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| CAS No.: | 642-78-4 |
|---|---|
| Name: | Sodium cloxacillin |
| Molecular Structure: | |
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| Formula: | C19H18 Cl N3 O5 S . Na |
| Molecular Weight: | 457.87 |
| Synonyms: | 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-,monosodium salt (8CI); 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-,monosodium salt, (2S,5R,6R)- (9CI);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-,monosodium salt, [2S-(2a,5a,6b)]-;3-(o-Chlorophenyl)-5-methyl-4-isoxazolylpenicillin sodium salt; Ankerbin;Austrastaph; BRL 1621 sodium salt; Cloxacillin sodium; Cloxacillin sodium salt;Cloxapen; Ekvacillin; Gelstaph; Monosodium cloxacillin; Orbenin; Orbeninsodium; Prevencilina P; Prostaphilin A; Prostaphlin A; Sodium3-(O-chlorophenyl)-5-methyl-4-isoxazolylpenicillin; Sodium cloxacillin; Sodiumorbenin; Sodium syntarpen; Staphybiotic; Syntarpen sodium salt; Tegopen |
| EINECS: | 211-390-9 |
| Melting Point: | 170°C |
| Solubility: | Toxicity da">
50 mg/ml
Stability
Toxicology
Toxicity da |
| Appearance: | white powder |
| Hazard Symbols: | Xn |
| Risk Codes: | 36/37/38-42/43 |
| Safety: | Moderately toxic by intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of Cl−, NOx, SOx, Na2O. |
| PSA: | 140.87000 |
| LogP: | 1.54280 |
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Chemistry
Molecular Structure of Cloxacillin sodium (CAS NO.642-78-4):
EINECS: 211-390-9
IUPAC Name: Sodium (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-carboxylate
Molecular Formula: C19H17ClN3NaO5S
Molecular Weight: 457.863150 g/mol
Appearance: white crystalline powder
H-Bond Donor: 1
H-Bond Acceptor: 6
Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]
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-].[Na+]
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
Flash Point: 370.9 °C
Enthalpy of Vaporization: 106.17 kJ/mol
Boiling Point: 689.7 °C at 760 mmHg
Vapour Pressure: 5.65E-20 mmHg at 25 °C
Melting Point: 170 °C
Storage Temp.: 2-8 °C
Toxicity Data With Reference
| 1. | orl-rat LD50:5 g/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 2. | ipr-rat LD50:1350 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 15 (1965),322. | ||
| 3. | scu-rat LD50:4200 mg/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 4. | ivn-rat LD50:1660 mg/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 5. | orl-mus LD50:5 g/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 6. | ipr-mus LD50:1170 mg/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 7. | scu-mus LD50:1500 mg/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),232. | ||
| 8. | ivn-mus LD50:916 mg/kg | FATOAO Farmakologiya i Toksikologiya (Moscow). 31 (1968),232. | ||
| 9. | ims-mus LD50:1220 mg/kg | NIIRDN |
Safety Profile
Safety Information of Cloxacillin sodium (CAS NO.642-78-4):
Hazard Codes: Xn 
Risk Statements: 36/37/38-42/43
R36/37/38:Irritating to eyes, respiratory system and skin
R42/43:May cause sensitization by inhalation and skin contact
Safety Statements: 26-36-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
S22:Do not breathe dust
WGK Germany: 2
RTECS: XH8920000
Moderately toxic by intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of Cl−, NOx, SOx, Na2O.
Specification
Cloxacillin sodium with CAS registry number of 642-78-4 is a semisynthetic antibiotic in the same class as penicillin, also called for 3-o-Chlorophenyl-5-methyl-4-isoxazolylpenicillin sodium ; Ankerbin ; Austrastaph ; BRL 1621 sodium salt ; BRL-1621 sodium salt ; Cloxacillin sodium anhydrous ; Cloxapen ; Ekvacillin ; Gelstaph ; Monosodium cloxacillin ; Orbenin sodium ; Prevencilina P ; Prostaphilin A ; Prostaphlin A ; Sodium 3-(o-chlorophenyl)-5-methyl-4-isoxazolylpenicillin ; Sodium cloxacillin ; Sodium orbenin ; Sodium syntarpen ; Staphybiotic ; Syntarpen sodium salt ; Tegopen ; UNII-MWQ645MKMF ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)- ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta))- ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-, monosodium salt . Cloxacillin was discovered and developed by Beecham. It is sold under a number of trade names such as Cloxapen and Orbenin. It is used against staphylococci but has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions. It has been suggested that increased use of cloxacillin may permit reduced use of vancomycin.