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CYCLANDELATE

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Classification   |    Detailed evidence-based information

Substances Included Synonyms

Therapeutic Toxic Class

    A) Cyclandelate is a vasodilator that produces peripheral vasodilatation by a direct effect on vascular smooth muscle.

Specific Substances

    1) 3,3,5-trimethylcyclohexyl ester
    2) Arto-espasmol
    3) Benzeneacetic acid, alpha-hydroxy-
    4) BS 572
    5) Mandelic acid, 3,3,5-trimethylcyclohexyl ester
    6) Trimethylcyclohexanol alpha phenyl alpha hydroxy acetate
    7) CAS 456-59-7
    1.2.1) MOLECULAR FORMULA
    1) C17-H24-O3

Available Forms Sources

    A) FORMS
    1) Brand names include Cyclomandol (Swed), and Cyclospasmol (Australia, Bel, Can, Denm, Fr, and others). Manufactured by Brocades in UK and Wyeth in the USA.
    2) Other names include Spasmocyclon (R), Arto-Espasol (Spain), Cyclan (Major), Ciclospasmol (Italy), Cyclobral (Manufactured by Norgine of the UK), Dilatan, Perebral, Saiclate, Sancyclan, Sepyron, Spasmione, Spasmocyclon (Germ), Capilan, and Vasodyl (Spain) (RTECS , 2001; S Sweetman , 2001; Grant & Schuman, 1993).
    3) The usual dosage is 200 or 400 mg tablets or capsules.
    B) USES
    1) Cyclandelate is a vasodilator used in the management of cerebrovascular and peripheral vascular disorders (S Sweetman , 2001), however the FDA has classified cyclandelate ineffective for its labeled indications including adjunctive therapy in intermittent claudication, arteriosclerosis obliterans, thrombophlebitis, nocturnal leg cramps, Raynaud's phenomenon, and selected cases of ischemic cerebrovascular disease (USPDI , 2001).

Overview

Life Support

    A) This overview assumes that basic life support measures have been instituted.

Clinical Effects

    0.2.1) SUMMARY OF EXPOSURE
    A) WITH POISONING/EXPOSURE
    1) Cyclandelate toxicity is considered very low. In higher doses, flushing, tingling of the extremities, nausea, vomiting, and headache may be seen, but no overdose cases could be found.
    2) THERE WAS NO INFORMATION on SPECIFIC CLINICAL EFFECTS OF EXPOSURE TO THIS AGENT IN AVAILABLE REFERENCES AT THE TIME OF THIS REVIEW.
    0.2.5) CARDIOVASCULAR
    A) WITH THERAPEUTIC USE
    1) A fast heart beat was reported as a side effect.
    B) WITH POISONING/EXPOSURE
    1) It is unknown if tachycardia would be seen in overdose.
    0.2.7) NEUROLOGIC
    A) WITH THERAPEUTIC USE
    1) Side effects have included dizziness, headache, weakness, and a tingling sensation in the extremities.
    B) WITH POISONING/EXPOSURE
    1) Dizziness, headache, weakness, and a tingling sensation in the extremities may occur in overdose.
    0.2.8) GASTROINTESTINAL
    A) WITH THERAPEUTIC USE
    1) Nausea and vomiting are possible, as is belching and heartburn.
    0.2.13) HEMATOLOGIC
    A) WITH THERAPEUTIC USE
    1) Platelet inhibition is seen with cyclandelate used therapeutically.
    B) WITH POISONING/EXPOSURE
    1) Observe for platelet abnormalities in overdose.
    0.2.14) DERMATOLOGIC
    A) WITH THERAPEUTIC USE
    1) Flushing may be seen when excessive doses have been taken.
    0.2.20) REPRODUCTIVE
    A) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    B) Pregnancy Category C
    0.2.21) CARCINOGENICITY
    A) At the time of this review, no data were available to assess the carcinogenic or mutagenic potential of this agent.

Laboratory Monitoring

    A) A number of chemicals produce abnormalities of the hematopoietic system, liver, and kidneys. Monitoring complete blood count, urinalysis, and liver and kidney function tests is suggested for patients with significant exposure.
    B) Cyclandelate does affect platelet function. In an overdose situation, monitor platelet function.

Treatment Overview

    0.4.2) ORAL/PARENTERAL EXPOSURE
    A) Cyclandelate is not known to be very toxic and the LD50's in animals are in the grams per kilogram range. There is no established toxic dose in man. Cyclandelate is not known to cause burns or seizures. There is no specific antidote. Treatment is symptomatic and supportive.
    B) ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old.

Range Of Toxicity

    A) There is no specific toxic dose in man. The oral LD50's in animals are in the 5 to 10 gram per kilogram range.

Clinical Effects

Summary Of Exposure

    A) WITH POISONING/EXPOSURE
    1) Cyclandelate toxicity is considered very low. In higher doses, flushing, tingling of the extremities, nausea, vomiting, and headache may be seen, but no overdose cases could be found.
    2) THERE WAS NO INFORMATION on SPECIFIC CLINICAL EFFECTS OF EXPOSURE TO THIS AGENT IN AVAILABLE REFERENCES AT THE TIME OF THIS REVIEW.

Heent

    3.4.3) EYES
    A) WITH THERAPEUTIC USE
    1) LACK OF EFFECT - There did not appear to be any alteration in intraocular pressure or a change in the axial depth of the anterior chamber for 4 to 5 hours after cyclandelate administration of 200 mg doses to patients with open-angle glaucoma (Grant & Schuman, 1993).

Cardiovascular

    3.5.1) SUMMARY
    A) WITH THERAPEUTIC USE
    1) A fast heart beat was reported as a side effect.
    B) WITH POISONING/EXPOSURE
    1) It is unknown if tachycardia would be seen in overdose.
    3.5.2) CLINICAL EFFECTS
    A) TACHYARRHYTHMIA
    1) WITH THERAPEUTIC USE
    a) A fast heart beat has been reported as an adverse effect following therapeutic administration of cyclandelate (S Sweetman , 2001; USPDI , 2001).

Neurologic

    3.7.1) SUMMARY
    A) WITH THERAPEUTIC USE
    1) Side effects have included dizziness, headache, weakness, and a tingling sensation in the extremities.
    B) WITH POISONING/EXPOSURE
    1) Dizziness, headache, weakness, and a tingling sensation in the extremities may occur in overdose.
    3.7.2) CLINICAL EFFECTS
    A) DIZZINESS
    1) WITH THERAPEUTIC USE
    a) SIDE EFFECTS have included dizziness, headache, weakness, and a tingling sensation in the extremities (S Sweetman , 2001; USPDI , 2001) Winsor & Hyman, 1961).

Gastrointestinal

    3.8.1) SUMMARY
    A) WITH THERAPEUTIC USE
    1) Nausea and vomiting are possible, as is belching and heartburn.
    3.8.2) CLINICAL EFFECTS
    A) NAUSEA AND VOMITING
    1) WITH THERAPEUTIC USE
    a) Nausea, vomiting, heartburn, stomach pain, and belching may occur more frequently during initial therapy of cyclandelate and appear to be dose-related (S Sweetman , 2001; USPDI , 2001) Winsor & Hyman, 1961).
    3.8.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) ANOREXIA
    a) RATS - Anorexia (possibly due to the disagreeable taste) was seen in sub-acute studies done in rats at oral doses of 500 to 1000 times the human dose level (Bijlsma et al, 1956).

Hematologic

    3.13.1) SUMMARY
    A) WITH THERAPEUTIC USE
    1) Platelet inhibition is seen with cyclandelate used therapeutically.
    B) WITH POISONING/EXPOSURE
    1) Observe for platelet abnormalities in overdose.
    3.13.2) CLINICAL EFFECTS
    A) PLATELET AGGREGATION
    1) WITH THERAPEUTIC USE
    a) PLATELET INHIBITION - Cyclandelate, and one of its metabolites, cyclandelate alcohol, prevented platelet aggregation in a dose dependent manner. Another metabolite, cyclandelate acid, did not show this property (van den Hoven & Hall, 1987).

Dermatologic

    3.14.1) SUMMARY
    A) WITH THERAPEUTIC USE
    1) Flushing may be seen when excessive doses have been taken.
    3.14.2) CLINICAL EFFECTS
    A) FLUSHING
    1) WITH THERAPEUTIC USE
    a) SIDE EFFECTS - Flushing has been seen as an adverse effect (USPDI , 2001).

Reproductive

    3.20.1) SUMMARY
    A) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    B) Pregnancy Category C
    3.20.2) TERATOGENICITY
    A) LACK OF INFORMATION
    1) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    3.20.3) EFFECTS IN PREGNANCY
    A) PREGNANCY CATEGORY
    CYCLANDELATEC
    Reference: Briggs et al, 1998
    3.20.4) EFFECTS DURING BREAST-FEEDING
    A) LACK OF INFORMATION
    1) At the time of this review, no data were available to assess the potential effects of exposure to this agent during lactation.

Carcinogenicity

    3.21.1) IARC CATEGORY
    A) IARC Carcinogenicity Ratings for CAS456-59-7 (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004):
    1) Not Listed
    3.21.2) SUMMARY/HUMAN
    A) At the time of this review, no data were available to assess the carcinogenic or mutagenic potential of this agent.
    3.21.3) HUMAN STUDIES
    A) LACK OF INFORMATION
    1) At the time of this review, no data were available to assess the carcinogenic or mutagenic potential of this agent.

Laboratory Monitoring

Monitoring Parameters Levels

    4.1.1) SUMMARY
    A) A number of chemicals produce abnormalities of the hematopoietic system, liver, and kidneys. Monitoring complete blood count, urinalysis, and liver and kidney function tests is suggested for patients with significant exposure.
    B) Cyclandelate does affect platelet function. In an overdose situation, monitor platelet function.
    4.1.2) SERUM/BLOOD
    A) COAGULATION STUDIES
    1) No specific laboratory measures are indicated.
    2) In therapeutic doses platelets are affected, so during an overdose platelet function should be monitored.
    3) Although increased bleeding time has been seen in animals, this has not been seen in humans (Prod Info, 1988).

Methods

    A) CHROMATOGRAPHY
    1) GC - One study indicated that gas chromatography could be used to determine the quantities of cyclandelate and its metabolites in the plasma.
    a) However, GC is unable to detect with sufficient sensitivity the quantities of mandelic acid (the major cyclandelate metabolite) at levels of 100 to 1000 ng/mL (Andermann & Dietz, 1983; Kojima et al, 1988).
    2) HPLC - High performance liquid chromatography can also be used to determine the levels of cyclandelate and is more accurate in determining the levels of mandelic acid (Kojima et al, 1988).

Treatment

Life Support

    A) Support respiratory and cardiovascular function.

Monitoring

    A) A number of chemicals produce abnormalities of the hematopoietic system, liver, and kidneys. Monitoring complete blood count, urinalysis, and liver and kidney function tests is suggested for patients with significant exposure.
    B) Cyclandelate does affect platelet function. In an overdose situation, monitor platelet function.

Oral Exposure

    6.5.1) PREVENTION OF ABSORPTION/PREHOSPITAL
    A) GENERAL
    1) Cyclandelate is not known to be very toxic and the LD50's in animals are in the grams per kilogram range. There is no established toxic dose in man. Treatment is symptomatic and supportive. Until definitive quantitative data are available, gastric decontamination may be warranted.
    B) ACTIVATED CHARCOAL
    1) PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION
    a) Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002).
    1) In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis.
    2) The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.2) PREVENTION OF ABSORPTION
    A) SUMMARY
    1) Cyclandelate is not thought to be very toxic, but until more data are known gastric decontamination may be warranted.
    B) ACTIVATED CHARCOAL
    1) CHARCOAL ADMINISTRATION
    a) Consider administration of activated charcoal after a potentially toxic ingestion (Chyka et al, 2005). Administer charcoal as an aqueous slurry; most effective when administered within one hour of ingestion.
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.3) TREATMENT
    A) SUPPORT
    1) There is no specific antidote, treatment is symptomatic and supportive.
    2) No information was available about specific clinical effects of exposure to this agent; no specific treatment recommendations can be made.

Range Of Toxicity

Summary

    A) There is no specific toxic dose in man. The oral LD50's in animals are in the 5 to 10 gram per kilogram range.

Therapeutic Dose

    7.2.1) ADULT
    A) GENERAL
    1) INITIAL - 1.2 to 1.6 grams orally daily in divided doses before meals and at bedtime. After a clinical response occurs, decrease dose in 200 milligram increments until a maintenance dose is reached (USPDI , 2001).
    2) MAINTENANCE - 400 to 800 milligrams orally daily in two to four divided doses (USPDI , 2001).
    7.2.2) PEDIATRIC
    A) GENERAL
    1) The safety and efficacy of cyclandelate administration in the pediatric population has not been established (USPDI , 2001).

Workplace Standards

    A) ACGIH TLV Values for CAS456-59-7 (American Conference of Governmental Industrial Hygienists, 2010):
    1) Not Listed

    B) NIOSH REL and IDLH Values for CAS456-59-7 (National Institute for Occupational Safety and Health, 2007):
    1) Not Listed

    C) Carcinogenicity Ratings for CAS456-59-7 :
    1) ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed
    2) EPA (U.S. Environmental Protection Agency, 2011): Not Listed
    3) IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed
    4) NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed
    5) MAK (DFG, 2002): Not Listed
    6) NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed

    D) OSHA PEL Values for CAS456-59-7 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
    1) Not Listed

Toxicity Information

    7.7.1) TOXICITY VALUES
    A) ANIMAL DATA
    1) LD50- (INTRAPERITONEAL)MOUSE:
    a) 3780 mg/kg (RTECS, 2001)
    2) LD50- (ORAL)MOUSE:
    a) >8 g/kg (Bijlsma et al, 1956)
    b) >10 g/kg (RTECS, 2001)
    3) LD50- (INTRAPERITONEAL)RAT:
    a) 2570 mg/kg (RTECS, 2001)
    4) LD50- (ORAL)RAT:
    a) 5 g/kg (RTECS, 2001)

Pharmacology Toxicology

Pharmacologic Mechanism

    A) When used for open-angle glaucoma, no significant alteration of intraocular pressure was found during four to five hours. The axial depth of the anterior chamber was not altered significantly (Grant & Schuman, 1993).
    1) Another study indicated that this agent increased flow to retinal arteries and yet reduced ophthalmic blood pressure (Hayatsu et al, 1966).
    B) Cyclandelate appears to have several effects, including a direct vasodilatory effect, an anti-platelet aggregatory effect, an increased deformability of red blood cells and an inhibition of cholesterol biosynthesis.
    1) Several enzymes may be affected, including inhibition of aldose reductase, and several phosphodiesterases. Calcium antagonism is also involved (Timmerman, 1984).

Toxicologic Mechanism

    A) It is hypothesized that cyclandelate's property of platelet inhibition may be due to the calcium modulating properties of the drug (van den Hoven & Hall, 1987; Timmerman, 1987).

Physicochemical

Physical Characteristics

    A) The powder has a slight odor of methanol (USPDI, 1988) and a bitter taste (JEF Reynolds , 1988).

Molecular Weight

    A) 276.4

References

General Bibliography

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