Gatifloxacin sesquihydrateProduct ingredient for Gatifloxacin

Name
Gatifloxacin sesquihydrate
Drug Entry
Gatifloxacin

Gatifloxacin is an antibiotic agent and a member of the fourth-generation fluoroquinolone family. It works by inhibiting the bacterial enzymes DNA gyrase and topoisomerase IV. It was first introduced by Bristol-Myers Squibb in 1999 under the brand name Tequin® for the treatment of respiratory tract infections. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. It is also available as eye drops under the brand name Zymar® marketed by Allergan.

The FDA withdrew its approval for the use of non-ophthalmic drug products containing gatifloxacin due to the high prevalence of gatifloxacin-associated dysglycemia adverse event reports and the high incidence of hyperglycemic and hypoglycemic episodes in patients taking gatifloxacin compared to those on macrolide antibiotics.5,6

Accession Number
DBSALT001829
Structure
Synonyms
Gatifloxacin / Gatifloxacin hydrate
External IDs
AM-1155 / BMS-206584-01 / BMS-20658401 / PD-135432
UNII
L4618BD7KJ
CAS Number
180200-66-2
Weight
Average: 804.846
Monoisotopic: 804.35056278
Chemical Formula
C38H50F2N6O11
InChI Key
RMJMZKDEVNTXHE-UHFFFAOYSA-N
InChI
InChI=1S/2C19H22FN3O4.3H2O/c2*1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26;;;/h2*7,9-11,21H,3-6,8H2,1-2H3,(H,25,26);3*1H2
IUPAC Name
bis(1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid) trihydrate
SMILES
O.O.O.COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1.COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1
ChemSpider
4445543
Predicted Properties
PropertyValueSource
Water Solubility0.631 mg/mLALOGPS
logP-0.23ALOGPS
logP-0.58Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.69Chemaxon
pKa (Strongest Basic)8.73Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area82.11 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity98.82 m3·mol-1Chemaxon
Polarizability38.22 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon