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Details

Stereochemistry ACHIRAL
Molecular Formula C6H13NO3S
Molecular Weight 179.237
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLAMIC ACID

SMILES

OS(=O)(=O)NC1CCCCC1

InChI

InChIKey=HCAJEUSONLESMK-UHFFFAOYSA-N
InChI=1S/C6H13NO3S/c8-11(9,10)7-6-4-2-1-3-5-6/h6-7H,1-5H2,(H,8,9,10)

HIDE SMILES / InChI

Description

Cyclamic acid (Cyclamate) is banned in the United States but it is used in many other Western countries without safety concerns. Cyclamate interacts with the sweet taste receptor subunit T1R3 transmembrane domain. Initially it was recommended for use in treatment of obese patients and by individuals with diabetes but in August 27, 1970 FDA concluded that there was no substantial evidence of effectiveness of cyclamate compounds at any level for treatment of obese patients and individuals with diabetes and therefore prohibited continued sale of cyclamate containing products with drug labeling. cyclamate is the putative carcinogenic agent. Cyclamate was tested in the Maximal Electroshock Seizure model (mice, ip), showing moderate anticonvulsant activity.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.1 mM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Sucaryl
Primary
Sucaryl
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
400 ng/mL
2.2 g 3 times / day steady-state, oral
CYCLOHEXYLAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1912 ng × h/mL
2.2 g 3 times / day steady-state, oral
CYCLOHEXYLAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
2.2 g 3 times / day steady-state, oral
CYCLOHEXYLAMINE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
5 mg cyclamate/kg bodyweight/day or less
Route of Administration: Oral
In Vitro Use Guide
The addition of sodium cyclamate (75 mM) to the culture of the native bacterial population of the caecum concurrent with the progressive dilution of the growth medium promoted metabolism of cyclamate to cyclohexylamine (sulphamatase activity) within 4 wk. The maximum formation of cyclohexylamine was attained in about 8 wk and was equivalent to a 2-3% molar conversion of cyclamate to cyclohexylamine.