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

General Information of Drug (ID: DR0898)
Drug Name
Ivacaftor
Synonyms
Ivacaftor; Ivacaftor (VX-770); Ivacaftor [USAN:INN]; Kalydeco; Kalydeco (TN); Tube715; VX 770; VX-770; ivacaftorum; 1Y740ILL1Z; 3-Quinolinecarboxamide, N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-1,4-dihydro-4-oxo-; 3-Quinolinecarboxamide, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-; 873054-44-5; CHEBI:66901; N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide; N-[2,4-Bis(tert-butyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-3-quinolinecarboxamide; UNII-1Y740ILL1Z; VX770
Indication Cystic fibrosis [ICD11: CA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 392.5 Topological Polar Surface Area 78.4
Heavy Atom Count 29 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
16220172
PubChem SID
24902571 ; 28764112 ; 40723266 ; 104253162 ; 118855344 ; 123051083 ; 124757031 ; 124950685 ; 125163835 ; 125299328 ; 125434146 ; 126661313 ; 126731535 ; 131480767 ; 134964550 ; 135264255 ; 135626653 ; 135653729 ; 135692075 ; 135727452 ; 136367331 ; 136367911 ; 136926964 ; 137031731 ; 137626819 ; 137626820 ; 144116089 ; 152134181 ; 152258419 ; 160645564 ; 160647255 ; 160874442 ; 162011579 ; 162037465 ; 162202744 ; 163894050 ; 164042021 ; 172919866 ; 175266660 ; 175427103 ; 178101159 ; 184819711 ; 187072829 ; 198993065 ; 223381530 ; 223471420 ; 223683825 ; 223705162 ; 224174132 ; 226685555
ChEBI ID
ChEBI:66901
CAS Number
873054-44-5
TTD Drug ID
D0W7WC
Formula
C24H28N2O3
Canonical SMILES
CC(C)(C)C1=CC(=C(C=C1NC(=O)C2=CNC3=CC=CC=C3C2=O)O)C(C)(C)C
InChI
1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)
InChIKey
PURKAOJPTOLRMP-UHFFFAOYSA-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
M1 (hydroxymethyl-ivacaftor) DM001046
46897962
Oxidation - Hydroxylation 1 [3] , [2]
M6 (ivacaftor-carboxylate) DM001047
46917263
Oxidation - Oxidation 1 [3] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002855 Ivacaftor M1 (hydroxymethyl-ivacaftor) Oxidation - Hydroxylation CYP3A4 ... [3], [2]
MR002856 Ivacaftor M6 (ivacaftor-carboxylate) Oxidation - Oxidation CYP3A4 [3], [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
References
1 Ivacaftor was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Sensitivity of ivacaftor to drug-drug interactions with rifampin, a cytochrome P450 3A4 inducer. Pediatr Pulmonol. 2018 May;53(5):E6-E8.
3 PharmGKB summary: ivacaftor pathway, pharmacokinetics/pharmacodynamics Pharmacogenet Genomics. 2017 Jan;27(1):39-42. doi: 10.1097/FPC.0000000000000246.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.