Details of the Drug

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]

ATC Code

J01MA21: Sitafloxacin

J01MA: Fluoroquinolones

J01M: QUINOLONE ANTIBACTERIALS

J01: ANTIBACTERIALS FOR SYSTEMIC USE

J: ANTIINFECTIVES FOR SYSTEMIC USE

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

409.8

Logarithm of the Partition Coefficient

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

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: CHEMBL4304
CAS Number: 127254-12-0
UNII: 9TD681796G
DrugBank ID: DB13261
VARIDT ID: DR01687

Drug ADMET Endpoint Profile (DAE)^NEW

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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)

MIA Detail

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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.