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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H12N6O10S2.2Na
Molecular Weight 510.367
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARUMONAM SODIUM

SMILES

[Na+].[Na+].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=BGGXRVPCJUKHTQ-AHCAJXDVSA-L
InChI=1S/C12H14N6O10S2.2Na/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);;/q;2*+1/p-2/b17-7-;;/t5-,8+;;/m1../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 C12H12N6O10S2
Molecular Weight 464.388
Charge -2
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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
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
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
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
Comparative epileptogenic properties of two monobactam derivatives in C57, Swiss and DBA/2 mice.
1996 Sep
Patents

Sample Use Guides

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 15:19:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:20 GMT 2023
Record UNII
B4J4M4939D
Record Status Validated (UNII)
Record Version
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Name Type Language
CARUMONAM SODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
AMA 1080
Code English
RO-172301006
Code English
ACETIC ACID, (((2-((2-(((AMINOCARBONYL)OXY)METHYL)-4-OXO-1-SULFO-3-AZETIDINYL)AMINO)-1-(2-AMINO-4-THIAZOLYL)-2-OXOETHYLIDEN)AMINO)OXY)-, DISODIUM SALT, (2S-(2.ALPHA.,3.ALPHA.(Z)))-
Systematic Name English
CARUMONAM SODIUM [JAN]
Common Name English
CARUMONAM DISODIUM SALT
MI  
Common Name English
Carumonam sodium [WHO-DD]
Common Name English
AMA-1080
Code English
RO 17-2301/006
Code English
CARUMONAM SODIUM [USAN]
Common Name English
AMASULIN
Brand Name English
CARUMONAM DISODIUM SALT [MI]
Common Name English
RO-17-2301/006
Code English
CARUMONAM SODIUM [MART.]
Common Name English
(Z)-[[[(2-Amino-4-thiazolyl)[[(2S,3S)-2-(hydroxymethyl)-4-oxo-1-sulfo-3-azetidinyl]carbamoyl]methylene]amino]oxy]acetic acid, carbamate (ester), disodium salt
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
Code System Code Type Description
PUBCHEM
9568618
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
SMS_ID
100000084877
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL1614658
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID1046712
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
USAN
U-111
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
NCI_THESAURUS
C79905
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
FDA UNII
B4J4M4939D
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
CAS
86832-68-0
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
CHEBI
31363
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
EVMPD
SUB01073MIG
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY
MERCK INDEX
m3141
Created by admin on Fri Dec 15 15:19:20 GMT 2023 , Edited by admin on Fri Dec 15 15:19:20 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY