Identification

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Name
Nitroglycerin
Accession Number
DB00727  (APRD00153)
Type
Small Molecule
Groups
Approved, Investigational
Description

Nitroglycerin is a vasodilator drug used for the treatment of chest pain and high blood pressure.12,13 It was first approved in 2000 and is currently marketed by Pfizer, and other companies, depending on the dosage form.12,15 Nitroglycerin is available in various forms, including a spray form, sublingual tablet form, intravenous form, extended-release tablet form, and transdermal form. A less commonly known fact is that in addition to treating angina, nitroglycerin is also used in an ointment to treat the pain that accompanies anal fissures. The rectal ointment form of nitroglycerin was approved by the FDA in 1955.14

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GonitroPowder400 ug/1SublingualEspero Pharmaceuticals, Inc.2016-07-01Not applicableUs
MinitranPatch0.4 mgTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
MinitranPatch0.2 mgTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
MinitranPatch0.6 mgTransdermalValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Minitran - Patch Trd 72mg/26.6 Sq CmPatchTransdermalGraceway PharmaceuticalsNot applicableNot applicableCanada
Nitro-durPatch160 mg/1TransdermalMerck Sharp & Dohme Limited1995-04-042018-04-25Us
Nitro-durPatch20 mg/1TransdermalIngenus Pharmaceuticals, LLC2017-12-06Not applicableUs
Nitro-durPatch20 mg/1TransdermalMerck Sharp & Dohme Limited1995-04-042018-04-25Us
Nitro-durPatch120 mg/1TransdermalIngenus Pharmaceuticals, LLC2017-12-06Not applicableUs
Nitro-durPatch20 mg/1TransdermalPhysicians Total Care, Inc.1995-07-262005-12-31Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-nitroglycerinSublingualApotex Corporation2013-09-23Not applicableCanada
MinitranPatch36000 ug/1Transdermal3M Company1996-08-302006-12-29Us
MinitranPatch5 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
MinitranPatch18 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
MinitranPatch18000 ug/1Transdermal3M Company1996-08-302006-12-29Us
MinitranPatch2.5 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
MinitranPatch9 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
MinitranPatch9000 ug/1Transdermal3M Company1996-08-302006-12-29Us
MinitranPatch18 mg/1[USP'U]TransdermalPhysicians Total Care, Inc.2012-02-212012-06-30Us
MinitranPatch15 mg/1dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nitroglycerin In 5% Dextrose Inj.-100mcg/mlNitroglycerin (10 mg) + Dextrose, unspecified form (5 g)SolutionIntravenousBaxter Laboratories1995-12-312016-02-26Canada
Nitroglycerin In 5% Dextrose Inj.-200mcg/mlNitroglycerin (20 mg) + Dextrose, unspecified form (5 g)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada
Nitroglycerin In 5% Dextrose Inj.-400mcg/mlNitroglycerin (40 mg) + Dextrose, unspecified form (5 g)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nitro-TimeNitroglycerin (2.5 mg/1)CapsuleOralMajor2004-01-29Not applicableUs
Nitro-TimeNitroglycerin (2.5 mg/1)CapsuleOralCarilion Materials Management2004-01-29Not applicableUs
Nitro-timeNitroglycerin (9 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUs
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralCarilion Materials Management2004-01-29Not applicableUs00904 0644 60 nlmimage10 66353349
Nitro-timeNitroglycerin (6.5 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUs
Nitro-timeNitroglycerin (2.5 mg/1)CapsuleOralTIME CAP LABORATORIES, INC2014-06-19Not applicableUs
Nitro-TimeNitroglycerin (9.0 mg/1)CapsuleOralMajor2004-01-29Not applicableUs
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralMajor2004-01-29Not applicableUs0904 064420180907 15195 1t18elc
Nitro-TimeNitroglycerin (6.5 mg/1)CapsuleOralAvera McKennan Hospital2015-04-242018-06-28Us
NitroglycerinNitroglycerin (2.5 mg/1)CapsuleOralPD-Rx Pharmaceuticals, Inc.2014-06-19Not applicableUs
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)
Categories
UNII
G59M7S0WS3
CAS number
55-63-0
Weight
Average: 227.0865
Monoisotopic: 227.002578773
Chemical Formula
C3H5N3O9
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

Pharmacology

Indication

Nitroglycerin is indicated for various purposes.15 It is indicated to prevent and treat angina or chest pain due to cardiovascular disease, as well as to treat peri-operative hypertension or induce intra-operative hypotension.13,16 It is also indicated to treat acute heart failure in patients with myocardial infarction.16 In the ointment form, nitroglycerin is indicated to treat pain caused by anal fissures.14 The transdermal form is applied directly to the skin to prevent acute anginal attacks.20

The intravenous form is used off-label in emergency settings and is commonly used to treat acute coronary spasm caused by cocaine, hypertensive emergencies, as well as acute congestive heart failure exacerbations.12 Some other off-label uses of nitroglycerin include management of variceal hemorrhage10, management of esophageal spasticity11, and induction of uterine relaxation.9

Associated Conditions
Pharmacodynamics

Nitroglycerin causes the relaxation of vascular smooth muscles, causing arteriolar and venous dilatation. It reduces cardiac preload and afterload and reduces coronary artery spasm, decreasing systemic vascular resistance as well as systolic and diastolic blood pressure.13 The reduction of cardiac work by nitroglycerin is thought to cause the most relief of anginal symptoms, with some contributions from arteriolar dilatation effects.12

Mechanism of action

Nitroglycerin is converted by mitochondrial aldehyde dehydrogenase (mtALDH) to nitric oxide (NO), an active substance which then activates the enzyme guanylate cyclase.2 The activation of this enzyme is followed by the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP), activating a cascade of protein kinase-dependent phosphorylation events in smooth muscles. This process eventually leads to the dephosphorylation of the myosin light chain of smooth muscles, causing relaxation and increased blood flow in veins, arteries and cardiac tissue.3,12. The above processes lead to decreased work of the heart decreased blood pressure, relief of anginal symptoms, and increased blood flow to the myocardium.3,12,17One in vitro study using mouse aorta suggests that nitric oxide (an activated metabolite of nitroglycerin) targets the natriuretic peptide receptors.7

TargetActionsOrganism
AAtrial natriuretic peptide receptor 1
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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Absorption

Nitroglycerin is rapidly absorbed and is often used in emergency situations for this reason.12 After a sublingual dose of 0.5 mg of nitroglycerin, peak concentration was reached by an average of in 4.4 minutes after administration and was measured to be 2.56 ng/ml.4

Cmax following a 0.6mg dose of sublingual nitroglycerin was measured to be 2.1 ng/mL and AUC was 14.9 minutes, and Tmax was 7.2 minutes.13 Absolute bioavailability after the administration of sublingual nitroglycerin tablets is about 40%. The bioavailability of nitroglycerin depends on factors such as mucosal metabolism and hydration status, which both affect the absorption of sublingual drugs.13

Volume of distribution

The volume of distribution of nitroglycerin is 3 L/kg.16

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%.13

Metabolism

The enzyme mitchochondrial aldehyde dehydrogenase is known to cause the bioactivation of nitroglycerin. Nitroglycerin is metabolized to nitrite, 1,2-glyceryl dinitrate, and 1,3 glyceryl dinitrate.8,16 Nitrite is then metabolized to nitric oxide or S-nitrosothiol.8 The 1,2-and 1,3-dinitroglycerols are less potent in strength than nitroglycerin, but they have longer half-lives, explaining some prolonged effects of nitrates. Both dinitrates are subsequently metabolized to mononitrates that are not active on the blood vessels, and to glycerol and carbon dioxide in the final step of metabolism.6,16

Route of elimination

Metabolism is the main route by which nitroglycerin is eliminated from the body.13

Half life

In a pharmacokinetic study, the plasma half-life of intravenously administered nitroglycerin was 2.8 ± 0.9 minutes.5 The FDA label for the intravenous form of nitroglycerin indicates a similar plasma half-life of about 3 minutes.16 A pharmacokinetic study using sublingual nitroglycerin estimated the plasma half-life to be approximately 6 minutes.4 The elimination half-lives of 1,2- and 1,3-dinitroglycerin (metabolites of nitroglycerin)range between 32-26 minutes.13

Clearance

The FDA label for the intravenous form of nitroglycerin estimates clearance to be 1 L/kg/min.16 Apparent clearance after a sublingual dose was measured to be 21.9 L/min in a pharmacokinetic study of 22 patients with ischemic heart disease and angina.4

Toxicity

LD50 information 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.18

Overdose information An overdose of nitroglycerin can lead to a variety of hemodynamic effects. General effects may include vertigo, fever, flushed skin, and diaphoresis. Cardiorespiratory symptoms may include syncope, dyspnea, decreased heart rate, or palpitations. Neurologic manifestations can include paralysis, seizures, coma, and death.16 There are no known antidotes to an overdose of nitroglycerin, and it is not known whether its metabolites can be removed from the circulation.13,16 If hypotension occurs due to an overdose with nitroglycerin, elevate the lower limbs and administer an intravenous infusion of normal saline or other fluids if necessary to maintain central fluid volume.13,16

Affected organisms
  • Humans and other mammals
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
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Nitroglycerin.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Nitroglycerin.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Nitroglycerin.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Nitroglycerin.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Nitroglycerin.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Nitroglycerin.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Nitroglycerin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Nitroglycerin.
AbediterolAbediterol may decrease the antihypertensive activities of Nitroglycerin.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Nitroglycerin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Avoid alcohol.
  • Dissolve under the tongue.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

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. [PubMed:12060725]
  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. [PubMed:12048254]
  3. Ferreira JC, Mochly-Rosen D: Nitroglycerin use in myocardial infarction patients. Circ J. 2012;76(1):15-21. Epub 2011 Nov 1. [PubMed:22040938]
  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. [PubMed:3125063]
  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. [PubMed:6101155]
  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. [PubMed:3086541]
  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. [PubMed:12890708]
  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. [PubMed:17055381]
  9. Smith GN, Brien JF: Use of nitroglycerin for uterine relaxation. Obstet Gynecol Surv. 1998 Sep;53(9):559-65. [PubMed:9751938]
  10. Burns SM, Martin M, Merrill P, Luer J, Stone DD: Evaluation and revision of a vasopressin/nitroglycerin protocol for use in variceal bleeding. Am J Crit Care. 1993 May;2(3):202-7. [PubMed:8364671]
  11. Swamy N: Esophageal spasm: clinical and manometric response to nitroglycerine and long acting nitrites. Gastroenterology. 1977 Jan;72(1):23-7. [PubMed:401445]
  12. Kyle H. Kim; Derek J. Schaller (2019). Nitroglycerin. Stat Pearls publishing.
  13. Nitrostat® (Nitroglycerin) FDA Label [Link]
  14. Rectiv FDA label [Link]
  15. FDA Label: Apadaz [Link]
  16. Nitroglycerin in Dextrose FDA label [Link]
  17. Nitroglycerin pump spray monograph [Link]
  18. Nitroglycerin MSDS, Pfizer [Link]
  19. MSDS, Nitroglycerin [Link]
  20. Transdermal nitroglycerin [Link]
External Links
Human Metabolome Database
HMDB0014865
KEGG Drug
D00515
KEGG Compound
C07455
PubChem Compound
4510
PubChem Substance
46509120
ChemSpider
4354
ChEBI
28787
ChEMBL
CHEMBL730
Therapeutic Targets Database
DNC001024
PharmGKB
PA450644
HET
TNG
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nitroglycerin
ATC Codes
C01DA02 — Glyceryl trinitrateC01DA52 — Glyceryl trinitrate, combinationsC05AE01 — Glyceryl trinitrate
AHFS Codes
  • 24:12.08 — Nitrates and Nitrites
PDB Entries
4fr8

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingBasic ScienceRadial Artery Injury Prevetion1
0CompletedScreeningAdenomatous Polyp of Colon / Colorectal Cancers / Neoplasms, Colorectal1
0CompletedSupportive CareControlled Hypotension for Nasal Surgeries1
1Active Not RecruitingTreatmentRectal Carcinoma1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableInflammatory Reaction1
1CompletedDiagnosticErectile Dysfunction (ED)1
1CompletedTreatmentCoronary Artery Disease1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentRaynaud's Phenomenon2
1RecruitingOtherHigh Blood Pressure (Hypertension)1
1, 2CompletedPreventionCatheter-Associated Infections / Catheter-Related Infections1
1, 2RecruitingBasic ScienceMicrovascular Dysfunction1
2CompletedTreatmentCardiac Failure / Heart Failure / Reduced Ventricular Ejection Fraction1
2CompletedTreatmentCerebral Oxygenation1
2CompletedTreatmentCoronary Artery Disease1
2CompletedTreatmentDiabetic Peripheral Neuropathy (DPN)1
2CompletedTreatmentDigital Ulcer of Scleroderma1
2CompletedTreatmentPrinzmetal's variant angina1
2CompletedTreatmentRaynaud's Disease1
2CompletedTreatmentRaynaud's Phenomenon Secondary to Connective Tissue Disease1
2CompletedTreatmentSickle Cell Disorders / Thoracic Pain1
2CompletedTreatmentStroke, Acute1
2RecruitingTreatmentColic / Functional disorders of the biliary tract1
2RecruitingTreatmentErectile Dysfunction (ED)1
2RecruitingTreatmentIntracerebral Hemorrhage / Stroke, Ischemic1
2RecruitingTreatmentMenopausal Hot Flashes1
2RecruitingTreatmentShock, Hemorrhagic1
2TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Unknown StatusTreatmentLocally Advanced Non Small-Cell Lung Canger1
2Unknown StatusTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Unknown StatusTreatmentLung Cancers1
2Unknown StatusTreatmentTendonitis1
2, 3Active Not RecruitingPreventionPerfusion; Complications1
2, 3CompletedPreventionRaynaud Secondary to Other Autoimmune Disease / Raynaud's Disease / Raynaud's Disease Secondary to Scleroderma1
2, 3CompletedTreatmentCardiac Catheterizations / Spasms1
2, 3CompletedTreatmentHeart Failure1
2, 3CompletedTreatmentInduction of Labor Affected Fetus / Newborn1
2, 3CompletedTreatmentPain After Stapled Haemorrhoidopexy1
2, 3RecruitingHealth Services ResearchAcute Heart Failure (AHF)1
2, 3TerminatedPreventionERCP / Pancreatitis1
2, 3TerminatedTreatmentExternal Cephalic Version1
3CompletedPreventionCardiac Catheterisation1
3CompletedPreventionOcclusion of Artery / Radial Artery Injury at Wrist and Hand Level / Vasodilation1
3CompletedPreventionOsteopenia / Osteoporosis1
3CompletedPreventionOsteoporosis1
3CompletedTreatmentAutoimmune Diseases / Raynaud's Disease / Scleroderma1
3CompletedTreatmentCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction / Myocardial Ischemia1
3CompletedTreatmentChronic Anal Fissures1
3CompletedTreatmentFissure in Ano / Pain NOS1
3CompletedTreatmentHeart Failure / High Blood Pressure (Hypertension)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3CompletedTreatmentOsteoporosis1
3CompletedTreatmentPain NOS1
3CompletedTreatmentRaynaud's Disease1
3CompletedTreatmentRheumatoid Arthritis1
3CompletedTreatmentSepsis / Shock, Septic1
3Not Yet RecruitingTreatmentPain NOS1
3RecruitingPreventionInjury of Radial Artery1
3RecruitingPreventionTotal Atherosclerotic Occlusion of Radial Artery / Transradial Catheterization, Radial Artery Occlusion1
3RecruitingTreatmentErectile Dysfunction (ED)1
3RecruitingTreatmentMyocardial Reperfusion Injury1
3Unknown StatusTreatmentRaynaud's Disease1
3Unknown StatusTreatmentRaynaud's Disease / Raynaud's Disease Secondary to Other Autoimmune Disease / Raynaud's Disease Secondary to Scleroderma1
3Unknown StatusTreatmentStrokes1
4Active Not RecruitingTreatmentAcute Heart Failure (AHF)1
4CompletedDiagnosticCoronary Artery Disease1
4CompletedOtherCardiopulmonary Bypass / Coronary Artery Bypass Graft Surgery Patients1
4CompletedPreventionContrast Induced Nephropathy (CIN)1
4CompletedSupportive CareManaging Preterm Labor1
4CompletedTreatmentAcute Decompensated Heart Failure (ADHF)1
4CompletedTreatmentAcute Myocardial Infarction (AMI) / Percutaneous Coronary Intervention1
4CompletedTreatmentAngina Pectoris1
4CompletedTreatmentCoronary Slow Flow Phenomenon / ST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentEndotoxin, Escherichia Coli / Regional Blood Flow / Retina1
4CompletedTreatmentEsophageal Food Bolus Obstruction1
4CompletedTreatmentHeart Transplantation / High Blood Pressure (Hypertension)1
4CompletedTreatmentIUD Insertion1
4CompletedTreatmentNormal, or Near Normal Coronary Angiography / Slow Coronary Flow / Stable Angina (SA)1
4CompletedTreatmentPlacenta, Retained2
4CompletedTreatmentProlonged Second Stage of Labor1
4CompletedTreatmentRenal Failure1
4Not Yet RecruitingTreatmentAngina Pectoris1
4Not Yet RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4RecruitingHealth Services ResearchCerebral Vasospasm1
4RecruitingPreventionAnginal Pain / Coronary Artery Disease / Radial Artery Spasm1
4RecruitingPreventionRadial Artery Injury1
4RecruitingSupportive CareCoronary Artery Disease1
4RecruitingSupportive CareDeliberate Hypotension / Sinus Endoscopic Surgery / Tissue Perfusion1
4RecruitingTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD)1
4Unknown StatusTreatmentMicrocirculation / Severe Sepsis1
4Unknown StatusTreatmentStable Angina (SA)1
4WithdrawnTreatmentAnal Fissures1
Not AvailableCompletedBasic ScienceFamilial Hemiplegic Migraine1
Not AvailableCompletedBasic ScienceGlaucoma1
Not AvailableCompletedBasic ScienceNitric Oxide / Oral Soft Tissue Conditions / Vasodilation1
Not AvailableCompletedBasic SciencePsychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedBasic ScienceRetinal Hypoxia1
Not AvailableCompletedPreventionContraception / Pain NOS1
Not AvailableCompletedPreventionInjury of Radial Artery1
Not AvailableCompletedPreventionMicrocirculation / Neoplasms, Esophageal1
Not AvailableCompletedTreatmentAchilles Tendinopathy / Achilles Tendon Pain / Tendinopathy1
Not AvailableCompletedTreatmentAnaesthesia therapy / Arterial Hypotension1
Not AvailableCompletedTreatmentArterial Line1
Not AvailableCompletedTreatmentBreech Presentation / Complication of Pregnancy1
Not AvailableCompletedTreatmentBreech Presentation / Complications, Pregnancy1
Not AvailableCompletedTreatmentCVA (Cerebrovascular Accident) / Intracerebral Hemorrhage / Intracranial Hemorrhages1
Not AvailableCompletedTreatmentCoronaropathy1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentHypertensive Anal Canal1
Not AvailableCompletedTreatmentMastectomy Flap Necrosis1
Not AvailableCompletedTreatmentMyofascial Trigger Points1
Not AvailableCompletedTreatmentPostpartum Haemorrhage (PPH)1
Not AvailableEnrolling by InvitationTreatmentCardiovascular Disease (CVD)1
Not AvailableRecruitingNot AvailableAortic Valve Stenosis / Hypertension,Essential / Impaired Renal Function / Secondary Hypertension1
Not AvailableRecruitingNot AvailableCoronary Ischemia1
Not AvailableRecruitingTreatmentAnal Fissures1
Not AvailableRecruitingTreatmentHypotension,Controlled1
Not AvailableTerminatedOtherEnd Stage Renal Disease (ESRD)1
Not AvailableTerminatedTreatmentChronic Kidney Disease (CKD)1
Not AvailableUnknown StatusEducational/Counseling/TrainingHealthy Volunteers1
Not AvailableUnknown StatusSupportive CareBleeding / Lactic Acidosis1
Not AvailableWithdrawnNot AvailableCoronary Heart Disease (CHD)1
Not AvailableWithdrawnHealth Services ResearchHealthy Volunteers1

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
PowderSublingual400 ug/1
PatchTransdermal0.2 mg
PatchTransdermal0.4 mg
PatchTransdermal0.6 mg
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
PatchTransdermal
Aerosol, meteredSublingual
OintmentTopical20 mg/1g
PatchTransdermal120 mg/1
PatchTransdermal160 mg/1
PatchTransdermal20 mg/1
PatchTransdermal40 mg/1
PatchTransdermal60 mg/1
PatchTransdermal80 mg/1
CapsuleOral9.0 mg/1
Tablet, extended releaseBuccal
Aerosol, meteredSublingual400 ug/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
SolutionIntravenous
InjectionIntravenous10 mg/100mL
InjectionIntravenous20 mg/100mL
InjectionIntravenous40 mg/100mL
Injection, solutionIntravenous100 ug/1mL
Injection, solutionIntravenous200 ug/1mL
Injection, solutionIntravenous400 ug/1mL
LiquidIntravenous
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
SolutionIntravenous
OintmentTopical
SprayOral400 ug/1
Spray, meteredSublingual400 ug/1
Spray, meteredOral400 ug/1
Aerosol, sprayTransmucosal400 ug/1
Injection, solutionIntravenous1 mg/1mL
Tablet, extended releaseOral
TabletOral0.3 mg/1
TabletOral0.6 mg/1
TabletSublingual0.3 mg
TabletSublingual0.4 mg/1
TabletSublingual0.6 mg
OintmentRectal4 mg/1g
Patch, extended releaseTransdermal12.5 mg/1
Patch, extended releaseTransdermal25 mg/1
Patch, extended releaseTransdermal50 mg/1
Patch, extended releaseTransdermal75 mg/1
Patch, extended releaseTransdermal
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)
US5186938No1993-02-162010-02-16Us
US7872049No2011-01-182028-03-14Us
US6500456No2002-12-312018-09-16Us
US5869082No1999-02-092016-04-16Us
US9101592No2015-08-112032-03-11Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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

Taxonomy

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
Alkyl nitrate / Organic nitro compound / Organic nitric acid or derivatives / Organic 1,3-dipolar compound / Allyl-type 1,3-dipolar organic compound / Organic nitrogen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
nitroglycerol (CHEBI:28787) / a small molecule (CPD-143)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. [PubMed:12890708]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [PubMed:20543077]
  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. [PubMed:12048254]

Drug created on June 13, 2005 07:24 / Updated on September 17, 2019 03:41