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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
Structure for Cyclandelate (DB04838)
- 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.
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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.
Target Actions Organism UVoltage-dependent calcium channel subunit alpha-2/delta-1 inhibitorHumans ULiver carboxylesterase 1 Not Available Humans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Cyclandelate can be increased when it is combined with Abametapir. Acarbose The risk or severity of hypoglycemia can be increased when Cyclandelate is combined with Acarbose. Acebutolol Acebutolol may increase the arrhythmogenic activities of Cyclandelate. Aceclofenac The risk or severity of hyperkalemia can be increased when Cyclandelate is combined with Aceclofenac. Acemetacin The risk or severity of hyperkalemia can be increased when Cyclandelate is combined with Acemetacin. - Food Interactions
- Take with food. Food reduces irritation.
Products
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- Capilan (Takeda) / Cyclergine / Cyclospasmol (lves)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cyclospasmol Tablets 200mg Tablet 200 mg / tab Oral Wyeth Ayerst Canada Inc. 1994-12-31 1997-08-14 Canada 
Categories
- ATC Codes
- C04AX01 — Cyclandelate
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Antiarrhythmic agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Cardiovascular Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Hydroxy Acids
- Mandelic Acids
- Peripheral Vasodilators
- Vasodilating Agents
- 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
- External Links
- Human Metabolome Database
- HMDB0015586
- PubChem Compound
- 2893
- PubChem Substance
- 46505740
- ChemSpider
- 2790
- BindingDB
- 50239973
- 2970
- ChEBI
- 3988
- ChEMBL
- CHEMBL1480987
- PharmGKB
- PA164748026
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cyclandelate
- MSDS
- Download (73.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Spectrum Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet, coated Tablet Oral 200 mg / tab - Prices
Unit description Cost Unit Cyclandelate powder 8.18USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 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. boiling point (°C) 193 °C at 1.40E+01 mm Hg PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0995 mg/mL ALOGPS logP 3.79 ALOGPS logP 3.72 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 11.99 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 78.06 m3·mol-1 Chemaxon Polarizability 30.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.8761 Caco-2 permeable + 0.7443 P-glycoprotein substrate Non-substrate 0.551 P-glycoprotein inhibitor I Inhibitor 0.6324 P-glycoprotein inhibitor II Non-inhibitor 0.6209 Renal organic cation transporter Non-inhibitor 0.8746 CYP450 2C9 substrate Non-substrate 0.7769 CYP450 2D6 substrate Non-substrate 0.9047 CYP450 3A4 substrate Substrate 0.6148 CYP450 1A2 substrate Non-inhibitor 0.8485 CYP450 2C9 inhibitor Inhibitor 0.7116 CYP450 2D6 inhibitor Non-inhibitor 0.9365 CYP450 2C19 inhibitor Non-inhibitor 0.7518 CYP450 3A4 inhibitor Non-inhibitor 0.9024 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9469 Ames test Non AMES toxic 0.8703 Carcinogenicity Non-carcinogens 0.7047 Biodegradation Not ready biodegradable 0.9626 Rat acute toxicity 1.7115 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9942 hERG inhibition (predictor II) Non-inhibitor 0.8132
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-0900000000-85c7942741dc3b7e0e52 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-0290000000-afef79013d7207e1ce02 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0910000000-727dd028342c50a417ab Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-6920000000-7485402760736c599c60 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-6900000000-a08c008521b4283c73e1 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-9800000000-14c9b5e6254e75b6e30f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1900000000-3c1aa48aac49a6498890 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.4083567 predictedDarkChem Lite v0.1.0 [M-H]- 166.49065 predictedDeepCCS 1.0 (2019) [M+H]+ 173.7310567 predictedDarkChem Lite v0.1.0 [M+H]+ 168.84865 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.6181567 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.9418 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel (PubMed:35293990). Plays an important role in excitation-contraction coupling (By similarity)
- Specific Function
- metal ion binding
- Gene Name
- CACNA2D1
- Uniprot ID
- P54289
- Uniprot Name
- Voltage-dependent calcium channel subunit alpha-2/delta-1
- Molecular Weight
- 124566.93 Da
References
- 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
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
- Specific Function
- carboxylesterase activity
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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 at September 26, 2007 15:09 / Updated at February 21, 2021 18:51