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

[H][C@]12SCC(CN3N=NC(C)=N3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(=O)OCOC(=O)C(C)(C)C

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 1064
Penicillin-binding protein 1B 22 Target ID: CHEMBL1814 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Binding Agent 1064
Penicillin-binding protein 3 7 Target ID: CHEMBL4269 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.e-search.ne.jp/~jpr/PDF/TOYAMA05.PDF	Curative		Approved 8429	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

PubMed

Title	Date	PubMed
In vitro activity of Ro 15-8074 and Ro 19-5247, two orally administered cephalosporin metabolites.	1986 Jun	3729361
In vitro activity of Ro 19-5247 (T-2525) and interpretive criteria for disk diffusion susceptibility testing.	1987 Jul	3112176
Preliminary antimicrobial susceptibility interpretive criteria for cefetamet (Ro 15-8074) and cefteram (Ro 19-5247) disk tests.	1987 Sep	3654953

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 `Sat Dec 16 05:42:44 UTC 2023` Edited by `admin` on `Sat Dec 16 05:42:44 UTC 2023`
Record UNII	0OD86RT58C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFTERAM PIVOXIL

Common Name

English

CEFTERAM PIVALOYLOXYMETHYL ESTER

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