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Grepafloxacin

Grepafloxacin structure

CAS No:
119914-60-2
Formula:
C19H22FN3O3
Chemical Name:
Grepafloxacin
Synonyms:
3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-;1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;Grepafloxacin;Tomefloxacin;1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;dl-Grepafloxacin;126292-40-8;146863-02-7
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Solid

Grepafloxacin is a member of quinolines, a quinolone antibiotic and a fluoroquinolone antibiotic.|Grepafloxacin is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Due to the QTc-prolonging potential, as indicated by the changes in the QT interval on the electrocardiogram, and the risk for cardiovascular adverse events, grepafloxacin was withdrawn in the United States.

Grepafloxacin Basic Attributes

Molecular Weight：

359.39

Exact Mass：

359.39

EC Number：

1806241-263-5

DSSTox ID：

DTXSID2048321

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

72.9

XLogP3：

2.9

Appearance：

Solid

Density：

1.366

Melting Point：

189-192 °C

Boiling Point：

610.0±55.0 °C(Predicted)

Flash Point：

322.7ºC

Water Solubility：

6.32e-01 g/L

Safety Information

Precautionary statement(s)：

P264, P270, P301+P310, P321, P330, P405, P501

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.

Protein Binding：

50%

Drug Information

Drug Indication：

For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.

Pharmacology：

Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.

MeSH：

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.

Metabolism/Metabolites：

Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity

Biological Half-Life：

15 ± 3 hours

Mechanism of Action：

Grepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA.

MeSH Entry Terms：

(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

Grepafloxacin Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:359.4
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:359.16451973
Monoisotopic Mass:359.16451973
Topological Polar Surface Area:72.9
Heavy Atom Count:26
Complexity:636
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes