Cloxacillin(1-)

Base Information

• Chemical Name: Cloxacillin(1-)
• CAS No.: 642-78-4
• Molecular Formula: C19H18 Cl N3 O5 S . Na
• Molecular Weight: 457.87
• Hs Code.: 2941109900
• European Community (EC) Number: 211-390-9
• Wikidata: Q27122554
• NCI Thesaurus Code: C47460
• Mol file: 642-78-4.mol

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

Chemical Property of Cloxacillin(1-)

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 170°C
• PSA: 140.87000
• LogP: 1.54280
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in water
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 434.0577445
• Heavy Atom Count: 29
• Complexity: 716

Purity/Quality:

95% ^*data from raw suppliers

4-Acetyloxy-N-despropyl Ropivacaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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 EU Clinical Trials: Short-course antibiotic regimen compared to conventional antibiotic treatment for gram-positive cocci infective endocarditis: randomized clinical trial
• Description: Cloxacillin is a β-lactam antibiotic and a derivative of oxacillin . It is active against clinical isolates of the Gram-positive bacteria S. aureus and S. epidermidis (MICs = 0.004-0.4 and 0.1-0.8 μg/ml, respectively) but not 34 Gram-negative bacteria (MICs = >128 μg/ml for all). Cloxacillin binds to S. aureus penicillin-binding protein 1 (PBP1), PBP2, PBP3, and PBP4 (IC50s = 0.04, 0.12, 0.21, and 2.5 μg/ml, respectively). It also binds to recombinant type Ib penicillinase, as well as P. vulgaris and C. freundii cephalosporinase (Kis = 15, 0.27, and 0.027 μM, respectively). Cloxacillin decreases the number of staphylococci in the mammary gland in a mouse model of acute, but not chronic, mastitis induced by Staphylococcus infection.
• Uses: Cloxacillin-13C4 SodiuM Salt 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. Cloxacillin-13C4 SodiuM Salt, an antibiotic that belongs to the group of the isoxazolylpenicillins. Cloxacillin is used to treat infections caused by species of staphylococci that produce beta-lac tamase due to its inhibitory effects on beta-lactamase binding. Labelled S-Form of Dropropizine. Cough suppressive phenylpiperazine derivative. Antitussive.
• Therapeutic Function: Antibacterial

Technology Process of Cloxacillin(1-)

There total 3 articles about Cloxacillin(1-) 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:

6-Aminopenicillanic Acid (551-16-6) + 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride (25629-50-9) → cloxacillin sodium (642-78-4)

Guidance literature:

With ammonium hydroxide; In ethyl acetate; pH=2 - 9;

Reference yield:

2-chloro-benzaldehyde (89-98-5) → cloxacillin sodium (642-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydroxylamine sulfate / methanol / 1 h / 20 - 40 °C

1.2: 24 h / 0 - 20 °C / pH ~ 9.5 / Inert atmosphere

1.3: pH ~ 7 - 7.5

2.1: phosphorus pentachloride / toluene

3.1: ammonium hydroxide / ethyl acetate / pH 2 - 9

With ammonium hydroxide; phosphorus pentachloride; hydroxylamine sulfate; In methanol; ethyl acetate; toluene;

Reference yield:

3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid (23598-72-3) → cloxacillin sodium (642-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus pentachloride / toluene

2: ammonium hydroxide / ethyl acetate / pH 2 - 9

With ammonium hydroxide; phosphorus pentachloride; In ethyl acetate; toluene;

upstream raw materials:

2-chloro-benzaldehyde

6-Aminopenicillanic Acid

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

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

Downstream raw materials:

(3S,5R,6R)-benzyl 6-[3'-(o-chlorophenyl)-5'-methyl-4'-isoxazolyl]carbonylamino penicillinate

C₂₂H₂₂ClN₃O₇S

<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-6-<<3-(2-chlorophenyl)-5-methyl-4-isoxazolyl>carboxamido>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-6-<<3-(2-chlorophenyl)-5-methyl-4-isoxazolyl>carboxamido>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Refernces