セフチゾキシム

Ceftizoxime

HCID 6533629
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基本情報

CAS
68401-81-0
標準SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=CCS[C@H]12)c1csc(N)n1
InChIKey
NNULBSISHYWZJU-LLKWHZGFSA-N
分子式
C13H13N5O5S2
平均分子量
383.4 g/mol
単同位体質量
383.03581052

概要

Ceftizoxime is a parenteral third-generation cephalosporin, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position. It has a role as an antibacterial drug. It is a conjugate acid of a ceftizoxime(1-).

名称と識別子

優先名称
Ceftizoxime
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
現地名
セフチゾキシム
英語名
Ceftizoxime
分子式
C13H13N5O5S2
分子量
383.4

名称と別名

ceftizoxime68401-81-0CeftizoximaCeftizoximumFK-749(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidsyn-7-(2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acidC43C467DPECHEBI:553473ceftizoximum alapivoxilumDTXSID5022772SKF 88373
名称をさらに表示
(7R)-7β-[2-(2-アミノ-4-チアゾリル)-2-(メトキシイミノ)アセチルアミノ]セファム-3-エン-4-カルボン酸セフィゾックスセフチックス(7R)-7-[[2-(2-アミノチアゾール-4-イル)-2-(メトキシイミノ)-1-オキソエチル]アミノ]セファム-3-エン-4-カルボン酸セフチソミンエポセリン(6R,7R)-7α-[2-(2-イミノ-4-チアゾリン-4-イル)-2-[(Z)-メトキシイミノ]アセチルアミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸(6R,7R)-7-[(Z)-2-(2-アミノ-4-チアゾリル)-2-メトキシイミノアセチルアミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸CZX【セフチゾキシム】セフチゾキシムセフチゾックスセフチゾオキシム(6R,7R)-7-[(2Z)-2-(2-イミノ-2,3-ジヒドロ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸(6R,7R)-7-[2-(2-アミノ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セフチゾクス(6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCefimxCeftizoxEPOCELINFR-13749CeftisominCeftizoxime >CEFTIZOXIME ACIDCeftizoxime (350 mg)
FR13749SK&F 883732(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-(6R,7R)-7-(((2Z)-2-(2-AMINO-1,3-THIAZOL-4-YL)-2-METHOXYIMINOACETYL)AMINO)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID(6R,7R)-7-((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid7-(2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino)-8-oxo-5-thia-1-aza-bicyclo(4.2.0)oct-2-ene-2-carboxylic acid7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

データベース識別子

CAS
68401-81-0
PubChem CID
6533629
DTXSID
DTXSID5022772
ChEMBL
CHEMBL528
ChEBI
CHEBI:553473
UNII
C43C467DPE
EC Number
685-309-4
Nikkaji
J37.178E

物性

構造計算による物性

XLogP
0
極性表面積
201 Ų
水素結合供与体数
3
水素結合受容体数
10
回転可能結合数
5
重原子数
25

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Solubility2.29e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Physical DescriptionSolid

物理化学的性質

融点
227 ° · 227° (dec)
比重(密度)
1.89 · 1.89±0.1 g/cm3(Predicted)
貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2–8 °C
溶解性
Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
外見
個体
酸解離定数(Pka)
2.1 · pKa 2.1 (Uncertain)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (50%)

毒性情報

Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

ceftizoxime

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

rtecs
XI0367375
毒性
LD50 intravenous in rat: 8gm/kg
hs_code
2941906000

化学と産業

薬理情報

ATC Code · 2 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding30% protein-bound across the standard concentration range.
Pharmacodynamics · 1 件

Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.

Mechanism of Action · 1 件

Ceftizoxime is an aminothiazolyl cephalosporin with an extended spectrum of activity against many gram-negative, nosocomially acquired pathogens. It has excellent beta-lactamase stability, with good in vitro activity against Haemophilus influenzae, Neisseria gonorrhoeae and Klebsiella pneumoniae. Ceftizoxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it 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 ceftizoxime interferes with an autolysin inhibitor.

Metabolism/MetabolitesCeftizoxime is not metabolized and is excreted virtually unchanged by the kidneys in 24 hours.
FDA Pharmacological Classification · 5 件

C43C467DPE

CEFTIZOXIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Ceftizoxime is a Cephalosporin Antibacterial.

応用分野 · 2 件

説明In ceftizoxime, the whole C-3 side chain has been omitted to prevent deactivation by hydrolysis. It rather resembles cefotaxime in its properties; however, not being subject to metabolism, its pharmacokinetic properties are much less complex.

使用Ceftizoxime is used for bacterial infections of the lower respiratory tract, infections of the urinary tract, infections of the bones, joints, skin, soft tissues, and abdominal infections. Synonyms of this drug are ceftix and eposerin.

上流・下流製品情報

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国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

補足説明

定義ChEBI: A parenteral third-generation cephalosporin, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position.

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