7081-44-9

Basic information

• Product Name: Cloxacillin sodium
• Synonyms: bactopen;brl-1621sodiumsaltmonohydrate;cloxacillinsodiummonohydrate;orbeninsodiumhydrate;prostaphlin-amonohydrate;sodiumcloxacillinmonohydrate;staphobristol-250;thyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-,sodiumsalt,monohydrate
• CAS NO: 7081-44-9
• Molecular Formula: C₁₉H₁₇ClN₃O₅S*H₂O*Na
• Molecular Weight: 475.88
• EINECS: 211-390-9
• Product Categories: Antibiotics for Research and Experimental Use;beta-Lactams (Antibiotics for Research and Experimental Use);Biochemistry;Interferes with Cell Wall SynthesisEPA;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Mechanism of Action;NeatsAntibiotics;Penicillins and Cephalosporins (beta-Lactams);Spectrum of Activity;1694 Pharmaceuticals&Personal Care Products;BactericidalAntibiotics;beta-Lactam StructureAlphabetic;Chemical Structure;CI - CLEPA;Principle;Antibiotics;C;Neats;Peptide Synthesis/Antibiotics;TEGOPEN
• Mol File: 7081-44-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 170℃
• Boiling Point: 689℃
• Flash Point: >110°(230°F)
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble50mg/mL
• Water Solubility: Soluble in water
• Merck: 13,2444
• BRN: 5403885
• CAS DataBase Reference: Cloxacillin sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Cloxacillin sodium(7081-44-9)
• EPA Substance Registry System: Cloxacillin sodium(7081-44-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: XH8920000
• Hazardous Substances Data: 7081-44-9(Hazardous Substances Data)

Usage

Brand Name(s) in US

Cloxapen, Orbenin, Tegopen

Uses

Different sources of media describe the Uses of 7081-44-9 differently. You can refer to the following data:
1. Penicillin antibacterial.
2. Targets primarily Gram-positive bacteria, especially -lactamase producing Staphylococci

Clinical Use

The chlorine atom ortho to the position of attachment of thephenyl ring to the isoxazole ring enhances the activity ofcloxacillin sodium, [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin sodium monohydrate (Tegopen), over that ofoxacillin, not by increasing its intrinsic antibacterial activitybut by enhancing its oral absorption, leading to higher plasmalevels. In almost all other respects, it resembles oxacillin.

Safety Profile

Moderately toxic by intraperitoneal, intramuscular, subcutaneous, and intravenous routes. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of Cl-, NOx, Na2O, and SOx.

Veterinary Drugs and Treatments

Cloxacillin is used via intramammary infusion in dry and lactating dairy cattle.

InChI:InChI=1/C19H18ClN3O5S.Na.H2O/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;;/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);;1H2/t13-,14+,17-;;/m1../s1

Synthetic route

3-(2'-chlorophenyl)-5-methyl-4-isoxazolyl chloride → cloxacillin sodium salt monohydrate (7081-44-9)

Conditions	Yield
	90%

2-Ethylhexanoic acid (149-57-5) + 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid (23598-72-3) + sodium 2-ethylhexanoic acid → cloxacillin sodium salt monohydrate (7081-44-9) + 6(3-(o-chlorophenyl)-5-methyl-4-isoxazolylcarboxyamido)penicillanic acid sodium salt

Conditions	Yield
With phosphorus pentachloride; triethylamine In hexane; dichloromethane; water; 4-methyl-2-pentanone	A 78.8% B n/a

Upstream product

• 149-57-5 2-Ethylhexanoic acid 
• 23598-72-3 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid 

Relevant articles and documents

Manufacture of semi-synthetic penicillin antibiotics

Improvements in or relating to the manufacture of semi-synthetic penicillin antibiotics are described. More particularly an improved process for the preparation of a 6β-acylamino penicillanic acid antibiotic product is described in which 6β-aminopenicillanic acid (6-APA) is reacted in an inert solvent with a silylating agent to form a silylated compound of formula (I) STR1 wherein R1 represents a hydrogen atom or a tri(C1-6 alkyl)silyl group, and R2 represents a tri(C1-6 alkyl)silyl group and the compound of formula (I) is thereafter contacted with an acyl chloride or protected acyl chloride corresponding to the desired 6β-acylamino group, the silyl groups are cleaved and the desired antibiotic product is recovered, silylation being effected using a tri(C1-6 alkyl) silylurea or tri(C1-6 alkyl) halosilane and the compound of formula (I) produced being reacted without intermediate isolation with the acyl chloride or protected acyl chloride, wherein acylation is effected in the presence of a hydrogen halide acceptor mixture comprising in excess of 0.15 and preferably up to 3.00 moles of urea per mole of 6-APA; in excess of 0.15, and preferably up to 1.30 moles of bis-tri-(C1-6 alkyl)silylurea per mole of 6-APA; and in excess of 0.25, and preferably up to 3.30 moles of tri-(C1-6 alkyl)-ammonium halide per mole of 6-APA. The process is especially useful for the preparation of ampicillin and amoxycillin in high yield and high purity.

Pharmaceutical formulations

Microcapsules which have an average diameter of from 100μ to 300μ and which comprise 94% to 99.9% of a medicament coated by 0.1% to 6% of a coating agent may be formed into a powder with 0% to 95% excipients or a tablet or capsule with a carrier.