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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 1.030
Experimentelle und physikochemische Eigenschaften
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℃)
- Farbe
- White to Off-White
- InChIKey
- XDZKBRJLTGRPSS-BGZQYGJUSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\OC)=O)C1=O)SCC(CSC1=NC(C)=C(CC(O)=O)S1)=C2C(O)=O
- CAS Datenbank
- 69739 · 69739-16-8(CAS DataBase Reference)
Sicherheit und Regulatorisches
Gefahrenhinweise
Regulatory Information
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
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Darstellung
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
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
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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