CEFTERAM PIVOXIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27N9O7S2
Molecular Weight	593.636
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(CN3N=NC(C)=N3)=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C)C4=CSC(N)=N4

InChI

InChIKey=UIYAXIPXULMHAI-JLGRZTKVSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H27N9O7S2
Molecular Weight	593.636
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF

Cefteram is a semisynthetic cephalosporin formulated for oral administration as the prodrug ester, cefteram pivoxil. The mechanism of action of cefteram is inhibition of bacterial cell wall synthesis. Cefteram exerts its bactericidal activity by strongly binding to penicillin-binding protein (PBP) 3, 1A, and 1Bs. The drug is available in Japan and is used for the treatment of bacterial infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 1A 45 Target ID: CHEMBL1813 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Binding Agent 1076
Penicillin-binding protein 1B 22 Target ID: CHEMBL1814 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Binding Agent 1076
Penicillin-binding protein 3 7 Target ID: CHEMBL4269 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Curative		Approved 8583	TOMIRON Approved Use To treat pharyngitis/laryngitis, tonsillitis (including peritonsillitis and peritonsillar abscess), acute bronchitis, pneumonia, and secondary infections in chronic respiratory lesion; cystitis, pyelonephritis and urethritis; bartholinitis, intrauterine infection and uterine adnexitis; otitis media and sinusitis; periodontitis, pericoronitis and gnathitis

C_max

Value	Dose	Analyte	Population
1.32 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.65 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1.73 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
2.79 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.89 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
4.76 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18498914/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20166432/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFTERAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
200 mg 3 times / day multiple, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15587753/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/15587753/	Sources: https://pubmed.ncbi.nlm.nih.gov/15587753/

PubMed

Title	Date	PubMed
Preliminary antimicrobial susceptibility interpretive criteria for cefetamet (Ro 15-8074) and cefteram (Ro 19-5247) disk tests.	1987-09	3654953
In vitro activity of Ro 19-5247 (T-2525) and interpretive criteria for disk diffusion susceptibility testing.	1987-07	3112176
In vitro activity of Ro 15-8074, Ro 19-5247, A-56268, and roxithromycin (RU 28965) against Neisseria gonorrhoeae and Chlamydia trachomatis.	1987-03	2953304
In vitro activity and beta-lactamase stability of two oral cephalosporins, ceftetrame (Ro 19-5247) and cefetamet (Ro 15-8074).	1986-09	3490827
In vitro activity of Ro 15-8074 and Ro 19-5247, two orally administered cephalosporin metabolites.	1986-06	3729361

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage for oral use is 150 − 600 mg (potency) of cefteram pivoxil daily in 3 divided doses after meals.

Route of Administration: Oral

In Vitro Use Guide

The activity of cefteram was compared with that of other P-lactams against a total of 491 bacterial strains. The drug was highly active (MIC for 90% of the strains tested [MIC90] < 2 ug/ml) against the majority of the members of the family Enterobacteriaceae, Haemophilus influenzae, Neisseria spp., and Streptococcuspneumoniae, being at least 16-fold more active than cephalexin and 8-fold more active than cefuroxime. There was no activity against Pseudomonas aeruginosa, Enterobacter sp., and Citrobacter sp. Staphylococcus aureus was moderately susceptible to cefteram (MIC90, 8 ug/ml).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:32:27 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:27 GMT 2025`
Record UNII	0OD86RT58C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFTERAM PIVALOYLOXYMETHYL ESTER

Preferred Name

English

CEFTERAM PIVOXIL

Common Name

English

Cefteram pivoxil [WHO-DD]

Common Name

English

T-2588

Code

English

PIVALOYLOXYMETHYL (Z)-7-(2-(2-AMINOTHIAZOL-4-YL)-2-METHOXYIMINOACETAMIDO)-3-(5-METHYL-2H-TETRAZOL-2-YLMETHYL)-3-CEPHEM-4-CARBOXYLATE

Common Name

English

CEFTERAM PIVALOYLOXYMETHYL ESTER [MI]

Common Name

English

RO 19-5248

Code

English

ANTIBIOTIC T 2588

Code

English

CEFTERAM PIVOXIL [MART.]

Common Name

English

T 2588

Code

English

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)-

Common Name

English

RO-19-5248

Code

English

TOMIRON

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357