CEFBUPERAZONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H29N9O9S2
Molecular Weight	627.651
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)[C@H](NC(=O)N4CCN(CC)C(=O)C4=O)[C@H](C)O)OC)C(O)=O

InChI

InChIKey=SMSRCGPDNDCXFR-CYWZMYCQSA-N

InChI=1S/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H29N9O9S2
Molecular Weight	627.651
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://apps.who.int/medicinedocs/documents/h5774e/h5774e.pdf
Curator's Comment: Description was created based on several sources, including https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C81029 and http://www.ncbi.nlm.nih.gov/pubmed/6348335

Cefbuperazone (cefalosporin antibiotic) is marketed under the brand name Keiperazon by Kaken, and Tomiproan by Toyama, Japan. It is powder for injection 0.5 and 1 g/ampoule. It is indicated to treat infections with susceptible microorganisms. It has been proposed especially against Pseudomonas infections. Cefbuperazone binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacteroides fragilis growth 2 Target ID: Bacteroides fragilis growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3874597	Inhibitor 8297
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/18765691	Inhibitor 8297
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.genome.jp/dbget-bin/www_bget?D03423+D01736	Inhibitor 8297
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/6348338	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pneumonia 90 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6348336	Curative		Approved 8429	Tomiporan Approved Use Indications: infections with susceptible microorganisms. Launch Date 4.810752E11
Urinary tract infections 205 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3661345	Curative		Approved 8429	Tomiporan Approved Use Indications: infections with susceptible microorganisms. Launch Date 4.810752E11

PubMed

Title	Date	PubMed
In vitro activity of cefbuperazone compared with that of other new beta-lactam agents against anaerobic gram-negative bacilli and contribution of beta-lactamase to resistance.	1985 May	3874597
In vivo bacterial regrowth-inhibition effect of cefbuperazone and amikacin in puerperal uterine cavity.	1995 Nov	8904147
Pharmacokinetic profile of cefbuperazone in healthy Chinese volunteers after single and multiple drip intravenous infusion by HPLC-MS/MS.	2016 Sep 10	27394175

Patents

Sample Use Guides

In Vivo Use Guide

intravenous injection at a daily dose of 2g (1g - 2 times)

Route of Administration: Intravenous

In Vitro Use Guide

Cefbuperazone inhibited Bacteroides fragilis growth with MIC50 16 ug/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:28 UTC 2023` Edited by `admin` on `Fri Dec 15 15:25:28 UTC 2023`
Record UNII	T0785J3X40
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFBUPERAZONE

Official Name

English

CEFBUPERAZONE [USAN]

Common Name

English

cefbuperazone [INN]

Common Name

English

BMY-25182

Code

English

CEFBUPERAZONE [MI]

Common Name

English

T-1982

Code

English

Cefbuperazone [WHO-DD]

Common Name

English

CEFBUPERAZONE [MART.]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((2-(((4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL)AMINO)-3-HYDROXY-1-OXOBUTYL)AMINO)-7-METHOXY-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.ALPHA.,7(2R*,3S*)))-

Common Name

English

(6R,7S)-7-[(2R,3S)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357