Identification

Summary

Nitroglycerin is a nitrate vasodilator used to treat or prevent angina, heart failure, hypertension, and anal fissures.

Brand Names
Gonitro, Minitran, Mylan-nitro, Nitro-bid, Nitro-dur, Nitroject, Nitrolingual, Nitromist, Nitrostat, Rectiv, Trinipatch
Generic Name
Nitroglycerin
DrugBank Accession Number
DB00727
Background

Nitroglycerin, also known as glyceryl trinitrate,2 is an organic nitrate and a vasodilating agent 17 that was first discovered in 1847.9 Originally used to dynamite, its antianginal effects were identified in the late 1860s after it produced headaches in factory workers while workers with angina pectoris or heart failure experienced relief from chest pain.1,3 Its use as a treatment for angina dates back to 1879 and is still used to treat and prevent angina.10 Nitroglycerin causes vasodilation in both arteries and veins.3

Nitroglycerin is used in a variety of different conditions, including angina pectoris due to coronary artery disease,12,14,17,15 peri-operative hypertension, congestive heart failure,11 and chronic anal fissure.16 It is also used to induce intraoperative hypotension.11

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 227.0865
Monoisotopic: 227.002578773
Chemical Formula
C3H5N3O9
Synonyms
  • 1,2,3-propanetrioltrinitrate
  • 1,2,3-propanetriyl nitrate
  • Glycerin trinitrate
  • Glycerol trinitrate
  • Glycerol, nitric acid triester
  • Glyceroli trinitratis
  • Glyceroltrinitrat
  • Glyceryl trinitrate
  • NG
  • Nitroglicerina
  • Nitroglycerin
  • Nitroglycerine
  • Nitroglycerol
  • Nitromed
  • Propane-1,2,3-triyl trinitrate
  • Trinitrine
  • Trinitroglycerin
  • Trinitroglycerol
External IDs
  • DR 66
  • IMX-150

Pharmacology

Indication

Sublingual nitroglycerin is indicated for the acute relief of an attack or acute prophylaxis of angina pectoris due to coronary artery disease.12,17,15 Transdermal nitroglycerin is indicated for the prevention of angina pectoris due to coronary artery disease.14

Intravenous nitroglycerin is indicated for the treatment of peri-operative hypertension; for control of congestive heart failure in the setting of acute myocardial infarction; for treatment of angina pectoris in patients who have not responded to sublingual nitroglycerin and beta (β)-blockers; and for induction of intraoperative hypotension.11

Topical nitroglycerin ointment is used to treat moderate to severe pain associated with chronic anal fissure.16

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Nitroglycerin causes the relaxation of vascular smooth muscles, causing arteriolar and venous dilatation.17 It increases blood flow to the myocardium and reduces cardiac preload and afterload, decreasing myocardial wall stress and ameliorating anginal symptoms.3,10,12 Nitroglycerin also reduces coronary artery spasm, decreasing systemic vascular resistance as well as systolic and diastolic blood pressure.17

Like other organic nitrates, repeated and prolonged administration of nitroglycerin can lead to the development of tolerance or desensitization of vascular smooth muscle to further nitroglycerin-induced vasorelaxation. This loss of efficacy may be associated with the inhibition of mitochondrial aldehyde dehydrogenase, which is an important enzyme involved in the bioactivation of nitroglycerin.1,2,3 Nitroglycerin tolerance may be accompanied by pro-oxidant effects, endothelial dysfunction, and increased sensitivity to vasoconstrictors.3

Mechanism of action

Nitroglycerin is converted by mitochondrial aldehyde dehydrogenase in smooth muscle cells to nitric oxide (NO), a potent vasodilator. NO activates the enzyme guanylate cyclase, which converts guanosine triphosphate (GTP) to cyclic guanosine 3',5'-monophosphate (cGMP) in vascular smooth muscle and other tissues.1,2,10 cGMP is an endogenous vasodilator of vascular smooth muscle:3 it causes protein kinase-dependent phosphorylation and activates downstream cascades that promote relaxation and increased blood flow in veins, arteries and cardiac tissue.3,10 An in vitro study using mouse aorta suggests that nitric oxide, an active metabolite of nitroglycerin, targets the natriuretic peptide receptors.7

TargetActionsOrganism
UAtrial natriuretic peptide receptor 1
agonist
Humans
Absorption

Nitroglycerin is rapidly absorbed and is often used in emergency situations for this reason.10 After a sublingual dose of 0.5 mg of nitroglycerin in patients with ischemic heart disease, the peak concentration (Cmax) was 2.56 ng/mL and the mean Tmax was 4.4 minutes.4

The Cmax following a 0.6mg dose of sublingual nitroglycerin was 2.1 ng/mL and the Tmax was 7.2 minutes.17 The absolute bioavailability following sublingual administration was about 40%. The bioavailability of nitroglycerin depends on several factors, such as mucosal metabolism and hydration status, which both affect the absorption of sublingual drugs.17

Volume of distribution

The volume of distribution of nitroglycerin is 3 L/kg.11

Protein binding

After a sublingual dose of nitroglycerin, at concentrations in the plasma ranging from 50 to 500 ng/mL, plasma protein binding of nitroglycerin is about 60%. The plasma protein binding of the metabolites 1,2-dinitroglycerin is 60% and that of 1,3-dinitroglycerin is 30%.17

Metabolism

Mitochondrial aldehyde dehydrogenase 2 (ALDH2) promotes the bioactivation of nitroglycerin. Nitroglycerin is metabolized to nitrite; 1,2-glyceryl dinitrate; and 1,3 glyceryl dinitrate.1,8,11 Nitrite is further metabolized to nitric oxide. 1,2- and 1,3-dinitroglycerols are less biologically active than nitroglycerin but they have longer half-lives, which explains some prolonged effects of nitrates. Both dinitrates are finally metabolized to glycerol, carbon dioxide, and mononitrates that do not have vasodilatory actions.6,11

Nitroglycerin can also chemically react with a thiol to generate an intermediate S-nitrosothiol, which resulted in further production of nitric oxide.1,3,8

Hover over products below to view reaction partners

Route of elimination

Metabolism is the main route by which nitroglycerin is eliminated from the body.17

Half-life

Following intravenous administration, the plasma half-life is about three minutes.5,11 The estimated plasma half-life following sublingual administration is approximately six minutes.4 The elimination half-lives of metabolites 1,2-dinitroglycerin and 1,3-dinitroglycerin range between 32 to 26 minutes.17

Clearance

The estimated clearance following intravenous administration is 1 L/kg/min.11 The apparent clearance after a sublingual dose was 21.9 L/min in a pharmacokinetic study of patients with ischemic heart disease and angina.4

Adverse Effects
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Toxicity

The oral LD50 of nitroglycerin in rats is 105 mg/kg and the LD50 of the intravenous form in rats is 23.2 mg/kg.13

Nitrate overdosage can result in following conditions: severe hypotension, persistent throbbing headache, vertigo, palpitation, visual disturbance, flushing and perspiring skin (later becoming cold and cyanotic), nausea and vomiting (possibly with colic and even bloody diarrhea), syncope (especially in the upright posture), methemoglobinemia with cyanosis and anorexia, initial hyperpnea, dyspnea and slow breathing, slow pulse (dicrotic and intermittent), heart block, increased intracranial pressure with cerebral symptoms of confusion and moderate fever, paralysis and coma followed by clonic convulsions, and possibly death due to circulatory collapse.17

Methemoglobinemia can rarely occur at conventional doses of organic nitrates. This condition is dose-related and it can be even more pronounced in patients with genetic abnormalities of hemoglobin that favor methemoglobin formation. Methemoglobinemia can be managed with the administration of methylene blue unless the patient has a known G-6-PD deficiency.17

There are no known antidotes to an overdose of nitroglycerin, and it is not known whether its metabolites can be removed from the circulation.17,11 Hypotension associated with nitroglycerin overdose can be managed with different symptomatic and supportive measures, including the elevation of the lower limbs, administration of intravenous saline or other fluids to maintain central fluid volume, and administration of oxygen and artificial ventilation. Gastric lavage may be used in case of ingestion of excess nitroglycerin.17

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololNitroglycerin may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Acemetacin.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Nitroglycerin.
Acetylsalicylic acidThe serum concentration of Nitroglycerin can be increased when it is combined with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Alclofenac.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Nitroglycerin.
AlfentanilAlfentanil may decrease the antihypertensive activities of Nitroglycerin.
AlfuzosinAlfuzosin may increase the hypotensive activities of Nitroglycerin.
AliskirenNitroglycerin may increase the hypotensive activities of Aliskiren.
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Food Interactions
  • Avoid alcohol. Alcohol can increase the risk of hypotension.

Products

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Product Images
International/Other Brands
Deponit (UCB Pharma) / Dermatrans (Bayer) / Gen-Nitro (Genpharm ULC) / Glytrin (Sanofi-Aventis) / Glytrin Spray (Sanofi-Aventis) / Natispray (Teofarma) / Nitrocap (Orion) / Nitroderm TTS (Novartis) / Nitrolingual Pump Spray (Arbor Pharmaceuticals) / Rectogesic (ProStrakan) / Stangyl / Transderm-Nitro (Novartis) / Tridil / Trimonit (Sanofi-Aventis) / Trinipatch (Paladin) / Triniplas (Novartis) / Trinispray (Sanofi Aventis) / Trinitrin Simplex Laleuf (Sanofi) / Trinitron (Quesada) / Trinitrosan (Merck) / Trintek (Goldshield) / Trocer (Incepta) / Trocer SR (Incepta) / Vasolator (Sanwa Kagaku) / Vasovin (Torrent) / Venitrin (Meda) / Vernies (Parke Davis) / Willlong (Will-Pharma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GonitroPowder400 ug/1SublingualEspero Pharmaceuticals, Inc.2016-07-01Not applicableUS flag
GonitroPowder400 ug/1SublingualAllegis Pharmaceuticals, Inc.2019-07-012023-06-30US flag
MinitranPatch0.6 mg / hourTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-312021-03-19Canada flag
MinitranPatch0.2 mg / hourTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-312021-03-19Canada flag
MinitranPatch0.4 mg / hourTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-312021-03-19Canada flag
Minitran - Patch Trd 72mg/26.6 Sq CmPatch72 mg / 26.6 sq cmTransdermalGraceway PharmaceuticalsNot applicableNot applicableCanada flag
Nitro-durPatch160 mg/1TransdermalIngenus Pharmaceuticals, LLC2017-12-06Not applicableUS flag
Nitro-durPatch60 mg/1TransdermalIngenus Pharmaceuticals, LLC2017-12-06Not applicableUS flag
Nitro-durPatch80 mg/1TransdermalMerck Sharp & Dohme Corp.1995-04-042017-06-02US flag
Nitro-durPatch40 mg/1TransdermalPhysicians Total Care, Inc.1993-08-132005-12-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-nitroglycerinSpray, metered0.4 mg / actSublingualApotex Corporation2013-09-23Not applicableCanada flag
MinitranPatch5 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUS flag
MinitranPatch54 mg/1TransdermalBausch Health US, LLC2012-02-212021-03-02US flag
MinitranPatch9 mg/1TransdermalBausch Health US, LLC2012-02-212021-10-01US flag
MinitranPatch18000 ug/1Transdermal3M Company1996-08-302006-12-29US flag
MinitranPatch18 mg/1[USP'U]TransdermalPhysicians Total Care, Inc.2012-02-212012-06-30US flag
MinitranPatch15 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUS flag
MinitranPatch2.5 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUS flag
MinitranPatch36 mg/1TransdermalBausch Health US, LLC2012-02-212020-11-03US flag
MinitranPatch54000 ug/1Transdermal3M Company1996-08-302006-12-29US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ANGISED TABLET 0.5 mgTablet0.5 mgOralGLAXOSMITHKLINE PTE LTD1988-06-24Not applicable
GLYTRIN SPRAYSpray400 mcg/spraySubmucosalJOYSON PTE. LTD.1997-01-21Not applicable
MYONIT INSTA NITROGLYCERIN SUBLINGUAL TABLETS USP 0.5MGTablet0.5 mgSublingualTRINITY PHARMACEUTICALS & FOOD PTE. LTD.2019-05-31Not applicable
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Nitroglycerin In 5% Dextrose Inj.-100mcg/mlNitroglycerin (10 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)SolutionIntravenousBaxter Laboratories1995-12-312016-02-26Canada flag
Nitroglycerin In 5% Dextrose Inj.-200mcg/mlNitroglycerin (20 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada flag
Nitroglycerin In 5% Dextrose Inj.-400mcg/mlNitroglycerin (40 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Nitro-timeNitroglycerin (2.5 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUS flag
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralAvera McKennan Hospital2015-04-242017-05-24US flag
Nitro-TimeNitroglycerin (2.5 mg/1)CapsuleOralMajor Pharmaceuticals2004-01-292022-10-31US flag
Nitro-TimeNitroglycerin (2.5 mg/1)CapsuleOralCarilion Materials Management2004-01-29Not applicableUS flag
Nitro-timeNitroglycerin (9 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUS flag
Nitro-TimeNitroglycerin (9.0 mg/1)CapsuleOralMajor Pharmaceuticals2004-01-292022-12-31US flag
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralCarilion Materials Management2004-01-29Not applicableUS flag
Nitro-timeNitroglycerin (6.5 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUS flag
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralMajor Pharmaceuticals2004-01-292022-02-28US flag
NitroglycerinNitroglycerin (9.0 mg/1)CapsuleOralCarilion Materials Management2004-01-29Not applicableUS flag

Categories

ATC Codes
C01DA02 — Glyceryl trinitrateC01DA52 — Glyceryl trinitrate, combinationsC05AE01 — Glyceryl trinitrate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organic oxoanionic compounds
Sub Class
Organic nitrates
Direct Parent
Alkyl nitrates
Alternative Parents
Organic nitro compounds / Organic nitric acids and derivatives / Organooxygen compounds / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Alkyl nitrate / Allyl-type 1,3-dipolar organic compound / Hydrocarbon derivative / Organic 1,3-dipolar compound / Organic nitric acid or derivatives / Organic nitro compound / Organic nitrogen compound / Organic oxide / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
nitroglycerol (CHEBI:28787) / a small molecule (CPD-143)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
G59M7S0WS3
CAS number
55-63-0
InChI Key
SNIOPGDIGTZGOP-UHFFFAOYSA-N
InChI
InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
IUPAC Name
1,3-bis(nitrooxy)propan-2-yl nitrate
SMILES
[O-][N+](=O)OCC(CO[N+]([O-])=O)O[N+]([O-])=O

References

Synthesis Reference

Izhak Blank, "Nitroglycerin preparations." U.S. Patent US4482534, issued December, 1979.

US4482534
General References
  1. Ignarro LJ: After 130 years, the molecular mechanism of action of nitroglycerin is revealed. Proc Natl Acad Sci U S A. 2002 Jun 11;99(12):7816-7. doi: 10.1073/pnas.132271799. [Article]
  2. Chen Z, Zhang J, Stamler JS: Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc Natl Acad Sci U S A. 2002 Jun 11;99(12):8306-11. doi: 10.1073/pnas.122225199. Epub 2002 Jun 4. [Article]
  3. Ferreira JC, Mochly-Rosen D: Nitroglycerin use in myocardial infarction patients. Circ J. 2012;76(1):15-21. Epub 2011 Nov 1. [Article]
  4. Blagodatskikh SV, Piotrovskii VK, Metelits VI, Riabokon' OS, Martsevich SIu: [Pharmacokinetics of glycerin trinitrate (nitroglycerin) after sublingual administration in patients with chronic ischemic heart disease]. Farmakol Toksikol. 1987 Nov-Dec;50(6):59-63. [Article]
  5. McNiff EF, Yacobi A, Young-Chang FM, Golden LH, Goldfarb A, Fung HL: Nitroglycerin pharmacokinetics after intravenous infusion in normal subjects. J Pharm Sci. 1981 Sep;70(9):1054-8. [Article]
  6. Cossum PA, Roberts MS, Yong AC, Kilpatrick D: Distribution and metabolism of nitroglycerin and its metabolites in vascular beds of sheep. J Pharmacol Exp Ther. 1986 Jun;237(3):959-66. [Article]
  7. Madhani M, Scotland RS, MacAllister RJ, Hobbs AJ: Vascular natriuretic peptide receptor-linked particulate guanylate cyclases are modulated by nitric oxide-cyclic GMP signalling. Br J Pharmacol. 2003 Aug;139(7):1289-96. [Article]
  8. Chen Z, Stamler JS: Bioactivation of nitroglycerin by the mitochondrial aldehyde dehydrogenase. Trends Cardiovasc Med. 2006 Nov;16(8):259-65. doi: 10.1016/j.tcm.2006.05.001. [Article]
  9. Marsh N, Marsh A: A short history of nitroglycerine and nitric oxide in pharmacology and physiology. Clin Exp Pharmacol Physiol. 2000 Apr;27(4):313-9. doi: 10.1046/j.1440-1681.2000.03240.x. [Article]
  10. Kim KH, Kerndt CC, Adnan G, Schaller DJ: Nitroglycerin . [Article]
  11. FDA Approved Drug Products: Nitroglycerin in 5% Dextrose Injection, for intravenous use [Link]
  12. Health Canada Approved Drug Products: NITROLINGUAL PUMPSPRAY (Nitroglycerin) Sublingual Spray [Link]
  13. Pfizer: Nitroglycerin MSDS [Link]
  14. FDA Approved Drug Products: NITRO-DUR (nitroglycerin) Transdermal Infusion System [Link]
  15. FDA Approved Drug Products: NitroMist (nitroglycerin) lingual aerosol [Link]
  16. DailyMed Label: RECTIV (nitroglycerin) Ointment 0.4%, for intra-anal use [Link]
  17. DailyMed Label: NITROSTAT (nitroglycerin) sublingual tablet [Link]
Human Metabolome Database
HMDB0014865
KEGG Drug
D00515
KEGG Compound
C07455
PubChem Compound
4510
PubChem Substance
46509120
ChemSpider
4354
RxNav
4917
ChEBI
28787
ChEMBL
CHEMBL730
ZINC
ZINC000008214625
Therapeutic Targets Database
DNC001024
PharmGKB
PA450644
PDBe Ligand
TNG
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nitroglycerin
PDB Entries
4fr8

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticCoronary Artery Disease (CAD)1
4CompletedOtherCardiopulmonarybypass / Coronary Artery Bypass Grafting (CABG)1
4CompletedPreventionAnginal Pain / Coronary Artery Disease (CAD) / Radial Artery Spasm1
4CompletedPreventionProphylaxis of Contrast-induced nephropathy1
4CompletedSupportive CareDeliberate Hypotension / Sinus Endoscopic Surgery / Tissue Perfusion1
4CompletedSupportive CareManaging Preterm Labor1
4CompletedTreatmentAcute Decompensated Heart Failure (ADHF)1
4CompletedTreatmentAcute Heart Failure (AHF)1
4CompletedTreatmentAcute Myocardial Infarction (AMI) / Percutaneous Coronary Intervention (PCI)1
4CompletedTreatmentAngina Pectoris1

Pharmacoeconomics

Manufacturers
  • Novadel pharma inc
  • Pohl boskamp
  • Graceway pharmaceuticals llc
  • Key pharmaceuticals inc sub schering plough corp
  • Hercon laboratories corp
  • Kremers urban co
  • Mylan technologies inc
  • Novartis pharmaceuticals corp
  • G pohl boskamp gmbh and co
  • Sanofi aventis us llc
  • Abraxis pharmaceutical products
  • Hospira inc
  • International medication systems ltd
  • Luitpold pharmaceuticals inc
  • Smith and nephew solopak div smith and nephew
  • Baxter healthcare corp
  • Rorer pharmaceutical corp sub rorer group
  • Parke davis div warner lambert co
  • E fougera div altana inc
  • Pfizer pharmaceuticals ltd
Packagers
  • 3M Health Care
  • Akrimax Pharmaceuticals
  • American Regent
  • A-S Medication Solutions LLC
  • Baxter International Inc.
  • Bradley Pharmaceuticals Inc.
  • Bristol-Myers Squibb Co.
  • C.O. Truxton Inc.
  • Cardinal Health
  • Concord Labs
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E. Fougera and Co.
  • Eon Labs
  • Ethex Corp.
  • G Pohl Boskamp GmbH and Co. KG
  • Glenmark Generics Ltd.
  • Glenmark Pharmaceuticals
  • Graceway Pharmaceuticals
  • H and H Laboratories
  • Heartland Repack Services LLC
  • Hercon Laboratories Corp.
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Konec Inc.
  • Lake Erie Medical and Surgical Supply
  • Lohmann Tiererahrung GmbH
  • LTS Lohmann Therapy Systems Corp.
  • Luitpold Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nippon Kayaku Co. Ltd.
  • North Safety Products
  • Novartis AG
  • Nubenco Enterprises Inc.
  • Nycomed Inc.
  • Pfizer Inc.
  • Pharmedix
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sanofi-Aventis Inc.
  • Savage Labs
  • Schering Corp.
  • Schwarz Pharma Inc.
  • Sciele Pharma Inc.
  • Shire Inc.
  • Southwood Pharmaceuticals
  • Summit Pharmaceuticals
  • Time-Cap Labs
  • TriMarc Labs
  • United Research Laboratories Inc.
  • Valsynthese Ltd.
  • Vangard Labs Inc.
  • Vision Pharma LLC
Dosage Forms
FormRouteStrength
PatchTransdermal10 MG
PatchTransdermal15 MG
PatchTransdermal5 MG
TabletOral0.5 mg
SolutionIntravenous25 mg
PatchTransdermal10 MG/24H
PatchTransdermal15 MG/24H
PatchTransdermal5 MG/24H
InjectionIntravenous
InjectionParenteral1 mg/ml
Injection, solutionIntravenous1 mg/ml
SolutionIntravenous1.000 MG/ML
InjectionIntravenous1 mg/1ml
Spray0.4 mg
SpraySubmucosal400 mcg/spray
SolutionSublingual400 mcg
PowderSublingual400 ug/1
TabletOral500 mcg
PatchTransdermal0.4 mg / hour
PatchTransdermal0.6 mg / hour
PatchTransdermal18 mg/1
PatchTransdermal18 mg/1[USP'U]
PatchTransdermal18000 ug/1
PatchTransdermal36 mg/1
PatchTransdermal36000 ug/1
PatchTransdermal54 mg/1
PatchTransdermal54000 ug/1
PatchTransdermal9 mg/1
PatchTransdermal9000 ug/1
PatchTransdermal72 mg / 26.6 sq cm
PlasterCutaneous36 mg
Aerosol, meteredSublingual0.4 mg / act
TabletSublingual0.5 mg
SpraySublingual
TabletSublingual
SolutionIntravenous1 mg/ml
OintmentTopical20 mg/1g
PatchTransdermal
PatchTransdermal120 mg/1
PatchTransdermal160 mg/1
PatchTransdermal20 mg/1
PatchTransdermal40 mg/1
PatchTransdermal60 mg/1
PatchTransdermal80 mg/1
Patch, extended releaseTransdermal0.2 mg / hour
Patch, extended releaseTransdermal60 mg / 15 sq cm
Patch, extended releaseTransdermal0.6 mg / hour
Patch, extended releaseTransdermal0.8 mg / hour
PatchTransdermal10 MG/24ORE
PatchTransdermal15 MG/24ORE
PatchTransdermal5 MG/24ORE
Ointment
Patch, extended releaseTransdermal10 mg/24hr
PlasterCutaneous10 mg
Patch, extended releaseTransdermal10 mg/24h
Patch, extended releaseTransdermal5 mg/24hr
PlasterCutaneous5 mg
Patch, extended releaseTransdermal5 mg/24h
Tablet, extended releaseBuccal1 mg
SolutionParenteral5 mg
SolutionIntravenous
SolutionIntravenous50 mg
SolutionParenteral50 mg
SolutionIntravenous20 mg
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous
Aerosol, meteredSublingual400 ug/1
CapsuleOral9.0 mg/1
Film, extended releaseTransdermal20.8 mg/1
Film, extended releaseTransdermal37.4 mg/1
Injection, solutionIntravenous5 mg/1mL
Injection, solution, concentrateIntravenous5 mg/1mL
PatchTransdermal0.1 mg/1h
PatchTransdermal0.4 mg/1h
PatchTransdermal0.6 mg/1h
TabletOral0.4 mg/1
TabletSublingual0.3 mg/1
TabletSublingual0.6 mg/1
Tablet, orally disintegratingSublingual0.3 mg/1
Tablet, orally disintegratingSublingual0.4 mg/1
Tablet, orally disintegratingSublingual0.6 mg/1
InjectionIntravenous10 mg/100mL
InjectionIntravenous20 mg/100mL
InjectionIntravenous40 mg/100mL
Injection, solutionIntravenous100 ug/1mL
Injection, solutionIntravenous200 ug/1mL
Injection, solutionIntravenous400 ug/1mL
LiquidIntravenous5 mg / mL
CapsuleOral2.5 mg/1
CapsuleOral6.5 mg/1
CapsuleOral9 mg/1
PatchTransdermal10 mg/1d
PatchTransdermal15 mg/1d
PatchTransdermal2.5 mg/1d
PatchTransdermal5 mg/1d
PatchTransdermal0.2 mg/1h
Patch, extended releaseTransdermal0.1 mg/1h
Patch, extended releaseTransdermal0.2 mg/1h
Patch, extended releaseTransdermal0.4 mg/1h
Patch, extended releaseTransdermal0.6 mg/1h
SolutionIntravenous10 mg / 10 mL
SolutionIntravenous50 mg / 10 mL
Capsule, extended releaseOral
OintmentTopical2 %
SprayOral400 ug/1
Spray, meteredSublingual400 ug/1
SprayOral0.4 mg
SprayOral0.41 mg
Spray, meteredOral400 ug/1
Spray, meteredSublingual0.4 mg / act
Aerosol, sprayTransmucosal400 ug/1
Injection, solutionIntravenous1 mg/1mL
Tablet, extended releaseOral2.6 mg
Aerosol, spraySublingual
TabletOral0.3 mg/1
TabletOral0.6 mg/1
TabletSublingual0.3 mg
TabletSublingual0.4 mg/1
TabletSublingual0.6 mg
InjectionParenteral
OintmentRectal4 mg/1g
OintmentRectal
OintmentTopical0.2 % w/w
Patch, extended releaseTransdermal12.5 mg/1
Patch, extended releaseTransdermal25 mg/1
Patch, extended releaseTransdermal50 mg/1
Patch, extended releaseTransdermal75 mg/1
Patch, extended releaseTransdermal0.4 mg / hour
Patch, extended releaseTransdermal100 mg / srd
PatchTransdermal0.2 mg / hour
Patch, extended releaseTransdermal15 mg/24hr
Injection, solutionIntravenous5 MG/1.5ML
Injection, solutionIntravenous50 MG/50ML
Injection, solution, concentrateIntravenous; Parenteral5 MG/1.5ML
Injection, solution, concentrateIntravenous; Parenteral50 MG/50ML
Tablet, coated0.3 MG
Injection, solution, concentrateIntravenous5 mg
Injection, solution, concentrateIntravenous5 MG/1.5ML
Solution5 mg/1ml
Prices
Unit descriptionCostUnit
Nitrolingual 0.4 mg/spray Solution 12 gm Bottle242.83USD bottle
Nitrolingual 0.4 mg/spray Solution 4.9 gm Bottle141.43USD bottle
Nitro-Dur 30 0.6 mg/hr Patches Box130.86USD box
Nitro-Dur 30 0.8 mg/hr Patches Box130.86USD box
Nitro-Dur 30 0.3 mg/hr Patches Box120.68USD box
Nitro-Dur 30 0.4 mg/hr Patches Box117.1USD box
Minitran 30 0.6 mg/hr Patches Box114.01USD box
Nitro-Dur 30 0.1 mg/hr Patches Box106.09USD box
Nitro-Dur 30 0.2 mg/hr Patches Box105.6USD box
Minitran 30 0.4 mg/hr Patches Box105.18USD box
Minitran 30 0.2 mg/hr Patches Box93.86USD box
Minitran 30 0.1 mg/hr Patches Box92.36USD box
Nitroglycerin 30 0.6 mg/hr Patches Box63.55USD box
Nitroglycerin 5 mg/ml kit62.38USD kit
Nitroglycerin 30 0.4 mg/hr Patches Box57.62USD box
Nitroglycerin 30 0.2 mg/hr Patches Box50.44USD box
Nitrostat 100 0.4 mg Sublingual Tabs Bottle29.88USD bottle
Nitromist 400 mcg spray28.5USD g
Nitrostat 100 0.3 mg Sublingual Tabs Bottle27.75USD bottle
Nitrostat 100 0.6 mg Sublingual Tabs Bottle24.99USD bottle
Nitroglycerin 100 0.6 mg Sublingual Tabs Bottle23.99USD bottle
Nitroglycerin 100 0.3 mg Sublingual Tabs Bottle22.99USD bottle
Nitrostat 25 0.4 mg Sublingual Tabs Bottle19.31USD bottle
Nitroglycerin 25 0.4 mg Sublingual Tabs Bottle9.5USD bottle
Nitro-dur 0.6 mg/hr patch4.19USD patch
Nitro-dur 0.8 mg/hr patch4.19USD patch
Nitro-dur 0.3 mg/hr patch3.87USD patch
Nitro-dur 0.4 mg/hr patch3.87USD patch
Minitran 0.6 mg/hr patch3.51USD patch
Nitro-dur 0.2 mg/hr patch3.45USD patch
Nitro-dur 0.1 mg/hr patch3.4USD patch
Minitran 0.4 mg/hr patch3.24USD patch
Minitran 0.2 mg/hr patch2.89USD patch
Minitran 0.1 mg/hr patch2.84USD patch
Nitroglycerin CR 6.5 mg capsule1.66USD capsule
Nitroglycerin 0.1 mg/hr Patches1.64USD patch
Nitroglycerin CR 9 mg capsule1.27USD capsule
Nitro-Dur 0.8 0.8 mg/hr Patch1.16USD patch
Nitroglycerin er 9 mg capsule1.0USD capsule
Transderm-Nitro 0.4 0.4 mg/hr Patch0.81USD patch
Transderm-Nitro 0.6 0.6 mg/hr Patch0.81USD patch
Minitran 0.4 0.4 mg/hr Patch0.74USD patch
Minitran 0.6 0.6 mg/hr Patch0.74USD patch
Nitroglycerin er 6.5 mg capsule0.72USD capsule
Transderm-Nitro 0.2 0.2 mg/hr Patch0.71USD patch
Nitro-Dur 0.4 0.4 mg/hr Patch0.67USD patch
Nitro-Dur 0.6 0.6 mg/hr Patch0.67USD patch
Trinipatch 0.4 0.4 mg/hr Patch0.67USD patch
Trinipatch 0.6 0.6 mg/hr Patch0.67USD patch
Minitran 0.2 0.2 mg/hr Patch0.66USD patch
Nitrol 2 % Ointment0.64USD g
Nitro-Dur 0.2 0.2 mg/hr Patch0.59USD patch
Trinipatch 0.2 0.2 mg/hr Patch0.59USD patch
Nitroglycerin 9 mg capsule sa0.53USD capsule
Nitro-bid 2% ointment0.48USD g
Nitroglycerin CR 2.5 mg capsule0.47USD capsule
Nitro-time er 9 mg capsule0.37USD capsule
Nitroglycerin 0.4 mg tablet sl0.36USD tablet
Nitrostat 0.4 mg tablet sl0.35USD tablet
Nitro-time er 6.5 mg capsule0.33USD capsule
Nitro-time er 2.5 mg capsule0.29USD capsule
Nitroglycerin er 2.5 mg capsule0.28USD capsule
Nitroglycerin 6.5 mg capsule sa0.22USD capsule
Nitroquick 0.3 mg tablet sl0.19USD tablet
Nitroglycerin 2.5 mg capsule sa0.18USD capsule
Nitroglycerin 2% ointment0.17USD g
Nitrostat 0.6 mg tablet sl0.16USD tablet
Nitroglycerin 0.3 mg tablet sl0.14USD tablet
Nitroglycerin 0.6 mg tablet sl0.14USD tablet
Nitrostat 0.3 mg Sublingual Tablet0.13USD tablet
Nitrostat 0.6 mg Sublingual Tablet0.13USD tablet
Nitrolingual Pumpspray 0.4 mg/dose Metered Dose Spray0.08USD dose
Nitroquick 0.4 mg tablet sl0.08USD tablet
Nitroquick 0.6 mg tablet sl0.08USD tablet
Nitrostat 0.3 mg tablet sl0.07USD tablet
Mylan-Nitro 0.4 mg/dose Metered Dose Spray0.04USD dose
Ntg 25 mg/250 ml in d5w0.04USD ml
Rho-Nitro Pumpspray 0.4 mg/dose Metered Dose Spray0.04USD dose
Ntg 50 mg/500 ml in d5w0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5186938No1993-02-162010-02-16US flag
US7872049No2011-01-182028-03-14US flag
US6500456No2002-12-312018-09-16US flag
US5869082No1999-02-092016-04-16US flag
US9101592No2015-08-112032-03-11US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)13.5 http://www.inchem.org/documents/icsc/icsc/eics0186.htm
boiling point (°C)160http://www.inchem.org/documents/icsc/icsc/eics0186.htm
water solubilitypoor solubility in waterhttp://www.inchem.org/documents/icsc/icsc/eics0186.htm
logP1.62http://www.inchem.org/documents/icsc/icsc/eics0186.htm
logS-3http://www.hmdb.ca/metabolites/HMDB0014865
pKa-5.6http://www.hmdb.ca/metabolites/HMDB0014865
Predicted Properties
PropertyValueSource
Water Solubility0.204 mg/mLALOGPS
logP1.25ALOGPS
logP0.26Chemaxon
logS-3ALOGPS
pKa (Strongest Basic)-5.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area157.11 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity37.59 m3·mol-1Chemaxon
Polarizability15.68 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7613
Blood Brain Barrier+0.9113
Caco-2 permeable-0.5775
P-glycoprotein substrateNon-substrate0.8322
P-glycoprotein inhibitor INon-inhibitor0.671
P-glycoprotein inhibitor IINon-inhibitor0.9005
Renal organic cation transporterNon-inhibitor0.8325
CYP450 2C9 substrateNon-substrate0.8982
CYP450 2D6 substrateNon-substrate0.9022
CYP450 3A4 substrateNon-substrate0.5255
CYP450 1A2 substrateNon-inhibitor0.8022
CYP450 2C9 inhibitorNon-inhibitor0.7789
CYP450 2D6 inhibitorNon-inhibitor0.9106
CYP450 2C19 inhibitorNon-inhibitor0.72
CYP450 3A4 inhibitorNon-inhibitor0.9173
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8638
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.6822
BiodegradationReady biodegradable0.9479
Rat acute toxicity2.9173 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.512
hERG inhibition (predictor II)Non-inhibitor0.9382
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.71 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Curator comments
This is a possible target of nitroglycerin, supported by an in vitro study.
General Function
Protein kinase activity
Specific Function
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate ...
Gene Name
NPR1
Uniprot ID
P16066
Uniprot Name
Atrial natriuretic peptide receptor 1
Molecular Weight
118918.11 Da
References
  1. Madhani M, Scotland RS, MacAllister RJ, Hobbs AJ: Vascular natriuretic peptide receptor-linked particulate guanylate cyclases are modulated by nitric oxide-cyclic GMP signalling. Br J Pharmacol. 2003 Aug;139(7):1289-96. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Electron carrier activity
Specific Function
Not Available
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
Molecular Weight
56380.93 Da
References
  1. Badejo AM Jr, Hodnette C, Dhaliwal JS, Casey DB, Pankey E, Murthy SN, Nossaman BD, Hyman AL, Kadowitz PJ: Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010 Sep;299(3):H819-26. doi: 10.1152/ajpheart.00959.2009. Epub 2010 Jun 11. [Article]
  2. Chen Z, Zhang J, Stamler JS: Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc Natl Acad Sci U S A. 2002 Jun 11;99(12):8306-11. doi: 10.1073/pnas.122225199. Epub 2002 Jun 4. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 06, 2022 07:57