Cefodizime

HCID 5361871CAS 69739-16-8

Grundinformationen

Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CSc3nc(C)c(CC(=O)O)s3)CS[C@H]12)c1csc(N)n1
InChIKey
XDZKBRJLTGRPSS-BGZQYGJUSA-N
Summenformel
C20H20N6O7S4
Durchschnittliche Molmasse
584,7 g/mol
Monoisotopische Masse
584,02763098

Überblick

Cefodizime is a cephalosporin compound having 5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It has a role as an antibacterial drug and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a cephalosporin, an oxime O-ether and a member of 1,3-thiazoles.

Namen und Bezeichner

Bevorzugter Name
Cefodizime
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Englischer Name
Cefodizime
Summenformel
C20H20N6O7S4
Molmasse
584.67

Namen und Synonyme

Cefodizime69739-16-8CefodizimaCefodizimumCDZMTimecefHR 221 FREE ACIDTHR 221 FREE ACID(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHR-221HR-221 FREE ACIDS 77 1221 B FREE ACID
Weitere Namen anzeigen
FIR-221EstrofanCefodizmeCefodizimCefodizime,CDZMCefodizMe SodiuMSodium cefodizimeCefodizime USP/EP/BPCEFODIZIME FREE ACID
THR-221 FREE ACIDZ31298J4HQS-77-1221-B FREE ACIDDTXSID2022757CHEBI:63214(6R,7R)-3-(((5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl)sulfanyl)methyl)-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-ene-2-carboxylic acid(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-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-ene-2-carboxylic acid(6R,7R)-7-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl)amino)-3-((5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Datenbank-Bezeichner

CAS
69739-16-8
PubChem CID
5361871
DTXSID
DTXSID2022757
ChEMBL
CHEMBL2303613
ChEBI
CHEBI:63214
UNII
Z31298J4HQ
EC Number
700-301-3
Nikkaji
J22.238K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
304 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
15
Frei drehbare Bindungen
10
Schwere Atome
37

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Antibiotics

Physikochemische Eigenschaften

Schmelzpunkt
170 °C · >170°C (dec.)
Dichte
1.86 · 1.86±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
DMSO (Slightly), Methanol (Slightly, Heated)
Aggregatzustand
Solid
pka
1 · pK1 2.85; pK2 3.37; pK3 4.18(at 25℃)

Sicherheit und Regulatorisches

Gefahrenhinweise

Regulatory Information · 1 Eintrag

REACH registered substance: (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EC: 700-301-3)

Sicherheitsdaten

risk_code
36/37/38-42/43
hazard_code
Xi
safety_code
22-26-36/37/39

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Mechanism of ActionCefodizime is a cephalosporin antibiotic that is bactericidal by binding PBPs and blocking peptidoglycan synthesis, leading to filamentation or lysis.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Darstellung · 1 Eintrag

synthetischeThe synthesis of cefodizime involved the following steps:Dissolve 6.1g of (2-mercapto-4-methylthiazol-5-yl) acetic acid in water and adjust the pH to 6.5 by adding 2 mol/L sodium hydroxide.Heat the solution to 70°C and then add a solution of 12g of cefotaxime in 75ml of water with stirring.Keep stirring the mixture at 70°C for 3 hours while maintaining the pH at 6.5 by adding 2 mol/L sodium hydroxide.Cool the mixture to room temperature and acidify it to pH 2.8.Filter the resulting precipitate and wash it with water.Dry the precipitate under vacuum and in the presence of phosphorus pentoxide.As a result, 10g of cefodizime is obtained.Cefodizime, an aminothiazolylcephalosporin. V. Synthesis and structure-activity relationships in the cefodizime series. DOI: 10.7164/antibiotics.40.29

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [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]
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Cefodizime is a cephalosporin compound having 5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It has a role as an antibacterial drug and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a cephalosporin, a member of 1,3-thiazoles and an oxime O-ether.

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