Basic information
- CAS
1173-88-2- Standard SMILES
Cc1onc(-c2ccccc2)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O- InChIKey
UWYHMGVUTGAWSP-JKIFEVAISA-N- Molecular formula
- C19H19N3O5S
- Average molar mass
- 401.4 g/mol
- Monoisotopic mass
- 401.10454189
Overview
Oxacillin is a penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6beta. It has a role as an antibacterial agent and an antibacterial drug. It is a conjugate acid of an oxacillin(1-).
Names & identifiers
- Preferred name
- Oxacillin
- IUPAC
- (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- OXACILLIN
- Molecular formula
- C19H19N3O5S
- Molecular weight
- 401.44
Names & synonyms
oxacillin66-79-5OxazocillinOxazocillineOxacilinaOxacillineOxacillinum5-Methyl-3-phenyl-4-isoxazolyl-penicillin(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidResistopenOxabel
Show more names
OxazinaBactocilPenstaphoOXACILLIN USP/EP/BPAnnamycin Impurity 100UWYHMGVUTGAWSP-JKIFEVAISA-NOxacillinQ: What is Oxacillin Q: What is the CAS Number of Oxacillin[2S-(2,5,6)]-3,3-dimethyl-6-(methyl-3-phenylisoxaz-4-ole-carboxamide-7-oxy-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(2S,5R,6R)-3,3-Dimethyl-6-[(5-methyl-3-phenylisoxazol-4-yl)carbonylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CHEBI:7809UH95VD7V76Staphcillin V(5-methyl-3-phenyl-4-isoxazolyl)penicillin6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acidDTXSID8023397(2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 680
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics (Penicillins)
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP2.4
Solubility8.62e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Access group antibiotics
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Physical DescriptionSolid
Dissociation Constants2.72
Collision Cross Section
195.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
193.63 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187.73 Ų [M+H]+
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (40%): 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 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety Information
IMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, monosodium salt, [2S-(2.alpha.,5.alpha.,6.beta.)]-: Environment tier I assessment
IMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, [2S-(2.alpha.,5.alpha.,6.beta.)]-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (40%)
Toxicology
Hepatotoxicity
Oxacillin has been linked to two forms of hepatotoxicity, first an acute andtransient elevation in serum aminotransferase levels occurring with highdoses of intravenous therapy; and second, a more prolonged, usuallycholestatic, idiosyncratic liver injury that is similar to thehepatotoxicity of other second-generation penicillins such as dicloxacillin,flucloxacillin, and nafcillin.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01CF02
Protein Binding94.2 +/- 2.1% (binds to serum protein, mainly albumin)
Pharmacodynamics
Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Mechanism of Action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Oxacillin interferes with an autolysin inhibitor.
Biological Half-Life20 to 30 minutes
FDA Pharmacological Classification
UH95VD7V76
OXACILLIN
Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial
Chemical Structure [CS] - Penicillins
Oxacillin is a Penicillin-class Antibacterial.
OXACILLIN
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Related reactions
0 records
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Compound notes
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