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
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
SNIOPGDIGTZGOP-UHFFFAOYSA-N
InChIKey
1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
Cross-matching ID
PubChem CID
4510
ChEBI ID
CHEBI:28787
CAS Number
55-63-0
DrugBank ID
DB00727
INTEDE ID
DR2513

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
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [5]
Aldehyde dehydrogenase, mitochondrial (ALDH2) OTKJ9I3N ALDH2_HUMAN Gene/Protein Processing [6]
Beta-2-microglobulin (B2M) OTDWN6NX B2MG_HUMAN Gene/Protein Processing [7]
Calcitonin (CALCA) OTZ11LHB CALC_HUMAN Gene/Protein Processing [8]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [9]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Protein Interaction/Cellular Processes [10]
Complement C3 (C3) OTCH5GS0 CO3_HUMAN Gene/Protein Processing [11]
Endothelin-1 (EDN1) OTZCACEG EDN1_HUMAN Gene/Protein Processing [12]
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 (GNB3) OTA6HYBA GBB3_HUMAN Drug Response [13]
Guanylate cyclase soluble subunit beta-1 (GUCY1B1) OTSHPHVB GCYB1_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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 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.
6 Decrease in endogenous CGRP release in nitroglycerin tolerance: role of ALDH-2. Eur J Pharmacol. 2007 Sep 24;571(1):44-50.
7 [Evaluation of the renal function during hypotensive anesthesia induced by nitroglycerin, prostaglandin E1 or nitroglycerin+prostaglandin E1]. Masui. 1993 Jul;42(7):1009-12.
8 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.
9 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.
10 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.
11 Cardiopulmonary bypass exacerbates oxidative stress but does not increase proinflammatory cytokine release in patients with diabetes compared with patients without diabetes: regulatory effects of exogenous nitric oxide. J Thorac Cardiovasc Surg. 2000 Jul;120(1):1-11. doi: 10.1067/mtc.2000.106835.
12 Effects of nitroglycerin and dexamethasone on nitric oxide and endothelin derived from alveolar macrophages in patients with mild and middle asthma. Hunan Yi Ke Da Xue Xue Bao. 2000 Aug 28;25(4):363-6.
13 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.
14 Glyceryl trinitrate treatment up-regulates soluble guanylyl cyclase in rat dura mater. Neuroreport. 2001 Dec 21;12(18):3993-6. doi: 10.1097/00001756-200112210-00028.