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

CCN1CCN(C(=O)N[C@H]([C@H](C)O)C(=O)N[C@@]2(OC)[C@H]3SCC(CSC4=NN=NN4C)=C(N3C2=O)C(O)=O)C(=O)C1=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 8504
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/18765691	Inhibitor 8504
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.genome.jp/dbget-bin/www_bget?D03423+D01736	Inhibitor 8504
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/6348338	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pneumonia 91 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6348336	Curative		Approved 8583	Tomiporan Approved Use Indications: infections with susceptible microorganisms. Launch Date 1985
Urinary tract infections 207 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3661345	Curative		Approved 8583	Tomiporan Approved Use Indications: infections with susceptible microorganisms. Launch Date 1985

C_max

Value	Dose	Analyte	Population
44.7 μg/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
86.7 μg/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
168 μg/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
94.9 μg/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g 2 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
21.9 μg/g CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/3165475/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
116 μg × h/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
224 μg × h/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
427 μg × h/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
240 μg × h/mL CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g 2 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.9 h CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.8 h CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.9 h CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.9 h CLINICAL TRIAL https://doi.org/10.1016/j.jpba.2016.06.029	1 g 2 times / day steady-state, intravenous dose: 1 g route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CEFBUPERAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.6 h REVIEW 10.2165/00003495-198700342-00008	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE serum	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.03 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/3165475/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFBUPERAZONE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 g 2 times / day steady-state, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: steady-state Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27394175/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27394175/	Sources: https://pubmed.ncbi.nlm.nih.gov/27394175/

PubMed

Title	Date	PubMed
Pharmacokinetic profile of cefbuperazone in healthy Chinese volunteers after single and multiple drip intravenous infusion by HPLC-MS/MS.	2016-09-10	27394175
In vivo bacterial regrowth-inhibition effect of cefbuperazone and amikacin in puerperal uterine cavity.	1995-11	8904147
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.	1985-05	3874597

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 `Mon Mar 31 17:57:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:14 GMT 2025`
Record UNII	T0785J3X40
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BMY-25182

Preferred Name

English

CEFBUPERAZONE

Official Name

English

CEFBUPERAZONE [USAN]

Common Name

English

cefbuperazone [INN]

Common Name

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