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Cyclandelate

PubChem CID
2893
Structure
Cyclandelate_small.png
Cyclandelate_3D_Structure.png
Molecular Formula
Synonyms
  • cyclandelate
  • 456-59-7
  • Cyclomandol
  • Cyclospasmol
  • Cyclolyt
Molecular Weight
276.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Cyclandelate is the ester obtained by formal condensation of mandelic acid and 3,3,5-tricyclohexanol. It is a direct-acting smooth muscle relaxant used to dilate blood vessels. It has a role as a vasodilator agent. It is a carboxylic ester and a secondary alcohol. It is functionally related to a mandelic acid and a 3,3,5-trimethylcyclohexanol.
A direct-acting smooth muscle relaxant used to dilate blood vessels. It may cause gastrointestinal distress and tachycardia. Cyclandelate is not approved for use in the U.S. or Canada, but is approved in various European countries.
CYCLANDELATE is a small molecule drug with a maximum clinical trial phase of IV and is indicated for cardiovascular disease.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cyclandelate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

WZHCOOQXZCIUNC-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1CC(CC(C1)(C)C)OC(=O)C(C2=CC=CC=C2)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H24O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

28283-32-1, 54110-27-9
28283-32-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 PharmGKB ID

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Cyclandelate
  • Cyclospasmol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
276.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
276.17254462 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
276.17254462 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
46.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
331
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Color / Form

CRYSTALS
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 352

3.2.3 Boiling Point

193 °C at 1.40E+01 mm Hg
PhysProp
192-194 °C @ 14 MM HG
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 352

3.2.4 Melting Point

50-53
Nauta, W.T.; U.S. Patent 2,707,193; April 26,1955; assigned to N.V. Koninklijke Pharmaceutische Fabrieken Voorbeen Brocades Stheeman & Pharmacia, Netherlands.
50-53 °C
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 352
56 °C

3.2.5 Solubility

PRACTICALLY INSOL IN WATER; SOL IN LIPOIDS & THEIR SOLVENTS
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 352
FREELY SOL IN PETROLEUM ETHER, ETHANOL; SOL IN DIETHYL ETHER, ACETONE
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 34
9.97e-02 g/L

3.2.6 Collision Cross Section

186.2 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

161.09 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

184.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

156.39 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.7 Kovats Retention Index

Standard non-polar
1890 , 1903

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 5
View All
NIST Number
247795
Library
Main library
Total Peaks
64
m/z Top Peak
107
m/z 2nd Highest
69
m/z 3rd Highest
79
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
246608
Library
Replicate library
Total Peaks
61
m/z Top Peak
107
m/z 2nd Highest
69
m/z 3rd Highest
83
Thumbnail
Thumbnail

4.2 IR Spectra

4.2.1 FTIR Spectra

Technique
FILM
Source of Sample
Ives Laboratories, Inc.
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

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

7.2 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.

7.3 Drug Warnings

...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

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

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.

8.2 MeSH Pharmacological Classification

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

8.3 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AX - Other peripheral vasodilators

C04AX01 - Cyclandelate

8.4 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)

8.5 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)

8.6 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

8.7 Human Metabolite Information

8.7.1 Cellular Locations

Membrane

9 Use and Manufacturing

9.1 Uses

MEDICATION

9.2 Methods of Manufacturing

PREPD BY ESTERIFICATION OF MANDELIC ACID WITH 3, 3,5-TRIMETHYLCYCLOHEXANOL USING SULFURIC ACID AS CATALYST: BROCK ET AL, ARZNEIMITTEL-FORSCH 2, 165 (1952); FUNCKE ET AL, IBID 3, 503 (1953)...BRITISH PATENT 707.227 (1954 TO BROCADES-STHEEMAN). PURIFICATION: FLITTER, US PATENT 3,663,597 (1972 TO AMERICAN HOME PRODUCTS).
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 352

9.3 Formulations / Preparations

DRUG IS AVAILABLE IN 100-MG TABLETS & 200-MG CAPSULES.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 736

9.4 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester: ACTIVE

10 Identification

10.1 Analytic Laboratory Methods

CYCLOSPASMOL IS ONE OF 13 DRUGS WHOSE UV SPECTRA ARE TABULATED FOR THEIR DETERMINATION IN PHARMACEUTICAL PREPARATIONS.
KRACMAR J ET AL; ULTRAVIOLET SPECTROPHOTOMETRY IN DRUG CONTROL. PART 18. NEW DRUGS WITH SUBSTITUTED BENZENE NUCLEI; PHARMAZIE 31(6) 363-367 (1976)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H319 (97.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Precautionary Statement Codes

P264+P265, P280, P305+P351+P338, and P337+P317

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Eye Irrit. 2 (97.4%)

12 Toxicity

12.1 Toxicological Information

12.1.1 Acute Effects

12.1.2 Human Toxicity Excerpts

CYCLANDELATE APPEARS TO PRODUCE LITTLE SERIOUS TOXICITY. HOWEVER, ORAL DOSES OF 200 MG OR MORE ARE ASSOC WITH SIGNIFICANT INCIDENCE OF UNPLEASANT SIDE EFFECTS, INCL GASTROINTESTINAL UPSETS, FLUSHING, TINGLING, HEADACHE, DIZZINESS, & SWEATING.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 737
SIDE EFFECTS INCLUDE...NAUSEA...& HYPOTENSION.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 787
...IT HAS BEEN CLAIMED THAT CYCLANDELATE REDUCED OPHTHALMIC BLOOD PRESSURE BUT INCR FLOW IN RETINAL ARTERIES. IT APPEARS THAT CYCLANDELATE PRESENTS NO SIGNIFICANT THREAT OF RAISING OCULAR PRESSURE IN OPEN-ANGLE GLAUCOMA NOR ANY THREAT OF PRECIPITATING ANGLE-CLOSURE GLAUCOMA...
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 340

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Drug-Drug Interactions

16.3 Drug-Food Interactions

Take with food. Food reduces irritation.

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: ATC

18.5 WHO ATC Classification System

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 NORMAN Suspect List Exchange Classification

18.10 CCSBase Classification

18.11 EPA DSSTox Classification

18.12 EPA TSCA and CDR Classification

18.13 EPA Substance Registry Services Tree

18.14 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
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    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
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    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
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  19. Metabolomics Workbench
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  21. NIST Mass Spectrometry Data Center
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    https://www.pharmgkb.org/page/policies
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  34. EPA Substance Registry Services
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS