CAS No.68401-81-0,Ceftizoxime Suppliers

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Basic Information

Molecular Structure:
CAS No.:	68401-81-0
Name:	Ceftizoxime
Article Data:	7

Formula:	C₁₃H₁₃N₅O₅S₂
Molecular Weight:	383.409
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;
Density:	1.89 g/cm³
Melting Point:	227° (dec)
Solubility:	soluble in water, slightly soluble in methanol, a few not soluble in alcohol, acetone, chloroform, ether or ethyl acetate
Appearance:	white or light ashy-yellow crystalline powder
Hazard Symbols:	Xi
PSA:	200.75000
LogP:	0.35420

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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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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,