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Revision as of 16:27, 21 October 2011

Cyclizine
Clinical data
Trade namesMarezine
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
Routes of
administration		Oral, IM, IV
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismN-demethylated to inactive norcyclizine
Elimination half-life20 hours
Identifiers
  • 1-benzhydryl-4-methyl-piperazine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.314 Edit this at Wikidata
Chemical and physical data
FormulaC18H22N2
Molar mass266.381 g/mol g·mol−1
3D model (JSmol)
  • c1c(cccc1)C(c2ccccc2)N3CCN(CC3)C
  • InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3 checkY
  • Key:UVKZSORBKUEBAZ-UHFFFAOYSA-N checkY
  (verify)

Cyclizine is an antihistamine drug used to treat nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operatively following administration of general anaesthesia and opioids.

Indications

Nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operatively following administration of general anaesthesia and opioids. An off-label use is as an opioid/opiate potentiator [1] or alone as an deliriant as it causes intense hallucinations in high doses, even as high as 800 mg – 16 times the normal dose.

The drug Diconal is a combination of cyclizine with the opioid dipipanone.[2] Diconal has been discontinued in the US for its high abuse potential.

Contraindications

Its antimuscarinic action warrants caution in patients with prostatic hypertrophy, urinary retention, or glaucoma. Liver disease exacerbates its sedative effects.[1]

Adverse effects

Common (over 10%) – Drowsiness, xerostomia (dry mouth)

Uncommon (1% to 10%) – Headache, psychomotor impairment, and antimuscarinic effects such as urinary retention, diplopia (blurred vision), dermatitis, and gastro-intestinal disturbances.

Rare – Hypersensitivity reactions (bronchospasm, angioedema, anaphylaxis, rashes and photosensitivity reactions), extrapyramidal effects, dizziness, confusion, depression, sleep disturbances, tremor, liver dysfunction and hallucinations

Formulations

As cyclizine hydrochloride 50 mg tablets and cyclizine lactate solution for intramuscular or intravenous injection (brand names: Valoid[1] in UK and Marezine, Marzine and Emoquil in US). Cyclizine HCl 25 mg is marketed as Bonine for Kids in the US.[3]

Pharmacology

Cyclizine is a piperazine derivative with histamine H1-receptor antagonist (antihistamine) activity. The precise mechanism of action in inhibiting the symptoms of motion sickness is not well understood. It may have effects directly on the labyrinthine apparatus and on the chemoreceptor trigger zone. Cyclizine exerts a central anticholinergic (antimuscarinic) action.[1]

History

Cyclizine was developed in the American division of pharmacy company Burroughs Wellcome (today GlaxoSmithKline) during a research involving many drugs of the antihistamine group. Cyclizine was quickly clinically found as a potent and long-acting antiemetic. Company named the substance – or more precisely cyclizine's hydrochloride form which it usually appears in – "marezine hydrochloride" and started to sell it in the United States under trade name Marezine. Selling was begun in France under trade name Marzine in 1965.[4][5]

The substance received more credit when NASA chose it as a space antiemetic for the first occupied moon flight. Cyclizine then spread into many West countries as a common antiemetic. It's still an over-the-counter drug in many countries because it has been well tolerated, although it's not very much studied.[4]

Recreational use

Some people using methadone recreationally combine cyclizine with their methadone dose, a combination that is known to produce strong psychoactive effects.[6] It has also been used recreationally by teenagers for its anticholinergic effects to induce hallucinations.[7]

See also

References

  1. ^ a b c d Valoid Tablets by Amdipharm. Electronic Medicines Compendium.
  2. ^ Diconal Tablets by Amdipharm. Electronic Medicines Compendium.
  3. ^ Bonine for Kids
  4. ^ a b Sneader, Walter (2005). Drug discovery: a history. John Wiley & Sons. p. 404.
  5. ^ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. William Andrew. p. 406.
  6. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2775912, please use {{cite journal}} with |pmid=2775912 instead.
  7. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8765114, please use {{cite journal}} with |pmid=8765114 instead.
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