CAS 7081-44-9|CAS 642-78-4|5-Methyl-3-(o-chlorophenyl)-4-isoxazolyl] pencillin|CLOXACILLIN SODIUM SALT|sodium (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia...

General Information

Structure

Molecular Formula

C₁₉H₁₇ClN₃NaO₅S

Molecular Mass

457.86315

Exact Mass

457.04751362

Charge

InChI

InChI=1S/C19H18ClN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1

InChIKey

SCLZRKVZRBKZCR-SLINCCQESA-M

Canonic Smiles

[O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl.[Na+]

Isomeric Smiles

[Na+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)c3c(onc3c3ccccc3Cl)C)[C@H]2SC1(C)C

Calculated Properties

JChem

Acid pKa

3.7497845

H Acceptors

H Donor

LogD (pH = 5.5)

0.55099535

LogD (pH = 7.4)

-0.9830029

Log P

2.3017397

Molar Refractivity

117.4742

Polarizability

41.823692

Polar Surface Area

115.57

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

5-Methyl-3-(o-chlorophenyl)-4-isoxazolyl] pencillinCLOXACILLIN SODIUM SALTCloxacillin sodium saltOrbenin Sodium(2S,5R,6R)-6-[[[3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium SaltEkvacillin6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Monosodium SaltAustrastaphProstaphilin ASyntarpen Sodium SaltGelstaphPrevencilina PProstaphlin ABRL 1621 Sodium SaltTegopenSodium 3-(O-Chlorophenyl)-5-methyl-4-isoxazolylpenicillinStaphybiotic3-(o-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin Sodium SaltOrbeninAnkerbinCloxapenSodium Cloxacillin

IUPAC name

sodium (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

IUPAC Traditional name

sodium cloxacillin(1-)

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem CID

PubChem SID

Beilstein Number

MDL Number

Registration numbers

Properties

Safety Information

RTECS

XH8920000

XH8750000

Storage Condition

2-8°C

MSDS Link

Download link

German water hazard class

Storage Temperature

2-8°C

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

Certificate of Analysis

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Purity

≥97.0% (HPLC)

Impurities

≤5% water

Empirical Formula (Hill Notation)

C19H17ClN3NaO5S

Derivatives & analogs of Natural Compounds

Na+

Physical Property

Solubility

H2O: soluble50 mg/mL, clear, colorless

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150702

Sodium Salt
White micro-crystalline powder
pH 6.0-7.5
Antibacterial

Sigma Aldrich

27555

Biochem/physiol Actions
Cloxacillin interferes with the last stage of bacterial cell wall synthesis by binding to penicillin-binding proteins. This inhibits the necessary cross-linking and leads to autolysis of the bacteria by autolysins.
Application
Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is used against staphylococci that produce β-lactamase. It is used to study the role of pH in antibiotic effectiveness1 and how oxgall, acid, and hydrogen peroxide stress effects the susceptibility of Bifidobacteria2.

TRC

C587460

Cloxacillin is an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lactamase due to its inhibitory effects on beta-lactamase binding.

Molecule Details

References

PubChem Literature

From Data Sources

• Gibbs, D.L. et al.: Curr. Microbiol., 2, 239 (1979)

• Dmitrova, D. et al.: Farmat., 48, 28 (1979)

• CRaven, N. et al.: Res. Vet. Sci., 29, 57 (1979)

References

Bioactivity

PubChem BioAssay

Bioactivity