7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 176852
• Molecular Formular: C21H22ClFN4O3
• Molecular Mass: 432.8757832
• Monoisotopic Mass: 432.13644648
• SMILES: c1(c(c(c2c(c1)c(=O)c(cn2C1CC1)C(=O)O)C#N)N1C[C@@H]2[C@H](C1)CCCN2)F.Cl
• Canonical SMILES: N#Cc1c(N2C[C@@H]3[C@H](C2)CCCN3)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1.Cl
• InChI: InChI=1S/C21H21FN4O3.ClH/c22-16-6-13-18(26(12-3-4-12)9-15(20(13)27)21(28)29)14(7-23)19(16)25-8-11-2-1-5-24-17(11)10-25;/h6,9,11-12,17,24H,1-5,8,10H2,(H,28,29);1H/t11-,17+;/m0./s1
• InChIKey: WUPBAVNMWVWXBI-VFZPIINCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: pradofloxacin hydrochloride
• Synonyms: 8-Cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic Acid Hydrochloride; (4aS-cis)-Pradofloxacin Hydrochloride; Veraflox Hydrochloride; Pradofloxacin Hydrochloride

Database IDs

• CAS Number: 195532-14-0
• PubChem SID: 164232762
• PubChem CID: 9802883

CALCULATED PROPERTIES

• Acid pKa: 4.521389
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.52591366
• LogD (pH = 7.4): -0.4945108
• Log P: -0.49288157
• Molar Refractivity: 105.4824 cm^3
• Polarizability: 38.899277 Å^3
• Polar Surface Area: 96.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P699400

Cyanofluorinated quinoline antibiotic. Antibacterial.

REFERENCES

• Krebber, R., et al.: J. Vet. Pharmacol. Ther., 26, 102 (2003)