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

General Information of Drug (ID: DR0703)
Drug Name
Flucloxacillin
Synonyms
Floxacillin (USAN); Floxacillin [USAN]; Floxapen; Floxapen (TN); Flucloxacilina [INN-Spanish]; Flucloxacillin; Flucloxacillin (INN); Flucloxacillin [INN]; Flucloxacillin-Sodium; Flucloxacilline; Flucloxacilline [INN-French]; Flucloxacillinum; Flucloxacillinum [INN-Latin]; Fluorochloroxacillin; FLOXACILLIN; flucloxacilina; 1847-24-1; 3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin; 43B2M34G2V; 5250-39-5; BRL 2039; C19H17ClFN3O5S; CHEBI:5098; EINECS 226-051-0; UNII-43B2M34G2V
Indication Staphylococcus infection [ICD11: 1B73] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 453.9 Topological Polar Surface Area 138
Heavy Atom Count 30 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
21319
PubChem SID
13913 ; 592659 ; 8165699 ; 11406647 ; 14833460 ; 15478401 ; 29288717 ; 46508276 ; 47206142 ; 48416015 ; 50064858 ; 57304807 ; 57330858 ; 77367777 ; 81065485 ; 103510783 ; 104133797 ; 104352937 ; 117541883 ; 124766224 ; 134338408 ; 134984533 ; 135968014 ; 137003738 ; 137272193 ; 160849692 ; 160963649 ; 162173005 ; 163413556 ; 163848983 ; 175442217 ; 179316780 ; 196392852 ; 198978091 ; 223557234 ; 223672511 ; 226395928 ; 251912553 ; 251916662
ChEBI ID
ChEBI:5098
CAS Number
5250-39-5
TTD Drug ID
D0Q2AT
Formula
C19H17ClFN3O5S
Canonical SMILES
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI
1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
InChIKey
UIOFUWFRIANQPC-JKIFEVAISA-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
5-hydroxymethyl-flucloxacillin DM006672 N. A. Oxidation - Oxidationn 1 [2]
Flucloxacillin penicilloic acids DM006674 N. A. Hydrolysis - Hydrolysis 1 [2]
5-hydroxymethyl-flucloxacillin penicilloic acids DM006673 N. A. Hydrolysis - Hydrolysis 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007190 Flucloxacillin 5-hydroxymethyl-flucloxacillin Oxidation - Oxidationn CYP3A4 ... [2]
MR007192 Flucloxacillin Flucloxacillin penicilloic acids Hydrolysis - Hydrolysis Unclear [2]
MR007191 5-hydroxymethyl-flucloxacillin 5-hydroxymethyl-flucloxacillin penicilloic acids Hydrolysis - Hydrolysis Unclear [2]
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
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT03632642) Penicillin Against Flucloxacillin Treatment Evaluation.
2 Characterization of kinetics of human cytochrome P450s involved in bioactivation of flucloxacillin: inhibition of CYP3A-catalysed hydroxylation by sulfaphenazole. Br J Pharmacol. 2019 Feb;176(3):466-477.

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