Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H12NO3S.Na |
Molecular Weight | 201.219 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-]S(=O)(=O)NC1CCCCC1
InChI
InChIKey=UDIPTWFVPPPURJ-UHFFFAOYSA-M
InChI=1S/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1
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 | C6H12NO3S |
Molecular Weight | 178.229 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdfCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/10653518 |https://www.ncbi.nlm.nih.gov/pubmed/22579423
Sources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/10653518 |https://www.ncbi.nlm.nih.gov/pubmed/22579423
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: 83756.0 Gene Symbol: TAS1R3 |
3.1 mM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Sucaryl Approved UseUnknown Launch Date-5.36457609E11 |
|||
Primary | Sucaryl Approved UseUnknown Launch Date-5.36457609E11 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
400 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/ |
2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOHEXYLAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1912 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/ |
2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOHEXYLAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/ |
2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOHEXYLAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
[Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design]. | 2006 Oct |
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Artificial sweeteners and salts producing a metallic taste sensation activate TRPV1 receptors. | 2007 Aug |
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Simultaneous determination of nine intense sweeteners in foodstuffs by high performance liquid chromatography and evaporative light scattering detection--development and single-laboratory validation. | 2007 Jul 20 |
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[Restless legs due to ingestion of 'light' beverages containing saccharine. Results of an N-of-1 trial]. | 2007 Jun |
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Structures of artificial sweeteners--cyclamic acid and sodium cyclamate with other cyclamates. | 2007 Jun |
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Rapid determination of cyclamate in foods by solid-phase extraction and capillary electrophoresis. | 2007 Jun 22 |
|
Estimated intake of intense sweeteners from non-alcoholic beverages in Denmark. | 2007 Mar |
|
A conductive pathway generated from fragments of the human red cell anion exchanger AE1. | 2007 May 15 |
|
Influence of artificial sweeteners on the kinetic and metabolic behavior of Lactobacillus delbrueckii subsp. bulgaricus. | 2007 Oct |
|
Synthesis, characterization and antimycobacterial activity of Ag(I)-aspartame, Ag(I)-saccharin and Ag(I)-cyclamate complexes. | 2007 Oct |
|
The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor. | 2007 Oct 12 |
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Influence of artificial sweetener on human blood glucose concentration. | 2007 Oct 5 |
|
Life-span exposure to low doses of aspartame beginning during prenatal life increases cancer effects in rats. | 2007 Sep |
|
Molecular mechanism of action of monocyclam versus bicyclam non-peptide antagonists in the CXCR4 chemokine receptor. | 2007 Sep 14 |
|
Chemical carcinogenesis studies in nonhuman primates. | 2008 |
|
[Compound preservative and cyclamat determinated by gas chromatography]. | 2008 Jul |
|
Catalyzed oxidative corrosion of porous silicon used as an optical transducer for ligand-receptor interactions. | 2008 Jul 21 |
|
Simultaneous square-wave voltammetric determination of aspartame and cyclamate using a boron-doped diamond electrode. | 2008 Jul 30 |
|
Estimated intake of intense sweeteners from non-alcoholic beverages in Denmark, 2005. | 2008 Jun |
|
Direct NMR detection of the binding of functional ligands to the human sweet receptor, a heterodimeric family 3 GPCR. | 2008 Jun 11 |
|
The capsaicin receptor participates in artificial sweetener aversion. | 2008 Nov 28 |
|
Spanish Ketogenic Mediterranean Diet: a healthy cardiovascular diet for weight loss. | 2008 Oct 26 |
|
Determination of cyclamate in foods by ultraperformance liquid chromatography/tandem mass spectrometry. | 2008 Sep-Oct |
|
Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion. | 2009 |
|
Simultaneous determination of nonnutritive sweeteners in foods by HPLC/ESI-MS. | 2009 Apr 22 |
|
A phase II study on safety and efficacy of high-dose N-acetylcysteine in patients with cystic fibrosis. | 2009 Aug 12 |
|
Genetic and molecular basis of individual differences in human umami taste perception. | 2009 Aug 21 |
|
Magnetic behaviour of nickel-cyclam complexes in mesoporous silica: EPR investigations. | 2009 Feb 18 |
|
Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study. | 2009 Jan-Feb |
|
Zolpidem, a clinical hypnotic that affects electronic transfer, alters synaptic activity through potential GABA receptors in the nervous system without significant free radical generation. | 2009 Jan-Mar |
|
Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT). | 2009 Jul |
|
Development and single-laboratory validation of an HPLC method for the determination of cyclamate sweetener in foodstuffs. | 2009 May |
|
Evaluation of certain food additives. Seventy-first report of the Joint FAO/WHO Expert Committee on Food Additives. | 2010 |
|
Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review. | 2010 |
|
[Determination of five synthetic sweeteners in wines using high performance liquid chromatography-tandem mass spectrometry]. | 2010 Aug |
|
Sensory quality of functional beverages: bitterness perception and bitter masking of olive leaf extract fortified fruit smoothies. | 2010 Aug 1 |
|
Novel monocyclam derivatives as HIV entry inhibitors: Design, synthesis, anti-HIV evaluation, and their interaction with the CXCR4 co-receptor. | 2010 Aug 2 |
|
Effects of artificial sweeteners on body weight, food and drink intake. | 2010 Dec |
|
An attempt to use sweeteners as a material for accident dosimetry. | 2010 Feb |
|
Oxovanadium(IV) cyclam and bicyclam complexes: potential CXCR4 receptor antagonists. | 2010 Feb 1 |
|
Tailored adsorption of His6-tagged protein onto nickel(II)-cyclam grafted mesoporous silica. | 2010 Feb 21 |
|
Anionic leak currents through the Na+/monocarboxylate cotransporter SMCT1. | 2010 Jan |
|
Gain weight by "going diet?" Artificial sweeteners and the neurobiology of sugar cravings: Neuroscience 2010. | 2010 Jun |
|
Performance of conventional multi-barrier drinking water treatment plants for the removal of four artificial sweeteners. | 2010 Jun |
|
Responses of single chorda tympani taste fibers of the calf (Bos taurus). | 2010 Jun |
|
Chronic consumption of fructose rich soft drinks alters tissue lipids of rats. | 2010 Jun 23 |
|
Positive allosteric modulators of the human sweet taste receptor enhance sweet taste. | 2010 Mar 9 |
|
Key amino acid residues involved in multi-point binding interactions between brazzein, a sweet protein, and the T1R2-T1R3 human sweet receptor. | 2010 May 14 |
|
[Simultaneous determination of six synthetic sweeteners in food by high performance liquid chromatography-tandem mass spectrometry]. | 2010 Nov |
|
Retention behaviour of some high-intensity sweeteners on different SPE sorbents. | 2010 Oct 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf
Curator's Comment: It is unnecessary to decide the acceptable daily intake and safe conditions for use issues.
5 mg cyclamate/kg bodyweight/day or less
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2416656
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:22:34 UTC 2023
by
admin
on
Fri Dec 15 15:22:34 UTC 2023
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Record UNII |
1I6F42RME1
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CODEX ALIMENTARIUS (GSFA) |
INS-952(IV)
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JECFA EVALUATION |
INS-952(IV)
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CFR |
21 CFR 189.135
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NCI_THESAURUS |
C283
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23665706
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100000083527
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1I6F42RME1
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205-348-9
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DTXSID6020355
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42195
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SODIUM CYCLAMATE
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56467
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C84153
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CHEMBL273977
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139-05-9
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