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

General Information of Drug (ID: DR4633)
Drug Name
Sitafloxacin
Synonyms
127254-12-0; Gracevit; Sitafloxacin Sesquihydrate; DU 6859; 163253-35-8; UNII-3GJC60U4Q8; DU-6859a; Sitafloxacin isomer II; DU 6859A; C19H18ClF2N3O3; 3GJC60U4Q8; CHEBI:4304; 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid; Sitafloxacin [INN]; 7-((S)-7-AMINO-5-AZASPIRO[2.4]HEPTAN-5-YL)-8-CHLORO-6-FLUORO-1-((1R,2S)-2-FLUOROCYCLOPROPYL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID; STFX; DU-6859; 127254-10-8; Sitafloxacin isomer III (RRS); 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxo-3-quinolinecarboxylic acid; 7-[(7S)-7-azanyl-5-azaspiro[2.4]heptan-5-yl]-8-chloranyl-6-fluoranyl-1-[(1R,2S)-2-fluoranylcyclopropyl]-4-oxidanylidene-quinoline-3-carboxylic acid; SITAFLOXACIN ISOMER III(RRS); SITAFLOXACINISOMER; SCHEMBL74553; 7-((7S)-Amino-5-azaspiro(2,4)heptan-5-yl)-8-chloro-6-fluoro-1-((1R,2R)-cis-2-fluoro-1-cyclopropyl)-1,4-dihydro-4-oxoquinolone-3-carboxylic acid; 7-(7-Amino-5-azaspiro(2.4)heptan-5-yl)-8-chloro-6-fluoro-1-(2-fluorocyclopropyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid sesquihydrate; SITAFLOXACINISOMER(RRS); SITAFLOXACINISOMER(RSR); DU6859a; CHEMBL108821; AMSP00027; GTPL11040; HY-B0395; ZINC3795983; AKOS015962212; AC-1388; ACN-048224; AM85541; compound 33 [PMID: 7932562]; YF10030; (-)-7-((7S)-Amino-5-azaspiro(2,4)hept-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-1,4-dihydro-4-oxoq-3-uinolonecarboxylic acid; 3-Quinolinecarboxylic acid, 7-(7-amino-5-azaspiro(2.4)hept-5-yl)-8-chloro-6-fluoro-1-(2-fluorocyclopropyl)-1,4-dihydro-4-oxo-, (1R-(1alpha(S*),2alpha))-; 3-Quinolinecarboxylic acid, 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-; 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxo-quinoline-3-carboxylic acid; AT-21032; AB01568244_01; 253S358; A805671; A805673; J-519022; (-)-7-[(7s)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1r,2s)-2-fluoro-1-cyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid; 273401-03-9; 3-Quinolinecarboxylic acid, 7-((7S)-7-amino-5-azaspiro(24)hept-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-1,4-dihydro-4-oxo-; 7-((7S)-7-Amino-5-azaspiro[2.4]hept-5-yl)-1-((1S,2S)-2-fluorocyclopropyl)-8-chloro-6-fluoro-4-oxohydroquinoline-3-carboxylic acid; 7-((S)-7-Amino-5-azaspiro[2.4]Heptan-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-[(7S)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1 R,2S)-2-fluorocyclopropyl]-4-oxo-1,4-dihydro-3-quinolinecarboxyli c acid; rel-7-((R)-7-Amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1S,2R)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Indication Escherichia coli infection [ICD11: 1A03] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 409.8 Topological Polar Surface Area 86.9
Heavy Atom Count 28 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
461399
ChEBI ID
CHEBI:4304
CAS Number
127254-12-0
TTD Drug ID
D6DT3X
Formula
C19H18ClF2N3O3
Canonical SMILES
C1CC12CN(C[C@H]2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)[C@@H]5C[C@@H]5F)F
InChI
InChI=1S/C19H18ClF2N3O3/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28)/t10-,12+,13+/m0/s1
InChIKey
PNUZDKCDAWUEGK-CYZMBNFOSA-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
Sitafloxacin metabolite M1 DM017242 N. A. Conjugation - Glucuronidation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008323 Sitafloxacin Sitafloxacin metabolite M1 Conjugation - Glucuronidation UGT1A1 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT02537847) Sitafloxacin and Ertapenem Treatment for Acute Pyelonephritis Caused by Escherichia Coli (SETAP). U.S. National Institutes of Health.
2 Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes

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