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Cyclandelate

Cyclandelate

Synopsis, Chemistry

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Also known as: 456-59-7, Cyclomandol, Cyclolyt, Cyclospasmol, Perebral, Ciclospasmol

Molecular Formula

C₁₇H₂₄O₃

Molecular Weight

276.4 g/mol

InChI Key

WZHCOOQXZCIUNC-UHFFFAOYSA-N

FDA UNII

4139O1OAY2

A direct-acting SMOOTH MUSCLE relaxant used to dilate BLOOD VESSELS.

1 2D Structure

Cyclandelate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate

2.1.2 InChI

InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3

2.1.3 InChI Key

WZHCOOQXZCIUNC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1CC(CC(C1)(C)C)OC(=O)C(C2=CC=CC=C2)O

2.2 Other Identifiers

2.2.1 UNII

4139O1OAY2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cyclospasmol

2.3.2 Depositor-Supplied Synonyms

1. 456-59-7

2. Cyclomandol

3. Cyclolyt

4. Cyclospasmol

5. Perebral

6. Ciclospasmol

7. Cyclergine

8. Spasmocyclon

9. Spasmocyclone

10. Capilan

11. Clandilon

12. Saiclate

13. Sancyclan

14. Sepyron

15. Spasmione

16. Arto-espasmol

17. 3,3,5-trimethylcyclohexyl Mandelate

18. 3,5,5-trimethylcyclohexyl Mandelate

19. Ciclandelato

20. Cyclobral

21. Novodil

22. Natil

23. 3,5,5-trimethylcyclohexyl Amygdalate

24. Cyclandelatum

25. Cyclandelatum [inn-latin]

26. Ciclandelato [inn-spanish]

27. Mandelic Acid 3,3,5-trimethylcyclohexyl Ester

28. Bs 572

29. 3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate

30. (3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate

31. Spasmocyclon (3m)

32. Cyclandelate (mixture Of Isomers)

33. Mandelic Acid, 3,3,5-trimethylcyclohexyl Ester

34. 3,5,5-trimethylcyclohexanol, Mandelic Acid Ester

35. Nsc-758910

36. Chebi:3988

37. 3,3,5-trimethylcyclohexanol Alpha-phenyl-alpha-hydroxyacetate

38. 3,3,5-trimethylcyclohexyl Hydroxy(phenyl)acetate

39. 4139o1oay2

40. Benzeneacetic Acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl Ester

41. 3,3,5-trimethylcyclohexyl Mandelate (mixture Of Isomers)

42. Ncgc00159506-02

43. Pericyclon

44. Hacosan

45. Lisospasm

46. Eparan

47. Cyclandelic Acid

48. Rythmol [vasodilator]

49. Hsdb 3046

50. Einecs 207-271-6

51. Mandelic

52. Unii-4139o1oay2

53. Benzeneacetic Acid, Alpha-hydroxy-, 3,3,5-trimethylcyclohexyl Ester

54. Cyclandelate [usp:inn:ban:jan]

55. Mfcd00056623

56. Alpha-hydroxybenzeneacetic Acid 3,3,5-trimethylcyclohexyl Ester

57. Cyclandelate [mi]

58. Cyclospasmol (tn)

59. Dsstox_cid_2862

60. Cyclandelate [inn]

61. Cyclandelate [jan]

62. Cyclandelate [hsdb]

63. Schembl5123

64. Cyclandelate [vandf]

65. Dsstox_rid_76763

66. Dsstox_gsid_22862

67. Cyclandelate [mart.]

68. Cyclandelate [usp-rs]

69. Cyclandelate [who-dd]

70. Cyclandelate (jan/usp/inn)

71. (3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenyl-acetate

72. Chembl1480987

73. Dtxsid4022862

74. Hms3264k11

75. Hms3652b09

76. Pharmakon1600-01505082

77. Cyclandelate [usp Impurity]

78. Hy-b1170

79. Tox21_111725

80. Nsc758910

81. S4189

82. Zinc00000189

83. Zinc00405331

84. Zinc00968262

85. Akos015902290

86. Ccg-213926

87. Cs-4770

88. Db04838

89. Ks-5317

90. Nsc 758910

91. Ncgc00159506-03

92. Ncgc00159506-05

93. Ncgc00159506-06

94. Cas-456-59-7

95. Sbi-0207036.p001

96. Ft-0735837

97. M0821

98. Sw220003-1

99. D00286

100. D91389

101. Ab01563218_01

102. Ab01563218_02

103. A913217

104. Sr-01000872740

105. 3,3,5-trimethylcyclohexyl Hydroxy(phenyl)acetate #

106. Q1147309

107. Sr-01000872740-1

108. .alpha.-hydroxybenzeneacetic Acid 3,3,5-trimethylcyclohexyl Ester

109. 3,3,5-trimethylcyclohexanol .alpha.-phenyl-.alpha.-hydroxyacetate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₄O₃
Molecular Weight	276.4 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	276.17254462 g/mol
Monoisotopic Mass	276.17254462 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	331
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	3
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

IT RELAXES VASCULAR SMOOTH MUSCLE & ERRATICALLY INCR BLOOD FLOW. IT IS USED IN TREATMENT OF THROMBOPHLEBITIS, RAYNAUD'S DISEASE, THROMBO-ANGIITIS OBLITERANS, DIABETIC ANGIOSES, INTERMITTENT CLAUDICATION, ARTERIOSCLEROSIS, ERYTHROCYANOSIS, FROSTBITE, & REFRACTORY SKIN ULCERS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 787

CYCLANDELATE HAS BEEN USED IN ALMOST EVERY KNOWN TYPE OF VASCULAR DISEASE, BUT ITS VALUE HAS NOT BEEN CONVINCINGLY DEMONSTRATED IN ANY.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 736

CYCLANDELATE CAN PRODUCE MILD VASODILATION IN MAN. THIS HAS BEEN NOTED PARTICULARLY AS INCR IN DIGITAL PULSE VOL & SKIN TEMP, BUT INCR IN CEREBRAL & MUSCLE BLOOD FLOW HAVE ALSO BEEN REPORTED.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 736

For more Therapeutic Uses (Complete) data for CYCLANDELATE (7 total), please visit the HSDB record page.

4.2 Drug Warning

...WHETHER REDUCTION OF PRESSURE IN ARTERIES SUPPLYING OPTIC NERVEHEAD MIGHT RENDER OPTIC NERVE MORE VULNERABLE TO INJURY IN GLAUCOMA REMAINS TO BE EVALUATED.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 340

4.3 Drug Indication

Used in the treatment of various blood vessel diseases (e.g., claudication, arteriosclerosis and Raynaud's disease) and nighttime leg cramps.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cyclandelate is in a class of drugs called vasodilators. Cyclandelate relaxes veins and arteries, which makes them wider and allows blood to pass through them more easily.

5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AX - Other peripheral vasodilators

C04AX01 - Cyclandelate

5.4 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.

MAX UPTAKE @ 1 HR FOR MOST RAT TISSUES WHILE BRAIN, DIAPHRAGM, STOMACH, & VEIN SHOWED MAX LEVELS @ 24 HR. LEVELS NEGLIGIBLE IN 28 DAYS.

ORR A, WHITTIER JR; DISTRIBUTION OF TRITIATED CYCLANDELATE, VASOACTIVE DRUG. PRELIMINARY OBSERVATIONS BY LIQUID SCINTILLATION SPECTROMETRY; INT J NUCL MED BIOL 1(4) 205-213 (1974)

5.5 Biological Half-Life

(3-)-H-LABELED CYCLANDELATE WAS DETECTED & QUANTITATED. EFFECTIVE HALF-LIFE VALUES IN VARIOUS RAT TISSUES WERE 2.8-4.1 DAYS.

ORR A, WHITTIER JR; DISTRIBUTION OF TRITIATED CYCLANDELATE, VASOACTIVE DRUG. PRELIMINARY OBSERVATIONS BY LIQUID SCINTILLATION SPECTROMETRY; INT J NUCL MED BIOL 1(4) 205-213 (1974)

5.6 Mechanism of Action

Cyclandelate produces peripheral vasodilation by a direct effect on vascular smooth muscle. Pharmacological action may be due to calcium-channel antagonism.

...MOST OF ITS PHARMACOLOGICAL PROPERTIES ARE VERY SIMILAR TO THOSE OF PAPAVERINE & OF MANY SYNTHETIC ANTISPASMODICS PROMOTED PRIMARILY FOR EFFECTS ON SMOOTH MUSCLE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 736

PAPAVERINE IS POTENT INHIBITOR OF CYCLIC NUCLEOTIDE PHOSPHODIESTERASE FOUND IN MANY TISSUES & CAN INCR CONCN OF CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE (CYCLIC AMP). SINCE CYCLIC AMP HAS BEEN IMPLICATED AS POSSIBLE MEDIATOR OF BETA-ADRENERGIC RELAXATION OF SMOOTH MUSCLE, SUCH MECHANISM OF ACTION...IS PLAUSIBLE. /PAPAVERINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 735