26924-74-3

Basic information

• Product Name: deacetoxycephalosporin C
• Synonyms: deacetoxycephalosporin C;(6R)-3-Methyl-7α-[[(R)-5-amino-5-carboxy-1-oxopentyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid;(6R,7R)-7-[[(R)-5-Amino-5-carboxy-1-oxopentyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Antibiotic WS-3442A;WS-3442A
• CAS NO: 26924-74-3
• Molecular Formula: C₁₄H₁₉N₃O₆S
• Molecular Weight: 357.38216
• Mol File: 26924-74-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 786.3°Cat760mmHg
• Flash Point: 429.3°C
• Appearance: /
• Density: 1.54g/cm³
• Vapor Pressure: 4.1E-27mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: deacetoxycephalosporin C(CAS DataBase Reference)
• NIST Chemistry Reference: deacetoxycephalosporin C(26924-74-3)
• EPA Substance Registry System: deacetoxycephalosporin C(26924-74-3)

Safety Data

• Hazardous Substances Data: 26924-74-3(Hazardous Substances Data)

Usage

Description

Deacetoxycephalosporin C is a semi-synthetic antibiotic derived from cephalosporin C, belonging to the cephalosporin class of antibiotics. It is effective against a broad spectrum of bacteria and is primarily utilized in the treatment of various infections.
Used in Pharmaceutical Industry:
Deacetoxycephalosporin C is used as an antibiotic for treating a wide range of bacterial infections due to its ability to inhibit bacterial cell wall synthesis, leading to the disruption of cell structure and bacterial death.
Used in Treatment of Respiratory Infections:
Deacetoxycephalosporin C is used as a therapeutic agent for respiratory infections, such as pneumonia, due to its effectiveness in combating the causative bacteria and reducing inflammation in the respiratory system.
Used in Treatment of Urinary Tract Infections:
Deacetoxycephalosporin C is used as a treatment for urinary tract infections to eliminate the bacteria causing the infection and alleviate symptoms such as pain and discomfort.
Used in Treatment of Skin Infections:
Deacetoxycephalosporin C is used as a medication for skin infections to clear the bacteria responsible for conditions like cellulitis and impetigo, promoting healing and preventing the spread of infection.
Used in Parenteral Administration:
Deacetoxycephalosporin C is used as an injectable antibiotic, allowing for direct introduction into the bloodstream to quickly reach the site of infection and exert its antibacterial effects.

InChI:InChI=1/C14H19N3O6S/c1-6-5-24-12-9(11(19)17(12)10(6)14(22)23)16-8(18)4-2-3-7(15)13(20)21/h7,9,12H,2-5,15H2,1H3,(H,16,18)(H,20,21)(H,22,23)/t7-,9-,12-/m1/s1

Upstream product

• 525-94-0 penicillin N 
• 328-50-7 α-ketoglutaric acid 

Relevant articles and documents

Studies on deacetoxycephalosporin C synthase support a consensus mechanism for 2-oxoglutarate dependent oxygenases

Deacetoxycephalosporin C synthase (DAOCS) catalyzes the oxidative ring expansion of penicillin N (penN) to give deacetoxycephalosporin C (DAOC), which is the committed step in the biosynthesis of the clinically important cephalosporin antibiotics. DAOCS belongs to the family of non-heme iron(II) and 2-oxoglutarate (2OG) dependent oxygenases, which have substantially conserved active sites and are proposed to employ a consensus mechanism proceeding via formation of an enzyme·Fe(II)·2OG·substrate ternary complex. Previously reported kinetic and crystallographic studies led to the proposal of an unusual ping-pong mechanism for DAOCS, which was significantly different from other members of the 2OG oxygenase superfamily. Here we report pre-steady-state kinetics and binding studies employing mass spectrometry and NMR on the DAOCS-catalyzed penN ring expansion that demonstrate the viability of ternary complex formation in DAOCS catalysis, arguing for the generality of the proposed consensus mechanism for 2OG oxygenases.

Cephalosporin C Biosynthesis; a Branched Pathway Sensitive to a Kinetic Isotope Effect

Incubation of penicillin N with preparations of deacetoxycephalosporin C/deacetylcephalosporin C synthetase activity from Cephalosporium acremonium CO 728 gave, along with the normal product deacetoxycephalosporin C, another β-lactam metabolite, namely 7β--3β-hydroxy-3α-methyl4-2H)-cepham-4α-carboxylic acid.This material arises as a result of a deuterium isotope effect on a branched pathway in the enzymic mechanism.The 3β-hydroxy group in this substance arises from molecular oxygen.

THE ENZYMATIC RING EXPANSION OF PENICILLINS TO CEPHALOSPORINS: SIDE CHAIN SPECIFICITY

Structural variants of the acylamino side chain of penicillins have been tested as substrates for Deacetoxy/Deacetyl Cephalosporin C Synthetase from C. acremonium CO 728.A six carbon chain terminating in a carboxyl group was found to permit efficient ring expansion to cephems, with the exception of δ-(L-α-aminoadipoyl).