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Details

Stereochemistry ACHIRAL
Molecular Formula C3H5N3O9
Molecular Weight 227.0865
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITROGLYCERIN

SMILES

[O-][N+](=O)OCC(CO[N+]([O-])=O)O[N+]([O-])=O

InChI

InChIKey=SNIOPGDIGTZGOP-UHFFFAOYSA-N
InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2

HIDE SMILES / InChI

Molecular Formula C3H5N3O9
Molecular Weight 227.0865
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Nitroglycerin was first invented in 1847 and has been used as an active ingredient in the manufacture of explosives, mostly dynamite. Nitroglycerin came into medical use in 1878 as as a potent vasodilator (dilation of the vascular system) to treat heart conditions, such as angina pectoris and chronic heart failure. Upon administration, nitroglycerin is converted to nitric oxide (NO) by mitochondrial aldehyde dehydrogenase. NO is a potent activator of guanylyl cyclase (GC) by heme-dependent mechanisms.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Effect of profound normovolemic hypotension and moderate hypothermia on circulating cytokines and adhesion molecules.
1999 Nov
Glyceryl trinitrate induces attacks of migraine without aura in sufferers of migraine with aura.
1999 Sep
Coronary spastic angina induced by anticholinesterase medication for myasthenia gravis--a case report.
2000 Dec
Paradoxical hypertensive response to nitroglycerin during cardiac catheterization.
2000 Dec
Glyceryl trinitrate for chronic anal fissure--healing or headache? Results of a multicenter, randomized, placebo-controled, double-blind trial.
2000 Feb
Audit of topical glyceryl trinitrate for treatment of fissure-in-ano.
2000 Jan
Effects of long-term nitroglycerin treatment on endothelial nitric oxide synthase (NOS III) gene expression, NOS III-mediated superoxide production, and vascular NO bioavailability.
2000 Jan 7
Glyceryl trinitrate induced headache in migraineurs - relation to attack frequency.
2000 Jul
Cardiopulmonary bypass exacerbates oxidative stress but does not increase proinflammatory cytokine release in patients with diabetes compared with patients without diabetes: regulatory effects of exogenous nitric oxide.
2000 Jul
Headache characteristics during the development of tolerance to nitrates: pathophysiological implications.
2000 Jun
Acute myocardial ischemia after administration of ondansetron hydrochloride.
2000 Mar
Hypotensive interaction of sildenafil and nicorandil in rats through the cGMP pathway but not by K(ATP) channel activation.
2000 Nov
Topical diltiazem and bethanechol decrease anal sphincter pressure and heal anal fissures without side effects.
2000 Oct
Nitric oxide-induced headache in patients with chronic tension-type headache.
2000 Sep
[Reactivity of cerebral vessels in patients with circulatory encephalopathy, arterial hypertension and cerebral hypoperfusion risk].
2001
The effect of transdermal glyceryl trinitrate, a nitric oxide donor, on blood pressure and platelet function in acute stroke.
2001
Glyceryl trinitrate and acute uterine relaxation: a literature review.
2001 Apr
Does nitric oxide play a role in the aetiology of pre-eclampsia?
2001 Apr
Nonadrenergic, noncholinergic relaxation of human isolated corpus cavernosum induced by scorpion venom.
2001 Apr
Topical diltiazem ointment in the treatment of chronic anal fissure.
2001 Apr
Nitric oxide modulation of blood vessel tone identified by arterial waveform analysis.
2001 Apr
S-Transnitrosylation of albumin in human plasma and blood in vitro and in vivo in the rat.
2001 Apr 7
Improved analysis of brachial artery ultrasound using a novel edge-detection software system.
2001 Aug
[Aspirin and nitroglycerine: a good combination for gastric mucosa].
2001 Aug-Sep
Investigations into migraine pathogenesis: time course for effects of m-CPP, BW723C86 or glyceryl trinitrate on appearance of Fos-like immunoreactivity in rat trigeminal nucleus caudalis (TNC).
2001 Feb
Cardiac natriuretic peptides--hope or hype?
2001 Feb
Continued cigarette smoking after coronary artery bypass surgery reduces endothelium-dependent vasodilation in internal thoracic artery grafts.
2001 Feb
Insulin resistance adds to endothelial dysfunction in hypertensive patients and in normotensive offspring of subjects with essential hypertension.
2001 Feb
Reduced venous responsiveness to endothelin-1 but not noradrenaline in hypertensive chronic renal failure.
2001 Feb
Does renal failure cause an atherosclerotic milieu in patients with end-stage renal disease?
2001 Feb 15
Migraine with aura after administration of sublingual nitroglycerin tablets.
2001 Jan
Impaired vasodilator response to organic nitrates in isolated basilar arteries.
2001 Jan
Effect of isosorbide dinitrate on nitric oxide synthase under hypoxia.
2001 Jan
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols.
2001 Jan
Effects of C-peptide on forearm blood flow and brachial artery dilatation in patients with type 1 diabetes mellitus.
2001 Jul
Different mechanisms of isoproterenol-induced and nitroglycerin-induced syncope during head-up tilt in patients with unexplained syncope: important role of epinephrine in nitroglycerin-induced syncope.
2001 Jul
Gender difference in age-related changes in vascular function.
2001 Jul
Potentiation of sildenafil-induced hypotension is minimal with nitrates generating a radical intermediate.
2001 Jul
Transoesophageal acoustic quantification for evaluation of cardiac function during laparoscopic surgery.
2001 Jul
The effect of nitric oxide donors and L-arginine on the gastric electrolyte barrier.
2001 Jun
Long-term outcome of patients with ergonovine induced coronary constriction not associated with ischemic electrocardiographic changes.
2001 Jun
Effect of acute blood pressure reduction on endothelial function in the brachial artery of patients with essential hypertension.
2001 Mar
Calcitonin gene-related peptide levels during nitric oxide-induced headache in patients with chronic tension-type headache.
2001 Mar
The BB-paraoxonase genotype is associated with impaired brachial reactivity after acute hypertriglyceridemia in healthy subjects.
2001 Mar
Comparison of provocative tests for unexplained syncope: isoprenaline and glyceryl trinitrate for diagnosing vasovagal syncope.
2001 Mar
Comparison of topically applied 0.2% glyceryl trinitrate ointment, incision and excision in the treatment of perianal thrombosis.
2001 May
Acute effects of vitamin C on platelet responsiveness to nitric oxide donors and endothelial function in patients with chronic heart failure.
2001 May
An update on nesiritide for treatment of decompensated heart failure.
2001 May
Glyceryl trinitrate ointment as a potential treatment for primary vaginismus.
2001 May
Functional immunohistochemistry of neuropeptides and nitric oxide synthase in the nerve fibers of the supratentorial dura mater in an experimental migraine model.
2001 May 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Nitroglycerin in 5% Dextrose Injection is intended for intravenous administration using sterile equipment. It should be administered only via an infusion pump that can maintain a constant infusion rate. For treatment of acute anginal attack, one tablet of Nitrostat should be dissolved under the tongue or in the buccal pouch at the first sign of an acute anginal attack. The dose may be repeated approximately every 5 minutes, until relief is obtained. If the pain persists after a total of 3 tablets in a 15-minute period, or the pain is different than is typically experienced, prompt medical attention is recommended. Nitrostat may be used prophylactically 5 to 10 minutes prior to engaging in activities which might precipitate an acute attack.
Route of Administration: Sublingual; Intravenous
In Vitro Use Guide
Vasoactivity of nitroglycerin was measured using an ex vivo assay. Mice thoracic aortae were removed, cleaned, and cut into 3-mm rings. Rings were mounted on strain gauge transducers under 1 g of resting tension, and maintained at 37°C in Krebs solution, bubbled continuously with 20% O2/5% CO2/75% N2. Rings were allowed to equilibrate for 1 h before active tension was induced with prostaglandin F2α. Application of Nitroglycerine relieve the F2α-induced strain with IC50 of 10-7 M for wt mice, and 10-5 for mtALDH-/- mice.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:56:49 UTC 2019
Edited
by admin
on Mon Oct 21 20:56:49 UTC 2019
Record UNII
G59M7S0WS3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITROGLYCERIN
HSDB   MI   ORANGE BOOK   USP   VANDF  
Systematic Name English
NITRO-DUR
Brand Name English
GLYCERYL TRINITRATE [WHO-DD]
Common Name English
RECTIV
Brand Name English
NITRO IV
Brand Name English
GLYCERIN TRINITRATE
Systematic Name English
NITROGLYCERIN TABLETS [JAN]
Common Name English
DILUTED NITROGLYCERIN [USP-RS]
Common Name English
NITROGLYCERIN [ORANGE BOOK]
Common Name English
PROPANE-1,2,3-TRIYL TRINITRATE
Systematic Name English
MINITRAN
Brand Name English
GLONOINUM [HPUS]
Common Name English
TRINITRIN
Common Name English
NITROGLYCERIN [MI]
Common Name English
NITORA
Common Name English
NTG
Common Name English
TRINITRINE
Common Name English
NITROGLYCERIN [VANDF]
Common Name English
NITROMIST
Brand Name English
NITRONAL
Brand Name English
NITROL
Brand Name English
GONITRO
Common Name English
GLONOINUM
HPUS  
Common Name English
C01DA02
Code English
NITROLINGUAL
Brand Name English
TRIDIL
Brand Name English
GLYCERYL TRINITRATE
MART.   WHO-DD  
Systematic Name English
NITROSTAT
Brand Name English
GLYCERYL TRINITRATE [MART.]
Common Name English
TRANSDERM-NITRO
Brand Name English
TRINITROGLYCERIN
Systematic Name English
NITRO-BID
Brand Name English
1,2,3-PROPANETRIOL, TRINITRATE
Systematic Name English
NITROGLYCERIN [USP]
Common Name English
DILUTED NITROGLYCERIN
USP-RS  
Common Name English
GLYCEROL TRINITRATE
Systematic Name English
IMX-150
Common Name English
NITROGLYCERIN [HSDB]
Common Name English
1,2,3-PROPANETRIOL TRINITRATE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC05AE01
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-VATC QC01DA02
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
CFR 21 CFR 250.102
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000007647
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000007647
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
EU-Orphan Drug EU/3/15/1435
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NCI_THESAURUS C29707
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-ATC C01DA52
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-ATC C05AE01
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
LIVERTOX 691
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000007647
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000009909
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 12.1
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-VATC QC01DA52
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000007647
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
NDF-RT N0000175415
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-ATC C01DA20
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
WHO-ATC C01DA02
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
200-240-8
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
PUBCHEM
4510
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
WIKIPEDIA
NITROGLYCERIN
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
HSDB
55-63-0
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
EVMPD
SUB11999MIG
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
EPA CompTox
55-63-0
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
NCI_THESAURUS
C29294
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
IUPHAR
7053
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
ChEMBL
CHEMBL730
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
MERCK INDEX
M7964
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY Merck Index
CAS
9010-02-0
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
SUPERCEDED
DRUG BANK
DB00727
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
LactMed
55-63-0
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
EVMPD
SUB13997MIG
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
CAS
55-63-0
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
RXCUI
4917
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY RxNorm
EVMPD
SUB90670
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
MESH
D005996
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
PRIMARY
EVMPD
SUB96541
Created by admin on Mon Oct 21 20:56:49 UTC 2019 , Edited by admin on Mon Oct 21 20:56:49 UTC 2019
ALTERNATIVE
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC