Details of the Drug

General Information of Drug (ID: DMSWJ5X)

Drug Name
Sildenafil citrate
Synonyms
Sildenafil (citrate); Sildenafil citrate; Sildenafil citrate [USAN]; Sildenafil citrate salt; UK 92480; UK-92480-10; UNII-BW9B0ZE037; Sildenafilcitrate; Sildenafil; 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine; 139755-83-2; 3M7OB98Y7H; 5-(2-Ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one; BNRNXUUZRGQAQC-UHFFFAOYSA-N; C22H30N6O4S; CHEBI:9139; CHEMBL192; HSDB 7305; Sildenafil [INN:BAN]; UK-92,480-10; UK-92480; UNII-3M7OB98Y7H; 1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate (1:1); 171599-83-0; BW9B0ZE037; CHEBI:58987; Caverta; DSSTox_CID_26076; DSSTox_GSID_46076; DSSTox_RID_81321
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski):
3		 Molecular Weight 666.7
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 12
Hydrogen Bond Donor Count 5
Hydrogen Bond Acceptor Count 15
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [1]
Clearance
The drug present in the plasma can be removed from the body at the rate of 9 mL/min/kg [2]
Elimination
7.5% of drug is excreted from urine in the unchanged form [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.2 hours [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.51885 micromolar/kg/day [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.04% [2]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.36 L/kg [2]
Water Solubility
The ability of drug to dissolve in water is measured as 3.5 mg/mL [1]
Chemical Identifiers
Formula
C28H38N6O11S
IUPAC Name
5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one;2-hydroxypropane-1,2,3-tricarboxylic acid
Canonical SMILES
CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI
InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey
DEIYFTQMQPDXOT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
135413523
ChEBI ID
CHEMBL1737
CAS Number
171599-83-0
INTEDE ID
DR1481
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [4]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [7]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 BDDCS applied to over 900 drugs
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Erectile dysfunction drugs changed the protein expressions and activities of drug-metabolising enzymes in the liver of male rats. Oxid Med Cell Longev. 2016;2016:4970906.
6 Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil. Br J Clin Pharmacol. 2001 Mar;51(3):239-48.
7 The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90.
8 Drug Interactions Flockhart Table