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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Amasulin
Curative
Amasulin
Curative
Amasulin
Curative
Amasulin
Curative
Amasulin

Cmax

ValueDoseCo-administeredAnalytePopulation
175 μg/mL
1 g single, intravenous
CARUMONAM plasma
Homo sapiens
192.2 μg/mL
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
300.7 μg/mL
2 g single, intravenous
CARUMONAM plasma
Homo sapiens
297.7 μg/mL
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
111 mg/L
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
105 mg/L
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
214 mg/L
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
208 mg/L
2 g 4 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
179 μg × h/mL
1020 mg single, intravenous
CARUMONAM plasma
Homo sapiens
493 μg × h/mL
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
783 μg × h/mL
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1302 μg × h/mL
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
56.9 μg × h/mL
500 mg single, intravenous
CARUMONAM plasma
Homo sapiens
113.4 μg × h/mL
1000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
230.4 μg × h/mL
2000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
107.4 μg × h/mL
1000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
117 μg × h/mL
1 g single, intravenous
CARUMONAM serum
Homo sapiens
186 μg × h/mL
1 g single, intravenous
CARUMONAM serum
Homo sapiens
602 μg × h/mL
1 g single, intravenous
CARUMONAM serum
Homo sapiens
1112 μg × h/mL
1 g single, intravenous
CARUMONAM serum
Homo sapiens
186.7 μg × h/mL
1 g single, intravenous
CARUMONAM plasma
Homo sapiens
156.4 μg × h/mL
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
330.6 μg × h/mL
2 g single, intravenous
CARUMONAM plasma
Homo sapiens
287.7 μg × h/mL
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
170 mg × h/L
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
147 mg × h/L
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
300 mg × h/L
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
293 mg × h/L
2 g 4 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
1020 mg single, intravenous
CARUMONAM plasma
Homo sapiens
4.5 h
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
6.6 h
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
11.3 h
1040 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1.76 h
500 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1.77 h
1000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1.93 h
2000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1.99 h
1000 mg single, intravenous
CARUMONAM plasma
Homo sapiens
1.53 h
1 g single, intravenous
CARUMONAM serum
Homo sapiens
2 h
1 g single, intravenous
CARUMONAM serum
Homo sapiens
5.08 h
1 g single, intravenous
CARUMONAM serum
Homo sapiens
12.8 h
1 g single, intravenous
CARUMONAM serum
Homo sapiens
1.3 h
1 g single, intravenous
CARUMONAM plasma
Homo sapiens
1.5 h
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
1.4 h
2 g single, intravenous
CARUMONAM plasma
Homo sapiens
1.5 h
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
1.5 h
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
1.3 h
1 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
1.4 h
2 g 3 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens
1.3 h
2 g 4 times / day multiple, intravenous
CARUMONAM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.82%
CARUMONAM plasma
Homo sapiens
72%
CARUMONAM plasma
Homo sapiens

Doses

PubMed

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
Record UNII
486890PI06
Record Status Validated (UNII)
Record Version