CARUMONAM

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 Search

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
Sources: http://211.103.242.133:8080/ziyuan/CDDPdf/med/base/111/%E6%8A%97%E7%94%9F%E7%B4%A0/2320.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3928279	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: http://211.103.242.133:8080/ziyuan/CDDPdf/med/base/111/%E6%8A%97%E7%94%9F%E7%B4%A0/2320.pdf	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.
Chronic respiratory infections 2 Sources: http://211.103.242.133:8080/ziyuan/CDDPdf/med/base/111/%E6%8A%97%E7%94%9F%E7%B4%A0/2320.pdf	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.
Biliary tract infections 2 Sources: http://211.103.242.133:8080/ziyuan/CDDPdf/med/base/111/%E6%8A%97%E7%94%9F%E7%B4%A0/2320.pdf	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.
Peritonitis 22 Sources: http://www.kmle.co.kr/viewDrug.php?m=%B6%F3%BD%C4&inx=7242&c=4582720816870505d09e6d5a5de7a3fd	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.
Sepsis 71 Sources: http://www.kmle.co.kr/viewDrug.php?m=%B6%F3%BD%C4&inx=7242&c=4582720816870505d09e6d5a5de7a3fd	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

Title	Date	PubMed
Comparative epileptogenic properties of two monobactam derivatives in C57, Swiss and DBA/2 mice.	1996 Sep	8889722

Patents

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 GMT 2023` Edited by `admin` on `Fri Dec 15 16:13:44 GMT 2023`
Record UNII	486890PI06
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARUMONAM

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