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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28N9O9S2.Na
Molecular Weight 649.632
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFBUPERAZONE SODIUM

SMILES

[Na+].[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=WNJOIIXGSLBJAS-FDVIUCIPSA-M
InChI=1S/C22H29N9O9S2.Na/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);/q;+1/p-1/t10-,12+,19+,22-;/m0./s1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C22H28N9O9S2
Molecular Weight 626.643
Charge -1
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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Bacteroides fragilis growth
2
Target ID: Bacteroides fragilis growth
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Staphylococcus aureus growth
27
Target ID: Staphylococcus aureus growth
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Tomiporan

Approved Use

Indications: infections with susceptible microorganisms.

Launch Date

1985
Curative
Approved
8429
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

Patents

CA1242699A1
2
EP0189942A2
2
US2016045480
2
US2016058717
3

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 18:32:23 GMT 2023
Edited
by admin
on Fri Dec 15 18:32:23 GMT 2023
Record UNII
1VX59V96BS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFBUPERAZONE SODIUM
MART.   WHO-DD  
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R,3S)-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-, SODIUM SALT (1:1), (6R,7S)-
Common Name English
CEFBUPERAZONE SODIUM [MART.]
Common Name English
CEFBUPERAZONE SODIUM SALT
MI  
Common Name English
CEFBUPERAZONE SODIUM SALT [MI]
Common Name English
Cefbuperazone sodium [WHO-DD]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(2-((2,3-DIOXO-4-ETHYL-1-PIPERAZINYL)FORMAMIDO)-3-HYDROXYBUTYRAMIDO)-7-METHOXY- 3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, MONOSODIUM SALT, (6R-(6-ALPHA,7-ALPHA,7(2R*,3S*)))-
Common Name English
CEFBUPERAZONE SODIUM [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
Code System Code Type Description
PUBCHEM
23663968
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
MERCK INDEX
m3189
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1908372
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
FDA UNII
1VX59V96BS
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
SMS_ID
100000084963
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
CAS
76648-01-6
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
NCI_THESAURUS
C98217
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
EVMPD
SUB01109MIG
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID50227467
Created by admin on Fri Dec 15 18:32:23 GMT 2023 , Edited by admin on Fri Dec 15 18:32:23 GMT 2023
PRIMARY
Related Record Type Details
Structure of CEFBUPERAZONE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CEFBUPERAZONE
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