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Accession NumberDB00727  (APRD00153)
TypeSmall Molecule
GroupsApproved, Investigational

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

1,2,3-PropanetrioltrinitrateNot AvailableNot Available
1,2,3-Propanetriyl nitrateNot AvailableNot Available
Glycerin trinitrateNot AvailableNot Available
Glycerol trinitrateNot AvailableNot Available
Glycerol, nitric acid triesterNot AvailableNot Available
Glyceroli trinitratis LatinINN
Glyceryl trinitrateNot AvailableNot Available
MinitranNot AvailableNot Available
NatisprayNot AvailableNot Available
NGNot AvailableNot Available
Nitro-durNot AvailableNot Available
NitroglicerinaNot AvailablePH: F.U. XII
NitroglycerinNot AvailableNot Available
NitroglycerineNot AvailableNot Available
NitroglycerolNot AvailableIS
NitrolingualNot AvailableNot Available
NitromedNot AvailableIS
NitromistNot AvailableNot Available
NitrostatNot AvailableNot Available
Propane-1,2,3-triyl trinitrateNot AvailableNot Available
RectogesicNot AvailableNot Available
Transderm nitroNot AvailableNot Available
TrinitroglycerinNot AvailableNot Available
TrinitroglycerolNot AvailableNot Available
SaltsNot Available
Brand names
DeponitUCB Pharma
Gen-NitroGenpharm ULC
Glytrin SpraySanofi-Aventis
MinitranMeda Pharma
Nitro-DurMerck Sharp & Dohme
Nitroderm TTSNovartis
NitrolingualNot Available
Nitrolingual Pump SprayArbor Pharmaceuticals
NitroMistNot Available
NitrostatNot Available
RectivNot Available
RhotrimineNot Available
StangylNot Available
SurmontilNot Available
TridilNot Available
TrinispraySanofi Aventis
Trinitrin Simplex LaleufSanofi
Trocer SRIncepta
VasolatorSanwa Kagaku
VerniesParke Davis
Brand mixtures
Brand NameIngredients
Alchemed NP-03aconite + apis mellifica + arnica montana + barberry root + calendula + cantharides + charcoal activated + echinacea angustifolia + hahnemann's causticum + hypericum perforatum + nitroglycerin + urtica urens
Alchemed NP-04aesculus hippocastanum + arnica montana + barium carbonate + belladonna + celandine + cinchona officinalis + nitroglycerin + oyster shells + sepia officinalis l + strophanthus hispidus
Alchemed NP-21belladonna + cantharides + german chamomile + nitroglycerin + phosphorus + sepia officinalis l + silver nitrate + valerian + zinc
Aribosan B31 - liqapis mellifica + barberry root + colchicine + convallaria majalis + nitroglycerin + poison oak + potassium iodide + quinine dihyrochloride
Cactus Compositum DPScactus grandiflorus + nitroglycerin + potassium carbonate + spigelia
CafinitrinaNitroglycerin and Caffeine
Cere Bosan B36 - liqbelladonna + hamamelis virginiana + nitroglycerin + saffron + trillium pendulum
Complex 12aesculus 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 15belladonna + cimicifuga racemosa + cinchona officinalis + glycyrrhiza glabra + nitroglycerin + oyster shells + platinum + pulsatilla + sanguinaria canadensis + sepia officinalis l + sulfur + tiger lily + vitex agnus castus
CRC-plexarnica 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-liqnitroglycerin + pulsatilla + sanguinaria canadensis + sepia officinalis l + vitex agnus castus
From time to timebelladonna + bryonia + charcoal activated + gelsemium sempervirens + lycopodium clavatum + melilot + nitroglycerin + silicon dioxide + sodium chloride + spigelia marylandica
Globuli no 51barium carbonate + cactus grandiflorus + gelsemium sempervirens + nitroglycerin
Homeo-form MI - liquidaluminum oxide + antimony trisulfide + cyclamen europaeum l. + lycopodium clavatum + melilot + nitroglycerin + silver nitrate
Homeo-form MI-tabaluminum oxide + antimony trisulfide + cyclamen europaeum l. + lycopodium clavatum + melilot + nitroglycerin + silver nitrate
Homeodel 24belladonna + charcoal activated + gelsemium sempervirens + iris versicolor + lycopodium + nitroglycerin + spigelia
Homeopathic Remedy THC no.4aconite + 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 DPSbarium chloride + gold + mistletoe + nitroglycerin
Ingr-bosan b34 - liqbelladonna + cimicifuga racemosa + gelsemium sempervirens + iris versicolor + nitroglycerin + spigelia anthelmia
Iper-bosan b44 - liqbaryta iodata + cactus grandiflorus + gelsemium sempervirens + nitroglycerin
L.122 - liq orlbryonia + cactus grandiflorus + nitroglycerin + potassium carbonate
L.15 DPSaconitinum + apocynum cannabinum + arnica montana + cactus grandiflorus + nitroglycerin
L.73 liqbelladonna + cocculus indicus + lead acetate + mugwort + nitroglycerin + periwinkle + pulsatilla + silver nitrate + valerian
L2apis mellifica + belladonna + juglans cinerea + nitroglycerin + phytolacca decandra + pulsatilla + spongia tosta + vitex agnus castus
Nova - 7041 - liqbelladonna + cantharides + german chamomile + nitroglycerin + phosphorus + sepia officinalis l + silver nitrate + valerian + zinc
Nova 7025 - liqaconite + apis mellifica + arnica montana + barberry root + calendula + cantharides + charcoal activated + echinacea angustifolia + hahnemann's causticum + hypericum perforatum + nitroglycerin + urtica urens
Nova 7028 - liqaesculus hippocastanum + arnica montana + barium carbonate + belladonna + calcium carbonate + celandine + cinchona officinalis + nitroglycerin + sepia officinalis l + strophanthus hispidus
Nova 7037 - liqbelladonna + calcium carbonate + cinchona officinalis + nitroglycerin + platinum + pulsatilla + sanguinaria canadensis + sulfur + tiger lily + tin
Pekana - complex nr. 47clematis erecta + cynara scolymus + dulcamara + euphrasia officinalis + ivy + nitroglycerin + ruta graveolens + tobacco
R 47 dpsasafetida + coffee + musk + nitroglycerin + pulsatilla
R-12 dpsarnica montana + barium chloride + calcium iodide + conium maculatum + lead acetate + nitroglycerin + phosphorus + potassium iodide
R12arnica montana + barium chloride + calcium iodide + conium maculatum + lead acetate + nitroglycerin + phosphorus + potassium iodide
R47asafetida + coffee + musk + nitroglycerin + pulsatilla
THC complex #15belladonna + cinchona officinalis + gelsemium sempervirens + nitroglycerin + sodium chloride + sulfur
THC complex #2aconite + 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 #37aconite + bellis perennis + caulophyllum thalictroides + cimicifuga racemosa + nitroglycerin + pulsatilla + sanguinaria canadensis + strontium carbonate
CAS number55-63-0
WeightAverage: 227.0865
Monoisotopic: 227.002578773
Chemical FormulaC3H5N3O9
2,3-bis(nitrooxy)propyl nitrate
Mass Specshow(7.71 KB)
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassOrganic Oxoanionic Compounds
SubclassOrganic Nitrates
Direct parentOrganic Nitrates
Alternative parentsNitrate Esters; Nitro Compounds; Polyamines
Substituentsorganic nitric acid or derivative; nitro compound; polyamine
Classification descriptionThis compound belongs to the organic nitrates. These are organic compounds containing the nitrate oxoanion, with the formula NO3-.
IndicationFor the prevention of angina
PharmacodynamicsNitroglycerin, 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 actionSimilar 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.
AbsorptionNot Available
Volume of distribution
  • 3 L/kg
Protein bindingNot Available

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

Route of eliminationNot Available
Half life3 minutes
  • 1 L/kg/min
ToxicityIncreased 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
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 substrate Non-inhibitor 0.7789
CYP450 2D6 substrate Non-inhibitor 0.9106
CYP450 2C19 substrate Non-inhibitor 0.72
CYP450 3A4 substrate 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
  • 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
Dosage forms
Aerosol, meteredSublingual
Solution / dropsOral
Spray, meteredSublingual
Unit descriptionCostUnit
Nitrolingual 0.4 mg/spray Solution 12 gm Bottle242.83USDbottle
Nitrolingual 0.4 mg/spray Solution 4.9 gm Bottle141.43USDbottle
Nitro-Dur 30 0.6 mg/hr Patches Box130.86USDbox
Nitro-Dur 30 0.8 mg/hr Patches Box130.86USDbox
Nitro-Dur 30 0.3 mg/hr Patches Box120.68USDbox
Nitro-Dur 30 0.4 mg/hr Patches Box117.1USDbox
Minitran 30 0.6 mg/hr Patches Box114.01USDbox
Nitro-Dur 30 0.1 mg/hr Patches Box106.09USDbox
Nitro-Dur 30 0.2 mg/hr Patches Box105.6USDbox
Minitran 30 0.4 mg/hr Patches Box105.18USDbox
Minitran 30 0.2 mg/hr Patches Box93.86USDbox
Minitran 30 0.1 mg/hr Patches Box92.36USDbox
Nitroglycerin 30 0.6 mg/hr Patches Box63.55USDbox
Nitroglycerin 5 mg/ml kit62.38USDkit
Nitroglycerin 30 0.4 mg/hr Patches Box57.62USDbox
Nitroglycerin 30 0.2 mg/hr Patches Box50.44USDbox
Nitrostat 100 0.4 mg Sublingual Tabs Bottle29.88USDbottle
Nitromist 400 mcg spray28.5USDg
Nitrostat 100 0.3 mg Sublingual Tabs Bottle27.75USDbottle
Nitrostat 100 0.6 mg Sublingual Tabs Bottle24.99USDbottle
Nitroglycerin 100 0.6 mg Sublingual Tabs Bottle23.99USDbottle
Nitroglycerin 100 0.3 mg Sublingual Tabs Bottle22.99USDbottle
Nitrostat 25 0.4 mg Sublingual Tabs Bottle19.31USDbottle
Nitroglycerin 25 0.4 mg Sublingual Tabs Bottle9.5USDbottle
Nitro-dur 0.6 mg/hr patch4.19USDpatch
Nitro-dur 0.8 mg/hr patch4.19USDpatch
Nitro-dur 0.3 mg/hr patch3.87USDpatch
Nitro-dur 0.4 mg/hr patch3.87USDpatch
Minitran 0.6 mg/hr patch3.51USDpatch
Nitro-dur 0.2 mg/hr patch3.45USDpatch
Nitro-dur 0.1 mg/hr patch3.4USDpatch
Minitran 0.4 mg/hr patch3.24USDpatch
Minitran 0.2 mg/hr patch2.89USDpatch
Minitran 0.1 mg/hr patch2.84USDpatch
Nitroglycerin CR 6.5 mg capsule1.66USDcapsule
Nitroglycerin 0.1 mg/hr Patches1.64USDpatch
Nitroglycerin CR 9 mg capsule1.27USDcapsule
Nitro-Dur 0.8 0.8 mg/hr Patch1.16USDpatch
Nitroglycerin er 9 mg capsule1.0USDcapsule
Transderm-Nitro 0.4 0.4 mg/hr Patch0.81USDpatch
Transderm-Nitro 0.6 0.6 mg/hr Patch0.81USDpatch
Minitran 0.4 0.4 mg/hr Patch0.74USDpatch
Minitran 0.6 0.6 mg/hr Patch0.74USDpatch
Nitroglycerin er 6.5 mg capsule0.72USDcapsule
Transderm-Nitro 0.2 0.2 mg/hr Patch0.71USDpatch
Nitro-Dur 0.4 0.4 mg/hr Patch0.67USDpatch
Nitro-Dur 0.6 0.6 mg/hr Patch0.67USDpatch
Trinipatch 0.4 0.4 mg/hr Patch0.67USDpatch
Trinipatch 0.6 0.6 mg/hr Patch0.67USDpatch
Minitran 0.2 0.2 mg/hr Patch0.66USDpatch
Nitrol 2 % Ointment0.64USDg
Nitro-Dur 0.2 0.2 mg/hr Patch0.59USDpatch
Trinipatch 0.2 0.2 mg/hr Patch0.59USDpatch
Nitroglycerin 9 mg capsule sa0.53USDcapsule
Nitro-bid 2% ointment0.48USDg
Nitroglycerin CR 2.5 mg capsule0.47USDcapsule
Nitro-time er 9 mg capsule0.37USDcapsule
Nitroglycerin 0.4 mg tablet sl0.36USDtablet
Nitrostat 0.4 mg tablet sl0.35USDtablet
Nitro-time er 6.5 mg capsule0.33USDcapsule
Nitro-time er 2.5 mg capsule0.29USDcapsule
Nitroglycerin er 2.5 mg capsule0.28USDcapsule
Nitroglycerin 6.5 mg capsule sa0.22USDcapsule
Nitroquick 0.3 mg tablet sl0.19USDtablet
Nitroglycerin 2.5 mg capsule sa0.18USDcapsule
Nitroglycerin 2% ointment0.17USDg
Nitrostat 0.6 mg tablet sl0.16USDtablet
Nitroglycerin 0.3 mg tablet sl0.14USDtablet
Nitroglycerin 0.6 mg tablet sl0.14USDtablet
Nitrostat 0.3 mg Sublingual Tablet0.13USDtablet
Nitrostat 0.6 mg Sublingual Tablet0.13USDtablet
Nitrolingual Pumpspray 0.4 mg/dose Metered Dose Spray0.08USDdose
Nitroquick 0.4 mg tablet sl0.08USDtablet
Nitroquick 0.6 mg tablet sl0.08USDtablet
Nitrostat 0.3 mg tablet sl0.07USDtablet
Mylan-Nitro 0.4 mg/dose Metered Dose Spray0.04USDdose
Ntg 25 mg/250 ml in d5w0.04USDml
Rho-Nitro Pumpspray 0.4 mg/dose Metered Dose Spray0.04USDdose
Ntg 50 mg/500 ml in d5w0.02USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
CountryPatent NumberApprovedExpires (estimated)
United States65004561998-09-162018-09-16
United States51869381993-02-162010-02-16
Experimental Properties
melting point13.5 °CPhysProp
boiling point250 °CPhysProp
water solubility1380 mg/L (at 20 °C)SEIDELL,A (1941)
logP1.62HANSCH,C ET AL. (1995)
logS-2.22ADME Research, USCD
Predicted Properties
Water Solubility0.204ALOGPS
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area165.15 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity40.6 m3·mol-1ChemAxon
Polarizability15.56 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
SpectraNot Available
Synthesis Reference

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

General ReferenceNot Available
External Links
KEGG DrugD00515
KEGG CompoundC07455
PubChem Compound4510
PubChem Substance46509120
Therapeutic Targets DatabaseDNC001024
Drug Product Database1926454
ATC CodesC01DA02
AHFS Codes
  • 24:12.08
  • 92:02.00*
PDB EntriesNot Available
FDA labelshow(801 KB)
MSDSNot Available
Drug Interactions
AlteplaseIV nitroglycerin may decrease the effect of alteplase.
AvanafilAdditive vasodilation. Concomitant therapy is contraindicated.
Azilsartan medoxomilPharmacodynamic synergist- increases effects.
DihydroergotaminePossible antagonism of action
ErgonovinePossible antagonism of action
ErgotaminePossible antagonism of action
MethylergometrinePossible antagonism of action
MethysergidePossible antagonism of action
SildenafilPossible significant hypotension with this combination
TadalafilThe vasodilatory effects of Nitroglycerin may be increased by Tadalafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
UdenafilThe vasodilatory effects of Nitroglycerin may be increased by Udenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
VardenafilThe vasodilatory effects of Nitroglycerin may be increased by Vardenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
Food Interactions
  • Avoid alcohol.
  • Dissolve under the tongue.
  • Take on empty stomach: 1 hour before or 2 hours after meals.


1. Atrial natriuretic peptide receptor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist


Name UniProt ID Details
Atrial natriuretic peptide receptor 1 P16066 Details


  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


1. Aldehyde dehydrogenase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate


Name UniProt ID Details
Aldehyde dehydrogenase, mitochondrial P05091 Details


  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

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Drug created on June 13, 2005 07:24 / Updated on January 07, 2014 11:25