Introduction：Basic information about CAS 61-72-3|Cloxacillin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Cloxacillin |
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| CAS Number | 61-72-3 | Molecular Weight | 435.881 |
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| Density | 1.6±0.1 g/cm3 | Boiling Point | 689.7±55.0 °C at 760 mmHg |
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| Molecular Formula | C19H18ClN3O5S | Melting Point | / |
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| MSDS | / | Flash Point | 370.9±31.5 °C |
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Names
| Name | cloxacillin |
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| Synonym | More Synonyms |
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Cloxacillin BiologicalActivity
| Description | Cloxacillin is an orally active antibacterial agent and β-lactamase inhibitor with an IC50 of 0.04 µM. Cloxacillin can suppress the S. aureus-induced inflammatory response by inhibiting the activation of MAPKs, NF-кB and NLRP3-related proteins[1][2][3]. |
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| Related Catalog | Research Areas >>CancerResearch Areas >>InfectionResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Anti-infection >>Bacterial |
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| Target | IC50: 0.04 µM (β-lactamase from wild type A.caviae), 0.3 µM (β-lactamase from mutant A.caviae)[3]. |
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| In Vitro | Cloxacillin (0-2048 µg/mL; 20-24 h) shows good antibacterial activity for S. aureus 8325-4 and DU1090 with MIC values both of 0.125 µg/mL[1]. Cloxacillin (0.015625 μg/mL; 6 h) inhibits the hemolytic activity of Hlα in vitro, and this inhibition is not only more pronounced when combined with TZ and TZ, but also suppresses the inflammatory response by inhibiting the activation of MAPKs, NF-кB and NLRP3-related proteins[1]. Cell Viability Assay[1] Cell Line: S. aureus 8325-4, S. aureus DU1090 (an Hlα-deleted strain) Concentration: 0-2048 µg/mL Incubation Time: 20-24 h Result: Inhibited S. aureus 8325-4 and DU1090 with MIC values both of 0.125 µg/mL. Western Blot Analysis[1] Cell Line: S. aureus 8325-4 Concentration: 0.015625 μg/mL (combines with Thioridazine (TZ, 0.25 μg/mL) and Tetracycline (TC, 0.03125 μg/mL)). Incubation Time: 6 h Result: Inhibited the expression of Hlα and the inhibition was more pronounced when combined with TZ and TC. Western Blot Analysis[1] Cell Line: RAW264.7 cells (exposes to S. aureus 8325-4/DU1090 or pure Hlα) Concentration: 0.015625 μg/mL (combines with TZ (0.25 μg/mL) and TC (0.03125 μg/mL)). Incubation Time: 6 h Result: Inhibited the activation of MAPKs, NF-кB and NLRP3-related proteins thereby inhibiting the inflammatory response when combined with TC and TZ. |
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| In Vivo | Cloxacillin (1.6125 mg/kg; s.c.; 12-h intervals for 72 h) protects mice from S. aureus peritonitis in vivo when combines with Thioridazine and Tetracycline[1]. Cloxacillin (7.5 mg/per; i.p.; twice daily from day 3 for 3 days) develops less severe synovitis and reduces bone erosions when combines with anti-IL-15 antibodies[3]. Animal Model: Female BALB/c mice (6-week-old; peritonitis model)[1]. Dosage: 1.6125 mg/kg (combines with TC (3.125 mg/kg) and TZ (25 mg/kg)) Administration: Subcutaneous injection; 12-h intervals for 72 h. Result: Reduced the degree of inflammatory cell infiltration in the mouse lung tissue and alveolar structures tended to be normal. Significantly reduced the pathological changes in spleen and liver tissue, as well as decreased the CFU counts of S. aureus in the peritoneal cavity. Animal Model: Female wildtype C57BL/6 mice (8-week-old; systemic S. aureus-induced arthritis model) Dosage: 7.5 mg/per (combines with 25 µg/per anti-IL-15 antibodies) Administration: Intraperitoneal injection; twice daily from day 3 (after bacterial inoculation) and stopped at day 6. Result: Showed activities of reducing severe synovitis and bone erosions when combined with anti-IL-15 antibodies. |
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| References | [1]. Zhou H, et al. The combination of cloxacillin, thioridazine and tetracycline protects mice against Staphylococcus aureus peritonitis by inhibiting α-Hemolysin-induced MAPK/NF-κB/NLRP3 activation. Int J Biol Macromol. 2022 Feb 15;198:1-10. [2]. Bergmann B, et al. Antibiotics with Interleukin-15 Inhibition Reduce Joint Inflammation and Bone Erosions but Not Cartilage Destruction in Staphylococcus aureus-Induced Arthritis. Infect Immun. 2018 Apr 23;86(5):e00960-17. [3]. Lupiola-Gómez PA, et al. Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics. Can J Microbiol. 2003 Mar;49(3):207-15. |
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Chemical & Physical Properties
| Density | 1.6±0.1 g/cm3 |
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| Boiling Point | 689.7±55.0 °C at 760 mmHg |
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| Molecular Formula | C19H18ClN3O5S |
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| Molecular Weight | 435.881 |
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| Flash Point | 370.9±31.5 °C |
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| Exact Mass | 435.065582 |
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| PSA | 138.04000 |
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| LogP | 2.53 |
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| Vapour Pressure | 0.0±2.3 mmHg at 25°C |
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| Index of Refraction | 1.685 |
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| InChIKey | LQOLIRLGBULYKD-JKIFEVAISA-N |
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| SMILES | Cc1onc(-c2ccccc2Cl)c1C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- XH8720000
- CHEMICAL NAME :
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-S-methyl-4- isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
- CAS REGISTRY NUMBER :
- 61-72-3
- LAST UPDATED :
- 199709
- DATA ITEMS CITED :
- 6
- MOLECULAR FORMULA :
- C19-H18-Cl-N3-O5-S
- MOLECULAR WEIGHT :
- 435.91
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 429 mg/kg/10D-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - interstitial nephritis Blood - eosinophilia
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 200 mg/kg/5D-I
- TOXIC EFFECTS :
- Liver - jaundice, other or unclassified Liver - liver function tests impaired
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 5600 mg/kg/5W-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - interstitial nephritis Nutritional and Gross Metabolic - body temperature increase
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intracerebral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 8100 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 7 gm/kg/4W-I
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - changes in lung weight Liver - changes in liver weight Endocrine - hypoglycemia
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Human Lymphocyte
- DOSE/DURATION :
- 400 mg/L
- REFERENCE :
- BSIBAC Bolletino della Societe Italiana di Biologia Sperimentale. (Casa Editrice Idelson, Via A. de Gasperi, 55, 80133 Naples, Italy) V.2- 1927- Volume(issue)/page/year: 60,2143,1984
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Synonyms
| xo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid |
| Cloxacillin (base and/or unspecified salts) |
| (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 |
| [5-Methyl-3-(o-chlorophenyl)-4-isoxazolyl]penicillin |
| MFCD00150735 |
| [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin |
| methocillins |
| [2S-(2a,5a,6b)]-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 |
| (2S,5R,6R)-6-({[3-(2-Chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| 3-dimethyl-7-oxo-thyl-4-isoxazolecarboxamido) |
| Orbenin Extra Dry Cow |
| brl1621 |
| 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)- |
| cloxacillin |
| Syntarpen |
| EINECS 200-514-7 |
| MCIPC |
| 6-<5-Methyl-3-(2-chlor-phenyl)-isoxazolyl-(4)-formamino>-penicillansaeure |
