ChemicalBook CAS DataBase List 61-72-3

61-72-3

Name	CLOXACILLIN
CAS	61-72-3
EINECS(EC#)	200-514-7
Molecular Formula	C19H18ClN3O5S
MDL Number	MFCD00242583
Molecular Weight	435.88
MOL File	61-72-3.mol

Synonyms

MCIPC brl1621 Syntarpen CLOXACILLIN methocillins Orbenin Extra Dry Cow Cloxacillin (base and/or unspecified salts) 3-dimethyl-7-oxo-thyl-4-isoxazolecarboxamido)- [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin xo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid 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]penicillanicacid 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolylcarboxamido]penicillanic acid 6-(((3-(2-chlorophenyl)-5-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicaci 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(3-(o-chlorophenyl)-5-me 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(3-(o-chlorophenyl)-s-me methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-,(2s-(2alpha,5alpha,6b 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-o 6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 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) (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 (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-[[[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 (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 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)]-

Chemical 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)
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). less more
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 Data

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
Hazardous Substances Data	61-72-3(Hazardous Substances Data)

Hazard Information

Description

Cloxacillin induced contact dermatitis in a pharmaceutical factory worker with positive reactions to ampicillin but not to penicillin.

Originator

Orbenin,Beecham,UK,1962

Uses

Antibacterial.

Definition

ChEBI: Cloxacillin is a semisynthetic penicillin antibiotic carrying a 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido group at position 6. It has a role as an antibacterial agent and an antibacterial drug. It is a semisynthetic derivative, a penicillin allergen and a penicillin. It is functionally related to an oxacillin. It is a conjugate acid of a cloxacillin(1-).

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-ochlorophenyl-5-methyl-4-isoxazolylpenicillin (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.

Brand name

Allypropymal;Alurate sodium;Aprozal;Isonal;Nervisal;Numal;Somnipron.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

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

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.]

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