基本情報
- CAS
1173-88-2- 標準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- 分子式
- C19H19N3O5S
- 平均分子量
- 401.4 g/mol
- 単同位体質量
- 401.10454189
概要
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-).
名称と識別子
- 優先名称
- 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
- 現地名
- オキサシリン
- 英語名
- OXACILLIN
- 分子式
- C19H19N3O5S
- 分子量
- 401.44
名称と別名
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
名称をさらに表示
MPI-ペニシリン(2S,5R,6R)-3,3-ジメチル-6-[(5-メチル-3-フェニルイソオキサゾール-4-イル)カルボニルアミノ]-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボン酸(2S,5β)-3,3-ジメチル-6α-[[(5-メチル-3-フェニル-4-イソオキサゾリル)カルボニル]アミノ]-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2β-カルボン酸オキサゾシリン6α-[[(5-メチル-3-フェニル-4-イソオキサゾリル)カルボニル]アミノ]ペニシラン酸オキシリンペンスタホミクロペニンオキサシリンオキサメートオキペンオキサジナバクトシル６（５メチル３フェニルイソキサゾル４イルカルボキサミド）ペニシラン酸(2S,5R,6R)-3,3-ジメチル-6-(5-メチル-3-フェニル-1,2-オキサゾール-4-アミド)-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン-2-カルボン酸
物性
構造計算による物性
- XLogP
- 2.4
- 極性表面積
- 138 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 7
- 回転可能結合数
- 4
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 680
実験および物理化学的性質
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]+
物理化学的性質
- 融点
- 188 °C · 188 °C
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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%)
毒性情報
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)
oxacillin
DILI Positive
Intravenous
DOI:10.1016/j.drudis.2019.09.022
化学と産業
薬理情報
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.
Absorption, Distribution and Excretion
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