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Home > Encyclopedia > Cyclandelate

Cyclandelate

pharmaceutical raw materials
Cyclandelate structure

Cyclandelate 

structure
  • CAS No:

    456-59-7

  • Formula:

    C17H24O3

  • Chemical Name:

    Cyclandelate

  • Synonyms:

    Benzeneacetic acid,α-hydroxy-,3,3,5-trimethylcyclohexyl ester;Mandelic acid,3,3,5-trimethylcyclohexyl ester;Cyclohexanol,3,3,5-trimethyl-,mandelate;BS 572;Cyclandelate;Cyclospasmol;3,5,5-Trimethylcyclohexanol,mandelic acid ester;3,3,5-Trimethylcyclohexanol α-phenyl-α-hydroxyacetate;3,5,5-Trimethylcyclohexyl amygdalate;3,3,5-Trimethylcyclohexyl mandelate;3,5,5-Trimethylcyclohexyl mandelate;Cyclolyt;Cyclomandol;Perebral;Spasmocyclon;Sepyron;Spasmione;Arto-Espasmol;Dilatan;Capilan;Ciclospasmol;Clandilon;Saiclate;Sancyclan;Natil;Novodil;Cyclergine;Cyclobral;(3,3,5-Trimethylcyclohexyl) 2-hydroxy-2-phenylacetate;28283-32-1;54110-27-9

  • Categories:

    Active Pharmaceutical Ingredients  >  Circulatory System Drugs

Description

Cyclandelate is a vasodilator used in the treatment of claudication, arteriosclerosis, and Raynaud's disease. It is also used to treat nighttime leg cramps, and has been investigated for its effect against migraine.


Solid


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 derives from 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.|A direct-acting SMOOTH MUSCLE relaxant used to dilate BLOOD VESSELS.

Cyclandelate Basic Attributes

276.37

276.37

207-271-6

4139O1OAY2

758910

DTXSID4022862

CRYSTALS

C - Cardiovascular system

2918199090

Characteristics

46.5

4.2

Solid

1.1±0.1 g/cm3

50-53 °C

192-194 °C @ Press: 14 Torr

150.1±15.1 °C

1.533

9.97e-02 g/L

LD50 oral in rat: 5gm/kg

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

Safety Information

NONH for all modes of transport

OO8200000

P305 + P351 + P338

H319

Toxicity

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

Drug Information

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

Vasodilator Agents|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.|CYCLANDELATE HAS BEEN USED IN ALMOST EVERY KNOWN TYPE OF VASCULAR DISEASE, BUT ITS VALUE HAS NOT BEEN CONVINCINGLY DEMONSTRATED IN ANY.|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.|For more Therapeutic Uses (Complete) data for CYCLANDELATE (7 total), please visit the HSDB record page.

...WHETHER REDUCTION OF PRESSURE IN ARTERIES SUPPLYING OPTIC NERVEHEAD MIGHT RENDER OPTIC NERVE MORE VULNERABLE TO INJURY IN GLAUCOMA REMAINS TO BE EVALUATED.

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.

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

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.

(3-)-H-LABELED CYCLANDELATE WAS DETECTED & QUANTITATED. EFFECTIVE HALF-LIFE VALUES IN VARIOUS RAT TISSUES WERE 2.8-4.1 DAYS.

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.|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/

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.|SIDE EFFECTS INCLUDE...NAUSEA...& HYPOTENSION.|...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...

Cyclandelate

Cyclandelate Use and Manufacturing

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).

Uses

vasodilator

DRUG IS AVAILABLE IN 100-MG TABLETS & 200-MG CAPSULES.

Benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester: ACTIVE

CYCLOSPASMOL IS ONE OF 13 DRUGS WHOSE UV SPECTRA ARE TABULATED FOR THEIR DETERMINATION IN PHARMACEUTICAL PREPARATIONS.

Computed Properties

Molecular Weight:276.4
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:276.17254462
Monoisotopic Mass:276.17254462
Topological Polar Surface Area:46.5
Heavy Atom Count:20
Complexity:331
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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