1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 121841
• Molecular Formular: C19H20F3N3O3
• Molecular Mass: 395.3756096
• Monoisotopic Mass: 395.14567618
• SMILES: c12c(n(cc(c1=O)C(=O)O)C1CC1)c(c(c(c2F)F)N1C[C@@H](N[C@@H](C1)C)C)F
• Canonical SMILES: C[C@@H]1N[C@H](C)CN(C1)c1c(F)c(F)c2c(c1F)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C19H20F3N3O3/c1-8-5-24(6-9(2)23-8)17-14(21)13(20)12-16(15(17)22)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6H2,1-2H3,(H,27,28)/t8-,9+
• InChIKey: QIPQASLPWJVQMH-DTORHVGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: orbifloxacin; 1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• Synonyms: 1-cyclopropyl-7-((3S,5R)-3,5-dimethylpiperazin-1-yl)-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Orbifloxacin; Orbax; 1-Cyclopropyl-5,6,8-trifluoro-1,4-dihydro-7-(cis-3,5-dimethyl-1-piperazinyl)-4-oxo-quinoline-3-carboxylic acid; Orbifloxacin; 1-环丙基-5,6,8-三氟-1,4-二羟基-7-(顺式-3,5-二甲基-1-哌嗪基)-4-氧代-喹啉-3-羧酸; 奥比沙星

Database IDs

• CAS Number: 113617-63-3
• MDL Number: MFCD00864858
• PubChem SID: 162216194; 24860808
• PubChem CID: 60605

CALCULATED PROPERTIES

• Acid pKa: 5.4919295
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.02530205
• LogD (pH = 7.4): 0.24292499
• Log P: 0.24618606
• Molar Refractivity: 97.2098 cm^3
• Polarizability: 35.475452 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Mechanism of Action: Inhibitor of bacterial DNA gyrase,; Prevents DNA supercoiling and synthesis

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Antibacterial agent; Antibiotic; Antiseptic
• Empirical Formula (Hill Notation): C19H20F3N3O3

DETAILS

Sigma Aldrich - 34041

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Eur. Pat., 1987, Dainippon, 242 789; CA, 108, 150325x, (synth, pharmacol)
• Miyamoto, T. et al., J. Med. Chem., 1990, 33, 1645-1656, (synth, pmr, ir, pharmacol)
• Morimura, T. et al., Chem. Pharm. Bull., 1995, 43, 1000-1004; 1997, 45, 373-377, (photodegradation)
• Nakamura, S. et al., Drugs, 1995, 49, 152-158, (rev)