Product Name

  • Name

    Ceftizoxime

  • EINECS
  • CAS No. 68401-81-0
  • Article Data7
  • CAS DataBase
  • Density 1.89 g/cm3
  • 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
  • Molecular Weight 383.409
  • Flash Point
  • Transport Information
  • Appearance white or light ashy-yellow crystalline powder
  • Safety
  • Risk Codes
  • 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;
  • PSA 200.75000
  • LogP 0.35420

Synthetic route

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
36923-17-8

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

C13H10N4O2S3

C13H10N4O2S3

ceftizoxime
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%
pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate
68881-44-7

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

A

ceftizoxime
68401-81-0

ceftizoxime

B

(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
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

(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;
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
36923-17-8

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

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
80756-85-0

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

ceftizoxime
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
iodomethyl pivaloate
53064-79-2

iodomethyl pivaloate

ceftizoxime
68401-81-0

ceftizoxime

pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate
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%
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCOCH3

XCH(CH3)OCOCH3

(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
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;
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2CH(CH3)2

XCH(CH3)OCO2CH(CH3)2

(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
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;
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2C2H5

XCH(CH3)OCO2C2H5

(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
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;
ceftizoxime
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

(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;
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(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
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;
ceftizoxime
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

(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
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-(2-tert-Butoxycarbonylamino-acetylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
249552-46-3

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

pivaloyloxymethyl 7β-[(Z)-2-[2-N-(tert-butoxycarbonyl)-(S)-alanylaminothiazol-4-yl]-2-methoxyiminoacetamido]-3-cephem-4-carboxylate
135790-89-5

pivaloyloxymethyl 7β-[(Z)-2-[2-N-(tert-butoxycarbonyl)-(S)-alanylaminothiazol-4-yl]-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: 50 percent / EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
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-isopropoxycarbonyloxy-ethyl ester
235099-14-6

(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-isopropoxycarbonyloxy-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
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-ethoxycarbonyloxy-ethyl ester
249552-52-1

(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-ethoxycarbonyloxy-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
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
249552-47-4

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
249552-48-5

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
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-cyclohexyloxycarbonyloxy-ethyl ester
235099-15-7

(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-cyclohexyloxycarbonyloxy-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
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-Amino-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; hydrochloride

(6R,7R)-7-{2-[2-((S)-2-Amino-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; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-6-Amino-2-tert-butoxycarbonylamino-hexanoylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
249552-50-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-Amino-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-isopropoxycarbonyloxy-ethyl ester; hydrochloride

(6R,7R)-7-{2-[2-((S)-2-Amino-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-isopropoxycarbonyloxy-ethyl ester; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

Ceftizoxime arapivoxil hydrochloride

Ceftizoxime arapivoxil hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: 50 percent / EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: 92 percent / HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-Amino-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-ethoxycarbonyloxy-ethyl ester; hydrochloride

(6R,7R)-7-{2-[2-((S)-2-Amino-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-ethoxycarbonyloxy-ethyl ester; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2-Amino-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-cyclohexyloxycarbonyloxy-ethyl ester; hydrochloride

(6R,7R)-7-{2-[2-((S)-2-Amino-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-cyclohexyloxycarbonyloxy-ethyl ester; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °C
View Scheme
ceftizoxime
68401-81-0

ceftizoxime

XCH(CH3)OCO2cHex

XCH(CH3)OCO2cHex

(6R,7R)-7-{2-[2-((S)-2,6-Diamino-hexanoylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester; compound with GENERIC INORGANIC NEUTRAL COMPONENT

(6R,7R)-7-{2-[2-((S)-2,6-Diamino-hexanoylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / dicyclohexylamine / N,N-dimethyl-acetamide / 2 h / -5 °C
2: EDC*HCl; DMAP / CH2Cl2 / 2 h / 20 °C
3: HCl / formic acid; propan-2-ol / 0.08 h / 0 - 5 °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,

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