U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
175 μg/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
192.2 μg/mL
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
300.7 μg/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
297.7 μg/mL
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
111 mg/L
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
105 mg/L
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
214 mg/L
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
208 mg/L
2 g 4 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
179 μg × h/mL
1020 mg single, intravenous
dose: 1020 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
493 μg × h/mL
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
783 μg × h/mL
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1302 μg × h/mL
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
56.9 μg × h/mL
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
113.4 μg × h/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
230.4 μg × h/mL
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
107.4 μg × h/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PROBENECID
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
117 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
186 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
602 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1112 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
186.7 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
156.4 μg × h/mL
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
330.6 μg × h/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
287.7 μg × h/mL
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
170 mg × h/L
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
147 mg × h/L
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
300 mg × h/L
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
293 mg × h/L
2 g 4 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
1020 mg single, intravenous
dose: 1020 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.5 h
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6.6 h
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11.3 h
1040 mg single, intravenous
dose: 1040 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.76 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.77 h
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.93 h
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.99 h
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PROBENECID
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.53 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.08 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
12.8 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.3 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.5 h
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.4 h
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.5 h
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.5 h
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.3 h
1 g 3 times / day multiple, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.4 h
2 g 3 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.3 h
2 g 4 times / day multiple, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.82%
CARUMONAM plasma
Homo sapiens
72%
CARUMONAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status:
Doses

Doses

DosePopulationAdverse events​
2 g 3 times / day multiple, intravenous
Highest studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
1 g 3 times / day multiple, parenteral
Studied dose
Dose: 1 g, 3 times / day
Route: parenteral
Route: multiple
Dose: 1 g, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Comparative epileptogenic properties of two monobactam derivatives in C57, Swiss and DBA/2 mice.
1996-09
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 Mon Mar 31 18:22:30 GMT 2025
Edited
by admin
on Mon Mar 31 18:22:30 GMT 2025
Record UNII
486890PI06
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMA 1080 FREE ACID
Preferred Name English
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
(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 Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
WHO-VATC QJ01DF02
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
NCI_THESAURUS C260
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
Code System Code Type Description
MERCK INDEX
m3141
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C79879
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
DRUG BANK
DB13553
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
SMS_ID
100000081331
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
PUBCHEM
6540466
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
WIKIPEDIA
CARUMONAM
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
INN
5508
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
CAS
87638-04-8
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048312
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
MESH
C044145
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL1614658
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
EVMPD
SUB06152MIG
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
CHEBI
55486
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
FDA UNII
486890PI06
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
DRUG CENTRAL
521
Created by admin on Mon Mar 31 18:22:30 GMT 2025 , Edited by admin on Mon Mar 31 18:22:30 GMT 2025
PRIMARY
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