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Alatrofloxacin

Alatrofloxacin structure

CAS No:
146961-76-4
Formula:
C26H25F3N6O5
Chemical Name:
Alatrofloxacin
Synonyms:
L-Alaninamide,L-alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-;L-Alaninamide,L-alanyl-N-[3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-,(1α,5α,6α)-;3-Azabicyclo[3.1.0]hexane,L-alaninamide deriv.;L-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninamide;Alatrofloxacin;157182-32-6
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Alatrofloxacin is a peptide.|Alatrofloxacin is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt. It was withdrawn from the U.S. market in 2001.

Alatrofloxacin Basic Attributes

Molecular Weight：

654.62

Exact Mass：

558.51

UNII：

7QVV6I50DT

DSSTox ID：

DTXSID4057893

Characteristics

PSA：

158

Density：

1.57±0.1 g/cm3(Predicted)

Boiling Point：

863.2±65.0 °C(Predicted)

Drug Information

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|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.)

MeSH Entry Terms：

alatrofloxacin

Alatrofloxacin Use and Manufacturing

This fourth-generation fluoroquinolone-class antibiotic (FW = 558.51 g/mol; CAS 146961-76-4; quickly hydrolyzes to form trovafloxacin), also named 7-[(1R,5S)-6-{[(2S)-1-{[(2S)-2-aminopropanoyl]amino}-1-oxopropan- 2-yl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6- fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid, is a systemic antibacterial that targets Type II DNA topoisomerases (gyrases) required for bacterial replication and transcription. This fluoroquinolone shows an extensive in vitro antibiotic spectrum, with high activity against Grampositive coccus, anaerobic and atypical pneumonia-producing bacteria. (For the prototypical member of this antibiotic class, See Ciprofloxacin) Intravenous alatrofloxacin, followed by oral trovafloxacin (TVX), is safe and well tolerated. Alatrofloxacin also lacks the phototoxicity, cardiovascular toxicity, and hemolytic anemia associated with earlier fluoroquinolones. Given its metabolism to trovafloxacin, it should be noted that the latter significantly increases the formation of nitrotyrosine in mice that are heterozygous for mitochondrial superoxide dismutase-2. Using the NO-selective probe DAF-2, TVX also increases the production of mitochondrial NO in immortalized human hepatocytes. Similarly, mitochondrial Ca2+ is increased by TVX, suggesting calcium ion-dependent activation of mitochondrial NOS activity. The relationship between these observations and trovafloxacin-induced leukopenia remains to be explored.

Computed Properties

Molecular Weight:558.5
XLogP3:-0.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:7
Exact Mass:558.18385241
Monoisotopic Mass:558.18385241
Topological Polar Surface Area:158
Heavy Atom Count:40
Complexity:1080
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes