Nitroglycerin

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

Similar Structures

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

Target	Actions	Organism
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 (C_max) was 2.56 ng/mL and the mean T_max was 4.4 minutes.⁴

The C_max following a 0.6mg dose of sublingual nitroglycerin was 2.1 ng/mL and the T_max 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

Nitroglycerin
- 1,2-glyceryl dinitrate + 1,3-glyceryl dinitrate + Nitrite
  - Nitric oxide + S-nitrosothiol

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.

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Nitroglycerin is combined with Abaloparatide.
Acebutolol	Nitroglycerin may increase the hypotensive activities of Acebutolol.
Aceclofenac	The therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Acemetacin.
Acetaminophen	The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Nitroglycerin.
Acetylsalicylic acid	The serum concentration of Nitroglycerin can be increased when it is combined with Acetylsalicylic acid.
Alclofenac	The therapeutic efficacy of Nitroglycerin can be decreased when used in combination with Alclofenac.
Aldesleukin	The risk or severity of adverse effects can be increased when Aldesleukin is combined with Nitroglycerin.
Alfentanil	Alfentanil may decrease the antihypertensive activities of Nitroglycerin.
Alfuzosin	Alfuzosin may increase the hypotensive activities of Nitroglycerin.

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Gonitro	Powder	400 ug/1	Sublingual	Espero Pharmaceuticals, Inc.	2016-07-01	Not applicable
Gonitro	Powder	400 ug/1	Sublingual	Allegis Pharmaceuticals, Inc.	2019-07-01	2023-06-30
Minitran	Patch	0.6 mg / hour	Transdermal	Valeant Canada Lp Valeant Canada S.E.C.	1995-12-31	2021-03-19
Minitran	Patch	18 mg/1	Transdermal	Kindeva Drug Delivery L.P.	2012-02-21	Not applicable
Minitran	Patch	0.2 mg / hour	Transdermal	Valeant Canada Lp Valeant Canada S.E.C.	1995-12-31	2021-03-19
Minitran	Patch	54 mg/1	Transdermal	Kindeva Drug Delivery L.P.	2012-02-21	Not applicable
Minitran	Patch	0.4 mg / hour	Transdermal	Valeant Canada Lp Valeant Canada S.E.C.	1995-12-31	2021-03-19
Minitran	Patch	36 mg/1	Transdermal	Kindeva Drug Delivery L.P.	2012-02-21	Not applicable
Minitran - Patch Trd 72mg/26.6 Sq Cm	Patch	72 mg / 26.6 sq cm	Transdermal	Graceway Pharmaceuticals	Not applicable	Not applicable
Nitro-dur	Patch	120 mg/1	Transdermal	Ingenus Pharmaceuticals, LLC	2017-12-06	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-nitroglycerin	Spray, metered	0.4 mg / act	Sublingual	Apotex Corporation	2013-09-23	Not applicable
Minitran	Patch	2.5 mg/1d	Transdermal	Graceway Pharmaceuticals	2007-04-01	Not applicable
Minitran	Patch	36000 ug/1	Transdermal	3M Company	1996-08-30	2006-12-29
Minitran	Patch	54 mg/1	Transdermal	Bausch Health US, LLC	2012-02-21	2021-03-02
Minitran	Patch	9 mg/1	Transdermal	Bausch Health US, LLC	2012-02-21	2021-10-01
Minitran	Patch	10 mg/1d	Transdermal	Graceway Pharmaceuticals	2009-08-10	Not applicable
Minitran	Patch	18000 ug/1	Transdermal	3M Company	1996-08-30	2006-12-29
Minitran	Patch	18 mg/1[USP'U]	Transdermal	Physicians Total Care, Inc.	2012-02-21	2012-06-30
Minitran	Patch	36 mg/1	Transdermal	Bausch Health US, LLC	2012-02-21	2020-11-03
Minitran	Patch	54000 ug/1	Transdermal	3M Company	1996-08-30	2006-12-29

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
ANGISED TABLET 0.5 mg	Tablet	0.5 mg	Oral	GLAXOSMITHKLINE PTE LTD	1988-06-24	Not applicable
GLYTRIN SPRAY	Spray	400 mcg/spray	Submucosal	JOYSON PTE. LTD.	1997-01-21	Not applicable
MYONIT INSTA NITROGLYCERIN SUBLINGUAL TABLETS USP 0.5MG	Tablet	0.5 mg	Sublingual	TRINITY PHARMACEUTICALS & FOOD PTE. LTD.	2019-05-31	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Nitroglycerin In 5% Dextrose Inj.-100mcg/ml	Nitroglycerin (10 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)	Solution	Intravenous	Baxter Laboratories	1995-12-31	2016-02-26
Nitroglycerin In 5% Dextrose Inj.-200mcg/ml	Nitroglycerin (20 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)	Solution	Intravenous	Baxter Laboratories	1995-12-31	Not applicable
Nitroglycerin In 5% Dextrose Inj.-400mcg/ml	Nitroglycerin (40 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL)	Solution	Intravenous	Baxter Laboratories	1995-12-31	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Basic Dental Emergency Kit	Nitroglycerin (0.4 mg/1) + Acetylsalicylic acid (325 mg/1) + D-glucose (4000 mg/1) + Diphenhydramine hydrochloride (50 mg/1mL) + Epinephrine (0.3 mg/0.3mL) + Salbutamol sulfate (108 ug/1)	Aerosol, metered; Injection; Kit; Tablet; Tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual	Best Dental Kit LLC	2023-01-30	Not applicable
Deluxe Dental Emergency Kit	Nitroglycerin (0.4 mg/1) + Acetylsalicylic acid (325 mg/1) + D-glucose (4000 mg/1) + Diphenhydramine hydrochloride (50 mg/1mL) + Diphenhydramine hydrochloride (12.5 mg/5mL) + Epinephrine (0.3 mg/0.3mL) + Epinephrine (0.15 mg/0.15mL) + Salbutamol sulfate (108 ug/1)	Aerosol, metered; Injection; Kit; Solution; Tablet; Tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual	Best Dental Kit LLC	2023-01-30	Not applicable
Nitro-Time	Nitroglycerin (9.0 mg/1)	Capsule	Oral	Major Pharmaceuticals	2004-01-29	2022-12-31
Nitro-Time	Nitroglycerin (6.5 mg/1)	Capsule	Oral	Carilion Materials Management	2004-01-29	Not applicable
Nitro-time	Nitroglycerin (2.5 mg/1)	Capsule	Oral	TIME CAP LABORATORIES, INC	2014-06-19	Not applicable
Nitro-Time	Nitroglycerin (6.5 mg/1)	Capsule	Oral	Major Pharmaceuticals	2004-01-29	2022-02-28
Nitro-time	Nitroglycerin (9 mg/1)	Capsule	Oral	TIME CAP LABORATORIES, INC	2014-06-19	Not applicable
Nitro-Time	Nitroglycerin (6.5 mg/1)	Capsule	Oral	Avera McKennan Hospital	2015-04-24	2017-05-24
Nitro-Time	Nitroglycerin (2.5 mg/1)	Capsule	Oral	Major Pharmaceuticals	2004-01-29	2022-10-31
Nitro-Time	Nitroglycerin (2.5 mg/1)	Capsule	Oral	Carilion Materials Management	2004-01-29	Not applicable

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

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]
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]
Ferreira JC, Mochly-Rosen D: Nitroglycerin use in myocardial infarction patients. Circ J. 2012;76(1):15-21. Epub 2011 Nov 1. [Article]
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]
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]
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]
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]
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]
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]
Kim KH, Kerndt CC, Adnan G, Schaller DJ: Nitroglycerin . [Article]
FDA Approved Drug Products: Nitroglycerin in 5% Dextrose Injection, for intravenous use [Link]
Health Canada Approved Drug Products: NITROLINGUAL PUMPSPRAY (Nitroglycerin) Sublingual Spray [Link]
Pfizer: Nitroglycerin MSDS [Link]
FDA Approved Drug Products: NITRO-DUR (nitroglycerin) Transdermal Infusion System [Link]
FDA Approved Drug Products: NitroMist (nitroglycerin) lingual aerosol [Link]
DailyMed Label: RECTIV (nitroglycerin) Ointment 0.4%, for intra-anal use [Link]
DailyMed Label: NITROSTAT (nitroglycerin) sublingual tablet [Link]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Completed	Diagnostic	Coronary Artery Disease (CAD)	1
4	Completed	Other	Cardiopulmonary Bypass / Coronary Artery Bypass Grafting (CABG)	1
4	Completed	Prevention	Anginal Pain / Coronary Artery Disease (CAD) / Radial Artery Spasm	1
4	Completed	Prevention	Prophylaxis of Contrast-induced nephropathy	1
4	Completed	Supportive Care	Deliberate Hypotension / Sinus Endoscopic Surgery / Tissue Perfusion	1
4	Completed	Supportive Care	Managing Preterm Labor	1
4	Completed	Treatment	Acute Decompensated Heart Failure (ADHF)	1
4	Completed	Treatment	Acute Heart Failure (AHF)	1
4	Completed	Treatment	Acute Myocardial Infarction (AMI) / Percutaneous Coronary Intervention (PCI)	1
4	Completed	Treatment	Angina Pectoris	1

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

Form	Route	Strength
Patch	Transdermal	10 MG
Patch	Transdermal	15 MG
Patch	Transdermal	5 MG
Solution	Intravenous	1.000 mg
Tablet	Oral	0.5 mg
Ointment	Rectal	0.4 %
Aerosol, metered; injection; kit; tablet; tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
Solution	Intravenous	50.000 mg
Patch	Transdermal	18.700 mg
Aerosol, metered; injection; kit; solution; tablet; tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
Solution	Intravenous	25 mg
Patch	Transdermal	10 MG/24H
Patch	Transdermal	15 MG/24H
Patch	Transdermal	5 MG/24H
Injection	Intravenous
Injection	Intravenous	50 mg/10ml
Injection	Parenteral	1 mg/ml
Injection, solution	Intravenous	1 mg/ml
Solution	Intravenous	1.000 MG/ML
Injection	Intravenous	1 mg/1ml
Spray		0.4 mg
Spray	Submucosal	400 mcg/spray
Solution	Sublingual	400 mcg
Powder	Sublingual	400 ug/1
Tablet	Oral	500 mcg
Patch	Transdermal	0.4 mg / hour
Patch	Transdermal	0.6 mg / hour
Patch	Transdermal	18 mg/1
Patch	Transdermal	18 mg/1[USP'U]
Patch	Transdermal	18000 ug/1
Patch	Transdermal	36 mg/1
Patch	Transdermal	36.000 mg
Patch	Transdermal	36000 ug/1
Patch	Transdermal	54 mg/1
Patch	Transdermal	54000 ug/1
Patch	Transdermal	9 mg/1
Patch	Transdermal	9000 ug/1
Patch	Transdermal	72 mg / 26.6 sq cm
Plaster	Cutaneous	36 mg
Aerosol, metered	Sublingual	0.4 mg / act
Tablet	Sublingual	0.5 mg
Spray	Sublingual
Tablet	Sublingual
Solution	Intravenous	1 mg/ml
Ointment	Topical	20 mg/1g
Patch	Transdermal
Patch	Transdermal	120 mg/1
Patch	Transdermal	160 mg/1
Patch	Transdermal	20 mg/1
Patch	Transdermal	40 mg/1
Patch	Transdermal	60 mg/1
Patch	Transdermal	80 mg/1
Patch, extended release	Transdermal	0.2 mg / hour
Patch, extended release	Transdermal	60 mg / 15 sq cm
Patch, extended release	Transdermal	0.6 mg / hour
Patch, extended release	Transdermal	0.8 mg / hour
Patch	Transdermal	10 MG/24ORE
Patch	Transdermal	15 MG/24ORE
Patch	Transdermal	5 MG/24ORE
Ointment
Patch	Transdermal	25.000 mg
Patch, extended release	Transdermal	10 mg/24hr
Plaster	Cutaneous	10 mg
Patch, extended release	Transdermal	10 mg/24h
Patch	Transdermal	50 mg
Patch, extended release	Transdermal	5 mg/24hr
Plaster	Cutaneous	5 mg
Patch, extended release	Transdermal	5 mg/24h
Patch	Transdermal	25 mg
Tablet, extended release	Buccal	1 mg
Solution	Parenteral	5 mg
Solution	Intravenous
Solution	Intravenous	50 mg
Solution	Parenteral	50 mg
Solution	Intravenous	20 mg
Injection, solution	Intravenous
Injection, solution, concentrate	Intravenous
Aerosol, metered	Sublingual	400 ug/1
Capsule	Oral	9.0 mg/1
Film, extended release	Transdermal	20.8 mg/1
Film, extended release	Transdermal	37.4 mg/1
Injection, solution	Intravenous	5 mg/1mL
Injection, solution, concentrate	Intravenous	5 mg/1mL
Patch	Transdermal	0.1 mg/1h
Patch	Transdermal	0.4 mg/1h
Patch	Transdermal	0.6 mg/1h
Tablet	Oral	0.4 mg/1
Tablet	Sublingual	0.3 mg/1
Tablet	Sublingual	0.6 mg/1
Tablet, orally disintegrating	Sublingual	0.3 mg/1
Tablet, orally disintegrating	Sublingual	0.4 mg/1
Tablet, orally disintegrating	Sublingual	0.6 mg/1
Injection	Intravenous	10 mg/100mL
Injection	Intravenous	20 mg/100mL
Injection	Intravenous	40 mg/100mL
Injection, solution	Intravenous	100 ug/1mL
Injection, solution	Intravenous	200 ug/1mL
Injection, solution	Intravenous	400 ug/1mL
Liquid	Intravenous	5 mg / mL
Capsule	Oral	2.5 mg/1
Capsule	Oral	6.5 mg/1
Capsule	Oral	9 mg/1
Patch	Transdermal	10 mg/1d
Patch	Transdermal	15 mg/1d
Patch	Transdermal	2.5 mg/1d
Patch	Transdermal	5 mg/1d
Patch	Transdermal	0.2 mg/1h
Patch, extended release	Transdermal	0.1 mg/1h
Patch, extended release	Transdermal	0.2 mg/1h
Patch, extended release	Transdermal	0.4 mg/1h
Patch, extended release	Transdermal	0.6 mg/1h
Solution	Intravenous	50 mg / 10 mL
Solution	Intravenous	10 mg / 10 mL
Capsule, extended release	Oral
Ointment	Topical	2 %
Spray	Oral	400 ug/1
Spray, metered	Sublingual	400 ug/1
Spray	Oral	0.4 mg
Spray	Oral	0.41 mg
Spray	Sublingual	0.4 mg
Spray, metered	Oral	400 ug/1
Spray, metered	Sublingual	0.4 mg / act
Aerosol, spray	Transmucosal	400 ug/1
Injection, solution	Intravenous	1 mg/1mL
Tablet, extended release	Oral	2.6 mg
Aerosol, spray	Sublingual
Tablet	Oral	0.3 mg/1
Tablet	Oral	0.6 mg/1
Tablet	Sublingual	0.3 mg
Tablet	Sublingual	0.4 mg/1
Tablet	Sublingual	0.6 mg
Injection	Parenteral	10 mg/10ml
Ointment	Rectal	4 mg/1g
Ointment	Rectal
Ointment	Rectal	4 mg/g
Ointment	Topical	0.2 % w/w
Ointment	Rectal	0.2 %
Patch, extended release	Transdermal	12.5 mg/1
Patch, extended release	Transdermal	25 mg/1
Patch, extended release	Transdermal	50 mg/1
Patch, extended release	Transdermal	75 mg/1
Patch, extended release	Transdermal	0.4 mg / hour
Patch, extended release	Transdermal	100 mg / srd
Patch	Transdermal	0.2 mg / hour
Patch, extended release	Transdermal	15 mg/24hr
Injection, solution	Intravenous	5 MG/1.5ML
Injection, solution	Intravenous	50 MG/50ML
Injection, solution, concentrate	Intravenous; Parenteral	5 MG/1.5ML
Injection, solution, concentrate	Intravenous; Parenteral	50 MG/50ML
Tablet, coated		0.3 MG
Injection, solution, concentrate	Intravenous	5 mg
Injection, solution, concentrate	Intravenous	5 MG/1.5ML
Solution		5 mg/1ml

Prices

Unit description	Cost	Unit
Nitrolingual 0.4 mg/spray Solution 12 gm Bottle	242.83USD	bottle
Nitrolingual 0.4 mg/spray Solution 4.9 gm Bottle	141.43USD	bottle
Nitro-Dur 30 0.6 mg/hr Patches Box	130.86USD	box
Nitro-Dur 30 0.8 mg/hr Patches Box	130.86USD	box
Nitro-Dur 30 0.3 mg/hr Patches Box	120.68USD	box
Nitro-Dur 30 0.4 mg/hr Patches Box	117.1USD	box
Minitran 30 0.6 mg/hr Patches Box	114.01USD	box
Nitro-Dur 30 0.1 mg/hr Patches Box	106.09USD	box
Nitro-Dur 30 0.2 mg/hr Patches Box	105.6USD	box
Minitran 30 0.4 mg/hr Patches Box	105.18USD	box
Minitran 30 0.2 mg/hr Patches Box	93.86USD	box
Minitran 30 0.1 mg/hr Patches Box	92.36USD	box
Nitroglycerin 30 0.6 mg/hr Patches Box	63.55USD	box
Nitroglycerin 5 mg/ml kit	62.38USD	kit
Nitroglycerin 30 0.4 mg/hr Patches Box	57.62USD	box
Nitroglycerin 30 0.2 mg/hr Patches Box	50.44USD	box
Nitrostat 100 0.4 mg Sublingual Tabs Bottle	29.88USD	bottle
Nitromist 400 mcg spray	28.5USD	g
Nitrostat 100 0.3 mg Sublingual Tabs Bottle	27.75USD	bottle
Nitrostat 100 0.6 mg Sublingual Tabs Bottle	24.99USD	bottle
Nitroglycerin 100 0.6 mg Sublingual Tabs Bottle	23.99USD	bottle
Nitroglycerin 100 0.3 mg Sublingual Tabs Bottle	22.99USD	bottle
Nitrostat 25 0.4 mg Sublingual Tabs Bottle	19.31USD	bottle
Nitroglycerin 25 0.4 mg Sublingual Tabs Bottle	9.5USD	bottle
Nitro-dur 0.6 mg/hr patch	4.19USD	patch
Nitro-dur 0.8 mg/hr patch	4.19USD	patch
Nitro-dur 0.3 mg/hr patch	3.87USD	patch
Nitro-dur 0.4 mg/hr patch	3.87USD	patch
Minitran 0.6 mg/hr patch	3.51USD	patch
Nitro-dur 0.2 mg/hr patch	3.45USD	patch
Nitro-dur 0.1 mg/hr patch	3.4USD	patch
Minitran 0.4 mg/hr patch	3.24USD	patch
Minitran 0.2 mg/hr patch	2.89USD	patch
Minitran 0.1 mg/hr patch	2.84USD	patch
Nitroglycerin CR 6.5 mg capsule	1.66USD	capsule
Nitroglycerin 0.1 mg/hr Patches	1.64USD	patch
Nitroglycerin CR 9 mg capsule	1.27USD	capsule
Nitro-Dur 0.8 0.8 mg/hr Patch	1.16USD	patch
Nitroglycerin er 9 mg capsule	1.0USD	capsule
Transderm-Nitro 0.4 0.4 mg/hr Patch	0.81USD	patch
Transderm-Nitro 0.6 0.6 mg/hr Patch	0.81USD	patch
Minitran 0.4 0.4 mg/hr Patch	0.74USD	patch
Minitran 0.6 0.6 mg/hr Patch	0.74USD	patch
Nitroglycerin er 6.5 mg capsule	0.72USD	capsule
Transderm-Nitro 0.2 0.2 mg/hr Patch	0.71USD	patch
Nitro-Dur 0.4 0.4 mg/hr Patch	0.67USD	patch
Nitro-Dur 0.6 0.6 mg/hr Patch	0.67USD	patch
Trinipatch 0.4 0.4 mg/hr Patch	0.67USD	patch
Trinipatch 0.6 0.6 mg/hr Patch	0.67USD	patch
Minitran 0.2 0.2 mg/hr Patch	0.66USD	patch
Nitrol 2 % Ointment	0.64USD	g
Nitro-Dur 0.2 0.2 mg/hr Patch	0.59USD	patch
Trinipatch 0.2 0.2 mg/hr Patch	0.59USD	patch
Nitroglycerin 9 mg capsule sa	0.53USD	capsule
Nitro-bid 2% ointment	0.48USD	g
Nitroglycerin CR 2.5 mg capsule	0.47USD	capsule
Nitro-time er 9 mg capsule	0.37USD	capsule
Nitroglycerin 0.4 mg tablet sl	0.36USD	tablet
Nitrostat 0.4 mg tablet sl	0.35USD	tablet
Nitro-time er 6.5 mg capsule	0.33USD	capsule
Nitro-time er 2.5 mg capsule	0.29USD	capsule
Nitroglycerin er 2.5 mg capsule	0.28USD	capsule
Nitroglycerin 6.5 mg capsule sa	0.22USD	capsule
Nitroquick 0.3 mg tablet sl	0.19USD	tablet
Nitroglycerin 2.5 mg capsule sa	0.18USD	capsule
Nitroglycerin 2% ointment	0.17USD	g
Nitrostat 0.6 mg tablet sl	0.16USD	tablet
Nitroglycerin 0.3 mg tablet sl	0.14USD	tablet
Nitroglycerin 0.6 mg tablet sl	0.14USD	tablet
Nitrostat 0.3 mg Sublingual Tablet	0.13USD	tablet
Nitrostat 0.6 mg Sublingual Tablet	0.13USD	tablet
Nitrolingual Pumpspray 0.4 mg/dose Metered Dose Spray	0.08USD	dose
Nitroquick 0.4 mg tablet sl	0.08USD	tablet
Nitroquick 0.6 mg tablet sl	0.08USD	tablet
Nitrostat 0.3 mg tablet sl	0.07USD	tablet
Mylan-Nitro 0.4 mg/dose Metered Dose Spray	0.04USD	dose
Ntg 25 mg/250 ml in d5w	0.04USD	ml
Rho-Nitro Pumpspray 0.4 mg/dose Metered Dose Spray	0.04USD	dose
Ntg 50 mg/500 ml in d5w	0.02USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5186938	No	1993-02-16	2010-02-16
US7872049	No	2011-01-18	2028-03-14
US6500456	No	2002-12-31	2018-09-16
US5869082	No	1999-02-09	2016-04-16
US9101592	No	2015-08-11	2032-03-11

Properties

State

Liquid

Experimental Properties

Property	Value	Source
melting point (°C)	13.5	http://www.inchem.org/documents/icsc/icsc/eics0186.htm
boiling point (°C)	160	http://www.inchem.org/documents/icsc/icsc/eics0186.htm
water solubility	poor solubility in water	http://www.inchem.org/documents/icsc/icsc/eics0186.htm
logP	1.62	http://www.inchem.org/documents/icsc/icsc/eics0186.htm
logS	-3	http://www.hmdb.ca/metabolites/HMDB0014865
pKa	-5.6	http://www.hmdb.ca/metabolites/HMDB0014865

Predicted Properties

Property	Value	Source
Water Solubility	0.204 mg/mL	ALOGPS
logP	1.25	ALOGPS
logP	0.26	Chemaxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-5.6	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	9	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	157.11 Å²	Chemaxon
Rotatable Bond Count	8	Chemaxon
Refractivity	37.59 m³·mol^-1	Chemaxon
Polarizability	15.68 Å³	Chemaxon
Number of Rings	0	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.7613
Blood Brain Barrier	+	0.9113
Caco-2 permeable	-	0.5775
P-glycoprotein substrate	Non-substrate	0.8322
P-glycoprotein inhibitor I	Non-inhibitor	0.671
P-glycoprotein inhibitor II	Non-inhibitor	0.9005
Renal organic cation transporter	Non-inhibitor	0.8325
CYP450 2C9 substrate	Non-substrate	0.8982
CYP450 2D6 substrate	Non-substrate	0.9022
CYP450 3A4 substrate	Non-substrate	0.5255
CYP450 1A2 substrate	Non-inhibitor	0.8022
CYP450 2C9 inhibitor	Non-inhibitor	0.7789
CYP450 2D6 inhibitor	Non-inhibitor	0.9106
CYP450 2C19 inhibitor	Non-inhibitor	0.72
CYP450 3A4 inhibitor	Non-inhibitor	0.9173
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8638
Ames test	AMES toxic	0.9107
Carcinogenicity	Carcinogens	0.6822
Biodegradation	Ready biodegradable	0.9479
Rat acute toxicity	2.9173 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.512
hERG inhibition (predictor II)	Non-inhibitor	0.9382

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (7.71 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Atrial natriuretic peptide receptor 1

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

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

Details1. Aldehyde dehydrogenase, mitochondrial

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

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]
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 September 30, 2023 15:27

Nitroglycerin

Identification

Structure for Nitroglycerin (DB00727)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

Enzymes

References