Details of the Drug

General Information of Drug (ID: DM4YDAJ)

Drug Name

Sildenafil

Synonyms

sildenafil; 139755-83-2; VIAGRA; Sildenafil [INN:BAN]; UK-92480; UNII-3M7OB98Y7H; UK-92,480-10; C22H30N6O4S; HSDB 7305; CHEMBL192; UK 92480-10; CHEBI:9139; 3M7OB98Y7H; BNRNXUUZRGQAQC-UHFFFAOYSA-N; Sildenafil

Indication

Disease Entry	ICD 11	Status	REF
Erectile dysfunction	HA01.1	Approved	[1]
Coronavirus Disease 2019 (COVID-19)	1D6Y	Phase 3	[2]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

474.6

Topological Polar Surface Area (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 60 min [3]
Clearance: The total body clearance of drug is 41 L/h [3]
Elimination: After either oral or intravenous administration, sildenafil is excreted as metabolites predominantly in the feces (approximately 80% of the administered oral dose) and to a lesser extent in the urine (approximately 13% of the administered oral dose) [F3850, F3853, F3856, F3859, F3883, F3886, L5611, L5614] [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 - 5 hours [4]
Metabolism: The drug is metabolized via the CYP3A4 hepatic microsomal isoenzymes [5]
Vd: The volume of distribution (Vd) of drug is 105 L [3]

Chemical Identifiers

Formula: C22H30N6O4S
IUPAC Name: 5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
Canonical SMILES: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C
InChI: InChI=1S/C22H30N6O4S/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/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
InChIKey: BNRNXUUZRGQAQC-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 135398744
ChEBI ID: CHEBI:9139
CAS Number: 139755-83-2
DrugBank ID: DB00203
TTD ID: D05ULR
ACDINA ID: D00622

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
HUMAN phosphodiesterase type 5 (PDE5)	TTRYFSB	PDE5A_HUMAN	Inhibitor	[6], [7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 206401.
2	ClinicalTrials.gov (NCT04304313) A Pilot Study of Sildenafil in COVID-19. U.S. National Institutes of Health.
3	Electronic Medicines Compendium: Sildenafil 25mg, 50mg, 100mg film-coated tablets Monograph
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Richards DM, Brogden RN: Ceftazidime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Feb;29(2):105-61. doi: 10.2165/00003495-198529020-00002.
6	Nitric oxide inhibits the replication cycle of severe acute respiratory syndrome coronavirus. J Virol. 2005 Feb;79(3):1966-9. doi: 10.1128/JVI.79.3.1966-1969.2005.
7	Any possible role of phosphodiesterase type 5 inhibitors in the treatment of severe COVID19 infections A lesson from urology. Clin Immunol. 2020 May;214:108414.