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Tox21_301008

Tox21_301008

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Also known as: Cyclohexylsulfamic acid, 100-88-9, Cyclamate, Cyclohexanesulfamic acid, N-cyclohexylsulfamic acid, Hexamic acid

Molecular Formula

C₆H₁₃NO₃S

Molecular Weight

179.24 g/mol

InChI Key

HCAJEUSONLESMK-UHFFFAOYSA-N

FDA UNII

HN3OFO5036

Salts and esters of cyclamic acid.

1 2D Structure

Tox21_301008

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

cyclohexylsulfamic acid

2.1.2 InChI

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

2.1.3 InChI Key

HCAJEUSONLESMK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCC(CC1)NS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

HN3OFO5036

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Calcium Cyclamate

2. Cyclamate

3. Cyclamate Calcium (2:1) Salt

4. Cyclamate, Calcium

5. Cyclamate, Calcium (2:1) Salt, Dihydrate

6. Cyclamate, Potassium

7. Cyclamate, Sodium

8. Cyclamate, Sodium Salt

9. Cyclamates

10. Potassium Cyclamate

11. Sodium Cyclamate

2.3.2 Depositor-Supplied Synonyms

1. Cyclohexylsulfamic Acid

2. 100-88-9

3. Cyclamate

4. Cyclohexanesulfamic Acid

5. N-cyclohexylsulfamic Acid

6. Hexamic Acid

7. Sucaryl

8. Sucaryl Acid

9. Cyclohexylaminesulphonic Acid

10. N-cyclohexylsulphamic Acid

11. Sulfamic Acid, Cyclohexyl-

12. Polycat 200

13. Cyclohexylamidosulfuric Acid

14. Cyclohexylaminesulfonic Acid

15. Cylamic Acid

16. Cyclohexylsulphamic Acid

17. Cyclohexanesulphamic Acid

18. Zyklamat

19. Cyclohexylamidosulphuric Acid

20. Cyclohexylamide Sulfate

21. Cyclohexylamine Sulfamic Acid

22. Sulfamic Acid, N-cyclohexyl-

23. Nsc 220327

24. Hexamic Acid (tn)

25. Nsc-220327

26. Cyclamate, Sodium Salt

27. Hn3ofo5036

28. Cyclohexylsulfamic Acid;cyclamate

29. Ins No.952(i)

30. Chebi:15964

31. Ins-952(i)

32. Asugryn

33. Nsc220327

34. Ncgc00165999-01

35. Cyclamic Acid (usan)

36. E-952(i)

37. Dsstox_cid_21809

38. Dsstox_rid_79849

39. Dsstox_gsid_41809

40. Cyclamic Acid [usan]

41. Cyclamates

42. Cyclamsaeure

43. Cyclamate, Calcium

44. Cyclamic Acid [usan:ban]

45. Cas-100-88-9

46. C6h13no3s

47. Cyclamate, Potassium

48. Hsdb 275

49. N-cyclohexylsulfamsaeure

50. Einecs 202-898-1

51. Sulfuric Acid Monoamide, N-cyclohexyl-

52. Brn 2208885

53. Unii-hn3ofo5036

54. Cyclamic-acid

55. N-(cyclohexyl)aminosulfonsaeure

56. Sucaryl Acidxine

57. Cyclamic Acid

58. Cyclamate Calcium (2:1) Salt

59. (cyclamic Acid)

60. Calciumlevulinate

61. Cyclohexylamide Sulphate

62. Cyclohexyl-sulfamic Acid

63. Cyclamic Acid-[d11]

64. N-cyclohexyl-sulfamic Acid

65. Bmse000657

66. N-?cyclohexylsulfamic Acid

67. N-cyclo-hexylsulphamic Acid

68. Cyclamic Acid [ii]

69. Cyclamic Acid [mi]

70. Schembl6227

71. Cyclamic Acid, Ban, Usan

72. Cyclamic Acid [hsdb]

73. 4-12-00-00102 (beilstein Handbook Reference)

74. Cyclamic Acid [mart.]

75. Cyclohexansulfamidsa Currencyure

76. Cyclohexylamine-n-sulfonic Acid

77. Cyclamic Acid [usp-rs]

78. Cyclamic Acid [who-dd]

79. Chembl1206440

80. Dtxsid5041809

81. Hms3264k03

82. Hms3652c17

83. Pharmakon1600-01301015

84. Hy-b0541

85. Zinc1529532

86. N-cyclohexyl-sulfuric Acid Monoamide

87. Tox21_112285

88. Tox21_301008

89. Mfcd00065234

90. Nsc760133

91. S4015

92. Stl356798

93. Akos015913947

94. Tox21_112285_1

95. Ccg-213726

96. Nsc-760133

97. Ncgc00165999-02

98. Ncgc00165999-03

99. Ncgc00254910-01

100. As-59382

101. N-cyclohexylsulfamic Acid, >=98.0% (t)

102. Ft-0624197

103. Sw219574-1

104. C02824

105. D02442

106. E78799

107. Ab01563182_01

108. Ab01563182_02

109. Sr-01000940120

110. J-000244

111. Q2130929

112. Sr-01000940120-2

113. Cyclamic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₃NO₃S
Molecular Weight	179.24 g/mol
XLogP3	0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	179.06161445 g/mol
Monoisotopic Mass	179.06161445 g/mol
Topological Polar Surface Area	74.8 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	200
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Minimum/Potential Fatal Human Dose

2. 2= SLIGHTLY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 5-15 G/KG, BETWEEN 1 PINT & 1 QUART FOR 70 KG PERSON (150 LB). /NA SALT/

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-243

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Sweetening Agents

Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)

5.2 Absorption, Distribution and Excretion

In pregnant rats, significant amounts of sodium cyclamate were distributed to fetal tissues. /Sodium cyclamate/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)

Absorption of cyclamate from the gut is incomplete, and absorbed cyclamate is excreted in the urine. When three men received 1 g calcium (14)C-cyclamate orally, 87-90% was recovered in the urine and feces in about equal amounts within four days. /Calcium cyclamate/

When given to lactating dogs and rats, calcium cyclamate reached higher concentrations in the milk than in the blood. /Calcium cyclamate/

In guinea-pigs, rats and rabbits, 30, 50 and 5% of orally administered cyclamate was excreted in the feces and 65, 40 and 95% in the urine, respectively, over two to three days. Cyclamate thus appears to be readily absorbed by rabbits but less readily by guinea-pigs and rats.

For more Absorption, Distribution and Excretion (Complete) data for CYCLAMATE (11 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

Most humans convert only small amounts of cyclamate to cyclohexylamine, and the majority converted < 0.1-8%; however, there is wide interindividual variation in the daily urinary excretion of cyclohexylamine, which can amount to 60% of a dose of cyclamate. Gastrointestinal microflora are the source of the conversion of unabsorbed cyclamate to cyclohexylamine.

Orally administered cyclamate appears to be readily absorbed by rabbits but less readily by guinea-pigs, rats and humans. All of these species convert cyclamate to cyclohexylamine, via the action of gastrointestinal microflora on unabsorbed cyclamate. The metabolism of cyclohexylamine to other products differs somewhat in humans and other species, although most cyclohexylamine is rapidly excreted unchanged in the urine. In rats, it is metabolized mainly by hydroxylation of the cyclohexane ring; in humans, it is metabolized by deamination; and in guinea-pigs and rabbits, it is metabolized by ring hydroxylation and deamination.

Two metabolites were definitely identified in the urine of volunteers who received an oral dose of (14)C-cyclohexylamine, namely cyclohexanol and trans-cyclohexane-1,2- diol. No N-hydroxycyclohexylamine was found in human urine.

...TO DETERMINE INDUCTION OF CYCLOHEXYLAMINE PRODUCTION...2 GROUPS OF RATS WERE FED NORMAL DIETS WITH & WITHOUT CYCLAMATE FOR 8 MO. BOTH GROUPS...WERE THEN GIVEN (14)C-CYCLAMATE...THOSE FED FORMER DIET CONVERTED 18% OF (14)C-DOSE INTO CYCLOHEXYLAMINE...THOSE FED LATTER CONVERTED LESS THAN 1%. ...DIETARY PRETREATMENT WITH CYCLAMATE IS USUALLY NECESSARY BEFORE.../BIOTRANSFORMATION/ TO CYCLOHEXYLAMINE...IN MAN, RAT, GUINEA-PIG, & RABBIT.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 149

For more Metabolism/Metabolites (Complete) data for CYCLAMATE (9 total), please visit the HSDB record page.

5.4 Biological Half-Life

(14)C-labelled cyclamate was shown to have an average serum half-life of 8 hours in dogs and rats.

WHO/FAO: Expert Committee on Food Additives. FAO Nutrition Meetings Report Series No. 48A: Calcium Cyclamate and Sodium Cyclamate (Including Cyclohexylamine) (1970). Available from, as of July 13, 2011: https://www.inchem.org/pages/jecfa.html

5.5 Mechanism of Action

The sweet taste receptor is a heterodimer of two G protein coupled receptors, T1R2 and T1R3. Previous experimental studies using sweet receptor chimeras and mutants show that there are at least three potential binding sites in this heterodimeric receptor. Receptor activity toward the artificial sweeteners aspartame and neotame depends on residues in the amino terminal domain of human T1R2. In contrast, receptor activity toward the sweetener cyclamate and the sweet taste inhibitor lactisole depends on residues within the transmembrane domain of human T1R3. Furthermore, receptor activity toward the sweet protein brazzein depends on the cysteine rich domain of human T1R3.

PMID:17168764 Cui M, et al; Curr Pharm Des 12 (35): 4591-4600 (2006)

The sweet protein brazzein [recombinant protein with sequence identical with the native protein lacking the N-terminal pyroglutamate (the numbering system used has Asp2 as the N-terminal residue)] activates the human sweet receptor, a heterodimeric G-protein-coupled receptor composed of subunits Taste type 1 Receptor 2 (T1R2) and Taste type 1 Receptor 3 (T1R3). In order to elucidate the key amino acid(s) responsible for this interaction, we mutated residues in brazzein and each of the two subunits of the receptor. The effects of brazzein mutations were assayed by a human taste panel and by an in vitro assay involving receptor subunits expressed recombinantly in human embryonic kidney cells; the effects of the receptor mutations were assayed by in vitro assay. We mutated surface residues of brazzein at three putative interaction sites: site 1 (Loop43), site 2 (N- and C-termini and adjacent Glu36, Loop33), and site 3 (Loop9-19). Basic residues in site 1 and acidic residues in site 2 were essential for positive responses from each assay. Mutation of Y39A (site 1) greatly reduced positive responses. A bulky side chain at position 54 (site 2), rather than a side chain with hydrogen-bonding potential, was required for positive responses, as was the presence of the native disulfide bond in Loop9-19 (site 3). Results from mutagenesis and chimeras of the receptor indicated that brazzein interacts with both T1R2 and T1R3 and that the Venus flytrap module of T1R2 is important for brazzein agonism. With one exception, all mutations of receptor residues at putative interaction sites predicted by wedge models failed to yield the expected decrease in brazzein response. The exception, hT1R2 (human T1R2 subunit of the sweet receptor):R217A/hT1R3 (human T1R3 subunit of the sweet receptor), which contained a substitution in lobe 2 at the interface between the two subunits, exhibited a small selective decrease in brazzein activity. However, because the mutation was found to increase the positive cooperativity of binding by multiple ligands proposed to bind both T1R subunits (brazzein, monellin, and sucralose) but not those that bind to a single subunit (neotame and cyclamate), we suggest that this site is involved in subunit-subunit interaction rather than in direct brazzein binding. Results from this study support a multi-point interaction between brazzein and the sweet receptor by some mechanism other than the proposed wedge models.

PMID:20302879 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2879441 Assadi-Porter FM, et al; J Mol Biol 398 (4): 584-94 (2010)