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Compound Detail

CHEMBL1737

SILDENAFIL CITRATE
💊 Approved Drug
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💊 Approved Drug
CCCc1nn(C)c2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12.O=C(O)CC(O)(CC(=O)O)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1737
Name SILDENAFIL CITRATE
Phase Approved
Structure Type MOL
InChI Key DEIYFTQMQPDXOT-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL192
Active Moiety CHEMBL192

Known Names

Aphrodil Granpidam Liqrev Mysildecard Nipatra NSC-744009 NSC-758669 Patrex Revatio Sildenafil (as citrate) Sildenafil actavis Sildenafil citrate +6 more
3
Targets
6
Activities
2
Assay Types
17
PK Parameters
20
Publications
18
Known Names
20
Indications
1
Mechanisms

Molecular Properties

474.6
MW (Da)
1.61
ALogP
8
HBA
1
HBD
113.4
PSA (Ų)
0.55
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral
USAN Stem -afil
USAN Year 1997

Extended Properties

Molecular Formula C28H38N6O11S
MW 666.71
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.51

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Phosphodiesterase 5A inhibitor INHIBITOR cGMP-specific 3',5'-cyclic phosphodiesterase ✓ ✓

Indications

Connective Tissue Diseases Erectile Dysfunction Erectile Dysfunction Familial Primary Pulmonary Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Pulmonary Arterial Hypertension Fetal Growth Retardation Heart Failure Prostatic Neoplasms, Castration-Resistant Raynaud Disease Scleroderma, Diffuse Scleroderma, Limited Scleroderma, Systemic Severe Acute Respiratory Syndrome Brain Concussion Brain Injuries Brain Neoplasms Emphysema Glioblastoma

Activity Summary

IC50 5 meas. best 8.66
EC50 1 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 8.66 8.47 2.2 3
Sus scrofa
CHEMBL613488
 EC50 7.42 7.42 38.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.57 4.57 26800.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 41.0 % Homo sapiens
F 41.0 % Rattus norvegicus
KA 1.08 uM Homo sapiens
KA 31.3 uM Homo sapiens
KA 13.4 uM Homo sapiens
KA 15.2 uM Homo sapiens
KA 16.8 uM Homo sapiens
KA 6.54 uM Homo sapiens
KA 2.37 uM Homo sapiens
KA 72.9 uM Homo sapiens
KA 34.0 uM Homo sapiens
KA 73.0 uM Homo sapiens
KA 27.5 uM Mus musculus
KA 32.4 uM Homo sapiens
T1/2 4.0 hr Homo sapiens
Tmax 60.0 hr Homo sapiens
Vss 105.0 L Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 2.2 nM 8.66 50% inhibitory concentration against phosphodiesterase 5 (PDE5) from porcine pla... 10891111
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 3.5 nM 8.46 Inhibition of human PDE5 isolated from corpus cavernosum after 30 to 60 mins by ... 22100260
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 5.1 nM 8.29 Inhibition of PDE5A1 catalytic domain (535 to 860 residues) (unknown origin) exp... 28686445
Sus scrofa EC50 = 38.0 nM 7.42 Vasorelaxant effect was evaluated on isolated porcine coronary arteries precontr... 10891111
ATP-binding cassette sub-family C member 4 IC50 = 26800.0 nM 4.57 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
30888810 10.1021/acs.jmedchem.9b00224 Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30148362 10.1021/acs.jmedchem.8b01209 Rattus norvegicus 3
28686445 10.1021/acs.jmedchem.7b00523 Rattus norvegicus 3
31035240 10.1016/j.ejmech.2019.04.020 Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' 3
19635671 10.1016/j.bmc.2009.07.019 Rattus norvegicus 3
31035240 10.1016/j.ejmech.2019.04.020 cGMP-specific 3',5'-cyclic phosphodiesterase 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 9 1
22100260 10.1016/j.bmc.2011.10.022 cGMP-specific 3',5'-cyclic phosphodiesterase 1
19635671 10.1016/j.bmc.2009.07.019 Serum 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 14 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 13 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 12 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 6 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 5B, mitochondrial 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 4 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 3 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 2 1
19635671 10.1016/j.bmc.2009.07.019 Carbonic anhydrase 1 1

Data from ChEMBL 36 via Core Engine