Cloxacillin

Base Information

• Chemical Name: Cloxacillin
• CAS No.: 61-72-3
• Deprecated CAS: 50763-55-8,8056-79-9
• Molecular Formula: C₁₉H₁₈ClN₃O₅S
• Molecular Weight: 435.888
• European Community (EC) Number: 211-390-9,200-514-7,629-588-2
• UNII: O6X5QGC2VB
• DSSTox Substance ID: DTXSID5022853
• Nikkaji Number: J4.818F
• Wikipedia: Cloxacillin
• Wikidata: Q422219
• NCI Thesaurus Code: C61688
• Metabolomics Workbench ID: 43369
• ChEMBL ID: CHEMBL891
• Mol file: 61-72-3.mol

Synonyms:Chloroxacillin;Cloxacillin;Cloxacillin Sodium;Cloxacillin, Sodium;Sodium Cloxacillin;Sodium, Cloxacillin;Syntarpen;Tegopen

Chemical Property of Cloxacillin

Chemical Property:

• Appearance/Colour: white to off white free flowing crystalline powder
• Vapor Pressure: 5.65E-20mmHg at 25°C
• Refractive Index: 1.685
• Boiling Point: 689.7 °C at 760 mmHg
• PKA: pKa 2.70±0.07(H2O t=35.0 c=0.0025) (Uncertain)
• Flash Point: 370.9 °C
• PSA: 138.04000
• Density: 1.56 g/cm³
• LogP: 2.87750
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 435.0655696
• Heavy Atom Count: 29
• Complexity: 722

Purity/Quality:

99% ^*data from raw suppliers

Cloxacillin 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
• Isomeric SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
• Recent ClinicalTrials: Non-inferiority Trial Comparing Cloxacillin vs Cefazolin in Methicillin-susceptible Staphylococcus Aureus Bacteremia
• Recent EU Clinical Trials: Accelerated treatment of infectious endocarditis
• 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. It comes as oral capsules of 250 and 500 mg, and in an injectable formulation of 250 mg, 500 mg, and 2 g. It is also available as an oral solution of 120 mg/5 ml.
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Cloxacillin

There total 6 articles about Cloxacillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-chloro benzaldehyde oxime (3717-28-0) → cloxacillin (61-72-3,7060-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Cl₂

2: (i) Na, MeOH, (ii) /BRN= 2502600/

3: aq. KOH / ethanol

4: SOCl₂

5: aq. NaOH, isobutyl methyl ketone

With potassium hydroxide; sodium hydroxide; thionyl chloride; chlorine; 4-methyl-2-pentanone; In ethanol;

DOI:10.1039/jr9630005838

Reference yield:

methyl 3-(2'-chlorophenyl)-5-methylisoxazole-4-carboxylate (4357-94-2) → cloxacillin (61-72-3,7060-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. KOH / ethanol

2: SOCl₂

3: aq. NaOH, isobutyl methyl ketone

With potassium hydroxide; sodium hydroxide; thionyl chloride; 4-methyl-2-pentanone; In ethanol;

DOI:10.1039/jr9630005838

Reference yield:

2-chloro-N-hydroxybenzimidoyl chloride (29568-74-9) → cloxacillin (61-72-3,7060-81-3)

Guidance literature:

Multi-step reaction with 4 steps

1: (i) Na, MeOH, (ii) /BRN= 2502600/

2: aq. KOH / ethanol

3: SOCl₂

4: aq. NaOH, isobutyl methyl ketone

With potassium hydroxide; sodium hydroxide; thionyl chloride; 4-methyl-2-pentanone; In ethanol;

DOI:10.1039/jr9630005838

upstream raw materials:

6-Aminopenicillanic Acid

3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride

2-chloro benzaldehyde oxime

3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid

Downstream raw materials:

cloxacillin methyl ester

Cloxacillin S-sulphoxide

Cloxacillin S-sulphoxide methylester

Refernces

• 1、 -. "Method of using deuterated calcium channel blockers". . . Retrieved 2008/06/13.