3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate

• ChemBase ID: 4382
• Molecular Formular: C17H24O3
• Molecular Mass: 276.37066
• Monoisotopic Mass: 276.17254463
• SMILES: O(C1CC(CC(C1)C)(C)C)C(=O)C(O)c1ccccc1
• Canonical SMILES: CC1CC(OC(=O)C(c2ccccc2)O)CC(C1)(C)C
• 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
• InChIKey: WZHCOOQXZCIUNC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate
• IUPAC Traditional name: cyclandelate
• Brand Name: Arto-espasmol; Capilan; Ciclospasmol; Clandilon; Cyclergine; Cyclobral; Cyclolyt; Cyclomandol; Cyclospasmol; Dilatan; Natil; Novodil; Perebral; Saiclate; Sancyclan; Sepyron; Spasmione; Spasmocyclon; Spasmocyclone; Vasodyl
• Synonyms: Cyclandelic acid; Ciclandelato [inn-spanish]; Cyclandelatum [inn-latin]; 3,5,5-Trimethylcyclohexyl mandelate; 3,5,5-Trimethylcyclohexyl amygdalate; 3,3,5-Trimethylcyclohexyl mandelate; Cyclandelate

Database IDs

• CAS Number: 456-59-7
• PubChem SID: 46505740; 160967814
• PubChem CID: 2893
• CHEBI ID: 3988
• ATC CODE: C04AX01
• Chemspider ID: 2790
• DrugBank ID: DB04838
• KEGG ID: D00286
• Unique Ingredient Identifier: 4139O1OAY2
• Wikipedia Title: Cyclandelate

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.9911
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.7150855
• LogD (pH = 7.4): 3.7150745
• Log P: 3.7150855
• Molar Refractivity: 78.0594 cm^3
• Polarizability: 31.23288 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.79
• LOG S: -3.44
• Solubility (Water): 9.97e-02 g/l

PROPERTIES

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB04838

• Drug Groups: approved
• 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.
• Indication: Used in the treatment of various blood vessel diseases (e.g., claudication, arteriosclerosis and Raynaud's disease) and nighttime leg cramps.
• 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.
• Toxicity: Acute oral toxicity (LD50): 3950 mg/kg [Guinea pig]
• Affected Organisms: Humans and other mammals
• Absorption: Well absorbed following oral administration.
• External Links: Drugs.com