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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H14N6O10S2
Molecular Weight 466.404
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARUMONAM

SMILES

NC(=O)OC[C@@H]1[C@H](NC(=O)C(=N/OCC(O)=O)\C2=CSC(N)=N2)C(=O)N1S(O)(=O)=O

InChI

InChIKey=UIMOJFJSJSIGLV-JNHMLNOCSA-N
InChI=1S/C12H14N6O10S2/c13-11-15-4(3-29-11)7(17-28-2-6(19)20)9(21)16-8-5(1-27-12(14)23)18(10(8)22)30(24,25)26/h3,5,8H,1-2H2,(H2,13,15)(H2,14,23)(H,16,21)(H,19,20)(H,24,25,26)/b17-7-/t5-,8+/m1/s1

HIDE SMILES / InChI
Molecular Formula C12H14N6O10S2
Molecular Weight 466.404
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/4073864 | https://www.ncbi.nlm.nih.gov/pubmed/3065522 | https://www.ncbi.nlm.nih.gov/pubmed/3377459

Carumonam is a monobactam antibacterial agent. It was highly active in vitro against members of the family Enterobacteriaceae, Pseudomonas aeruginosa, and Haemophilus influenzae and weakly active against Streptococcus pneumoniae, but it was not active against Staphylococcus aureus. The excellent activity of carumonam against Gram-negative bacteria is related to its high affinity for their penicillin-binding proteins. It is indicated for the treatment of urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis. Another factor that contributes to the excellent activity of carumonam against Gram-negative bacteria is its resistance to beta-lactamases. Adverse effects of the carumonam were limited to phlebitis at the intravenous infusion site; bloody diarrhea.

Originator

Takeda Chemical Industries
28
Curator's Comment: # Takeda Chemical Industries, Ltd. http://doi.org/10.1248/cpb.33.3798 | doi:10.7164/antibiotics.36.1421

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Amasulin

Approved Use

It is indicated for the treatment of infections, caused by sensitive bacteria: urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis.
Curative
Approved
8429
Amasulin

Approved Use

It is indicated for the treatment of infections, caused by sensitive bacteria: urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis.
Curative
Approved
8429
Amasulin

Approved Use

It is indicated for the treatment of infections, caused by sensitive bacteria: urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis.
Curative
Approved
8429
Amasulin

Approved Use

It is indicated for the treatment of infections, caused by sensitive bacteria: urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis.
Curative
Approved
8429
Amasulin

Approved Use

It is indicated for the treatment of infections, caused by sensitive bacteria: urinary tract infections, chronic respiratory infections, biliary tract infections, peritonitis, sepsis.
PubMed

PubMed

TitleDatePubMed
Patents

Patents

JP2002541233A
400
JP2003515526A
462

Sample Use Guides

In Vivo Use Guide
The usual dose is 1-2 g daily in two divided doses.
Route of Administration: Other
In Vitro Use Guide
Enterobacteriaceae were highly susceptible to carumonam, 90% of the isolates being inhibited at 0.5 ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:44 UTC 2023
Edited
by admin
on Fri Dec 15 16:13:44 UTC 2023
Record UNII
486890PI06
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARUMONAM
INN   MI   WHO-DD  
INN  
Official Name English
ACETIC ACID, (((2-((2-(((AMINOCARBONYL)OXY)METHYL)-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-1-(2-AMINO-4-THIAZOLYL)-2-OXOETHYLIDENE)AMINO)OXY)-, (2S-(2.ALPHA.,3.ALPHA.(Z)))-
Systematic Name English
AMA 1080 FREE ACID
Code English
(Z)-((((2-AMINO-4-THIAZOLYL)(((2S,3S)-2-(HYDROXYMETHYL)-4-OXO-1-SULFO-3-AZETIDINYL)CARBAMOYL)METHYLENE)AMINO)OXY)ACETIC ACID, CARBAMATE (ESTER)
Systematic Name English
CARUMONAM [MI]
Common Name English
Carumonam [WHO-DD]
Common Name English
carumonam [INN]
Common Name English
AMA-1080 FREE ACID
Code English
Classification Tree Code System Code
WHO-ATC J01DF02
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
WHO-VATC QJ01DF02
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
NCI_THESAURUS C260
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
Code System Code Type Description
MERCK INDEX
m3141
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C79879
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
DRUG BANK
DB13553
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
SMS_ID
100000081331
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
PUBCHEM
6540466
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
WIKIPEDIA
CARUMONAM
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
INN
5508
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
CAS
87638-04-8
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048312
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
MESH
C044145
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1614658
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
EVMPD
SUB06152MIG
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
CHEBI
55486
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
FDA UNII
486890PI06
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
DRUG CENTRAL
521
Created by admin on Fri Dec 15 16:13:45 UTC 2023 , Edited by admin on Fri Dec 15 16:13:45 UTC 2023
PRIMARY
Related Record Type Details
Structure of CARUMONAM SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CARUMONAM
ACTIVE MOIETY
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