Identification

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

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

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
  • Natispray
  • NG
  • Nitroglicerina
  • Nitroglycerin
  • Nitroglycerine
  • Nitroglycerol
  • Nitromed
  • Propane-1,2,3-triyl trinitrate
  • Rectogesic
  • Trinitrine
  • Trinitroglycerin
  • Trinitroglycerol
External IDs
C01DA02 / DR 66
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
MinitranPatch0.6 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
Minitran - Patch Trd 72mg/26.6 Sq CmPatch72 mgTransdermalGraceway PharmaceuticalsNot applicableNot applicableCanada
Nitro-durPatch120 mg/1TransdermalMerck Sharp & Dohme Limited1995-04-04Not applicableUs
Nitro-durPatch160 mg/1TransdermalMerck Sharp & Dohme Limited1995-04-04Not applicableUs
Nitro-durPatch40 mg/1TransdermalIngenus Pharmaceuticals Llc2017-12-06Not applicableUs
Nitro-durPatch40 mg/1TransdermalMerck Sharp & Dohme Limited1995-04-04Not applicableUs
Nitro-durPatch80 mg/1TransdermalIngenus Pharmaceuticals Llc2017-12-06Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-nitroglycerinSpray, metered0.4 mgSublingualApotex Corporation2013-09-23Not applicableCanada
MinitranPatch2.5 mg/dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
MinitranPatch36 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
MinitranPatch10 mg/dTransdermalGraceway Pharmaceuticals2009-08-10Not applicableUs
MinitranPatch18 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
MinitranPatch5 mg/dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
MinitranPatch54 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
MinitranPatch15 mg/dTransdermalGraceway Pharmaceuticals2007-04-01Not applicableUs
MinitranPatch9 mg/1TransdermalValeant Pharmaceuticals North America2012-02-21Not applicableUs
Mylan-nitro Patch 0.2Patch, extended release0.2 mgTransdermalMylan Pharmaceuticals2013-06-04Not applicableCanada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nitro-TimeCapsule9 mg/1OralCarilion Materials Management2004-01-29Not applicableUs
Nitro-timeCapsule2.5 mg/1OralTime Cap Laboratories2014-06-19Not applicableUs
Nitro-TimeCapsule2.5 mg/1OralMajor2004-01-29Not applicableUs
Nitro-TimeCapsule6.5 mg/1OralCarilion Materials Management2004-01-29Not applicableUs00904 0644 60 nlmimage10 66353349
Nitro-TimeCapsule9 mg/1OralMajor2004-01-29Not applicableUs
Nitro-timeCapsule9 mg/1OralTime Cap Laboratories2014-06-19Not applicableUs
Nitro-TimeCapsule6.5 mg/1OralAvera Mc Kennan Hospital2015-04-24Not applicableUs
Nitro-TimeCapsule2.5 mg/1OralCarilion Materials Management2004-01-29Not applicableUs
Nitro-timeCapsule6.5 mg/1OralTime Cap Laboratories2014-06-19Not applicableUs
Nitro-TimeCapsule6.5 mg/1OralMajor2004-01-29Not applicableUs
International/Other Brands
Deponit (UCB Pharma) / Dermatrans (Bayer) / Gen-Nitro (Genpharm ULC) / Glytrin (Sanofi-Aventis) / Glytrin Spray (Sanofi-Aventis) / Minitran / Natispray (Teofarma) / Nitro-dur / Nitrocap (Orion) / Nitroderm TTS (Novartis) / Nitrolingual / Nitrolingual Pump Spray (Arbor Pharmaceuticals) / Nitromist / Nitrostat / Rectogesic (ProStrakan) / Stangyl / Transderm nitro / 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)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nitroglycerin In 5% Dextrose Inj.-100mcg/mlNitroglycerin (10 mg) + Glucose (5 g)SolutionIntravenousBaxter Laboratories1995-12-312016-02-26Canada
Nitroglycerin In 5% Dextrose Inj.-200mcg/mlNitroglycerin (20 mg) + Glucose (5 g)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada
Nitroglycerin In 5% Dextrose Inj.-400mcg/mlNitroglycerin (40 mg) + Glucose (5 g)SolutionIntravenousBaxter Laboratories1995-12-31Not applicableCanada
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

For the prevention of angina

Structured Indications
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.

TargetActionsOrganism
AAtrial natriuretic peptide receptor 1
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AlfuzosinAlfuzosin may increase the hypotensive activities of Nitroglycerin.Approved, Investigational
AlteplaseThe serum concentration of Alteplase can be decreased when it is combined with Nitroglycerin.Approved
AvanafilAvanafil may increase the vasodilatory activities of Nitroglycerin.Approved
BromocriptineThe bioavailability of Bromocriptine can be increased when combined with Nitroglycerin.Approved, Investigational
CabergolineThe bioavailability of Cabergoline can be increased when combined with Nitroglycerin.Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Nitroglycerin.Investigational
DihydroergocornineThe bioavailability of Dihydroergocornine can be increased when combined with Nitroglycerin.Approved
DihydroergocristineThe bioavailability of Dihydroergocristine can be increased when combined with Nitroglycerin.Approved, Experimental
DihydroergocryptineThe bioavailability of Dihydroergocryptine can be increased when combined with Nitroglycerin.Experimental
DihydroergotamineThe bioavailability of Dihydroergotamine can be increased when combined with Nitroglycerin.Approved
Ergoloid mesylateThe bioavailability of Ergoloid mesylate can be increased when combined with Nitroglycerin.Approved
ErgonovineThe bioavailability of Ergonovine can be increased when combined with Nitroglycerin.Approved
ErgotamineThe bioavailability of Ergotamine can be increased when combined with Nitroglycerin.Approved
EthanolEthanol may increase the vasodilatory activities of Nitroglycerin.Approved
HeparinNitroglycerin may decrease the anticoagulant activities of Heparin.Approved, Investigational
LisurideThe bioavailability of Lisuride can be increased when combined with Nitroglycerin.Approved, Investigational
Lysergic Acid DiethylamideThe bioavailability of Lysergic Acid Diethylamide can be increased when combined with Nitroglycerin.Illicit, Investigational, Withdrawn
MetergolineThe bioavailability of Metergoline can be increased when combined with Nitroglycerin.Experimental
MethylergometrineThe bioavailability of Methylergometrine can be increased when combined with Nitroglycerin.Approved
MethysergideThe bioavailability of Methysergide can be increased when combined with Nitroglycerin.Approved
MirodenafilMirodenafil may increase the vasodilatory activities of Nitroglycerin.Investigational
MolsidomineMolsidomine may increase the hypotensive activities of Nitroglycerin.Approved, Investigational
NicergolineThe bioavailability of Nicergoline can be increased when combined with Nitroglycerin.Approved, Investigational
PergolideThe bioavailability of Pergolide can be increased when combined with Nitroglycerin.Approved, Investigational, Vet Approved, Withdrawn
RiociguatNitroglycerin may increase the hypotensive activities of Riociguat.Approved
RosiglitazoneThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Rosiglitazone.Approved, Investigational
SildenafilSildenafil may increase the vasodilatory activities of Nitroglycerin.Approved, Investigational
TadalafilTadalafil may increase the vasodilatory activities of Nitroglycerin.Approved, Investigational
TergurideThe bioavailability of Terguride can be increased when combined with Nitroglycerin.Experimental
UdenafilUdenafil may increase the vasodilatory activities of Nitroglycerin.Approved, Investigational
VardenafilVardenafil may increase the vasodilatory activities of Nitroglycerin.Approved
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
Not Available
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
C05AE01 — Glyceryl trinitrateC01DA52 — Glyceryl trinitrate, combinationsC01DA02 — Glyceryl trinitrate
AHFS Codes
  • 24:12.08 — Nitrates and Nitrites
PDB Entries
4fr8
FDA label
Download (801 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareControlled Hypotension for Nasal Surgeries1
1Active Not RecruitingTreatmentRectal Carcinoma1
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentCoronary Artery Disease1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentRaynaud's Phenomenon2
1RecruitingNot AvailableHigh Blood Pressure (Hypertension)1
2CompletedTreatmentAngina, Prinzmetal's1
2CompletedTreatmentCerebral Oxygenation1
2CompletedTreatmentCoronary Artery Disease1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentRaynaud's Disease1
2CompletedTreatmentRaynaud's Phenomenon Secondary to Connective Tissue Disease1
2CompletedTreatmentSickle Cell Disorders / Thoracic Pain1
2CompletedTreatmentStroke, Acute1
2Not Yet RecruitingTreatmentCardiac Failure / Heart Failure, Unspecified / Reduced Ventricular Ejection Fraction1
2RecruitingTreatmentColic / Functional disorders of the biliary tract1
2RecruitingTreatmentErectile Dysfunction (ED)1
2RecruitingTreatmentIntracerebral Hemorrhage / Stroke, Ischemic1
2RecruitingTreatmentMenopausal Hot Flashes1
2RecruitingTreatmentShock, Hemorrhagic1
2Unknown StatusTreatmentLocally Advanced Non Small-Cell Lung Canger1
2Unknown StatusTreatmentLung Cancers1
2, 3CompletedTreatmentCardiac Catheterizations / Spasms1
2, 3CompletedTreatmentHeart Failure, Unspecified1
2, 3CompletedTreatmentInduction of Labor Affected Fetus / Newborn1
2, 3CompletedTreatmentPain After Stapled Haemorrhoidopexy1
2, 3RecruitingHealth Services ResearchAcute Heart Failure (AHF)1
2, 3TerminatedTreatmentExternal Cephalic Version1
3CompletedPreventionCardiac Catheterisation1
3CompletedTreatmentCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction (MI) / Myocardial Ischemia1
3CompletedTreatmentChronic Anal Fissures1
3CompletedTreatmentFissure in Ano / Pain1
3CompletedTreatmentHeart Failure, Unspecified / High Blood Pressure (Hypertension)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3CompletedTreatmentPain1
3CompletedTreatmentBone destruction1
3Not Yet RecruitingPreventionInjury of Radial Artery1
3RecruitingPreventionTotal Atherosclerotic Occlusion of Radial Artery / Transradial Catheterization, Radial Artery Occlusion1
3Unknown StatusTreatmentRaynaud's Disease / Raynaud's Disease Secondary to Other Autoimmune Disease / Raynaud's Disease Secondary to Scleroderma1
3Unknown StatusTreatmentStrokes1
4CompletedOtherCardiopulmonary Bypass / Coronary Artery Bypass Graft1
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
4CompletedTreatmentIUD Insertion1
4CompletedTreatmentNormal, or Near Normal Coronary Angiography / Slow Coronary Flow / Stable Angina (SA)1
4CompletedTreatmentPlacenta, Retained1
4Not Yet RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4RecruitingHealth Services ResearchCerebral Vasospasm1
4RecruitingPreventionAnginal Pain / Coronary Artery Disease / Radial Artery Spasm1
4RecruitingPreventionContrast Induced Nephropathy (CIN)1
4RecruitingSupportive CareCoronary Artery Disease1
4RecruitingTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD)1
4RecruitingTreatmentEsophageal Food Bolus Obstruction1
4RecruitingTreatmentPlacenta, Retained1
4RecruitingTreatmentProlonged Second Stage of Labor1
4Unknown StatusTreatmentMicrocirculation / Severe Sepsis1
4Unknown StatusTreatmentStable Angina (SA)1
4WithdrawnTreatmentAnal Fissures1
Not AvailableCompletedBasic ScienceFamilial Hemiplegic Migraine1
Not AvailableCompletedBasic ScienceGlaucoma1
Not AvailableCompletedBasic ScienceRetinal Hypoxia1
Not AvailableCompletedOtherVascular Reaction to Medications1
Not AvailableCompletedPreventionMicrocirculation / Neoplasms, Esophageal1
Not AvailableCompletedTreatmentAnaesthesia therapy / Arterial Hypotension1
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 AvailableNot Yet RecruitingBasic SciencePsychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableNot Yet RecruitingDiagnosticCoronary Artery Disease1
Not AvailableNot Yet RecruitingDiagnosticMigraine Disorders / Migraine Without Aura / Migraine, Classic1
Not AvailableRecruitingNot AvailableAortic Valve Stenosis / Hypertension,Essential / Impaired Renal Function / Secondary Hypertension1
Not AvailableRecruitingTreatmentAchilles Tendinopathy / Achilles Tendon Pain / Tendinopathy1
Not AvailableTerminatedTreatmentChronic Kidney Disease (CKD)1
Not AvailableUnknown StatusSupportive CareAcidosis, Respiratory / Haemorrhage1

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
FormRouteStrength
PowderSublingual400 ug/1
PatchTransdermal0.4 mg
PatchTransdermal0.6 mg
PatchTransdermal10 mg/d
PatchTransdermal15 mg/d
PatchTransdermal18 mg/1
PatchTransdermal2.5 mg/d
PatchTransdermal36 mg/1
PatchTransdermal5 mg/d
PatchTransdermal54 mg/1
PatchTransdermal9 mg/1
PatchTransdermal72 mg
Aerosol, meteredSublingual0.4 mg
OintmentTopical20 mg/g
PatchTransdermal120 mg/1
PatchTransdermal160 mg/1
PatchTransdermal20 mg/1
PatchTransdermal40 mg/1
PatchTransdermal60 mg/1
PatchTransdermal80 mg/1
Patch, extended releaseTransdermal0.2 mg
Patch, extended releaseTransdermal60 mg
Patch, extended releaseTransdermal0.6 mg
Patch, extended releaseTransdermal0.8 mg
CapsuleOral9 mg/1
Tablet, extended releaseBuccal1 mg
Film, extended releaseTransdermal20.8 mg/1
Film, extended releaseTransdermal37.4 mg/1
Injection, solutionIntravenous5 mg/mL
TabletSublingual.3 mg/1
TabletSublingual.6 mg/1
Tablet, orally disintegratingSublingual.3 mg/1
Tablet, orally disintegratingSublingual.4 mg/1
Tablet, orally disintegratingSublingual.6 mg/1
CapsuleOral2.5 mg/1
CapsuleOral6.5 mg/1
SolutionIntravenous
InjectionIntravenous10 mg/100mL
InjectionIntravenous20 mg/100mL
InjectionIntravenous40 mg/100mL
Injection, solutionIntravenous100 ug/mL
Injection, solutionIntravenous200 ug/mL
Injection, solutionIntravenous400 ug/mL
LiquidIntravenous5 mg
Spray, meteredSublingual400 ug/1
PatchTransdermal.1 mg/h
PatchTransdermal.2 mg/h
PatchTransdermal.4 mg/h
PatchTransdermal.6 mg/h
Patch, extended releaseTransdermal.2 mg/h
Patch, extended releaseTransdermal.4 mg/h
Patch, extended releaseTransdermal.6 mg/h
SolutionIntravenous10 mg
SolutionIntravenous50 mg
OintmentTopical2 %
SprayOral400 ug/1
Spray, meteredOral400 ug/1
Spray, meteredSublingual0.4 mg
Aerosol, meteredSublingual400 ug/1
Tablet, extended releaseOral2.6 mg
TabletOral.3 mg/1
TabletOral.4 mg/1
TabletSublingual.4 mg/1
TabletSublingual0.3 mg
TabletSublingual0.6 mg
OintmentRectal4 mg/g
Patch, extended releaseTransdermal0.4 mg
Patch, extended releaseTransdermal100 mg
PatchTransdermal0.2 mg
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
US7872049No2008-03-142028-03-14Us
US6500456No1998-09-162018-09-16Us
US5869082No1996-04-162016-04-16Us
US9101592No2012-03-112032-03-11Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)13.5 °CPhysProp
boiling point (°C)250 °CPhysProp
water solubility1380 mg/L (at 20 °C)SEIDELL,A (1941)
logP1.62HANSCH,C ET AL. (1995)
logS-2.22ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.204 mg/mLALOGPS
logP1.25ALOGPS
logP0.94ChemAxon
logS-3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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)
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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
Human
Pharmacological action
Yes
Actions
Agonist
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]
  2. Bauersachs J: Aminoethyl nitrate--the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. doi: 10.1111/j.1476-5381.2009.00414.x. [PubMed:19732062]

Enzymes

Kind
Protein
Organism
Human
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]

Drug created on June 13, 2005 07:24 / Updated on January 22, 2018 10:45