General Information of Drug (ID: DMTV5XC)

Drug Name
Sitafloxacin
Synonyms
Sitafloxacin; Gracevit; Sitafloxacin Sesquihydrate; UNII-3GJC60U4Q8; Sitafloxacin isomer II; DU-6859a; C19H18ClF2N3O3; 3GJC60U4Q8; 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; 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
Indication
Disease Entry ICD 11 Status REF
Escherichia coli infection 1A03 Phase 2 [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
0
Molecular Weight 409.8
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 3
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 8
Chemical Identifiers
Formula
C19H18ClF2N3O3
IUPAC Name
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
Canonical SMILES
C1CC12CN(CC2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)C5CC5F)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
Cross-matching ID
PubChem CID
461399
ChEBI ID
CHEBI:4304
CAS Number
127254-12-0
DrugBank ID
DB13261
VARIDT ID
DR01687

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial DNA gyrase (Bact gyrase) TTN6J5F GYRA_STAAU ; GYRB_STAAU Inhibitor [2]
Bacterial DNA topoisomerase 4A (Bact parC) TTFK8YB PARC_ECOLI Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Biotransformations [4]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Biotransformations [4]
UDP-glucuronosyltransferase 1A7 OTY4JJ32 UD17_HUMAN Biotransformations [4]
UDP-glucuronosyltransferase 1A9 OTPCHAFX UD19_HUMAN Biotransformations [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02537847) Sitafloxacin and Ertapenem Treatment for Acute Pyelonephritis Caused by Escherichia Coli (SETAP). U.S. National Institutes of Health.
2 Dual-targeting properties of the 3-aminopyrrolidyl quinolones, DC-159a and sitafloxacin, against DNA gyrase and topoisomerase IV: contribution to reducing in vitro emergence of quinolone-resistant Streptococcus pneumoniae. J Antimicrob Chemother. 2008 Jul;62(1):98-104.
3 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
4 Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes. Drug Metab Dispos. 2005 Jun;33(6):803-11. doi: 10.1124/dmd.104.003178. Epub 2005 Mar 15.