245765-41-7 Usage
Description
Ozenoxacin is a novel, non-fluorinated quinolone antibiotic discovered by Toyama Chemical Co. Ltd. and developed by Maruho Co. Ltd. It is used to treat impetigo, a skin infection caused by bacteria, in adults and children 2 months of age and older. Ozenoxacin belongs to a class of medications called antibacterials and works by killing and stopping the growth of bacteria on the skin. Its mechanism of action involves the drug's affinity for DNA gyrase and DNA topoisomerase IV, which upon binding, triggers bacterial apoptosis.
Uses
Used in Pharmaceutical Industry:
Ozenoxacin is used as an antibacterial agent for treating impetigo caused by Staphylococcus aureus or Streptococcus pyogenes in adult and pediatric patients 2 months of age and older. It was approved by the PMDA of Japan in September 2015 for the treatment of acne and skin infections.
Used in Dermatology:
Ozenoxacin is used as a topical quinolone for treating acne and superficial skin infections. It exhibits antimicrobial activity against propionibacteria and staphylococci, which are commonly implicated in such skin conditions.
Used in Clinical Trials:
Ozenoxacin has been used in trials studying the treatment of impetigo, with the FDA approving Ferrer Internacional S.A.'s Xepi (ozenoxacin 1%) as a topically applied cream for this purpose on December 11, 2017.
Pharmacokinetics
Although the exposure response relationship for ozenoxacin after it has been applied topically has not yet been studied, a formal relationship is unlikely because systemic exposure of ozenoxacin following its topical application has been measured to be negligible .
Mechanism of action
Ozenoxacin is a quinolone antibiotic drug. And, like most quinolones, ozenoxacin predominately executes its mechanism of action by entering into bacterial cells and acting to inhibit the bacterial DNA replication enzymes DNA gyrase A and topoisomerase IV . As DNA gyrase A and topoisomerase IV are essential to bacterial DNA replication activities including supercoiling, supercoil relaxation, chromosomal condensation, chromosomal decatenation and more, their inhibition is the principal action of ozenoxacin's mechanism and it has been demonstrated to be bactericidal against S. aureus and S. pyogenes organisms.
Synthesis
A U.S. patent filed by co-workers at Toyama describes the
only publicly disclosed synthetic approach to this drug.12 The
drug’s assembly hinges upon a key Stille coupling between a
quinolonyl bromide and a stannylpyridine.
Buchwald-Hartwig coupling of commercially available 2,6-
dibromotoluene (22) and cyclopropylamine (23) gave Ncyclopropyl-
3-bromo-2-methylaniline 24 in 84% yield , and this step was followed by reaction with diethyl
ethoxymethylenemalonate (25) and subsequent cyclization
under acidic conditions to secure bromoquinoline 26 in 43%
yield over the two-step sequence. Stille coupling of 27 with
bromoquinoline 26 resulted in pyridyl quinoline adduct 28 in
80% yield. Saponification of ester 28 followed by acidic removal
of the N-acetyl group delivered the active pharmaceutical
ingredient ozenoxacin (III) in 75% yield.The preparation of key stannane 27, which is not
commercially available and began
with the conversion of commercially available 5-bromo-2-
chloro-3-methylpyridine (30) to aminopyridine derivative 31
upon treatment with aqueous methylamine at elevated
temperature in a sealed vessel. The resulting aminopyridine
was subjected to acetic anhydride in pyridine, resulting in
acetamide 32 in good yield, and this coupling was followed by a
modest-yielding palladium-catalyzed installation of the stannyl
group to deliver subunit 27.
Check Digit Verification of cas no
The CAS Registry Mumber 245765-41-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,5,7,6 and 5 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 245765-41:
(8*2)+(7*4)+(6*5)+(5*7)+(4*6)+(3*5)+(2*4)+(1*1)=157
157 % 10 = 7
So 245765-41-7 is a valid CAS Registry Number.
245765-41-7Relevant articles and documents
CRYSTALLINE FORM OF OZENOXACIN AND PROCESSES FOR PREPARATION THEREOF
-
, (2020/05/12)
The present invention relates to a crystalline form of 1-cyclopropyl-8-methyl-7- (5-methyl-6-(methylamino)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid the compound of formula-1, which is represented by the following structural formula-1. The
Preparation method of Ozenoxacin and intermediates thereof
-
, (2019/01/05)
The invention provides compounds represented by the formula (IIIb) and a preparation method thereof. The invention also provides an application of the compound represented by the formula (IIIb) as a key intermediate in Ozenoxacin preparation.
