26774-90-3

Basic information

• Product Name: EPICILLIN
• Synonyms: 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(2-amino-2-(1,4-cyclohex;d-adien-1-yl)acetamido)-;dihydroampicillin;EPICILLIN;(2S,5β)-6α-[[(R)-Amino(1,4-cyclohexadien-1-yl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid;6α-[[(R)-2-Amino-2-(1,4-cyclohexadien-1-yl)acetyl]amino]penicillanic acid;Dexacillin;Omnisan
• CAS NO: 26774-90-3
• Molecular Formula: C₁₆H₂₁N₃O₄S
• Molecular Weight: 351.42
• EINECS: 248-001-7
• Mol File: 26774-90-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 653°Cat760mmHg
• Flash Point: 348.7°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 9.76E-19mmHg at 25°C
• Refractive Index: 1.66
• PKA: pKa 2.77 (H2O t=35 I=0.5(KCl)) (Uncertain);7.17(H2O t=35 I=0.5(KCl)) (Uncertain)
• CAS DataBase Reference: EPICILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: EPICILLIN(26774-90-3)
• EPA Substance Registry System: EPICILLIN(26774-90-3)

Safety Data

• Hazardous Substances Data: 26774-90-3(Hazardous Substances Data)

Usage

Originator

Dexacilline,Squibb,France,1974

Uses

Antibacterial.

Definition

ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido group.

Manufacturing Process

See Cephradine for preparation of D-2-amino-2-(1,4-cyclohexadienyl)acetic acid and then its methyl acetoacetic ester enamine as the starting material.358 mg of 6-aminopenicillanic acid (APA) (1.66 mmol) are stirred well in 2.5 ml of water while 0.23 ml triethylamine is gradually added with the pH kept under 8.0. Final pH is 7.4; 0.85 ml acetone is added and the solution kept at - 10°C.469 mg methyl acetoacetate enamine of D-2-amino-2-(1,4- cyclohexadienyl)acetic acid sodium salt (1.715 mmol) are stirred in 4.25 ml acetone at -20°C. A microdrop of N-methylmorpholine is added followed by the slow addition of 198 mg of ice cold ethyl chloroformate. Water, 0.43 ml, is added at this point and a turbid solution results. The reaction mixture is stirred for 10 minutes at -20°C.The turbid solution of mixed anhydride is then added to the 6-APA solution. A complete solution is observed. The solution is stirred for 30 minutes at -10°C, then raised to room temperature, acidified to pH 2.0 with diluted HCl and, with good stirring, the pH is kept at that level for 10 minutes.The solution is then extracted with 5 ml xylene. The aqueous layer is layered with 5 ml methyl isobutyl ketone and the pH adjusted to 5.0 with 1 N NaOH and chilled overnight. The resulting crystals are filtered off, washed with water and air dried. Yield, 272 mg (44%), decomposes at 202°C.

Brand name

Dexacillin (Bristol- Myers Squibb).

Therapeutic Function

Antibacterial

Antimicrobial activity

An analog of ampicillin in which the benzene ring is partially saturated. It closely resembles ampicillin in its antibacterial properties. It is moderately well absorbed, a 500 mg oral dose producing mean peak plasma levels of 2–3 mg/L. Its behavior on intramuscular injection, distribution, excretion, toxicity and uses resemble those of ampicillin. It is of very limited availability.

InChI:InChI=1/C16H21N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-4,7,9-11,14H,5-6,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

Downstream Products

• 61-33-6 penicillin G 

Relevant articles and documents

Beta lactam production

A new process is described for the production of 6-alpha-amino-penicillins and 7-alpha-amino-desacetoxy-cephalosporins free from halogen-containing solvents by acylating 6-APA, 7-ADCA or a derivative thereof in a halogen-free solvent.