Ceftizoxime

HCID 6533629

Grundinformationen

CAS
68401-81-0
Standard-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
Summenformel
C13H13N5O5S2
Durchschnittliche Molmasse
383,4 g/mol
Monoisotopische Masse
383,03581052

Überblick

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-).

Namen und Bezeichner

Bevorzugter Name
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
Englischer Name
Ceftizoxime
Summenformel
C13H13N5O5S2
Molmasse
383.4

Namen und Synonyme

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
Weitere Namen anzeigen
(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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0
Polarare Oberfläche (TPSA)
201 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
10
Frei drehbare Bindungen
5
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

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

Physikochemische Eigenschaften

Schmelzpunkt
227 ° · 227° (dec)
Dichte
1.89 · 1.89±0.1 g/cm3(Predicted)
storage temp.
2 · under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit
Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
Aggregatzustand
Solid
pka
2.1 · pKa 2.1 (Uncertain)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (50%)

Toxikologische Informationen

Drug Induced Liver Injury · 5 Einträge

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

Sicherheitsdaten

hs_code
2941906000
RTECS-Nr.
XI0367375
Toxizität
LD50 intravenous in rat: 8gm/kg

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

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

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 Eintrag

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 Einträge

C43C467DPE

CEFTIZOXIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Ceftizoxime is a Cephalosporin Antibacterial.

Anwendungen · 2 Einträge

BeschreibungIn 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.

VerwendenCeftizoxime 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.

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]
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]

Ergänzende Hinweise

DefinitionChEBI: 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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