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Calcium Cyclamate

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Also known as: 139-06-0, Cyclamate calcium, Cyclan, Calcium bis(cyclohexylsulphamate), Calcium cyclohexanesulfamate, Calcium cyclamate(1:2)

Molecular Formula

C₁₂H₂₄CaN₂O₆S₂

Molecular Weight

396.5 g/mol

InChI Key

UKLJMHXGZUJRTL-UHFFFAOYSA-L

FDA UNII

X12LMJ1WYL

Salts and esters of cyclamic acid.

1 2D Structure

Calcium Cyclamate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

calcium;N-cyclohexylsulfamate

2.1.2 InChI

InChI=1S/2C6H13NO3S.Ca/c2*8-11(9,10)7-6-4-2-1-3-5-6;/h2*6-7H,1-5H2,(H,8,9,10);/q;;+2/p-2

2.1.3 InChI Key

UKLJMHXGZUJRTL-UHFFFAOYSA-L

2.1.4 Canonical SMILES

C1CCC(CC1)NS(=O)(=O)[O-].C1CCC(CC1)NS(=O)(=O)[O-].[Ca+2]

2.2 Other Identifiers

2.2.1 UNII

X12LMJ1WYL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cyclamate

2. Cyclamate Calcium (2:1) Salt

3. Cyclamate, Calcium

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

5. Cyclamate, Potassium

6. Cyclamate, Sodium

7. Cyclamate, Sodium Salt

8. Cyclamates

9. Cyclamic Acid

10. Potassium Cyclamate

11. Sodium Cyclamate

2.3.2 Depositor-Supplied Synonyms

1. 139-06-0

2. Cyclamate Calcium

3. Cyclan

4. Calcium Bis(cyclohexylsulphamate)

5. Calcium Cyclohexanesulfamate

6. Calcium Cyclamate(1:2)

7. Calcium;n-cyclohexylsulfamate

8. X12lmj1wyl

9. Calcium Cyclamate Anhydrous

10. Dietil

11. Cylan

12. Sucaryl Calcium

13. Cyclamate, Calcium Salt

14. Kalziumzyklamate

15. Kalziumzyklamate [german]

16. Calcium Cyclohexylsulphamate

17. Calcium Cyclohexane Sulphamate

18. Ccris 186

19. Hsdb 823

20. Calcium Cyclohexylsulfamate (1:2)

21. Einecs 205-349-4

22. Unii-x12lmj1wyl

23. Ai3-52126

24. Cyclohexanesulfamic Acid, Calcium Salt (2:1)

25. Sulfamic Acid, Cyclohexyl-, Calcium Salt (2:1)

26. Calciumcyclohexylsulfamat

27. Calcium Cyclohexylsulfamate

28. Calcium Cyclamate [mi]

29. Schembl1532404

30. Calcium Cyclamate [hsdb]

31. Calcium Cyclamate [inci]

32. Chembl2104112

33. Dtxsid9057892

34. Cyclamate Calcium Anhydrous

35. Calcium Cyclamate, Anhydrous

36. Calcium N-cyclohexylsulphamate

37. Cyclohexylsulfamic Acid Calcium Salt

38. Db-042461

39. Ft-0631808

40. D02444

41. Sulfamic Acid, N-cyclohexyl-, Calcium Salt (2:1)

42. Q27293257

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₄CaN₂O₆S₂
Molecular Weight	396.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	396.0701697 g/mol
Monoisotopic Mass	396.0701697 g/mol
Topological Polar Surface Area	155 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	187
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	3

4 Drug and Medication Information

4.1 Minimum/Potential Fatal Human Dose

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

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-406

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

...PREVIOUSLY THOUGHT TO BE METABOLICALLY STABLE. WHEN GIVEN ORALLY TO GUINEA PIGS, RABBITS, RATS, & HUMANS ON CYCLAMATE-FREE DIET IT IS EXCRETED LARGELY UNCHANGED. /CYCLAMATE/

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 449

...CYCLOHEXYLAMINE FORMED IN INTESTINE IS ALMOST COMPLETELY ABSORBED & EXCRETED IN URINE, IN COMPARISON TO CYCLAMATE, WHICH IS ABSORBED TO AN EXTENT OF ONLY 20-40%. /CYCLAMATE/

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. 264

...(14)C-CYCLAMATE, GIVEN IV TO WOMEN UNDERGOING THERAPEUTIC ABORTION, BY ABDOMINAL HYSTERECTOMY DURING EARLY PREGNANCY, CROSSED PLACENTA & DISPERSED IN FETAL TISSUES, PARTICULARLY IN LIVER, SPLEEN, PANCREAS, & KIDNEYS. ...MATERNAL BLOOD LEVELS...FELL RAPIDLY...INDICATING VERY RAPID ELIMINATION... /CYCLAMATE/

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. 150

MAX DAILY EXCRETION OF CYCLOHEXYLAMINE...RANGED FROM 0.1 TO 0.9% OF DAILY CYCLAMATE INTAKE (5 G); URINARY OUTPUT OF CYCLOHEXYLAMINE WAS ERRATIC & CONTINUED FOR 3-4 DAYS AFTER ADMIN HAD CEASED. /CYCLAMATE/

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. 265

For more Absorption, Distribution and Excretion (Complete) data for CALCIUM CYCLAMATE (6 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

/CALCIUM/ CYCLAMATE LABELLED WITH (35)S OR (14)C IS EXCRETED BY MAN & LABORATORY ANIMALS ALMOST ENTIRELY UNCHANGED, IN URINE & FECES, ALTHOUGH TRACES OF...CYCLOHEXYLAMINE (0.7% DOSE) HAVE BEEN FOUND IN URINE OF HUMANS & DOGS DOSED ORALLY...

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 165

...BIOTRANSFORMATION IN RATS...IS BROUGHT ABOUT BY GUT MICROFLORA. ...GUT MICROFLORA IN MAN & IN ANIMALS ACQUIRE CAPACITY TO METABOLIZE CYCLAMATE INTO CYCLOHEXYLAMINE, WHEN CYCLAMATE IS ADMIN CHRONICALLY. /CYCLAMATE/

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. 264

GUT MICRO-ORGANISMS, WHICH BECOME CYCLAMATE "CONVERTERS" ARE CLOSTRIDIA IN RATS, ENTEROBACTERIA IN RABBITS, & ENTEROCOCCI IN MAN. /CYCLAMATE/

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 347

...2 GROUPS OF WEANLING RATS WERE FED FOR 8 MO...WITH CHOW DIET OR...DIET CONTAINING 0.1% CA CYCLAMATE...THEN A SINGLE DOSE OF (14)C-CYCLAMATE BY STOMACH TUBE. ...7/11 CYCLAMATE-FED RATS CONVERTED CYCLAMATE INTO CYCLOHEXYLAMINE, TO...12-25% OF TOTAL (14)C IN URINE. 2 OF THE URINES CONTAINED TRACES OF DICYCLOHEXYLAMINE...

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. 264

WHEN GUINEA PIGS, RABBITS, RATS, & HUMANS WERE PLACED ON A DIET CONTAINING CALCIUM CYCLAMATE THEY DEVELOPED THE ABILITY TO CONVERT ORALLY ADMIN CYCLAMATE INTO CYCLOHEXYLAMINE & THE METABOLITES OF THE LATTER.

RENWICK ET AL; BIOCHEM J 129(4) 869 (1972)

5.4 Biological Half-Life

...IV DOSE OF 14(C)-CYCLAMATE TO PREGNANT RAT...T/2 OF CYCLAMATE WAS ABOUT 7 HR. /CYCLAMATE/

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. 150

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