HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cloxacillin
Syntarpen · MCIPC · brl1621 · CLOXACILLIN · methocillins · Cloxacillin 13C4 · Cloxacilline-13c4 · Cloxacillin Impurity
Identifiers & Physical Properties
| CAS No. | 61-72-3 |
|---|---|
| Molecular formula | C19H18ClN3O5S |
| Average molar mass | 435.9 g/mol |
| Monoisotopic mass | 435.06556936 g/mol |
| SMILES | Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O |
| InChIKey | LQOLIRLGBULYKD-JKIFEVAISA-N |
| PubChem CID | 6098 |
| ChEMBL | CHEMBL891 |
| ChEBI | CHEBI:49566 |
| EC No. | 200-514-7 |
| DTXSID | DTXSID5022853 |
Chemical & Physical Properties
| XLogP | 2.4 |
|---|---|
| Topological polar surface area | 138 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 4 |
| Heavy atoms | 29 |
| Formal charge | 0 |
| Complexity | 722 |
| Drugs | Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Penicillins)Pharmaceuticals -> Listed in ZINC15 |
| LogP (partition coefficient) | LogP = 2.4432.86 |
| Solubility | WHITE, CRYSTALLINE POWDERSOL IN ALCOHOLSLIGHTLY SOL IN ACETONE, CHLOROFORMAQ SOLN IS ALKALINEDECOMP BETWEEN 170 °C & 173 °CODORLESSBITTER TASTE /MONOHYDRATE/5.32e-02 g/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillinsAccess group antibiotics |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| Physical Description | Solid |
| Stability/Shelf Life | CLOXACILLIN IS RELATIVELY STABLE IN GASTRIC ACIDSTABLE IN LIGHTSLIGHTLY HYGROSCOPIC. /MONOHYDRATE/AQ SOLN FOR INJECTIONS ARE STABLE FOR AT LEAST 3 DAYS IF REFRIGERATED.Penicillinase-resistant penicillins are generally stable in the dry state @ room temp for several yrhowever, the drugs are stable only for short periods of time in soln unless frozen. Stability of the drugs is pH and temp dependent. Methicillin, nafcillin, and oxacillin are generally stable @ pH 5-8. /Penicillinase-resistant penicillins/ |
| Dissociation Constants | 2.78 |
| Collision Cross Section | 197.93 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]193.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]200.94 Ų [M-H]- |
| Other Experimental Properties | Microcryst powder, dec 170 °C, specific optical rotation +163 deg @ 20 °C/DpH 6.0-7.5. Soluble in water, methanol, ethanol, pyridine, ethylene glycol /Sodium monohydrate/ |
| Boiling point | 689.7±55.0 °C(Predicted) |
| Density | 1.2954 (rough estimate) |
| Refractive index | 1.6100 (estimate) |
| pKa (acidity coefficient) | pKa 2.70±0.07(H2O t=35.0 c=0.0025) (Uncertain) |
| InChIKey | LQOLIRLGBULYKD-JKIFEVAISA-N |
| SMILES | N12[C@@]([H])([C@H](NC(C3=C(C)ON=C3C3=CC=CC=C3Cl)=O)C1=O)SC(C)(C)[C@@H]2C(O)=O |
| FDA 21 CFR | 556.165 |
| FDA UNII | O6X5QGC2VB |
| ATC code | J01CF02 |
| GHS pictogram | GHS08 |
| Signal word | Danger |
| GHS hazard statements | H317-H334 |
| GHS precautionary statements | P261-P285-P304+P341-P342+P311-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501 |
| Hazardous substances data | 61-72-3(Hazardous Substances Data) |
Safety & Regulations
| GHS classification | DangerH315 (85.4%): Causes skin irritation [Warning Skin corrosion/irritation]P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| Other safety information | IMAP assessments - 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-(2.alpha.,5.alpha.,6.beta.)]-: Environment tier I assessment |
| FDA requirements | A tolerance is established for negligible residues of cloxacillin in the uncooked edible tissues of cattle and in milk.Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Hazard Classes and Categories | Skin Sens. 1 (100%)Skin Irrit. 2 (85.4%) |
| Storage conditions | Commercially available cloxacillin sodium capsules and powder for oral solution should be stored in tight containers at a temperature less than 40 °C, preferably between 15-30 °C. Following reconstitution, cloxacillin sodium oral solutions should be stored at 2-8 °C, and any unused soln should be discarded after 14 days. If stored at room temperature, the oral soln is stable for 3 days. /Cloxacillin sodium/ |
| Disposal methods | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Allowable Tolerances | A tolerance of 0.01 ppm is established for negligible residues of cloxacillin in the uncooked edible tissues of cattle and in milk. |
| Interactions | PENICILLINS SHOULD NOT BE ROUTINELY ADMIN WITH ERYTHROMYCIN. /PENICILLINS/OTHER PENICILLIN ANALOGS SHOWN TO INTERACT WITH PROBENECID ARE...CLOXACILLIN...TETRACYCLINE MAY ANTAGONIZE BACTERICIDAL EFFECT OF PENICILLIN... /PENICILLINS/Concurrent use of other hepatotoxic medications with cloxacillin ... may increase the potential for hepatotoxicity.For more Interactions (Complete) data for CLOXACILLIN (9 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | RASH & URTICARIA ARE PRINCIPAL ALLERGIC MANIFESTATIONS. NOT ALL PT ALLERGIC TO PENICILLIN G ARE SENSITIVE TO CLOXACILLIN, BUT CROSS-SENSITIZATION DOES OCCUR. CLOXACILLIN MAY ALSO CAUSE OCCASIONAL NAUSEA, VOMITING, ABDOMINAL DISCOMFORT, EPIGASTRIC FULLNESS, OR DIARRHEA. SUPERINFECTIONS OCCASIONALLY OCCUR. /MONOHYDRATE/SKIN RASHES OF ALL TYPES HAVE BEEN OBSERVED WHEN PENICILLIN SENSITIZATION HAS OCCURRED. ...VESICULAR, & BULLOUS ERUPTIONS MAY DEVELOP. PURPURIC LESIONS ARE UNCOMMON & ARE USUALLY RESULT OF VASCULITISTHROMBOPENIC PURPURA MAY OCCUR VERY RARELY. HENOCH-SCHOENLEIN PURPURA WITH RENAL INVOLVEMENT HAS BEEN RARE... /PENICILLINS/CONTACT DERMATITIS IS OBSERVED...IN PHARMACISTS, NURSES, & PHYSICIANS WHO PREPARE PENICILLIN SOLN... MORE SEVERE REACTIONS INVOLVING SKIN ARE EXFOLIATIVE DERMATITIS & EXUDATIVE ERYTHEMA MULTIFORME OF EITHER ERYTHEMATOPAPULAR OR VESICULOBULLOUS TYPE...CONSTITUTE CHARACTERISTIC STEVENS-JOHNSON SYNDROME. /PENICILLINS/VARIETY OF ORAL LESIONS HAVE RESULTED FROM SENSITIZATION TO PENICILLIN. AMONG THESE ARE ACUTE GLOSSITIS, SEVERE STOMATITIS WITH LOSS OF BUCCAL MUCOUS MEMBRANES, FURRED TONGUE, BLACK OR BROWN TONGUE, & CHEILOSIS. /PENICILLINS/For more Human Toxicity Excerpts (Complete) data for CLOXACILLIN (42 total), please visit the HSDB record page. |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)cloxacillinDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES /TO MICE, RATS, RABBITS/. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK... /PENICILLINS/IN HAMSTERS THE DRUG IS SOMEWHAT MORE TOXIC BY ORAL THAN BY SC ROUTE WHEN OBSERVED FOR 14 DAYS AFTER SINGLE DOSES. ... PERHAPS SENSITIVITY OF GUINEA PIGS IS RELATED TO EFFECTS ON INTESTINAL MICROFLORA. /PENICILLINS/...ENCEPHALOPATHY WITH MUSCULAR HYPERIRRITABILITY, MYOCLONUS, VISUAL & AUDITORY HALLUCINATIONS & GENERAL CONVULSIONS. ...ELICITED IN RATS & CATS WITH DOSES TO 3-4 MILLION UNITS/KG, & SYNDROME CAN BE REVERSED BY PENICILLINASE. /PENICILLINS/DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES /TO CATS & DOGS/. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK...ALSO TRUE FOR GUINEA PIGS EXCEPT THAT A LATE...GRADUALLY DEVELOPING TOXEMIA KILLED ALL SURVIVORS OF ACUTE RESPONSE. /PENICILLINS/ |
| Antidote and Emergency Treatment | 1. ESTABLISHMENT OF RESP & CREATION OF ARTIFICIAL AIRWAY... CHECK ADEQUACY OF TIDAL VOL... 2. ACUTE TOXICITY: HYPERSENSITIVITY REACTION. DRUG SHOULD BE IMMEDIATELY DISCONTINUED & PT OBSERVED FOR POSSIBILITY OF ANAPHYLACTIC SHOCK. ... 3. CHRONIC TOXICITY: DISCONTINUE USE OF DRUG. /PENICILLINS/4. PREVENTION OF ABSORPTION: A. EMESIS SHOULD BE INITIATED UNLESS PT IS COMATOSE, CONVULSING OR HAS LOST GAG REFLEX. B. ...ENDOTRACHEAL INTUBATION SHOULD PRECEDE GASTRIC LAVAGE WITH LARGE BORE TUBE. C. ACTIVATED CHARCOAL... D. SODIUM OR MAGNESIUM SULFATE...AS CATHARTIC... /PENICILLINS/ |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Non-Human Toxicity Values | LD50 MOUSE ORAL 5.0 G/KG |
| Signal word | Danger |
| GHS pictogram | GHS08 |
| GHS hazard statements | H317-H334 |
| GHS precautionary statements | P261-P285-P304+P341-P342+P311-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501 |
| Hazardous substances data | 61-72-3(Hazardous Substances Data) |
Applications & Uses
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.
Uses
Cloxacillin is a semisynthetic beta-lactamase resistant penicillin antibiotic with antibacterial activity. It is used to treat a wide variety of bacterial infections.