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    Cyclandelate

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 28Xls

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    2D Structure
    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

    2D Structure

    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 Weight 276.4 g/mol
    Molecular Formula C17H24O3
    XLogP34.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass276.17254462 g/mol
    Monoisotopic Mass276.17254462 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity331
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count3
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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