Cefoperazon

Cefoperazone

HCID 44187
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Grundinformationen

CAS
62893-19-0
Standard-SMILES
CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CS[C@H]23)c2ccc(O)cc2)C(=O)C1=O
InChIKey
GCFBRXLSHGKWDP-XCGNWRKASA-N
Summenformel
C25H27N9O8S2
Durchschnittliche Molmasse
645,7 g/mol
Monoisotopische Masse
645,1424012

Überblick

Cefoperazone is a semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance. It has a role as an antibacterial drug.

Namen und Bezeichner

Bevorzugter Name
Cefoperazone
IUPAC
(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Lokaler Name
Cefoperazon
Englischer Name
Cefoperazone
Summenformel
C25H27N9O8S2
Molmasse
645.67

Namen und Synonyme

cefoperazone62893-19-0CefoperazonumCefoperazonoPeracefCefoperazonCefoperazonaCHEBI:34937U75I1278DDTXSID2022759(6R,7R)-7-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Weitere Namen anzeigen
CEFOPERAZONE ACIDCefoperazone (Cefobid)(6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-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-carboxylicacid,7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-(4-hydroxyphenyl)acetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-,(6R,7R)-Cefobl~rdumMedocefcefoperazineCephaperazon
(6R,7R)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-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-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6-alpha,7-beta(R*)))-(6R,7R)-7-(((2R)-2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-(4-hydroxyphenyl)acetyl)amino)-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-((2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-(4-hydroxyphenyl)acetyl)amino)-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:918190DTXCID702759J01DA32263-749-4

Datenbank-Bezeichner

CAS
62893-19-0
PubChem CID
44187
DTXSID
DTXSID2022759
ChEMBL
CHEMBL507674
ChEBI
CHEBI:3493
UNII
7U75I1278D
EC Number
263-749-4
Nikkaji
J19.295C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
271 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
13
Frei drehbare Bindungen
9
Schwere Atome
44

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP-0.74
Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

Pharmaceuticals

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point188-190
Collision Cross Section · 2 Einträge

239.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

238.72 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
169 · 169-171 C
Dichte
1.77 · 1.77±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
Aggregatzustand
Solid
pka
2.6 · pKa 2.6 (Uncertain)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

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

Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationREACH registered substance: Cefoperazone (EC: 263-749-4)
Other Safety Information · 1 Eintrag

IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment

Hazard Classes and CategoriesSkin Sens. 1 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefoperazone

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

hs_code
29419000
RTECS-Nr.
XI0373900
risk_code
20/21/22-36/37/38
hazard_code
Xn
safety_code
26-36

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingThe degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.
PharmacodynamicsCefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis
Mechanism of Action · 1 Eintrag

Like all beta-lactam antibiotics, cefoperazone binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Biological Half-LifeThe mean serum half-life is approximately 2.0 hours, independent of the route of administration.
Metabolism/MetabolitesNo significant quanitity of metabolites have been identified in urine.

Verwendung und Herstellung

Use ClassificationPharmaceuticals
Anwendungen · 2 Einträge

BeschreibungCefoperazone has a C-7 side chain reminiscent of piperacillin's and also possesses the C-3 side chain (MTT ) that often is associated with the bleeding and alcohol intolerance problems among patients taking cephalosporins. Its useful activity against pseudomonads partly compensates for this, although it is not potent enough to be used as a single agent against this difficult pathogen. The C-7 side chain does not convey sufficient resistance to many β-lactamases, although the addition of clavulanic acid or sulbactam would presumably help.

VerwendenCefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others.

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.

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