Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D6DT3X
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| Drug Name |
Sitafloxacin
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| 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
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| Drug Type |
Small molecular drug
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| Indication | Escherichia coli infection [ICD-11: 1A03; ICD-10: A04, A04.4] | Phase 2 | [1] | |
| Structure |
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Download2D MOL |
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| Formula |
C19H18ClF2N3O3
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| Canonical SMILES |
C1CC12CN(CC2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)C5CC5F)F
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| 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
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| InChIKey |
PNUZDKCDAWUEGK-CYZMBNFOSA-N
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| CAS Number |
CAS 127254-12-0
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| PubChem Compound ID | ||||
| ChEBI ID |
CHEBI:4304
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroidaceae
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[2] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacteroidaceae was decreased by Sitafloxacin. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Enterobacteriaceae
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[2] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Enterobacteriaceae was decreased by Sitafloxacin. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridium difficile
Show/Hide Hierarchy
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[2] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Clostridium difficile was decreased by Sitafloxacin. | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Bacterial DNA gyrase (Bact gyrase) | Target Info | Inhibitor | [3] |
| Bacterial DNA topoisomerase 4A (Bact parC) | Target Info | Inhibitor | [3] | |
| References | Top | |||
|---|---|---|---|---|
| REF 1 | ClinicalTrials.gov (NCT02537847) Sitafloxacin and Ertapenem Treatment for Acute Pyelonephritis Caused by Escherichia Coli (SETAP). U.S. National Institutes of Health. | |||
| REF 2 | The effect of DU-6859a, a new potent fluoroquinolone, on fecal microflora in human volunteers. Jpn J Antibiot. 1995 Mar;48(3):368-79. | |||
| REF 3 | 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. | |||
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