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Gatifloxacin

Gatifloxacin structure

CAS No:
112811-59-3
Formula:
C19H22FN3O4
Chemical Name:
Gatifloxacin
Synonyms:
3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-;1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;AM 1155;PD 135432;(±)-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;BMS 206584-01;Gatifloxacin;1-Cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;Tequin;Gatiflo;Zymar;Tymer;Gatiquin;Gaity;Gatilox;Gatispan;G-Cebran;Gatifloxin;1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate;1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;Zymaxid;160738-57-8
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, it inhibits the bacterial enzymes DNA gyrase and topoisomerase IV.Target: AntibacterialGatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Gatifloxacin had activity equal to that of tosufloxacin and activity more potent than those of norfloxacin, ofloxacin, ciprofloxacin, and sparf

Solid

Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antiinfective agent, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and an antimicrobial agent. It is a quinolinemonocarboxylic acid, a N-arylpiperazine, an organofluorine compound, a quinolone and a quinolone antibiotic.|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.|A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.

Gatifloxacin Basic Attributes

Molecular Weight：

375.39

Exact Mass：

375.39

EC Number：

1308068-626-2

NSC Number：

758701

DSSTox ID：

DTXSID5045704

ATC Code：

J - Antiinfectives for systemic use|S - Sensory organs

HScode：

2933990090

Characteristics

PSA：

82.1

XLogP3：

-0.7

Appearance：

White powder

Density：

1.4±0.1 g/cm3

Melting Point：

167-168 °C

Boiling Point：

607.8±55.0°C at 760 mmHg

Flash Point：

321.4±31.5 °C

Refractive Index：

1.616

Water Solubility：

6.31e-01 g/L

Storage Conditions：

Store at 0-5°C

Vapor Pressure：

1.26E-15mmHg at 25°C

Collision Cross Section：

189.5 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

hazard class code：

20/21/22

safety instructions：

36/37

RTECS Number：

BT1750000

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (97.44%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Protein Binding：

20%

Drug Information

Drug Indication：

For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes|FDA Label

Pharmacology：

Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

MeSH：

Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)|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：

Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

Metabolism/Metabolites：

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

Biological Half-Life：

7-14 hours

Mechanism of Action：

The bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

MeSH Entry Terms：

1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

Gatifloxacin Use and Manufacturing

Uses

An antibacterial

Use Classification：

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

Computed Properties

Molecular Weight:375.4
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:375.15943435
Monoisotopic Mass:375.15943435
Topological Polar Surface Area:82.1
Heavy Atom Count:27
Complexity:653
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

By inhibiting bacterial DNA gyrase and topoisomerase IV, it inhibits bacterial DNA replication, transcription, and repair processes. It has antibacterial activity against the following microorganisms: 1. Gram-positive bacteria (such as Staphylococcus aureus, Streptococcus pneumoniae, etc.); 2. Gram-negative bacteria (such as Haemophilus, Moraxella catarrhalis, Escherichia coli, etc.); 3. Other microorganisms (such as Chlamydia pneumoniae, Legionella pneumophila, Mycoplasma pneumoniae).

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Gatifloxacin Capsules
Ingredients	The main ingredient of this product is gatifloxacin, chemical name: (±)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(-3-methyl-1-piperazine)-4-keto-3-quinolinecarboxylic acid sesquihydrate. Chemical structure: Molecular formula: C19H22FN3O4·1.5H2O Molecular weight: 402.42
Indication	1. This product can be used in combination with probenecid to slow down the elimination of gatifloxacin through the kidney. 2. When this product is used simultaneously with digoxin, no significant changes in the pharmacokinetics of gatifloxacin are observed, but increased digoxin blood concentrations are found in some subjects. Therefore, patients taking digoxin should be monitored for symptoms and signs of digoxin toxicity. For patients showing toxic symptoms and signs, the blood concentration of digoxin should be measured and the digoxin dose should be adjusted appropriately. However, it is not recommended to adjust the doses of the two drugs in advance. 3. The simultaneous use of gatifloxacin and drugs that affect glucose metabolism can increase the risk of abnormal blood glucose metabolism in patients (see Contraindications and Warnings: Abnormal Blood Glucose). Antidiabetic drugs: Pharmacodynamic changes that affect glucose metabolism have been observed after the combined use of glibenclamide and other hypoglycemic drugs. No significant pharmacokinetic interactions were observed when glibenclamide was used in combination with gatifloxacin.
Specifications	0.1g
Manufacturer	Tianjin Huajin Pharmaceutcial Co., Ltd.

Gatifloxacin
Manufacturer	Xiuzheng Pharmaceutical Group Liu HE Pharmaceutical Co., Ltd.

Gatifloxacin Mesylate Tablets
Ingredients	Methylcantharidin.
Indication	Not yet clear.
Specifications	0.1g (based on gatifloxacin)
Manufacturer	Tonghua Golden-Horse Pharmaceutical Industey Co., Ltd.

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Registered Holders

MATRIX PHARMACORP PRIVATE LTD

United States
Active
LUPIN LTD

United Kingdom
Active
キョーリン製薬グループ工場株式会社

Japan
Active

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