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Compound Detail

CHEMBL1963681

AVANAFIL
💊 Approved Drug
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💊 Approved Drug
COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C(=O)NCc2ncccn2)cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1963681
Name AVANAFIL
Phase Approved
Structure Type MOL
InChI Key WEAJZXNPAWBCOA-INIZCTEOSA-N
Therapeutic ✓ Yes

Known Names

Avanafil Avanafilo Spedra Stendra TA-1790
5
Targets
43
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

484.0
MW (Da)
2.43
ALogP
9
HBA
3
HBD
125.4
PSA (Ų)
0.42
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -afil
USAN Year 2000

Extended Properties

Molecular Formula C23H26ClN7O3
MW 483.96
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.29

Mechanism of Action

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

Indications

Erectile Dysfunction Erectile Dysfunction Kidney Diseases

ATC Classification

G04BE10
avanafil
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Activity Summary

IC50 42 meas. best 8.28
Ki 1 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 Ki 8.3 8.3 5.0 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL2304402
 IC50 8.28 8.28 5.2 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 8.15 7.5988 7.0 26
NCI-H1299
CHEMBL612255
 IC50 5.15 4.985 7100.0 2
NCI-H661
CHEMBL1075544
 IC50 5.09 4.6633 8200.0 3
A549
CHEMBL392
 IC50 4.91 4.77 12300.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
cGMP-specific 3',5'-cyclic phosphodiesterase Ki = 5.0 nM 8.3 Inhibition of PDE5 (unknown origin) 30245400
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 5.2 nM 8.28 Inhibition of dog lungs PDE5 using [3H]cGMP as substrate after 30 mins by scinti... 25455484
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 6.993 nM 8.15 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 8.557 nM 8.07 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 9.29 nM 8.03 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 10.77 nM 7.97 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 10.77 nM 7.97 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 10.77 nM 7.97 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 10.77 nM 7.97 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 10.77 nM 7.97 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 12.25 nM 7.91 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 12.53 nM 7.9 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 17.32 nM 7.76 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 20.86 nM 7.68 Caliper Mobility-Shift Assay: To a 96-well plate, 20 μL, of 10 μM FL-cGMP as the... -

Literature References

PubMed DOI Target Context # Activities
39149110 10.1039/d4md00364k A549 17
39149110 10.1039/d4md00364k NCI-H1299 14
39149110 10.1039/d4md00364k NCI-H661 13
25455484 10.1016/j.bmcl.2014.10.008 Unchecked 11
32663396 10.1021/acs.jmedchem.0c00853 cGMP-specific 3',5'-cyclic phosphodiesterase 10
39149110 10.1039/d4md00364k Unchecked 3
32631538 10.1016/j.bmcl.2020.127337 cGMP-specific 3',5'-cyclic phosphodiesterase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
25455484 10.1016/j.bmcl.2014.10.008 cGMP-specific 3',5'-cyclic phosphodiesterase 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
30245400 10.1016/j.ejmech.2018.09.028 cGMP-specific 3',5'-cyclic phosphodiesterase 1
30245400 10.1016/j.ejmech.2018.09.028 Unchecked 1
25455484 10.1016/j.bmcl.2014.10.008 Corpus cavernosum 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1

Data from ChEMBL 36 via Core Engine