Details of the Drug

General Information of Drug (ID: DMF72W3)

Drug Name
Glyceryl trinitrate
Synonyms
Gilustenon; Glycerol trinitrate; Glyceryl trinitrate; Lenitral; Minitran; Natispray; Nitro-Bid; Nitro-dur; Nitrocine; Nitroderm; Cordipatch; Corditrine; Epinitril; Nitroderm TTS; Nitroglicerina; Nitroglycerine; Nitroglycerol; Nitroglyn; Nitrolan; Nitrolingual; Nitronet; Nitrong; Nitroplast; Nitrorectal; Nitroretard; Nitrospan; Nitrostat; Perglottal; Perlinganit; Rectogesic; Susadrin; Sustonit; Transderm Nitro; Transderm-nitro; Tridil; Trinitrin; Trinitroglycerin; Trinitroglycerol; Trinitrolong; Trinitrosan; nitroglycerin; 55-63-0; Niong
Affected Organisms
Humans and other mammals
ATC Code
C01DA02: Glyceryl trinitrate
C01DA: Organic nitrates
C01D: VASODILATORS USED IN CARDIAC DISEASES
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
C01DA02: Glyceryl trinitrate
C01DA: Organic nitrates
C01D: VASODILATORS USED IN CARDIAC DISEASES
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
C01DA02: Glyceryl trinitrate
C01DA: Organic nitrates
C01D: VASODILATORS USED IN CARDIAC DISEASES
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
C01DA02: Glyceryl trinitrate
C01DA: Organic nitrates
C01D: VASODILATORS USED IN CARDIAC DISEASES
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
C05AE01: Glyceryl trinitrate
C05AE: Muscle relaxants
C05A: AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
C05: VASOPROTECTIVES
C: CARDIOVASCULAR SYSTEM
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 227.09
Logarithm of the Partition Coefficient (xlogp) 1.6
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Bioavailability
The bioavailability of drug is 40% []
Clearance
The clearance of drug is 1 L/min/kg [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.8 +/- 0.9 minutes (intravenously administered nitroglycerin) [2]
Metabolism
The drug is metabolized via the mitchochondrial aldehyde dehydrogenase [3]
Vd
The volume of distribution (Vd) of drug is 3 L/kg [1]
Chemical Identifiers
Formula
C3H5N3O9
IUPAC Name
1,3-dinitrooxypropan-2-yl nitrate
Canonical SMILES
C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
InChI
InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
InChIKey
SNIOPGDIGTZGOP-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4510
ChEBI ID
CHEMBL28787
CAS Number
55-63-0
UNII
G59M7S0WS3
DrugBank ID
DB00727
INTEDE ID
DR2513
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Microsomal glutathione S-transferase 1 (MGST1)
Main DME 		DEAPJSO MGST1_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldehyde dehydrogenase, mitochondrial (ALDH2) OTKJ9I3N ALDH2_HUMAN Gene/Protein Processing [5]
Calcitonin (CALCA) OTZ11LHB CALC_HUMAN Gene/Protein Processing [6]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Protein Interaction/Cellular Processes [7]
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 (GNB3) OTA6HYBA GBB3_HUMAN Drug Response [8]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [9]
Matrilysin (MMP7) OTVT3SEJ MMP7_HUMAN Gene/Protein Processing [10]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [11]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [12]
Vasodilator-stimulated phosphoprotein OTFC3010 VASP_HUMAN Post-Translational Modifications [13]
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References

1 Nitroglycerin in Dextrose FDA label
2 Nitroglycerin pharmacokinetics after intravenous infusion in normal subjects. J Pharm Sci. 1981 Sep;70(9):1054-8.
3 Tomlinson ES, Maggs JL, Park BK, Back DJ: Dexamethasone metabolism in vitro: species differences. J Steroid Biochem Mol Biol. 1997 Jul;62(4):345-52. doi: 10.1016/s0960-0760(97)00038-1.
4 Microsomal glutathione transferase 1: mechanism and functional roles. Drug Metab Rev. 2011 May;43(2):300-6.
5 Decrease in endogenous CGRP release in nitroglycerin tolerance: role of ALDH-2. Eur J Pharmacol. 2007 Sep 24;571(1):44-50.
6 NO-induced migraine attack: strong increase in plasma calcitonin gene-related peptide (CGRP) concentration and negative correlation with platelet serotonin release. Pain. 2003 Dec;106(3):461-470. doi: 10.1016/j.pain.2003.09.008.
7 Nitric oxide-induced down-regulation of beta-catenin in colon cancer cells by a proteasome-independent specific pathway. Gastroenterology. 2006 Oct;131(4):1142-52. doi: 10.1053/j.gastro.2006.07.017. Epub 2006 Jul 24.
8 Venous response to nitroglycerin is enhanced in young, healthy carriers of the 825T allele of the G protein beta3 subunit gene (GNB3). Clin Pharmacol Ther. 2003 Nov;74(5):499-504. doi: 10.1016/S0009-9236(03)00230-3.
9 Nitric oxide production is a proximal signaling event controlling exercise-induced mRNA expression in human skeletal muscle. FASEB J. 2007 Sep;21(11):2683-94. doi: 10.1096/fj.06-7477com. Epub 2007 Apr 30.
10 Nitroglycerin upregulates matrix metalloproteinase expression by human macrophages. J Am Coll Cardiol. 2002 Jun 19;39(12):1943-50. doi: 10.1016/s0735-1097(02)01907-1.
11 Glyceryl trinitrate inhibits hypoxia/reoxygenation-induced apoptosis in the syncytiotrophoblast of the human placenta: therapeutic implications for preeclampsia. Am J Pathol. 2007 Mar;170(3):909-20. doi: 10.2353/ajpath.2007.060665.
12 Comparison of atrial natriuretic peptide versus nitroglycerin for reducing blood pressure in acute myocardial infarction. Am J Cardiol. 1998 Mar 15;81(6):781-4. doi: 10.1016/s0002-9149(97)01033-3.
13 Inhibitory mechanisms of resveratrol in platelet activation: pivotal roles of p38 MAPK and NO/cyclic GMP. Br J Haematol. 2007 Nov;139(3):475-85. doi: 10.1111/j.1365-2141.2007.06788.x. Epub 2007 Sep 14.