Cyclandelate

Identification

Summary

Cyclandelate is a vasodilator used for the treatment of various blood vessel diseases, such as claudication and arteriosclerosis.

Generic Name
Cyclandelate
DrugBank Accession Number
DB04838
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 276.3707
Monoisotopic: 276.172544634
Chemical Formula
C17H24O3
Synonyms
  • 3,3,5-Trimethylcyclohexyl mandelate
  • 3,5,5-Trimethylcyclohexyl amygdalate
  • Ciclandelato
  • Cyclandelate
  • Cyclandelatum

Pharmacology

Indication

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

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
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.

Mechanism of action

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

TargetActionsOrganism
UVoltage-dependent calcium channel subunit alpha-2/delta-1
inhibitor
Humans
ULiver carboxylesterase 1Not AvailableHumans
Absorption

Well absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Acute oral toxicity (LD50): 3950 mg/kg [Guinea pig]

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Cyclandelate can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hypoglycemia can be increased when Cyclandelate is combined with Acarbose.
AcebutololThe risk or severity of bradycardia can be increased when Cyclandelate is combined with Acebutolol.
AceclofenacThe risk or severity of hyperkalemia can be increased when Cyclandelate is combined with Aceclofenac.
AcemetacinThe risk or severity of hyperkalemia can be increased when Cyclandelate is combined with Acemetacin.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Cyclandelate is combined with Acetohexamide.
AcetyldigitoxinCyclandelate may increase the arrhythmogenic activities of Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of hyperkalemia can be increased when Acetylsalicylic acid is combined with Cyclandelate.
AdenosineAdenosine may increase the arrhythmogenic activities of Cyclandelate.
AjmalineAjmaline may increase the arrhythmogenic activities of Cyclandelate.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
  • Take with food. Food reduces irritation.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
International/Other Brands
Capilan (Takeda) / Cyclergine / Cyclospasmol (lves)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cyclospasmol Tablets 200mgTablet200 mg / tabOralWyeth Ayerst Canada Inc.1994-12-311997-08-14Canada flag

Categories

ATC Codes
C04AX01 — Cyclandelate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Secondary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Aromatic alcohols
Substituents
Alcohol / Aromatic alcohol / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxylic ester, secondary alcohol (CHEBI:3988)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4139O1OAY2
CAS number
456-59-7
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0015586
PubChem Compound
2893
PubChem Substance
46505740
ChemSpider
2790
BindingDB
50239973
RxNav
2970
ChEBI
3988
ChEMBL
CHEMBL1480987
PharmGKB
PA164748026
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyclandelate
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, coated
TabletOral200 mg / tab
Prices
Unit descriptionCostUnit
Cyclandelate powder8.18USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)50-53Nauta, W.T.; U.S. Patent 2,707,193; April 26,1955; assigned to N.V. Koninklijke Pharmaceutische Fabrieken Voorbeen Brocades Stheeman & Pharmacia, Netherlands.
boiling point (°C)193 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
Kind
Protein
Organism
Humans
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-...
Gene Name
CACNA2D1
Uniprot ID
P54289
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight
124566.93 Da
References
  1. Pascual J: [New prospects in the treatment of migraine]. Neurologia. 1999 Dec;14 Suppl 6:26-35. [Article]
Kind
Protein
Organism
Humans
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 acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Drug created on September 26, 2007 15:09 / Updated on February 21, 2021 18:51