| Identification | Back Directory | [Name]
CLOXACILLIN | [CAS]
61-72-3 | [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)]- | [EINECS(EC#)]
200-514-7 | [Molecular Formula]
C19H18ClN3O5S | [MDL Number]
MFCD00242583 | [MOL File]
61-72-3.mol | [Molecular Weight]
435.88 |
| Chemical Properties | Back Directory | [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). | [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 |
| Hazard Information | Back Directory | [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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