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Compound Detail

CHEMBL1520

VARDENAFIL
💊 Approved Drug
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💊 Approved Drug
CCCc1nc(C)c2c(=O)nc(-c3cc(S(=O)(=O)N4CCN(CC)CC4)ccc3OCC)[nH]n12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1520
Name VARDENAFIL
Phase Approved
Structure Type MOL
InChI Key SECKRCOLJRRGGV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BAY-389456 BAY38-9456 Levitra Vardenafil Vivanza
14
Targets
38
Activities
2
Assay Types
9
PK Parameters
20
Publications
5
Known Names
8
Indications

Molecular Properties

488.6
MW (Da)
2.07
ALogP
8
HBA
1
HBD
112.9
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2003
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -afil
USAN Year 2001

Extended Properties

Molecular Formula C23H32N6O4S
MW 488.61
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.61

Indications

Erectile Dysfunction Hypertension, Pulmonary Cystic Fibrosis Prostatic Hyperplasia Raynaud Disease Tinnitus Urinary Bladder, Overactive Reperfusion Injury

ATC Classification

G04BE09
vardenafil
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Activity Summary

IC50 36 meas. best 10.54
Ki 2 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 10.54 9.4122 0.0 9
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 Ki 9.15 9.075 0.7 2
Phosphodiesterase 6
CHEMBL2097163
 IC50 9.0 8.3067 1.0 3
Unchecked
CHEMBL612545
 IC50 9.0 9.0 1.0 1
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A
CHEMBL2717
 IC50 6.89 6.755 130.0 2
Phosphodiesterase 1
CHEMBL2095150
 IC50 6.64 6.58 230.0 2
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
CHEMBL3535
 IC50 6.34 6.255 460.0 2
Phosphodiesterase 3
CHEMBL2094125
 IC50 6.24 5.96 580.0 2
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
 IC50 6.1 6.08 790.0 2
Phosphodiesterase 7
CHEMBL2111411
 IC50 5.72 5.72 1900.0 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
 IC50 5.51 5.51 3100.0 1
Phosphodiesterase 4
CHEMBL2093863
 IC50 5.42 5.385 3800.0 2
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
 IC50 4.8 4.8 15848.9 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.5 4.3 31622.8 2
A-type voltage-gated potassium channel KCND3
CHEMBL1964
 IC50 4.1 4.1 79432.8 1

Pharmacokinetic Data

Parameter Value Units Species
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
F 15.0 % Homo sapiens
Fu 0.05 - Homo sapiens
Fu 0.05 - Homo sapiens
MRT 3.8 hr Homo sapiens
T1/2 4.5 hr 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 = 0.029 nM 10.54 Inhibition of human platelets derived PDE5 using [3H]-cGMP as substrate incubate... 32870008
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.17 nM 9.77 Inhibition of PDE5A1 (unknwon origin) using [3H]cGMP as substrate after 30 mins ... 29293004
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.2 nM 9.7 Inhibition of human phosphodiesterase 5 15837326
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.5012 nM 9.3 Inhibition of PDE5 (unknown origin) 29620890
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.7 nM 9.15 Inhibition of Phosphodiesterase 5 from human platelets 12570368
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.7079 nM 9.15 Inhibition of PDE5 18656371
cGMP-specific 3',5'-cyclic phosphodiesterase Ki = 0.7 nM 9.15 Inhibition of PDE5 (unknown origin) 30245400
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.89 nM 9.05 Inhibition of recombinant human PDE5A 27606546
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.89 nM 9.05 Inhibition of PDE5A (unknown origin) 29549837
cGMP-specific 3',5'-cyclic phosphodiesterase Ki = 1.0 nM 9.0 Inhibition of human phosphodiesterase 5 15887951
Unchecked IC50 = 1.0 nM 9.0 Inhibition of PDE5 (unknown origin) 29574203
Phosphodiesterase 6 IC50 = 1.0 nM 9.0 Inhibition of human phosphodiesterase 6 15837326
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 1.0 nM 9.0 Inhibition of PDE5 (unknown origin) using FAM-cGMP as substrate after 60 mins by... 23313637
Phosphodiesterase 6 IC50 = 11.0 nM 7.96 Inhibition of human phosphodiesterase 6 15887951
Phosphodiesterase 6 IC50 = 11.0 nM 7.96 Inhibition of PDE6 (unknown origin) using FAM-cGMP as substrate after 60 mins by... 23313637
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A IC50 = 130.0 nM 6.89 Inhibition of human phosphodiesterase 11 15837326
Phosphodiesterase 1 IC50 = 230.0 nM 6.64 Inhibition of human phosphodiesterase 1 15837326
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A IC50 = 240.0 nM 6.62 Inhibition of PDE11 (unknown origin) using FAM-cGMP and FAM-cAMP as substrate af... 23313637
Phosphodiesterase 1 IC50 = 300.0 nM 6.52 Inhibition of PDE1 (unknown origin) using FAM-cGMP and FAM-cAMP as substrate aft... 23313637
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A IC50 = 460.0 nM 6.34 Inhibition of Phosphodiesterase 9 15837326

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
23313637 10.1016/j.ejmech.2012.12.009 Unchecked 10
20070106 10.1021/jm901371v Homo sapiens 8
29549837 10.1016/j.ejmech.2018.03.005 Unchecked 5
12570368 10.1021/jm0256068 Unchecked 4
18426954 10.1124/dmd.108.020479 ADMET 4
29549837 10.1016/j.ejmech.2018.03.005 Histone deacetylase 6 3
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated inwardly rectifying potassium channel KCNH2 3
25087753 10.1016/j.vascn.2014.07.002 Voltage-dependent L-type calcium channel subunit alpha-1C 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32870008 10.1021/acs.jmedchem.0c00960 ADMET 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
25087753 10.1016/j.vascn.2014.07.002 Sodium channel protein type 5 subunit alpha 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) 2
19445515 10.1021/jm900403j Homo sapiens 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine