Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0159)
Drug Name
Avanafil
Synonyms
Avanafil; DR5S136IVO; STENDRA; Spedra; TA 1790; TA-1790; (S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine; (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide; (S)-4-(3-Chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-N-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide; 330784-47-9; CHEBI:66876; UNII-DR5S136IVO
Indication Erectile dysfunction [ICD11: HA01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 483.9 Topological Polar Surface Area 125
Heavy Atom Count 34 Rotatable Bond Count 9
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
9869929
PubChem SID
14834924 ; 15132057 ; 17397370 ; 24160918 ; 45292193 ; 50284293 ; 57373612 ; 125299302 ; 126680642 ; 135264773 ; 136922931 ; 137082779 ; 137263447 ; 143177981 ; 160645587 ; 162255031 ; 164178031 ; 164194088 ; 164835991 ; 165222624 ; 165245576 ; 170502146 ; 174528935 ; 175267514 ; 175427065 ; 178104020 ; 185997047 ; 189480340 ; 198993783 ; 210275731 ; 210281392 ; 223635467 ; 223667975 ; 223700581 ; 223797060 ; 226490661 ; 241381281 ; 244115505 ; 249855750 ; 250163172 ; 250224291 ; 252066590 ; 252214915 ; 252436466
ChEBI ID
ChEBI:66876
CAS Number
330784-47-9
TTD Drug ID
D0Y5JC
Formula
C23H26ClN7O3
Canonical SMILES
COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCCC4CO)Cl
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
InChIKey
WEAJZXNPAWBCOA-INIZCTEOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Avanafil Metabolite M1 DM018052 N. A. Unclear - Unclear 1 [4] , [5]
Avanafil Metabolite M16 DM018055 N. A. Unclear - Unclear 1 [4] , [5]
Avanafil Metabolite M2 DM016711
145708474
Unclear - Unclear 1 [4] , [5]
Avanafil Metabolite M4-1 DM018053 N. A. Unclear - Unclear 1 [4] , [5]
Avanafil Metabolite M4-2 DM018054 N. A. Unclear - Unclear 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009880 Avanafil Avanafil Metabolite M1 Unclear - Unclear CYP3A4 ... [4], [5]
MR009881 Avanafil Avanafil Metabolite M2 Unclear - Unclear CYP3A4 ... [4], [5]
MR009882 Avanafil Avanafil Metabolite M4-1 Unclear - Unclear CYP3A4 ... [4], [5]
MR009883 Avanafil Avanafil Metabolite M4-2 Unclear - Unclear CYP3A4 ... [4], [5]
MR009884 Avanafil Avanafil Metabolite M16 Unclear - Unclear CYP3A4 ... [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Avanafil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA LABEL:Avanafil
3 An update on pharmacological treatment of erectile dysfunction with phosphodiesterase type 5 inhibitors. Expert Opin Pharmacother. 2013 Jul;14(10):1333-44.
4 LC-MS/MS determination of avanafil and its metabolites in rat plasma and brain: pharmacokinetic study after oral administration and transdermal film application
5 FDA:Avanafil

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