AVANAFIL

Search structure
Trade Names:
Synonyms:
Status: Approved (2011)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: G04BE10
UNII: DR5S136IVO

Structure
InChI Key WEAJZXNPAWBCOA-INIZCTEOSA-N
Smile COc1ccc(C/N=c2\[nH]c(N3CCC[C@H]3CO)ncc2C(=O)NCc2ncccn2)cc1Cl
InChI
InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H26ClN7O3
Molecular Weight 483.96
AlogP 1.85
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 128.62
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 34.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Phosphodiesterase 5A inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
- 5200-25000 - 5 66-84

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Erectile Dysfunction 4 D007172 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 12.1
Nervous system disorders Headache 10.5
General disorders and administration site conditions Flushing 10.1
Nervous system disorders Headache 8.1
Nervous system disorders Headache 6.9
Nervous system disorders Headache 5.6
General disorders and administration site conditions Flushing 5.1
Nervous system disorders Headache 5.1
Infections and infestations Nasopharyngitis 5.1
General disorders and administration site conditions Flushing 4.3
General disorders and administration site conditions Flushing 4.0
General disorders and administration site conditions Flushing 3.5
Infections and infestations Nasopharyngitis 3.4
Musculoskeletal and connective tissue disorders Back pain 3.2
General disorders and administration site conditions Flushing 3.2
Musculoskeletal and connective tissue disorders Back pain 3.0
Investigations Electrocardiogram abnormal 3.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 3.0
Infections and infestations Nasopharyngitis 3.0
Infections and infestations Upper respiratory tract infection 3.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.9
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 2.6
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.1
Musculoskeletal and connective tissue disorders Back pain 2.0
Cardiac disorders Dizziness 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.0
Infections and infestations Upper respiratory tract infection 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 1.8
Nervous system disorders Headache
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 1.1
Respiratory, thoracic and mediastinal disorders Nasal congestion
Musculoskeletal and connective tissue disorders Back pain
Cardiac disorders Dizziness 1.0
Investigations Electrocardiogram abnormal 1.0
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Nasal congestion
Respiratory, thoracic and mediastinal disorders Nasal congestion 1.0
Infections and infestations Nasopharyngitis 0.9

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
42.68
Injury, poisoning and procedural complications
8.25
Nervous system disorders
8.25
Reproductive system and breast disorders
6.19
Psychiatric disorders
5.67
Skin and subcutaneous tissue disorders
4.95
Vascular disorders
4.74
Gastrointestinal disorders
3.81
Cardiac disorders
2.68
Respiratory, thoracic and mediastinal disorders
2.47
Eye disorders
2.16
Investigations
2.06

Cross References

Resources Reference
CAS NUMBER 330784-47-9
ChEBI 66876
ChEMBL CHEMBL1963681
DrugBank DB06237
DrugCentral 4305
EPA CompTox DTXSID50186727
FDA SRS DR5S136IVO
Guide to Pharmacology 7448
PDB E6L
PubChem 9869929
SureChEMBL SCHEMBL118799
ZINC ZINC000011677857
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