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
Alveolar capillary dysplasia with misalignment of pulmonary veins N.A. Approved [1]
Erectile dysfunction HA01.1 Approved [2]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 3 [3]
Respiratory failure CB41 Investigative [1]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 474.6
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 60 min [4]
Clearance
The total body clearance of drug is 41 L/h [4]
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] [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 5 hours []
Metabolism
The drug is metabolized via the CYP3A4 hepatic microsomal isoenzymes [5]
Vd
The volume of distribution (Vd) of drug is 105 L [4]
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
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiotensin-converting enzyme (ACE) OTDF1964 ACE_HUMAN Drug Response [7]
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 (GNB3) OTA6HYBA GBB3_HUMAN Drug Response [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Sildenafil FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 206401.
3 ClinicalTrials.gov (NCT04304313) A Pilot Study of Sildenafil in COVID-19. U.S. National Institutes of Health.
4 Electronic Medicines Compendium: Sildenafil 25mg, 50mg, 100mg film-coated tablets Monograph
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 ACE gene I/D and NOS3 G894T polymorphisms and response to sildenafil in men with erectile dysfunction. Urology. 2003 Jul;62(1):152-7. doi: 10.1016/s0090-4295(03)00137-7.
8 Sildenafil response is influenced by the G protein beta 3 subunit GNB3 C825T polymorphism: a pilot study. J Urol. 2003 Mar;169(3):1048-51. doi: 10.1097/01.ju.0000058369.72348.ba.