头孢匹罗

Cefpirome

HCID 5479539CAS 84957-29-9

基本信息

标准SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3cccc4c3CCC4)CS[C@H]12)c1csc(N)n1
InChIKey: DKOQGJHPHLTOJR-WHRDSVKCSA-N
分子式: C22H22N6O5S2
平均分子量: 514.6 g/mol
单同位素质量: 514.1093098

概述

Cefpirome is a fourth-generation cephalosporin antibiotic having 6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It is a cephalosporin and a cyclopentapyridine.

名称与标识

首选名称: Cefpirome
IUPAC: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
中文名: 头孢匹罗
英文名: Cefpirome
分子式: C22H22N6O5S2
分子量: 514.58

名称与别名

CEFPIROME84957-29-9CefpiromaCefpiromumCefirHR 810HR-810 FREE BASES72Q2F09HY(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHR-810CHEBI:3503DTXSID2048244

展开更多名称

头孢匹罗头孢吡隆头孢匹隆氨噻奎吡戊头孢氨噻肟吡戊头孢无菌头孢匹罗(碳酸钠)化合物 Cefpirome头孢匹罗溶液,100PPMCEFPIROME SULPHATEKeitimCS-283CerfpiromeCefpirome-13C-D3Cefpiromum [latin]

810, HR5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-(6R,7R)-7-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl)amino)-3-(6,7-dihydro-5H-cyclopenta(b)pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate1-(((6R,7R)-2-carboxylato-7-(((2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5H,6H,7H-cyclopenta(b)pyridin-1-ium1-{[(6R,7R)-2-carboxylato-7-{[(2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium3-((2,3-cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylateRefChem:124246

数据库标识

CAS: 84957-29-9
PubChem CID: 5479539
DTXSID: DTXSID2048244
ChEMBL: CHEMBL65794
ChEBI: CHEBI:3503
UNII: S72Q2F09HY
Nikkaji: J32.848K

性质

结构计算性质

XLogP: 0.9
极性表面积: 207 Å²
氢键供体: 2
氢键受体: 10
可旋转键: 6
重原子: 35
形式电荷: 0
复杂度: 955

实验与物化性质

DrugsPharmaceuticals -> Antibiotics

物理化学性质

储存条件: 2 · 2-8°C(protect from light)

化学性质 · 1 条

白色至微黄白色结晶性粉末，略有特异臭。较易溶于水，几不溶于乙醇或乙醚。在Ph值为5～7时易溶于水，其水溶液稳定性可与头孢噻肟及其它第三代头孢菌素比拟。急性毒性LD50小鼠，大鼠(g/kg)：1.9～2.4，1.9～2.15静脉注射；3.8～4.2，5.8～6.55腹腔注射。硫酸头孢匹罗(Cefpirome Sulfate)：022H22N6O5S2H2SO4。[98753-19-6]。结晶，熔点198～202℃(分解)。[α]D23-4.7°(C=5，水)。UV最大吸收：265mn(ε21100)。在Ph=6.5的缓冲液中的溶解度＞50%。

安全与法规

毒理信息

Drug Induced Liver Injury · 4 条

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Cefpirome

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

安全数据

毒性: LD50 in mice, rats (g/kg): 1.9-2.4, 1.9-2.15 i.v.; 3.8-4.2, 5.8-6.55 i.p. (Donaubauer, Mayer)
安全说明: 22-26-36/37/39
危险品标志: Xi
危险类别码: 36/37/38-42/43

化学与工业

药理信息

ATC Code · 2 条

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Mechanism of ActionCefpirome is a β-lactam (cephalosporin) antibiotic that binds penicillin-binding proteins (PBPs) and inhibits peptidoglycan cross-linking in bacterial cell-wall synthesis.

MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.

应用领域

用途用于败血症及严重的尿道感染，呼吸道感染等。

制备方法

生产方法头孢噻肟(I)和2，3-环戊烯并吡啶在碘化钾存在下，于水中加热，即得头孢匹罗。或将其侧链转化为碘化物后，和2，3-环戊烯并吡啶在二氯甲烷中回流，也得头孢匹罗。或者用活性的化合物(Ⅲ)和化合物(Ⅳ)直接酰化，得到头孢匹罗。

上下游产品信息

上游原料

碘化钾碘海醇水解物头孢噻肟酸 2,3-环戊烯并吡啶

供应商50 家

北京华美互利生物化工010-56205725 · [email protected]

上海莉凯化工技术有限公司16628776521 · [email protected]

深圳市健竹科技有限公司0755-89218110 13480856786

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]

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