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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 of CEFBUPERAZONE

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
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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Tomiporan

Approved Use

Indications: infections with susceptible microorganisms.

Launch Date

1985
Curative
Tomiporan

Approved Use

Indications: infections with susceptible microorganisms.

Launch Date

1985
PubMed

PubMed

TitleDatePubMed
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
Pharmacokinetic profile of cefbuperazone in healthy Chinese volunteers after single and multiple drip intravenous infusion by HPLC-MS/MS.
2016 Sep 10
Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:28 GMT 2023
Record UNII
T0785J3X40
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFBUPERAZONE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
WHO-ATC J01DC13
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
WHO-VATC QJ01DC13
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
Code System Code Type Description
MESH
C035978
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
INN
5216
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908372
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
CAS
76610-84-9
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
WIKIPEDIA
CEFBUPERAZONE
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
CHEBI
135856
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
MERCK INDEX
m3189
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C81029
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
DRUG CENTRAL
3072
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
DRUG BANK
DB13638
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
PUBCHEM
127527
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
FDA UNII
T0785J3X40
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID701024595
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
SMS_ID
100000081813
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
EVMPD
SUB07380MIG
Created by admin on Fri Dec 15 15:25:28 GMT 2023 , Edited by admin on Fri Dec 15 15:25:28 GMT 2023
PRIMARY
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