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Identification
Name Nitroglycerin
Accession Number DB00727 (APRD00153)
Type small molecule
Groups approved
Description

A volatile vasodilator which relieves angina pectoris by stimulating guanylate cyclase and lowering cytosolic calcium. [PubChem]

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Glyceryl trinitrate
  • NG
  • nitroglycerin ointment
  • Nitroglycerine
  • NTG
  • TNG
  • Trinitroglycerin
Brand names
  • Cellegesic
  • Minitran
  • Natispray
  • Nitro-Dur
  • Nitrocap
  • Nitrolingual Pump Spray
  • Nitronet
  • Nitrong parenteral
  • Nitrospan
  • Nitrostat
  • Rectogesic
  • Transderm Nitro
  • Tridil
Brand name mixtures
  • Alchemed NP-03 (aconite + apis mellifica + arnica montana + barberry root + calendula + cantharides + charcoal activated + echinacea angustifolia + hahnemann's causticum + hypericum perforatum + nitroglycerin + urtica urens)
  • Alchemed NP-04 (aesculus hippocastanum + arnica montana + barium carbonate + belladonna + celandine + cinchona officinalis + nitroglycerin + oyster shells + sepia officinalis l + strophanthus hispidus)
  • Alchemed NP-21 (belladonna + cantharides + german chamomile + nitroglycerin + phosphorus + sepia officinalis l + silver nitrate + valerian + zinc)
  • Aribosan B31 - liq (apis mellifica + barberry root + colchicine + convallaria majalis + nitroglycerin + poison oak + potassium iodide + quinine dihyrochloride)
  • Cactus Compositum DPS (cactus grandiflorus + nitroglycerin + potassium carbonate + spigelia)
  • Cere Bosan B36 - liq (belladonna + hamamelis virginiana + nitroglycerin + saffron + trillium pendulum)
  • Complex 12 (aesculus hippocastanum + apis mellifica + arnica montana + barium carbonate + barium chloride + belladonna + calcium fluoride + celandine + charcoal activated + cinchona officinalis + collinsonia canadensis + conium maculatum + echinacea angustifolia + hamamelis virginiana + lycopodium clavatum + nitroglycerin + phosphorus + ruta graveolens + sepia officinalis l + sodium chloride + strophanthus hispidus + sulfur + tobacco)
  • Complex 15 (belladonna + cimicifuga racemosa + cinchona officinalis + glycyrrhiza glabra + nitroglycerin + oyster shells + platinum + pulsatilla + sanguinaria canadensis + sepia officinalis l + sulfur + tiger lily + vitex agnus castus)
  • CRC-plex (arnica montana + barium chloride + calcium lactate + charcoal activated + cholesterol + convallaria majalis + epinephrine + iodine + magnesium carbonate + nitroglycerin + phosphorus + picric acid + potassium iodide + strophanthus hispidus)
  • Ero-bosan B20-liq (nitroglycerin + pulsatilla + sanguinaria canadensis + sepia officinalis l + vitex agnus castus)
  • From time to time (belladonna + bryonia + charcoal activated + gelsemium sempervirens + lycopodium clavatum + melilot + nitroglycerin + silicon dioxide + sodium chloride + spigelia marylandica)
  • Globuli no 51 (barium carbonate + cactus grandiflorus + gelsemium sempervirens + nitroglycerin)
  • Homeo-form MI - liquid (aluminum oxide + antimony trisulfide + cyclamen europaeum l. + lycopodium clavatum + melilot + nitroglycerin + silver nitrate)
  • Homeo-form MI-tab (aluminum oxide + antimony trisulfide + cyclamen europaeum l. + lycopodium clavatum + melilot + nitroglycerin + silver nitrate)
  • Homeodel 24 (belladonna + charcoal activated + gelsemium sempervirens + iris versicolor + lycopodium + nitroglycerin + spigelia)
  • Homeopathic Remedy THC no.4 (aconite + arnica montana + belladonna + bryonia + cocculus indicus + gelsemium sempervirens + iris versicolor + lycopodium clavatum + nitroglycerin + potassium dichromate + pulsatilla + sanguinaria canadensis + silicon dioxide + silver nitrate + sodium chloride + spigelia marylandica + thuja occidentalis)
  • HPB Complex DPS (barium chloride + gold + mistletoe + nitroglycerin)
  • Ingr-bosan b34 - liq (belladonna + cimicifuga racemosa + gelsemium sempervirens + iris versicolor + nitroglycerin + spigelia anthelmia)
  • Iper-bosan b44 - liq (baryta iodata + cactus grandiflorus + gelsemium sempervirens + nitroglycerin)
  • L.122 - liq orl (bryonia + cactus grandiflorus + nitroglycerin + potassium carbonate)
  • L.15 DPS (aconitinum + apocynum cannabinum + arnica montana + cactus grandiflorus + nitroglycerin)
  • L.73 liq (belladonna + cocculus indicus + lead acetate + mugwort + nitroglycerin + periwinkle + pulsatilla + silver nitrate + valerian)
  • L2 (apis mellifica + belladonna + juglans cinerea + nitroglycerin + phytolacca decandra + pulsatilla + spongia tosta + vitex agnus castus)
  • Nova - 7041 - liq (belladonna + cantharides + german chamomile + nitroglycerin + phosphorus + sepia officinalis l + silver nitrate + valerian + zinc)
  • Nova 7025 - liq (aconite + apis mellifica + arnica montana + barberry root + calendula + cantharides + charcoal activated + echinacea angustifolia + hahnemann's causticum + hypericum perforatum + nitroglycerin + urtica urens)
  • Nova 7028 - liq (aesculus hippocastanum + arnica montana + barium carbonate + belladonna + calcium carbonate + celandine + cinchona officinalis + nitroglycerin + sepia officinalis l + strophanthus hispidus)
  • Nova 7037 - liq (belladonna + calcium carbonate + cinchona officinalis + nitroglycerin + platinum + pulsatilla + sanguinaria canadensis + sulfur + tiger lily + tin)
  • Pekana - complex nr. 47 (clematis erecta + cynara scolymus + dulcamara + euphrasia officinalis + ivy + nitroglycerin + ruta graveolens + tobacco)
  • R 47 dps (asafetida + coffee + musk + nitroglycerin + pulsatilla)
  • R-12 dps (arnica montana + barium chloride + calcium iodide + conium maculatum + lead acetate + nitroglycerin + phosphorus + potassium iodide)
  • R12 (arnica montana + barium chloride + calcium iodide + conium maculatum + lead acetate + nitroglycerin + phosphorus + potassium iodide)
  • R47 (asafetida + coffee + musk + nitroglycerin + pulsatilla)
  • THC complex #15 (belladonna + cinchona officinalis + gelsemium sempervirens + nitroglycerin + sodium chloride + sulfur)
  • THC complex #2 (aconite + apis mellifica + arnica montana + belladonna + bryonia + cocculus indicus + ferrum phosphoricum + gelsemium sempervirens + hydrastis canadensis + iris versicolor + lycopodium clavatum + magnesium phosphate dibasic + nitroglycerin + phosphorus + potassium dichromate + potassium phosphate dibasic + pulsatilla + sanguinaria canadensis + silicon dioxide + silver nitrate + sodium chloride + spigelia marylandica + thuja occidentalis)
  • THC complex #37 (aconite + bellis perennis + caulophyllum thalictroides + cimicifuga racemosa + nitroglycerin + pulsatilla + sanguinaria canadensis + strontium carbonate)
Categories
  • Vasodilator Agents
  • Tocolytic Agents
  • Nitrates and Nitrites
  • Explosive Agents
CAS number 55-63-0
Weight Average: 227.0865
Monoisotopic: 227.002578773
Chemical Formula C3H5N3O9
InChI Key InChIKey=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
Plain Text
IUPAC Name
2,3-bis(nitrooxy)propyl nitrate
SMILES
[O-][N+](=O)OCC(CO[N+]([O-])=O)O[N+]([O-])=O
Plain Text
Mass Spec show (7.7 KB)
Taxonomy
Kingdom Organic
Classes
  • Glycerol and Derivatives
Substructures
  • Glycerol and Derivatives
  • Oxoazaniums
  • Esters
  • Nitrates
Pharmacology
Indication For the prevention of angina
Pharmacodynamics Nitroglycerin, an organic nitrate, is available in many forms as a vasodilator. Nitroglycerin is used in the treatement of angina pectoris and perioperative hypertension, to produce controlled hypotension during surgical procedures, to treat hypertensive emergencies, and to treat congestive heart failure associated with myocardial infarction.
Mechanism of action Similar to other nitrites and organic nitrates, nitroglycerin is converted to nitric oxide (NO), an active intermediate compound which activates the enzyme guanylate cyclase. This stimulates the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP) which then activates a series of protein kinase-dependent phosphorylations in the smooth muscle cells, eventually resulting in the dephosphorylation of the myosin light chain of the smooth muscle fiber. The subsequent release of calcium ions results in the relaxation of the smooth muscle cells and vasodilation.
Absorption Not Available
Volume of distribution
  • 3 L/kg
Protein binding Not Available
Metabolism

Hepatic, cytochrome P450 (P450) is a key enzyme of organic nitrate biotransformation

Route of elimination Not Available
Half life 3 minutes
Clearance
  • 1 L/kg/min
Toxicity Increased intracranial pressure, with any or all of persistent throbbing headache, confusion, and moderate fever; Vertigo; Palpitations; Visual disturbances; Nausea and vomiting (possibly with colic and even bloody diarrhea); Syncope (especially in the upright posture); Air hunger and dyspnea, later followed by reduced ventilatory effort; Diaphoresis, with the skin either flushed or cold and clammy; Heart block and bradycardia; Paralysis; Coma; Seizures; Death.
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Dosage forms
Form Route Strength
Aerosol, metered Sublingual
Disc Transdermal
Liquid Intravenous
Liquid Oral
Ointment Topical
Patch Transdermal
Solution Intravenous
Solution / drops Oral
Spray, metered Sublingual
Tablet Oral
Tablet Sublingual
Prices
Unit description Cost Unit
Nitrolingual 0.4 mg/spray Solution 12 gm Bottle 242.83 USD bottle
Nitrolingual 0.4 mg/spray Solution 4.9 gm Bottle 141.43 USD bottle
Nitro-Dur 30 0.6 mg/hr Patches Box 130.86 USD box
Nitro-Dur 30 0.8 mg/hr Patches Box 130.86 USD box
Nitro-Dur 30 0.3 mg/hr Patches Box 120.68 USD box
Nitro-Dur 30 0.4 mg/hr Patches Box 117.1 USD box
Minitran 30 0.6 mg/hr Patches Box 114.01 USD box
Nitro-Dur 30 0.1 mg/hr Patches Box 106.09 USD box
Nitro-Dur 30 0.2 mg/hr Patches Box 105.6 USD box
Minitran 30 0.4 mg/hr Patches Box 105.18 USD box
Minitran 30 0.2 mg/hr Patches Box 93.86 USD box
Minitran 30 0.1 mg/hr Patches Box 92.36 USD box
Nitroglycerin 30 0.6 mg/hr Patches Box 63.55 USD box
Nitroglycerin 5 mg/ml kit 62.38 USD kit
Nitroglycerin 30 0.4 mg/hr Patches Box 57.62 USD box
Nitroglycerin 30 0.2 mg/hr Patches Box 50.44 USD box
Nitrostat 100 0.4 mg Sublingual Tabs Bottle 29.88 USD bottle
Nitromist 400 mcg spray 28.5 USD g
Nitrostat 100 0.3 mg Sublingual Tabs Bottle 27.75 USD bottle
Nitrostat 100 0.6 mg Sublingual Tabs Bottle 24.99 USD bottle
Nitroglycerin 100 0.6 mg Sublingual Tabs Bottle 23.99 USD bottle
Nitroglycerin 100 0.3 mg Sublingual Tabs Bottle 22.99 USD bottle
Nitrostat 25 0.4 mg Sublingual Tabs Bottle 19.31 USD bottle
Nitroglycerin 25 0.4 mg Sublingual Tabs Bottle 9.5 USD bottle
Nitro-dur 0.6 mg/hr patch 4.19 USD patch
Nitro-dur 0.8 mg/hr patch 4.19 USD patch
Nitro-dur 0.3 mg/hr patch 3.87 USD patch
Nitro-dur 0.4 mg/hr patch 3.87 USD patch
Minitran 0.6 mg/hr patch 3.51 USD patch
Nitro-dur 0.2 mg/hr patch 3.45 USD patch
Nitro-dur 0.1 mg/hr patch 3.4 USD patch
Minitran 0.4 mg/hr patch 3.24 USD patch
Minitran 0.2 mg/hr patch 2.89 USD patch
Minitran 0.1 mg/hr patch 2.84 USD patch
Nitroglycerin CR 6.5 mg capsule 1.66 USD capsule
Nitroglycerin 0.1 mg/hr Patches 1.64 USD patch
Nitroglycerin CR 9 mg capsule 1.27 USD capsule
Nitro-Dur 0.8 0.8 mg/hr Patch 1.16 USD patch
Nitroglycerin er 9 mg capsule 1.0 USD capsule
Transderm-Nitro 0.4 0.4 mg/hr Patch 0.81 USD patch
Transderm-Nitro 0.6 0.6 mg/hr Patch 0.81 USD patch
Minitran 0.4 0.4 mg/hr Patch 0.74 USD patch
Minitran 0.6 0.6 mg/hr Patch 0.74 USD patch
Nitroglycerin er 6.5 mg capsule 0.72 USD capsule
Transderm-Nitro 0.2 0.2 mg/hr Patch 0.71 USD patch
Nitro-Dur 0.4 0.4 mg/hr Patch 0.67 USD patch
Nitro-Dur 0.6 0.6 mg/hr Patch 0.67 USD patch
Trinipatch 0.4 0.4 mg/hr Patch 0.67 USD patch
Trinipatch 0.6 0.6 mg/hr Patch 0.67 USD patch
Minitran 0.2 0.2 mg/hr Patch 0.66 USD patch
Nitrol 2 % Ointment 0.64 USD g
Nitro-Dur 0.2 0.2 mg/hr Patch 0.59 USD patch
Trinipatch 0.2 0.2 mg/hr Patch 0.59 USD patch
Nitroglycerin 9 mg capsule sa 0.53 USD capsule
Nitro-bid 2% ointment 0.48 USD g
Nitroglycerin CR 2.5 mg capsule 0.47 USD capsule
Nitro-time er 9 mg capsule 0.37 USD capsule
Nitroglycerin 0.4 mg tablet sl 0.36 USD tablet
Nitrostat 0.4 mg tablet sl 0.35 USD tablet
Nitro-time er 6.5 mg capsule 0.33 USD capsule
Nitro-time er 2.5 mg capsule 0.29 USD capsule
Nitroglycerin er 2.5 mg capsule 0.28 USD capsule
Nitroglycerin 6.5 mg capsule sa 0.22 USD capsule
Nitroquick 0.3 mg tablet sl 0.19 USD tablet
Nitroglycerin 2.5 mg capsule sa 0.18 USD capsule
Nitroglycerin 2% ointment 0.17 USD g
Nitrostat 0.6 mg tablet sl 0.16 USD tablet
Nitroglycerin 0.3 mg tablet sl 0.14 USD tablet
Nitroglycerin 0.6 mg tablet sl 0.14 USD tablet
Nitrostat 0.3 mg Sublingual Tablet 0.13 USD tablet
Nitrostat 0.6 mg Sublingual Tablet 0.13 USD tablet
Nitrolingual Pumpspray 0.4 mg/dose Metered Dose Spray 0.08 USD dose
Nitroquick 0.4 mg tablet sl 0.08 USD tablet
Nitroquick 0.6 mg tablet sl 0.08 USD tablet
Nitrostat 0.3 mg tablet sl 0.07 USD tablet
Mylan-Nitro 0.4 mg/dose Metered Dose Spray 0.04 USD dose
Ntg 25 mg/250 ml in d5w 0.04 USD ml
Rho-Nitro Pumpspray 0.4 mg/dose Metered Dose Spray 0.04 USD dose
Ntg 50 mg/500 ml in d5w 0.02 USD ml
Patents
Country Patent Number Approved Expires
United States 6500456 1998-09-16 2018-09-16
United States 5186938 1993-02-16 2010-02-16
Properties
State liquid
Melting point 13.5oC
Experimental Properties
Property Value Source
water solubility Slightly soluble PhysProp
logP 1 PhysProp
logS -2.22 [ADME Research, USCD] PhysProp
Predicted Properties
Property Value Source
water solubility 2.04e-01 g/l ALOGPS
logP 1.25 ALOGPS
logP 0.94 ChemAxon Molconvert
logS -3.05 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 9 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 165.15 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 40.60 ChemAxon Molconvert
polarizability 15.56 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00515 Link_out
KEGG Compound C07455 Link_out
PubChem Compound 4510 Link_out
PubChem Substance 46509120 Link_out
ChemSpider 4354 Link_out
ChEBI 28787 Link_out
ChEMBL 28787 Link_out
Therapeutic Targets Database DNC001024 Link_out
PharmGKB PA450644 Link_out
Drug Product Database 1926454 Link_out
RxList http://www.rxlist.com/cgi/generic/ntg.htm Link_out
Drugs.com http://www.drugs.com/cdi/nitroglycerin.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nit1296.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Nitroglycerin Link_out
ATC Codes
  • C01DA02
AHFS Codes
  • 24:12.08
  • 92:02.00*
PDB Entries Not Available
FDA label show (800.7 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Dissolve under the tongue.
  • Take on empty stomach: 1 hour before or 2 hours after meals.
Targets

1. Atrial natriuretic peptide receptor A

Pharmacological action: yes
Actions: agonist

Receptor for atrial natriuretic peptide. Has guanylate cyclase activity on binding of ANF

Organism class: human
UniProt ID: P16066 Link_out
Gene: NPR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Bauersachs J: Aminoethyl nitrate—the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. Pubmed

Enzymes

1. Aldehyde dehydrogenase, mitochondrial

Actions: substrate
UniProt ID: P05091 Link_out
Gene: ALDH2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2010 Jun 11. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:42

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.