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Identification
NameCyclandelate
Accession NumberDB04838
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
3,3,5-Trimethylcyclohexyl mandelate
3,5,5-Trimethylcyclohexyl amygdalate
Ciclandelato
Cyclandelatum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyclospasmol Tablets 200mgtablet200 mgoralWyeth Ayerst Canada Inc.1994-12-311997-08-14Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CapilanTakeda
CyclergineNot Available
Cyclospasmollves
Brand mixturesNot Available
SaltsNot Available
Categories
UNII4139O1OAY2
CAS number456-59-7
WeightAverage: 276.3707
Monoisotopic: 276.172544634
Chemical FormulaC17H24O3
InChI KeyInChIKey=WZHCOOQXZCIUNC-UHFFFAOYSA-N
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
IUPAC Name
3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate
SMILES
CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the treatment of various blood vessel diseases (e.g., claudication, arteriosclerosis and Raynaud's disease) and nighttime leg cramps.
PharmacodynamicsCyclandelate 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.
Mechanism of actionCyclandelate produces peripheral vasodilation by a direct effect on vascular smooth muscle. Pharmacological action may be due to calcium-channel antagonism.
Related Articles
AbsorptionWell absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute oral toxicity (LD50): 3950 mg/kg [Guinea pig]
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.8761
Caco-2 permeable+0.7443
P-glycoprotein substrateNon-substrate0.551
P-glycoprotein inhibitor IInhibitor0.6324
P-glycoprotein inhibitor IINon-inhibitor0.6209
Renal organic cation transporterNon-inhibitor0.8746
CYP450 2C9 substrateNon-substrate0.7769
CYP450 2D6 substrateNon-substrate0.9047
CYP450 3A4 substrateSubstrate0.6148
CYP450 1A2 substrateNon-inhibitor0.8485
CYP450 2C9 inhibitorInhibitor0.7116
CYP450 2D6 inhibitorNon-inhibitor0.9365
CYP450 2C19 inhibitorNon-inhibitor0.7518
CYP450 3A4 inhibitorNon-inhibitor0.9024
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9469
Ames testNon AMES toxic0.8703
CarcinogenicityNon-carcinogens0.7047
BiodegradationNot ready biodegradable0.9626
Rat acute toxicity1.7115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9942
hERG inhibition (predictor II)Non-inhibitor0.8132
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral200 mg
Prices
Unit descriptionCostUnit
Cyclandelate powder8.18USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point50-53Nauta, W.T.; U.S. Patent 2,707,193; April 26,1955; assigned to N.V. Koninklijke Pharmaceutische Fabrieken Voorbeen Brocades Stheeman & Pharmacia, Netherlands.
boiling point193 °C at 1.40E+01 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0997 mg/mLALOGPS
logP3.79ALOGPS
logP3.72ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.99ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.06 m3·mol-1ChemAxon
Polarizability30.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Nauta, W.T.; U.S. Patent 2,707,193; April 26,1955; assigned to N.V. Koninklijke Pharmaceutische Fabrieken Voorbeen Brocades Stheeman & Pharmacia, Netherlands.
Flitter, D.; U.S. Patent 3,663,597; May 16, 1972; assigned to American Home Products
Corporation.

General ReferencesNot Available
External Links
ATC CodesC04AX01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated calcium channel activity
Specific Function:
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling (By similarity).
Gene Name:
CACNA2D1
Uniprot ID:
P54289
Molecular Weight:
124566.93 Da
References
  1. Pascual J: [New prospects in the treatment of migraine]. Neurologia. 1999 Dec;14 Suppl 6:26-35. [PubMed:10659603 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Heffron F, Middleton B, White DA: Inhibition of acyl coenzyme A: cholesterol acyl transferase by trimethylcyclohexanylmandelate (cyclandelate). Biochem Pharmacol. 1990 Feb 1;39(3):575-80. [PubMed:2306268 ]
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Drug created on September 26, 2007 09:09 / Updated on April 09, 2014 16:16