Cas no 82547-81-7 (Cefteram pivoxil)

Cefteram pivoxil is a third-generation cephalosporin antibiotic prodrug, designed to enhance oral bioavailability. Upon administration, it is hydrolyzed to the active form, cefteram, which exhibits broad-spectrum activity against Gram-positive and Gram-negative bacteria. Its key advantages include improved stability against β-lactamases, ensuring efficacy against resistant strains, and a favorable pharmacokinetic profile with prolonged serum half-life, allowing for less frequent dosing. The compound demonstrates high tissue penetration, particularly in respiratory and urinary tracts, making it suitable for treating infections in these regions. Its esterified pivoxil moiety facilitates better intestinal absorption, distinguishing it from earlier cephalosporins with limited oral efficacy. Clinical applications include respiratory, urinary, and soft tissue infections.
Cefteram pivoxil structure
Cefteram pivoxil structure
Product Name:Cefteram pivoxil
CAS No:82547-81-7
MF:C22H27N9O7S2
MW:593.635880708694
CID:60457
PubChem ID:5362114
Update Time:2025-06-07

Cefteram pivoxil Chemical and Physical Properties

Names and Identifiers

    • Cefteram pivoxil
    • Pivaloyloxymethyl (Z)-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylate
    • Antibiotic T 2588
    • CefteramPivoxilCefteramPivoxil
    • CEFTERAMPIVOXYL
    • Ro 19-5248
    • T 2588
    • Tomiron
    • Tomiron 100
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [6R-[6α,7β(Z)]]- (ZCI)
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R,7R)- (9CI)
    • starbld0016558
    • CFTM-PI
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-(METHOXYIMINO)ACETYL)AMINO)-3-((5-METHYL-2H-TETRAZOL-2-YL)METHYL)-8-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER, (6R,7R)-
    • InChI=1/C22H27N9O7S2/c1-10-26-29-30(27-10)6-11-7-39-18-14(25-16(32)13(28-36-5)12-8-40-21(23)24-12)17(33)31(18)15(11)19(34)37-9-38-20(35)22(2,3)4/h8,14,18H,6-7,9H2,1-5H3,(H2,23,24)(H,25,32)/b28-13-/t14-,18-/m1/s1
    • s5354
    • Cefteram pivaloyloxymethyl ester
    • UIYAXIPXULMHAI-JLGRZTKVSA-
    • CHEBI:31381
    • CHEMBL3137676
    • T-2588
    • SCHEMBL22718900
    • CS-0026074
    • BRN 4223783
    • D01686
    • CEFTERAM PIVOXIL [WHO-DD]
    • 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    • CEFTERAM PIVOXIL [MART.]
    • AKOS040745021
    • Tomiron (TN)
    • CEFTERAM PIVALOYLOXYMETHYL ESTER [MI]
    • UNII-0OD86RT58C
    • PIVALOYLOXYMETHYL (Z)-7-(2-(2-AMINOTHIAZOL-4-YL)-2-METHOXYIMINOACETAMIDO)-3-(5-METHYL-2H-TETRAZOL-2-YLMETHYL)-3-CEPHEM-4-CARBOXYLATE
    • 1ST161294
    • 0OD86RT58C
    • Cefteram pivoxil (JP17)
    • HY-106571
    • 82547-81-7
    • DTXSID401316612
    • NS00011587
    • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((5-methyl-2H-tetrazol-2-yl)methyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R-(6-alpha,7-beta(Z)))-
    • Cefteram pivoxil (JP18)
    • DA-62193
    • Cefterampivoxil
    • MDL： MFCD00941401
    • Inchi： 1S/C22H27N9O7S2/c1-10-26-29-30(27-10)6-11-7-39-18-14(25-16(32)13(28-36-5)12-8-40-21(23)24-12)17(33)31(18)15(11)19(34)37-9-38-20(35)22(2,3)4/h8,14,18H,6-7,9H2,1-5H3,(H2,23,24)(H,25,32)/b28-13-/t14-,18-/m1/s1
    • InChI Key： UIYAXIPXULMHAI-JLGRZTKVSA-N
    • SMILES： C(C1=C(CN2N=NC(C)=N2)CS[C@@H]2[C@@H](C(N12)=O)NC(=O)/C(/C1=CSC(N)=N1)=N\OC)(=O)OCOC(=O)C(C)(C)C

Computed Properties

  • Exact Mass: 593.14700
  • Monoisotopic Mass: 593.147486
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 14
  • Heavy Atom Count: 40
  • Rotatable Bond Count: 13
  • Complexity: 1100
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.1
  • Topological Polar Surface Area: 260

Experimental Properties

  • Density: 1.3216 (rough estimate)
  • Melting Point: 125-128°C
  • Boiling Point: Not available
  • Flash Point: Not available
  • Refractive Index: 1.7400 (estimate)
  • PSA: 259.65000
  • LogP: 0.72490
  • Vapor Pressure: Not available

Cefteram pivoxil Security Information

  • Signal Word：warning
  • Hazard Statement： H303+H313+H333
  • Warning Statement： P264+P280+P305+P351+P338+P337+P313
  • Safety Instruction： H303+H313+H333
  • Toxicity：LD50 in male, female mice, rats (g/kg): >6.00, 5.86, 5.63, 5.09 i.p.; in both species >6.00 s.c.; in male mice, rats, dogs (g/kg): >6.00, >6.00, >2.00 orally (Sato)
  • Storage Condition：storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

Cefteram pivoxil Pricemore >>

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Cefteram pivoxil Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Dichloromethane ,  Dimethylacetamide
1.2 -
Reference
Studies on β-lactam antibiotics for medicinal purpose. XVIII. Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-substituted methyl-3-cephem-4-carboxylic acid derivatives
Sadaki, Hiroshi; et al, Yakugaku Zasshi, 1986, 106(2), 129-46

Production Method 2

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ,  Tetrahydrofuran
1.2 Reagents: Triethylamine Solvents: Dichloromethane
Reference
Studies on β-lactam antibiotics for medicinal purposes. XIX. Synthesis and structure-activity relationships of 7β-(acylamino)-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-3-cephem-4-carboxylic acid, 7β-(acylamino)-3-[(5-chloro-1,2,4-triazol-1-yl)methyl]-3-cephem-4-carboxylic acid, and their derivatives
Sadaki, Hiroshi; et al, Yakugaku Zasshi, 1986, 106(2), 147-53

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ,  Dimethylformamide ;  20 min, 20 °C
1.2 20 °C; 2.5 h, 20 °C
Reference
Synthesis of cefteram pivoxil
Shi, Ke-jin; et al, Zhongguo Kangshengsu Zazhi, 2014, 39(7), 507-509

Production Method 4

Reaction Conditions
1.1 Reagents: Dicyclohexylamine Solvents: Dimethylacetamide
Reference
Studies on orally active cephalosporin esters
Fujimoto, Koichi; et al, Journal of Antibiotics, 1987, 40(3), 370-84

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylamine ,  Sodium pyrosulfite Solvents: Dichloromethane ;  rt → 0 °C; 3 h, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, pH 2.5 - 3, 0 °C → 5 °C
2.1 Reagents: Sodium methoxide Solvents: Methanol ,  Dimethylformamide ;  20 min, 20 °C
2.2 20 °C; 2.5 h, 20 °C
Reference
Synthesis of cefteram pivoxil
Shi, Ke-jin; et al, Zhongguo Kangshengsu Zazhi, 2014, 39(7), 507-509

Production Method 6

Reaction Conditions
1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Acetone
1.2 Reagents: Oxalic acid
2.1 Reagents: Phosphorus oxychloride Solvents: Dichloromethane ,  Dimethylacetamide
2.2 -
Reference
Studies on β-lactam antibiotics for medicinal purpose. XVIII. Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-substituted methyl-3-cephem-4-carboxylic acid derivatives
Sadaki, Hiroshi; et al, Yakugaku Zasshi, 1986, 106(2), 129-46

Production Method 7

Reaction Conditions
1.1 Reagents: (T-4)-(Dimethyl carbonate-κO′′)trifluoroboron ;  5 h, 35 °C
1.2 Reagents: Potassium hydroxide Solvents: Water ;  2 h, pH 3.5, 35 °C → 5 °C
2.1 Reagents: Triethylamine ,  Sodium pyrosulfite Solvents: Dichloromethane ;  rt → 0 °C; 3 h, 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, pH 2.5 - 3, 0 °C → 5 °C
3.1 Reagents: Sodium methoxide Solvents: Methanol ,  Dimethylformamide ;  20 min, 20 °C
3.2 20 °C; 2.5 h, 20 °C
Reference
Synthesis of cefteram pivoxil
Shi, Ke-jin; et al, Zhongguo Kangshengsu Zazhi, 2014, 39(7), 507-509

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