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
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16103363 |
https://www.ncbi.nlm.nih.gov/pubmed/22040938
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16103363 |
https://www.ncbi.nlm.nih.gov/pubmed/22040938
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
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22040938
Curator's Comment: Nitroglycerin was first synthesized by the Italian chemist Ascanio Sobrero in 1847, working under Théophile-Jules Pelouze at the University of Turin
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111348 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NITROSTAT Approved UseAcute relief of angina pectoris secondary to CAD; acute prophylactic management in situations likely to provoke angina attacks; and long-term prophylactic management of angina pectoris. Launch Date9.4703039E11 |
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Primary | NITROGLYCERIN Approved UseManagement of patients with acute myocardial infarction (MI). Nitroglycerin is one of the principal initial therapies of MI. Launch Date3.71174408E11 |
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Primary | NITROGLYCERIN Approved UseIV nitroglycerin is used to control BP in perioperative hypertension, especially hypertension associated with cardiovascular procedures; to control BP in patients with severe hypertension† or in hypertensive crises for the immediate reduction of BP in patients in whom such reduction is considered an emergency (hypertensive emergencies), especially those associated with coronary complications (e.g., coronary ischemia, acute coronary insufficiency, acute left ventricular failure, postoperative hypertension [especially following coronary bypass surgery]); and to produce controlled hypotension during surgical procedures. Launch Date3.71174408E11 |
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Primary | NITROGLYCERIN Approved UseIV nitroglycerin has been used in the management of acutely decompensated (e.g., congestive) heart failure and other low cardiac-output states. Launch Date3.71174408E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.7 pg/mL |
800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered: |
NITROGLYCERIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
84 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/ |
13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYCERYL 1,2-DINITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.3 pg × min/mL |
800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered: |
NITROGLYCERIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3380 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/ |
13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYCERYL 1,2-DINITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40 min |
800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered: |
NITROGLYCERIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
50 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/ |
13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLYCERYL 1,2-DINITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 ug/kg/min multiple, intravenous (starting) Dose: 1 ug/kg/min Route: intravenous Route: multiple Dose: 1 ug/kg/min Sources: |
pregnant, 26 years n = 16 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 16 Sources: |
Disc. AE: Hypotension... AEs leading to discontinuation/dose reduction: Hypotension (4 patients) Sources: |
8 ug/kg/min multiple, intravenous Dose: 8 ug/kg/min Route: intravenous Route: multiple Dose: 8 ug/kg/min Sources: |
pregnant, 26 years n = 1 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 1 Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (severe, 1 patient) Sources: Vomiting (severe, 1 patient) Headache (severe, 1 patient) |
35 ug/kg/min single, intravenous Dose: 35 ug/kg/min Route: intravenous Route: single Dose: 35 ug/kg/min Sources: |
unhealthy, 50 years (range: 19 ± 74 years) n = 105 Health Status: unhealthy Age Group: 50 years (range: 19 ± 74 years) Sex: M+F Population Size: 105 Sources: |
Disc. AE: Hemodynamic test abnormal... AEs leading to discontinuation/dose reduction: Hemodynamic test abnormal (8 patients) Sources: |
0.6 mg/h 1 times / day multiple, transdermal Highest studied dose Dose: 0.6 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.6 mg/h, 1 times / day Sources: |
unhealthy, 51.4 ±4.3 years n = 11 Health Status: unhealthy Condition: menopausal hot flashes Age Group: 51.4 ±4.3 years Sex: F Population Size: 11 Sources: |
|
2 % 6 times / day multiple, topical Dose: 2 %, 6 times / day Route: topical Route: multiple Dose: 2 %, 6 times / day Sources: |
unhealthy, 57 - 71 years n = 2 Health Status: unhealthy Age Group: 57 - 71 years Sex: M Population Size: 2 Sources: |
Disc. AE: Pruritic rash, Erythema edematous... AEs leading to discontinuation/dose reduction: Pruritic rash (2 patients) Sources: Erythema edematous (2 patients) Vesicular eruption (2 patients) |
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy, 80 years n = 1 Health Status: unhealthy Condition: angina pectoris Age Group: 80 years Sex: M Population Size: 1 Sources: |
Other AEs: Methemoglobinemia... Other AEs: Methemoglobinemia (grade 5, 1 patient) Sources: |
0.2 mg/h 1 times / day multiple, transdermal (starting) Recommended Dose: 0.2 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.2 mg/h, 1 times / day Sources: |
unhealthy, adult n = 307 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 307 Sources: |
Other AEs: Headache, Lightheadedness... Other AEs: Headache (63%) Sources: Lightheadedness (6%) Hypotension (4%) Syncope (4%) |
1.5 mg 2 times / day multiple, rectal Dose: 1.5 mg, 2 times / day Route: rectal Route: multiple Dose: 1.5 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Hypotension... AEs leading to discontinuation/dose reduction: Hypotension Sources: |
5 ug/kg 1 times / day single, subcutaneous Dose: 5 ug/kg, 1 times / day Route: subcutaneous Route: single Dose: 5 ug/kg, 1 times / day Sources: |
unhealthy, pediatric n = 57 Health Status: unhealthy Age Group: pediatric Population Size: 57 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | 4 patients Disc. AE |
1 ug/kg/min multiple, intravenous (starting) Dose: 1 ug/kg/min Route: intravenous Route: multiple Dose: 1 ug/kg/min Sources: |
pregnant, 26 years n = 16 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 16 Sources: |
Headache | severe, 1 patient Disc. AE |
8 ug/kg/min multiple, intravenous Dose: 8 ug/kg/min Route: intravenous Route: multiple Dose: 8 ug/kg/min Sources: |
pregnant, 26 years n = 1 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 1 Sources: |
Nausea | severe, 1 patient Disc. AE |
8 ug/kg/min multiple, intravenous Dose: 8 ug/kg/min Route: intravenous Route: multiple Dose: 8 ug/kg/min Sources: |
pregnant, 26 years n = 1 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 1 Sources: |
Vomiting | severe, 1 patient Disc. AE |
8 ug/kg/min multiple, intravenous Dose: 8 ug/kg/min Route: intravenous Route: multiple Dose: 8 ug/kg/min Sources: |
pregnant, 26 years n = 1 Health Status: pregnant Condition: Preterm labor Age Group: 26 years Sex: F Population Size: 1 Sources: |
Hemodynamic test abnormal | 8 patients Disc. AE |
35 ug/kg/min single, intravenous Dose: 35 ug/kg/min Route: intravenous Route: single Dose: 35 ug/kg/min Sources: |
unhealthy, 50 years (range: 19 ± 74 years) n = 105 Health Status: unhealthy Age Group: 50 years (range: 19 ± 74 years) Sex: M+F Population Size: 105 Sources: |
Erythema edematous | 2 patients Disc. AE |
2 % 6 times / day multiple, topical Dose: 2 %, 6 times / day Route: topical Route: multiple Dose: 2 %, 6 times / day Sources: |
unhealthy, 57 - 71 years n = 2 Health Status: unhealthy Age Group: 57 - 71 years Sex: M Population Size: 2 Sources: |
Pruritic rash | 2 patients Disc. AE |
2 % 6 times / day multiple, topical Dose: 2 %, 6 times / day Route: topical Route: multiple Dose: 2 %, 6 times / day Sources: |
unhealthy, 57 - 71 years n = 2 Health Status: unhealthy Age Group: 57 - 71 years Sex: M Population Size: 2 Sources: |
Vesicular eruption | 2 patients Disc. AE |
2 % 6 times / day multiple, topical Dose: 2 %, 6 times / day Route: topical Route: multiple Dose: 2 %, 6 times / day Sources: |
unhealthy, 57 - 71 years n = 2 Health Status: unhealthy Age Group: 57 - 71 years Sex: M Population Size: 2 Sources: |
Methemoglobinemia | grade 5, 1 patient | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy, 80 years n = 1 Health Status: unhealthy Condition: angina pectoris Age Group: 80 years Sex: M Population Size: 1 Sources: |
Hypotension | 4% | 0.2 mg/h 1 times / day multiple, transdermal (starting) Recommended Dose: 0.2 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.2 mg/h, 1 times / day Sources: |
unhealthy, adult n = 307 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 307 Sources: |
Syncope | 4% | 0.2 mg/h 1 times / day multiple, transdermal (starting) Recommended Dose: 0.2 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.2 mg/h, 1 times / day Sources: |
unhealthy, adult n = 307 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 307 Sources: |
Lightheadedness | 6% | 0.2 mg/h 1 times / day multiple, transdermal (starting) Recommended Dose: 0.2 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.2 mg/h, 1 times / day Sources: |
unhealthy, adult n = 307 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 307 Sources: |
Headache | 63% | 0.2 mg/h 1 times / day multiple, transdermal (starting) Recommended Dose: 0.2 mg/h, 1 times / day Route: transdermal Route: multiple Dose: 0.2 mg/h, 1 times / day Sources: |
unhealthy, adult n = 307 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 307 Sources: |
Hypotension | Disc. AE | 1.5 mg 2 times / day multiple, rectal Dose: 1.5 mg, 2 times / day Route: rectal Route: multiple Dose: 1.5 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[Reactivity of cerebral vessels in patients with circulatory encephalopathy, arterial hypertension and cerebral hypoperfusion risk]. | 2001 |
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The effect of transdermal glyceryl trinitrate, a nitric oxide donor, on blood pressure and platelet function in acute stroke. | 2001 |
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The use of intravenous nitroglycerin in a case of spasm of the sphincter of Oddi during laparoscopic cholecystectomy. | 2001 Apr |
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Treatment of anal fissure with glyceryl trinitrate in patients referred for surgical management. | 2001 Apr |
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Ultrasound vasography evaluation of radial arterial grafts used for coronary arterial bypass surgery. | 2001 Apr |
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Glyceryl trinitrate and acute uterine relaxation: a literature review. | 2001 Apr |
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Does nitric oxide play a role in the aetiology of pre-eclampsia? | 2001 Apr |
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Nonadrenergic, noncholinergic relaxation of human isolated corpus cavernosum induced by scorpion venom. | 2001 Apr |
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Topical diltiazem ointment in the treatment of chronic anal fissure. | 2001 Apr |
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Effects of nitrovasodilators on the human fetal-placental circulation in vitro. | 2001 Apr |
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Nitric oxide modulation of blood vessel tone identified by arterial waveform analysis. | 2001 Apr |
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S-Transnitrosylation of albumin in human plasma and blood in vitro and in vivo in the rat. | 2001 Apr 7 |
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Improved analysis of brachial artery ultrasound using a novel edge-detection software system. | 2001 Aug |
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[Aspirin and nitroglycerine: a good combination for gastric mucosa]. | 2001 Aug-Sep |
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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 |
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Effects of nitric oxide donors on the contractility and prostaglandin synthesis of myometrial strips from pregnant and non-pregnant women. | 2001 Feb |
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Cardiac natriuretic peptides--hope or hype? | 2001 Feb |
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Continued cigarette smoking after coronary artery bypass surgery reduces endothelium-dependent vasodilation in internal thoracic artery grafts. | 2001 Feb |
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Insulin resistance adds to endothelial dysfunction in hypertensive patients and in normotensive offspring of subjects with essential hypertension. | 2001 Feb |
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Effects of C-peptide on forearm blood flow and brachial artery dilatation in patients with type 1 diabetes mellitus. | 2001 Jul |
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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 |
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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 |
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Transoesophageal acoustic quantification for evaluation of cardiac function during laparoscopic surgery. | 2001 Jul |
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Pseudonormal diastolic filling unmasked with glyceryl trinitrate in patients with type 2 diabetes with poor metabolic control. | 2001 Jul |
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Reduction of organic nitrates catalysed by xanthine oxidoreductase under anaerobic conditions. | 2001 Jul 2 |
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The effect of nitric oxide donors and L-arginine on the gastric electrolyte barrier. | 2001 Jun |
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Long-term outcome of patients with ergonovine induced coronary constriction not associated with ischemic electrocardiographic changes. | 2001 Jun |
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Changes in endothelium-dependent vasodilatation and alpha-adrenergic responses in resistance vessels during the menstrual cycle in healthy women. | 2001 Jun |
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Reasons for failure of glyceryl trinitrate treatment of chronic fissure-in-ano: a multivariate analysis. | 2001 Jun |
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Effect of statin versus fibrate on postprandial endothelial dysfunction: role of remnant-like particles. | 2001 Jun |
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Nitric oxide in primary headaches. | 2001 Jun |
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Ecstasy induced acute myocardial infarction. | 2001 Jun |
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Augmentation of nitric oxide to treat detrusor-external sphincter dyssynergia in spinal cord injury. | 2001 Jun 16 |
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Technique for using video microscopy and indicator dilution for repeated measurements of cardiac output in small animals. | 2001 Mar |
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Effect of acute blood pressure reduction on endothelial function in the brachial artery of patients with essential hypertension. | 2001 Mar |
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Calcitonin gene-related peptide levels during nitric oxide-induced headache in patients with chronic tension-type headache. | 2001 Mar |
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The BB-paraoxonase genotype is associated with impaired brachial reactivity after acute hypertriglyceridemia in healthy subjects. | 2001 Mar |
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Comparison of topically applied 0.2% glyceryl trinitrate ointment, incision and excision in the treatment of perianal thrombosis. | 2001 May |
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Audit of topical glyceryl trinitrate for treatment of fissure-in-ano. | 2001 May |
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Endothelium-dependent and independent vasodilation studies at normoglycaemia in type I diabetes mellitus with and without microalbuminuria. | 2001 May |
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Myocardial Doppler tissue velocity improves following myocardial gene therapy with VEGF-A165 plasmid in patients with inoperable angina pectoris. | 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 |
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An update on nesiritide for treatment of decompensated heart failure. | 2001 May |
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Glyceryl trinitrate ointment as a potential treatment for primary vaginismus. | 2001 May |
|
Effects of in vivo nitroglycerin treatment on activity and expression of the guanylyl cyclase and cGMP-dependent protein kinase and their downstream target vasodilator-stimulated phosphoprotein in aorta. | 2001 May 1 |
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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 |
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[Nitrate headache in blasting work]. | 2001 May 15 |
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Heart preservation with celsior solution improved by the addition of nitroglycerine. | 2001 May 27 |
|
Treatment of chronic anal fissure with topical glyceryl trinitrate: a double-blind, placebo-controlled trial. | 2001 May-Jun |
Patents
Sample Use Guides
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:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103363
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC05AE01
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WHO-VATC |
QC01DA02
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CFR |
21 CFR 250.102
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NDF-RT |
N0000007647
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NDF-RT |
N0000007647
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EU-Orphan Drug |
EU/3/15/1435
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NCI_THESAURUS |
C29707
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WHO-ATC |
C01DA52
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WHO-ATC |
C05AE01
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LIVERTOX |
691
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NDF-RT |
N0000007647
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NDF-RT |
N0000009909
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WHO-ESSENTIAL MEDICINES LIST |
12.1
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WHO-VATC |
QC01DA52
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NDF-RT |
N0000007647
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NDF-RT |
N0000175415
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WHO-ATC |
C01DA20
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WHO-ATC |
C01DA02
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Code System | Code | Type | Description | ||
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Nitroglycerin (medication)
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200-240-8
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G59M7S0WS3
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G59M7S0WS3
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4510
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1952
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NITROGLYCERIN
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30
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SUB11999MIG
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DTXSID1021407
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C29294
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7053
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CHEMBL730
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M7964
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DB00727
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1466506
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Nitroglycerin
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SUB13997MIG
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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55-63-0
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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4917
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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SUB90670
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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34104
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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9010-02-0
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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28787
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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D005996
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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SUB96541
Created by
admin on Fri Dec 16 16:35:17 UTC 2022 , Edited by admin on Fri Dec 16 16:35:17 UTC 2022
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ALTERNATIVE |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)