
1410:
1399:
1379:
1327:
1291:
1277:Comptes Rendus
1260:
1211:
1173:
1127:
1081:
1080:
1078:
1075:
1066:
1063:
1061:
1058:
1034:blood pressure
1022:Thomas Brunton
989:
986:
916:(NO). Organic
900:which must be
893:
890:
882:defibrillation
839:
838:Adverse events
836:
835:
834:
831:
828:
825:
810:
807:
774:tendinopathies
769:
766:
740:
737:
704:
701:
688:
685:
669:PDE5 inhibitor
656:
653:
639:. It is taken
592:
591:
574:
573:
571:
570:
567:
565:
562:
554:
553:
552:
549:
548:
546:
545:
542:
534:
533:
532:
529:
528:
526:
525:
517:
515:
507:
506:
500:
494:
493:
490:
484:
478:
472:
467:
461:
460:
456:
455:
453:
452:
444:
442:
436:
435:
433:
432:
424:
422:
416:
415:
413:
412:
404:
402:
396:
395:
393:
392:
384:
382:
376:
375:
373:
372:
364:
362:
356:
355:
353:
352:
344:
342:
336:
335:
333:
332:
324:
322:
311:
310:
308:
307:
299:
297:
291:
290:
288:
287:
284:
276:
275:
274:
271:
270:
266:
265:
262:
256:
255:
252:
243:
242:
239:
233:
232:
229:
223:
222:
215:
214:
212:
211:
199:
186:
172:
170:
164:
163:
159:
158:
156:
155:
132:
130:
124:
123:
106:
104:administration
98:
97:
90:
84:
83:
76:
66:
65:
64:Nitrol, others
62:
56:
55:
51:
50:
42:
41:
15:
13:
10:
9:
6:
4:
3:
2:
4217:
4216:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4176:
4174:
4164:
4154:
4150:
4139:
4138:
4135:
4129:
4122:
4118:
4115:
4112:
4109:
4105:
4102:
4098:
4095:
4091:
4088:
4085:
4081:
4078:
4075:
4071:
4067:
4064:
4061:
4058:
4054:
4047:
4044:
4040:
4036:
4032:
4029:
4026:
4025:
4022:
4019:
4017:
4011:
4009:
4006:
4004:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3975:
3974:
3971:
3964:
3962:
3956:
3953:
3952:
3950:
3946:
3936:
3933:
3931:
3930:Calmidazolium
3928:
3927:
3925:
3923:
3919:
3913:
3910:
3908:
3905:
3903:
3900:
3898:
3895:
3893:
3890:
3888:
3885:
3883:
3880:
3878:
3871:
3869:
3866:
3865:
3863:
3861:
3857:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3793:
3791:
3787:
3781:
3778:
3776:
3765:
3763:
3752:
3750:
3747:
3746:
3744:
3742:
3738:
3732:
3729:
3727:
3724:
3722:
3711:
3709:
3698:
3696:
3685:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3653:
3650:
3648:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3614:
3612:
3610:
3606:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3574:
3572:
3561:
3559:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3501:
3499:
3497:
3493:
3490:
3488:
3484:
3481:
3477:
3471:
3467:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3435:
3434:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3406:
3403:
3401:
3398:
3396:
3392:
3389:
3388:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3341:
3340:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3318:
3315:
3314:
3311:
3308:
3306:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3235:
3233:
3229:
3227:
3224:
3222:
3220:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3198:Hexyl nitrite
3196:
3194:
3193:Ethyl nitrite
3191:
3189:
3186:
3184:
3181:
3179:
3173:
3161:
3159:
3155:
3151:
3150:
3147:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3001:
3000:
2998:
2994:
2988:
2984:
2974:
2971:
2968:
2967:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2913:
2912:
2910:
2908:
2904:
2901:
2899:
2895:
2889:
2886:
2884:
2881:
2879:
2876:
2875:
2873:
2871:
2867:
2863:
2860:
2857:
2850:
2845:
2843:
2838:
2836:
2831:
2830:
2827:
2815:
2812:
2810:
2807:
2805:
2802:
2801:
2799:
2795:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2735:
2734:
2731:
2728:
2726:
2725:Nitroglycerin
2723:
2721:
2717:
2716:
2713:
2710:
2708:
2705:
2703:
2699:
2698:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2676:
2675:
2673:
2671:
2667:
2662:
2658:
2654:
2646:
2641:
2639:
2634:
2632:
2627:
2626:
2623:
2607:
2605:
2602:
2601:
2599:
2596:
2593:
2590:
2588:
2585:
2584:
2580:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2475:
2473:
2469:
2463:
2460:
2459:
2457:
2454:
2450:
2444:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2406:
2403:
2400:
2397:
2394:
2393:Nitroglycerin
2391:
2390:
2388:
2386:
2382:
2377:
2373:
2369:
2362:
2357:
2355:
2350:
2348:
2343:
2342:
2339:
2330:
2326:
2322:
2318:
2314:
2310:
2306:
2302:
2297:
2293:
2289:
2285:
2281:
2277:
2273:
2270:(2): 156–67.
2269:
2265:
2260:
2256:
2252:
2247:
2242:
2238:
2234:
2230:
2226:
2222:
2217:
2216:
2211:
2194:
2190:
2184:
2181:
2169:
2165:
2159:
2156:
2143:
2137:
2134:
2129:
2125:
2121:
2117:
2113:
2109:
2102:
2099:
2094:
2090:
2084:
2080:
2079:
2071:
2068:
2062:
2058:
2053:
2048:
2044:
2040:
2036:
2029:
2026:
2020:
2016:
2012:
2005:
2002:
1998:
1992:
1989:
1984:
1980:
1976:
1972:
1968:
1964:
1963:Resuscitation
1957:
1954:
1941:
1937:
1930:
1927:
1914:
1910:
1906:
1900:
1897:
1891:
1888:
1882:
1879:
1873:
1870:
1864:
1861:
1856:
1852:
1847:
1842:
1837:
1832:
1828:
1824:
1820:
1813:
1810:
1805:
1801:
1797:
1793:
1789:
1785:
1777:
1774:
1769:
1765:
1761:
1757:
1754:(2): 238–44.
1753:
1749:
1742:
1739:
1734:
1730:
1725:
1720:
1716:
1712:
1708:
1704:
1700:
1693:
1690:
1685:
1681:
1676:
1671:
1667:
1663:
1659:
1655:
1651:
1644:
1641:
1636:
1632:
1628:
1624:
1620:
1616:
1612:
1608:
1601:
1598:
1593:
1589:
1583:
1580:
1567:
1563:
1559:
1553:
1550:
1538:
1534:
1529:
1524:
1520:
1516:
1512:
1505:
1502:
1490:
1486:
1480:
1477:
1464:
1460:
1456:
1450:
1447:
1442:
1438:
1436:9783527326693
1432:
1428:
1427:
1419:
1417:
1415:
1411:
1406:
1402:
1400:9783527607495
1396:
1392:
1391:
1383:
1380:
1374:
1369:
1365:
1361:
1357:
1353:
1349:
1345:
1341:
1334:
1332:
1328:
1323:
1322:Piroglicerina
1319:
1316:From p. 198:
1313:
1309:
1305:
1298:
1296:
1292:
1288:
1285:From p. 248:
1282:
1279:(in French).
1278:
1274:
1267:
1265:
1261:
1256:
1252:
1247:
1242:
1238:
1234:
1231:(5): 427–42.
1230:
1226:
1222:
1215:
1212:
1207:
1203:
1199:
1195:
1191:
1187:
1180:
1178:
1174:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1134:
1132:
1128:
1115:
1111:
1105:
1103:
1101:
1099:
1097:
1095:
1093:
1091:
1089:
1087:
1083:
1076:
1074:
1072:
1064:
1059:
1057:
1055:
1050:
1047:
1045:
1044:
1039:
1035:
1031:
1027:
1023:
1018:
1016:
1011:
1007:
1003:
999:
998:nitroglycerin
995:
987:
985:
983:
979:
975:
971:
967:
963:
959:
955:
951:
946:
944:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
899:
891:
889:
887:
883:
878:
876:
872:
868:
864:
860:
855:
853:
849:
845:
837:
832:
829:
826:
823:
822:
821:
818:
816:
808:
806:
804:
800:
796:
791:
789:
784:
782:
781:anal fissures
777:
775:
767:
765:
763:
759:
754:
753:tachyphylaxis
750:
746:
738:
736:
734:
730:
726:
725:intravenously
722:
718:
709:
702:
700:
694:
693:nitroglycerin
686:
684:
682:
678:
674:
670:
666:
662:
654:
652:
650:
646:
642:
638:
634:
630:
626:
622:
621:anal fissures
618:
614:
613:heart failure
610:
606:
602:
598:
597:Nitroglycerin
588:
581:
575:
566:
561:
557:
550:
541:
537:
530:
523:
519:
518:
516:
513:
508:
501:
499:
495:
468:
466:
462:
457:
450:
446:
445:
443:
441:
437:
430:
426:
425:
423:
421:
417:
410:
406:
405:
403:
401:
397:
390:
386:
385:
383:
381:
377:
370:
366:
365:
363:
361:
357:
350:
346:
345:
343:
341:
337:
330:
326:
325:
323:
316:
312:
305:
301:
300:
298:
296:
292:
283:
279:
272:
267:
263:
261:
257:
253:
251:
244:
240:
238:
234:
230:
228:
224:
220:
216:
210:
200:
197:
187:
184:
174:
173:
171:
169:
165:
160:
152:
147:
142:
137:
134:
133:
131:
129:
125:
122:
118:
114:
110:
107:
105:
99:
95:
91:
89:
85:
81:
77:
75:
71:
67:
63:
61:
57:
54:Clinical data
52:
48:
43:
39:
34:
30:Nitroglycerin
26:
22:
21:Nitroglycerin
4179:Antianginals
4133:
4132:
4108:paraxanthine
4084:beta blocker
4027:
3976:
3954:
3758:-ornithine (
3691:-ornithine (
3436:
3415:Feprosidnine
3410:Sydnonimines
3408:
3393:
3390:
3342:
3319:
3316:
3305:nitrosamines
3302:
3237:
3231:
3218:
3175:
3152:
3002:
2969:
2948:GSK-2181236A
2914:
2856:Nitric oxide
2718:
2712:Dexpanthenol
2700:
2677:
2670:Cicatrizants
2533:Levosimendan
2478:Benziodarone
2455:vasodilators
2368:Vasodilators
2307:(4): 313–9.
2304:
2300:
2267:
2263:
2231:(1): 15–21.
2228:
2224:
2197:. Retrieved
2192:
2183:
2171:. Retrieved
2167:
2158:
2146:. Retrieved
2136:
2114:(1): 181–3.
2111:
2107:
2101:
2077:
2070:
2042:
2038:
2028:
2018:
2014:
2004:
1996:
1991:
1969:(3): 145–8.
1966:
1962:
1956:
1944:. Retrieved
1929:
1917:. Retrieved
1908:
1899:
1890:
1881:
1872:
1863:
1826:
1822:
1812:
1787:
1783:
1776:
1751:
1747:
1741:
1709:(1): 12–20.
1706:
1702:
1692:
1657:
1653:
1643:
1613:(3): 36–49.
1610:
1606:
1600:
1591:
1582:
1570:. Retrieved
1561:
1552:
1540:. Retrieved
1518:
1514:
1504:
1492:. Retrieved
1488:
1479:
1467:. Retrieved
1458:
1449:
1425:
1389:
1382:
1347:
1343:
1321:
1317:
1311:
1307:
1286:
1280:
1276:
1228:
1224:
1214:
1192:(5): 403–9.
1189:
1185:
1146:(3): 343–9.
1143:
1139:
1118:. Retrieved
1068:
1051:
1048:
1041:
1026:amyl nitrite
1019:
1006:vasodilation
991:
960:(cGMP) from
947:
914:nitric oxide
895:
879:
856:
841:
819:
812:
799:Sophie Jamal
795:osteoporosis
792:
788:dysmenorrhea
785:
778:
771:
742:
714:
703:Medical uses
690:
658:
637:heart attack
617:hypertension
604:
600:
596:
595:
584:
578:
247:Elimination
168:Legal status
162:Legal status
25:
4121:simvastatin
3955:Precursors:
3892:epicatechin
3816:Indospicine
3771:-arginine (
3717:-arginine (
3652:AR-C 102222
3580:-arginine (
3567:-arginine (
3430:Sydnonimine
3163:Nitrite (NO
3146:Trolnitrate
3142:Tenitramine
3084:Nitrate (NO
2970:Inhibitors:
2953:Praliciguat
2933:BAY 60-4552
2928:BAY 41-8543
2923:BAY 41-2272
2738:Becaplermin
2694:Dextranomer
2594:from market
2558:Prenylamine
2523:Hexobendine
2483:Carbocromen
2462:Flosequinan
2443:Trolnitrate
2439:Tenitramine
2420:Molsidomine
2415:Linsidomine
2164:"Nitrostat"
2045:(1): 21–9.
2039:Circulation
1876:Gori et al.
1542:23 November
1521:(1): 2–17.
1065:Brand names
936:(CYP), and
904:, with the
859:vasodilator
844:hypotension
609:vasodilator
505: g·mol
429:CHEBI:28787
269:Identifiers
121:intravenous
113:transdermal
88:MedlinePlus
60:Trade names
4173:Categories
4094:sildenafil
4074:nifedipine
3977:Cofactors:
3966:N-Hydroxy-
3873:N-Hydroxy-
3662:Canavanine
3657:BYK-191023
3476:inhibitors
3405:REC15/2739
3384:V-PYRRO/NO
3074:Nicorandil
2963:Vericiguat
2862:modulators
2773:Nepidermin
2768:Ketanserin
2689:Crilanomer
2573:Vericiguat
2553:Pimobendan
2548:Oxyfedrine
2543:Nicorandil
2538:Nesiritide
2518:Heptaminol
2513:Gapicomine
2493:Cloridarol
2425:Nicorandil
1494:14 January
1469:14 January
1344:The Lancet
1314:: 195–201.
1283:: 247–248.
1120:8 December
1077:References
1043:The Lancet
1020:Following
1015:homeopathy
926:sulfhydryl
902:denitrated
875:vardenafil
867:sildenafil
865:, such as
852:compliance
768:Other uses
731:, or as a
673:sildenafil
510:3D model (
498:Molar mass
409:G59M7S0WS3
380:ChemSpider
340:IUPHAR/BPS
295:CAS Number
278:IUPAC name
237:Metabolism
109:Sublingual
16:Medication
4134:See also:
4080:Nebivolol
4039:captopril
3961:-Arginine
3902:norvaline
3897:ornithine
3811:GW-273629
3767:N-Methyl-
3713:N-Methyl-
3704:-lysine (
3576:N-Propyl-
3563:N-Methyl-
3544:ARL-17477
3437:Unsorted:
2987:NO donors
2958:Riociguat
2938:BI-703704
2918:Ataciguat
2859:signaling
2788:Trolamine
2783:Trafermin
2758:Enoxolone
2604:Phase III
2592:Withdrawn
2563:Serelaxin
2528:Imolamine
2508:Etafenone
2488:Cinepazet
2453:Quinolone
2021:(1): 3–5.
1562:drugs.com
1046:in 1879.
1002:headaches
871:tadalafil
809:Tolerance
665:pregnancy
611:used for
449:ChEMBL730
260:Excretion
254:3 minutes
249:half-life
194: P (
102:Routes of
80:Monograph
74:Drugs.com
4163:Medicine
4101:caffeine
4066:blockers
4057:bosentan
4043:losartan
3860:Arginase
3846:VAS-2381
3841:ONO-1714
3789:Unsorted
3549:Indazole
3455:FR146881
3450:FR144220
3440:Cimlanod
3395:Furoxans
3374:PROLI/NO
3344:NONOates
3294:SNO-t-PA
3158:nitrites
3069:NCX-4215
3064:NCX 4040
3059:NCX-4016
3054:NCX-2216
3004:Nitrates
2993:prodrugs
2568:Trapidil
2503:Efloxate
2370:used in
2329:12897126
2321:10779131
2284:18167491
2255:22040938
2189:"Brands"
2093:Archived
1946:30 March
1940:Archived
1913:Archived
1855:27551032
1804:20684913
1768:22244067
1733:30035035
1684:18446422
1635:26907571
1627:24113701
1572:31 March
1566:Archived
1537:18522770
1489:ClinCalc
1463:Archived
1459:ClinCalc
1441:Archived
1405:Archived
1255:20573078
1206:12196860
1168:46984485
1160:16526822
1114:Archived
1038:overdose
952:(GC) by
918:nitrates
661:headache
641:by mouth
607:), is a
587:(verify)
360:DrugBank
128:ATC code
117:by mouth
4119:(e.g.,
4117:Statins
4092:(e.g.,
4068:(e.g.,
4055:(e.g.,
4037:(e.g.,
3887:ginseng
3836:NXN-462
3831:NCX-456
3821:KD-7040
3801:CKD-712
3534:A-84643
3400:Furoxan
3299:SNO-vWF
3049:NCX-466
2898:Targets
2814:Trypsin
2736:other:
2720:nitrate
2498:Dilazep
2292:5141850
2246:3527093
2199:17 June
2193:Viatris
2173:17 June
2148:17 June
2128:3917597
2061:2866851
1983:9715773
1919:3 April
1846:5026510
1724:5982354
1675:2505250
1373:5901592
1246:2856043
1071:Viatris
988:History
910:reduced
906:nitrite
898:prodrug
727:, as a
677:nitrate
633:cocaine
503:227.085
465:Formula
369:DB00727
315:PubChem
304:55-63-0
148: (
146:C05AE01
144:)
138: (
136:C01DA02
94:a601086
4149:Portal
3948:Others
3907:lysine
3470:Enzyme
3445:FK-409
3359:GLO/NO
3310:SIN-1A
2657:ulcers
2653:wounds
2587:WHO-EM
2471:Others
2327:
2319:
2290:
2282:
2253:
2243:
2168:Pfizer
2126:
2085:
2059:
1981:
1853:
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