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

General Information of Drug (ID: DR2456)
Drug Name
Levofloxacin
Synonyms
Leroxacin; Lesacin; Levaquin; Levaquin (TN); Levofloxacin (INN); Levofloxacin [USAN:INN:JAN]; Levofloxacine; Levofloxacine [INN-French]; Levofloxacino; Levofloxacino [INN-Spanish]; Levofloxacinum; Levofloxacinum [INN-Latin]; Levokacin; Levoxacin; MP-376; Mosardal; Nofaxin; Ofloxacin S-(-)-form; Oftaquix; Oftaquix (TN); Quixin; Quixin (TN); R-Ofloxacin; Aeroquin; Cravit; Cravit (TN); Cravit Ophthalmic; D-Levofloxacin; DR 3354; DR-3355; DR-3355: L-isomer of ofloxacin; DR3355; Elequine; Floxacin; Floxel; Iquix (TN); L-Ofloxacin; RWJ 25213-097; RWJ-25213; Reskuin; S-(-)-Ofloxacin; Tavanic; Tavanic (TN); Volequin; (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid; (-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyridol[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid hemihydrate; (-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7Hpyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid hemihydrate; (3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; (R)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid; (R)-isomer; (S)-(-)-Ofloxacin; (S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid; (S)-Ofloxacin; HR 355; HR-355; Iquix; LEVAQUIN IN DEXTROSE 5% IN PLASTIC CONTAINER; LFX; LVX; Levofloxacin tablet, suspension or intravenous; Levox
Indication Bronchitis [ICD11: CA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 361.4 Topological Polar Surface Area 73.3
Heavy Atom Count 26 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
149096
PubChem SID
9862 ; 598046 ; 7979773 ; 10250227 ; 11364613 ; 11367175 ; 11369737 ; 11372008 ; 11374743 ; 11377899 ; 11485627 ; 11489492 ; 11490810 ; 11492937 ; 11495533 ; 11528725 ; 12014081 ; 14876841 ; 14901428 ; 24857060 ; 26612693 ; 26680408 ; 26719895 ; 46225907 ; 46386771 ; 46505134 ; 48185231 ; 48334772 ; 49665952 ; 49681682 ; 50064059 ; 50123181 ; 56314311 ; 57346857 ; 57648297 ; 76034622 ; 85261747 ; 85789483 ; 87558890 ; 89736102 ; 92124751 ; 92307928 ; 92308354 ; 92309286 ; 92710579 ; 96024810 ; 103165325 ; 104052737 ; 104179033 ; 104253435
ChEBI ID
CHEBI:63598
CAS Number
100986-85-4
TTD Drug ID
D02RSN
Formula
C18H20FN3O4
Canonical SMILES
CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
InChI
1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
InChIKey
GSDSWSVVBLHKDQ-JTQLQIEISA-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
Desmethyl levofloxacin DM000290
10958963
Oxidation - N-Demethylation 1 [4]
Glucuronide of Levofloxacin DM000292 N. A. Conjugation - Glucuronidation 1 [4]
Levofloxacin N-oxide DM000291
10970860
Oxidation - N-Oxidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003403 Levofloxacin Desmethyl levofloxacin Oxidation - N-Demethylation Unclear [4]
MR003404 Levofloxacin Levofloxacin N-oxide Oxidation - N-Oxidation Unclear [4]
MR003405 Levofloxacin Glucuronide of Levofloxacin Conjugation - Glucuronidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1023 Klebsiella pneumoniae
A0A378EHS6_KLEPR
3.5.2.6
[2]
Unclear metabolic mechanism (DME-unclear) DME1697 Prevotella amnii Not Available Not Available [3]
References
1 Levofloxacin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Analysis of the drug-resistant characteristics of Klebsiella pneumoniae isolated from the respiratory tract and CTX-M ESBL genes. Genet Mol Res. 2015 Oct 5;14(4):12043-8.
3 Antimicrobial susceptibility and beta-lactamase production of anaerobic and aerobic bacteria isolated from pus specimens from orofacial infections. J Chemother. 2007 Oct;19(5):495-9.
4 Pharmacokinetics, metabolism, excretion and plasma protein binding of 14C-levofloxacin after a single oral administration in the Rhesus monkey Xenobiotica. 2006 Jul;36(7):597-613. doi: 10.1080/00498250600674436.

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