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Cloxacillin

CAS No.: 61-72-3

Chemical Name:: Cloxacillin

Synonyms: Syntarpen;MCIPC;brl1621;CLOXACILLIN;methocillins;Cloxacillin 13C4;Cloxacillin Impurity;Orbenin Extra Dry Cow;CLOXACILLIN USP/EP/BP;Cloxacillin (base and/or unspecified salts)

CBNumber:: CB7163623

Molecular Formula:: C19H18ClN3O5S

Molecular Weight:: 435.88

MOL File:: 61-72-3.mol

MSDS File:: SDS

Modify Date:: 2024/8/21 22:41:43

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Cloxacillin Properties

Boiling point	689.7±55.0 °C(Predicted)
Density	1.2954 (rough estimate)
refractive index	1.6100 (estimate)
pka	pKa 2.70±0.07(H2O t=35.0 c=0.0025) (Uncertain)
InChIKey	LQOLIRLGBULYKD-JKIFEVAISA-N
SMILES	N12[C@@]([H])([C@H](NC(C3=C(C)ON=C3C3=CC=CC=C3Cl)=O)C1=O)SC(C)(C)[C@@H]2C(O)=O

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08
Signal word	Danger
Hazard statements	H317-H334
Precautionary statements	P261-P285-P304+P341-P342+P311-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501

Cloxacillin Chemical Properties,Uses,Production

Description

Cloxacillin induced contact dermatitis in a pharmaceutical factory worker with positive reactions to ampicillin but not to penicillin. The chemical formula of this is 3-o-chlorophenyl-5-methyl-4-isoxazolyl penicillin (Knudsen et al., 1962); this differs from oxacillin only by an additional chlorine atom.

Uses

Cloxacillin is a semisynthetic beta-lactamase resistant penicillin antibiotic with antibacterial activity. It is used to treat a wide variety of bacterial infections.

Manufacturing Process

The reaction between 6-aminopenicillanic acid (6.5 g) and 3-o-chlorophenyl-5- methylisoxazole4-carbonyl chloride (7.66 g) gave the sodium salt of 3-o-chlorophenyl-5-methyl-4-isoxazolylpenicillin（Cloxacillin） (9.98 g) as a pale yellow solid. Colorimetric assay with hydroxylamine against a benzylpenicillin standard indicated a purity of 68%.The 3-o-chlorophenyl-5-methylisoxazole-4-carboxylic acid, from which the acid chloride was prepared, was obtained by hydrolysis of the ester product of the reaction between o-chlorobenzohydroxamic chloride and ethyl acetoacetate in methanolic sodium methoxide. Reaction with thionyl chloride gave the starting material.

World Health Organization (WHO)

Ampicillin and cloxacillin are listed separately in the WHO Model List of Essential Drugs.

Contact allergens

Cloxacillin is a semisynthetic penicillin close to oxacillin. It induced contact dermatitis in a pharmaceutical factory worker with positive reactions to ampicillin, but not to penicillin. In cutaneous drug reactions such as acute generalized exanthematous pustulosis due to amoxicillin, cross-reactivity is frequent to cloxacillin (personal observations).

Side effects

Common side effects include Upset stomach, nausea, vomiting, diarrhea, gas, and mouth sores may occur.

Purification Methods

Purify mandelic acid by Soxhlet extraction with *C6H6 (about 6mL/g) and allow the extract to crystallise. It can also be recrystallised from CHCl3. The S-benzylisothiuronium salt has m 169o (166o) (from H2O). Dry it at room temperature under vacuum. [Beilstein 10 IV 565.]

Cloxacillin Preparation Products And Raw materials

Raw materials

6-Aminopenicillanic acid Ethyl acetoacetate

Preparation Products

Cloxacillin Suppliers

Global( 77)Suppliers

Supplier	Tel	Country	ProdList	Advantage	Inquiry
Medec Dragon Private Limited	+91-9768474716	Maharashtra, India	59	58	Inquiry
Ebenezer Industries		Gujarat, India	96	58	Inquiry
Pharma Affiliates	172-5066494	Haryana, India	6761	58	Inquiry
CLEARSYNTH LABS LTD.	+91-22-45045900	Hyderabad, India	6351	58	Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd	+91-172-5066494	Haryana, India	6773	58	Inquiry
Guangzhou Tosun Pharmaceutical Limited	+8618922120635	China	1000	58	Inquiry
Hebei Mojin Biotechnology Co., Ltd	+86 13288715578 +8613288715578	China	12446	58	Inquiry
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	China	5866	58	Inquiry
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	China	21667	55	Inquiry
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	China	9343	55	Inquiry

Supplier	Advantage
Medec Dragon Private Limited	58
Ebenezer Industries	58
Pharma Affiliates	58
CLEARSYNTH LABS LTD.	58
Pharmaffiliates Analytics and Synthetics P. Ltd	58
Guangzhou Tosun Pharmaceutical Limited	58
Hebei Mojin Biotechnology Co., Ltd	58
Hebei Chuanghai Biotechnology Co,.LTD	58
Henan Tianfu Chemical Co.,Ltd.	55
Hangzhou FandaChem Co.,Ltd.	55

61-72-3(Cloxacillin)Related Search:

Flucloxacillin sodium CLOXACILLIN BENZATHINE,Benzathine cloxacillin Dicloxacillin Sodium cloxacillin monohydrate Flucloxacillin

Cloxacillin-13C4 SodiuM Salt Dicloxacillin sodium Cloxacillin CLOXACILLIN NA OXACILLIN

Penicillin G Cloxacillin sodium sterile Ampicillin Sodium+Cloxacillin Sodium Cloxacillin acid Cloxacillin Sodium Sterile/oral

CLOXACILLIN BENZATHINE USP(CRM STANDARD) Cloxacillin sodium lyophilised ANTI-CLOXACILLIN,ANTI-CLOXACILLIN (INCLUDES BSA CONJUGATE)

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4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(3-(o-chlorophenyl)-s-me 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo- (8CI) 6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido) penicillanic acid 6-(5-Methyl-3-o-chlorophenylisoxazole-4-carboxamido) penicillanic acid 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolylcarboxamido]penicillanic acid Orbenin Extra Dry Cow Cloxacillin (base and/or unspecified salts) (2S,5R,6R)-6-[[[5-Methyl-3-(2-chlorophenyl)-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-1-aza-4-thiabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5β)-6α-[[[3-(2-Chlorophenyl)-5-methylisoxazole-4-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2β-carboxylic acid MCIPC (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-7-keto-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin 3-dimethyl-7-oxo-thyl-4-isoxazolecarboxamido)- 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(3-(o-chlorophenyl)-5-me CLOXACILLIN 6-(((3-(2-chlorophenyl)-5-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicaci 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-o 6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]penicillanicacid brl1621 methocillins methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-,(2s-(2alpha,5alpha,6b xo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid CLOXACILLIN USP/EP/BP Cloxacillin 13C4 CloxacillinQ: What is Cloxacillin Q: What is the CAS Number of Cloxacillin Syntarpen (2S,5R,6R)-6-[[[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid(cloxacillin), Cloxacillin Impurity Oxacillin Impurity 5 (Oxacillin EP Impurity E) 61-72-3 60-72-3 C19H18ClN3O5S C19H16N3ClO5S C19H18CL1N3O5S1