Welcome to LookChem.com Sign In|Join Free
  • or
Home > Products >  > 

Ceftizoxime
Related Products

Hot Products

Basic Information Post buying leads Suppliers Cas Database
Name

Ceftizoxime

 EINECS N/A
CAS No. 68401-81-0 Density 1.89 g/cm3
PSA 200.75000 LogP 0.35420
Solubility soluble in water, slightly soluble in methanol, a few not soluble in alcohol, acetone, chloroform, ether or ethyl acetate Melting Point 227° (dec)
Formula C13H13N5O5S2 Boiling Point N/A
Molecular Weight 383.409 Flash Point N/A
Transport Information N/A Appearance white or light ashy-yellow crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 68401-81-0 (Ceftizoxime) Hazard Symbols Xi
Synonyms

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-(9CI);Ceftisomin;Ceftizoxime;Epocelin;

Article Data 7

Ceftizoxime Synthetic route

36923-17-8

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

C13H10N4O2S3

68401-81-0

ceftizoxime

Conditions
ConditionsYield
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With dmap In dichloromethane at -8 - 0℃;
Stage #2: C13H10N4O2S3 With dmap In dichloromethane at -5 - 0℃; for 0.25h; Reagent/catalyst; Temperature;		97%
68881-44-7

pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

A

68401-81-0

ceftizoxime

B

102044-69-9

(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

C

(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions
ConditionsYield
With water In N,N-dimethyl-formamide at 37℃; Rate constant; phosphate buffer, var. pH;
36923-17-8

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

80756-85-0

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

68401-81-0

ceftizoxime

Conditions
ConditionsYield
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In chloroform for 0.333333h;
Stage #2: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate In chloroform at 35℃; for 4.5h; Temperature;		87 g
53064-79-2

iodomethyl pivaloate

68401-81-0

ceftizoxime

68881-44-7

pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;73%
68401-81-0

ceftizoxime

XCH(CH3)OCOCH3

XCH(CH3)OCOCH3

84725-07-5

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-acetoxy-ethyl ester

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;
68401-81-0

ceftizoxime

XCH(CH3)OCO2CH(CH3)2

XCH(CH3)OCO2CH(CH3)2

84089-74-7

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;
68401-81-0

ceftizoxime

XCH(CH3)OCO2C2H5

XCH(CH3)OCO2C2H5

84129-42-0

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-ethoxycarbonyloxy-ethyl ester

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;
68401-81-0

ceftizoxime

but-2,3-en-2,3-carbonate-1-yl halide

but-2,3-en-2,3-carbonate-1-yl halide

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

235099-09-9

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-cyclohexyloxycarbonyloxy-ethyl ester

Conditions
ConditionsYield
With N-cyclohexyl-cyclohexanamine In N,N-dimethyl acetamide at -5℃; for 2h; Esterification;
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-acetoxy-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme

Ceftizoxime Specification

The Ceftizoxime acid with CAS registry number of 68401-81-0 is also known as Ceftizoximum. The IUPAC name is (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. Its classification codes are Anti-Bacterial Agents; Anti-Infective Agents; Antibiotics; Drug/Therapeutic Agent. In addition, the formula is C13H13N5O5S2 and the molecular weight is 383.40. This chemical is a white or light ashy-yellow crystalline powder and soluble in water, slightly soluble in methanol.

Physical properties about Ceftizoxime acid are: (1)#H bond acceptors: 10; (2)#H bond donors: 4; (3)#Freely Rotating Bonds: 5; (4)Polar Surface Area:: 199.35Å2; (5)Rotatable Bond Count: 5; (6)Tautomer Count: 14; (7)Exact Mass: 383.03581; (8)MonoIsotopic Mass: 383.03581; (9)Topological Polar Surface Area: 201; (10)Heavy Atom Count: 25; (11)Complexity: 669; (12)Defined Atom StereoCenter Count: 2; (13)Defined Bond StereoCenter Count: 1; (14)Covalently-Bonded Unit Count: 1.

Preparation of Ceftizoxime acid. Firstly, chloride compounds (Ⅵ) is prepared by reaction of 2-methoxy-imino 2-(2-amino-1,3-thiazol-4-yl) acetic acid (V), phosphorus oxychloride, bis (trimethylsilyl) acetamide and dimethylformamide. Secondly, add trimethylsilyl acetamide to 7-ACA, then add the reaction mixture to chloride compounds (Ⅵ) . The reaction mixture is stirred at -10~-15 °C for 1 hour. At last, the reaction mixture is conducted with column chromatography and evaporated to obtained the product.

Ceftizoxime acid is prepared by reaction of chloride compounds (Ⅵ) with 7-ACA and trimethylsilyl acetamide.

Uses of Ceftizoxime acid: it is used as third-generation cephalosporins, and also used for respiratory infections caused by susceptible strains, urinary tract infections, biliary tract infections, bone and joint infections, skin and soft tissue infections, gynecological diseases, sepsis, peritonitis, meningitis and endocarditis. What's more, it is primarily used for the treatment of respiratory system, urinary system, such as bone and joint infections.

You can still convert the following datas into molecular structure:
1. SMILES: CON=C(c1csc(=[NH2+])[nH]1)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)[O-]
2. InChI: InChI=1/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-
3. InChIKey: NNULBSISHYWZJU-IDUWFGFVBF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intravenous 8gm/kg (8000mg/kg)   United States Patent Document. Vol. #4563522,
rat LD50 subcutaneous > 8gm/kg (8000mg/kg)   United States Patent Document. Vol. #4563522,

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 68401-81-0