Cyclizine

Source: Wikipedia, the free encyclopedia.

Cyclizine
Clinical data
Trade namesMarezine, Valoid, Nausicalm, others
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, IM, IV
ATC code
Legal status
Legal status
  • AU: S3 (Pharmacist only)
  • UK: P (
    Pharmacy medicines
    )
  • US: OTC
  • OTC (Netherlands)
Pharmacokinetic data
MetabolismN-demethylated to inactive norcyclizine[1]
Elimination half-life20 hours
Identifiers
  • 1-benzhydryl-4-methyl-piperazine
JSmol)
  • CN(CC1)CCN1C(C2=CC=CC=C2)C3=CC=CC=C3
  • 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, sold under a number of brand names, is a medication used to treat and prevent

injected into a vein.[3][4]

Common side effects include sleepiness, dry mouth,

low blood pressure and urinary retention.[5] It is not generally recommended in young children or those with glaucoma.[2][6] Cyclizine appears to be safe during pregnancy but has not been well studied.[7] It is in the anticholinergic and antihistamine family of medications.[3][6]

Cyclizine was discovered in 1947.

over the counter.[6]

Medical uses

Primary uses include

general anesthesia and opioids. It is sometimes given in hyperemesis gravidarum, although the manufacturer advises that it be avoided in pregnancy. Off-license use often occurs with specialists in hospitals to treat inpatients who have become severely dehydrated in pregnancy. An off-label use is as an opioid/opiate potentiator.[10]

The drug Diconal is a combination of cyclizine and the opioid

schedule I controlled substance in the US.[12]

Contraindications

Its antimuscarinic action warrants caution in patients with prostatic hypertrophy, urinary retention, or angle-closure glaucoma. Liver disease exacerbates its sedative effects.[10]

Adverse effects

Common (over 10%) —

Drowsiness, dry mouth
.

Uncommon (1% to 10%) — Headache, psychomotor impairment, dermatitis, and

antimuscarinic effects such as diplopia (double vision), tachycardia, constipation, urinary retention
and gastro-intestinal disturbances.

Rare (less than 1%) — Hypersensitivity reactions (bronchospasm, angioedema, anaphylaxis, rashes and photosensitivity reactions), extrapyramidal effects, dizziness, confusion, depression, sleep disturbances, tremor, liver dysfunction, and hallucinations.

Pharmacology

Cyclizine is a

antimuscarinic) action.[10]

Synthesis

Cyclizine may be prepared by the

1-methylpiperazine
in acetonitrile to form the hydrobromide salt of the drug.

History

Cyclizine was developed in the American division of pharmacy company

GlaxoSmithKline) during a research study involving many drugs of the antihistamine group. Cyclizine was quickly clinically found as a potent and long-acting antiemetic. The 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.[13][14]

The substance received more credit when NASA chose it as a space antiemetic for the first crewed Moon flight. Cyclizine was introduced to many countries as a common antiemetic. It is an over-the-counter drug in many countries because it has been well tolerated, although it has not been studied much.[13][15]

Society and culture

Some people using methadone recreationally combine cyclizine with their

psychoactive effects.[16]
It has also been used recreationally for its anticholinergic effects to induce hallucinations.[17]

It has been used illegally in greyhound racing to sabotage a dog's performance.[18]

Names

As cyclizine hydrochloride tablets and cyclizine lactate solution for intramuscular or intravenous injection (brand names: Valoid[10] in UK and South Africa and Marezine, Marzine and Emoquil in US). Cyclizine was marketed as Bonine for Kids in the US, but was discontinued in 2012, and replaced with meclizine.[19]

Cyclizine derivatives

Structural comparison of cyclizine
and related H1 antagonists[20]
Compound R1 R2
Cyclizine H
CH3
Chlorcyclizine Cl CH3
Meclizine Cl
Buclizine Cl
Oxatomide H
Hydroxyzine Cl
Cetirizine Cl

See also

References

  1. ^ "DrugBank: Cyclizine. Pharmacology: metabolism". DrugBank Database. Archived from the original on 30 January 2016. Retrieved 5 January 2016.
  2. ^ a b c "Cyclizine 50mg Tablets - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. 27 March 2015. Archived from the original on 20 December 2016. Retrieved 13 December 2016.
  3. ^
    ISBN 9781455749898. Archived
    from the original on 20 December 2016.
  4. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^ a b "Cyclizine Side Effects in Detail - Drugs.com". www.drugs.com. Archived from the original on 21 December 2016. Retrieved 13 December 2016.
  6. ^ a b c "Cyclizine: Indications, Side Effects, Warnings - Drugs.com". www.drugs.com. Archived from the original on 21 December 2016. Retrieved 13 December 2016.
  7. ^ "Cyclizine Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 21 December 2016. Retrieved 13 December 2016.
  8. ISBN 9781899163922. Archived
    from the original on 20 December 2016.
  9. hdl:10665/345533
    . WHO/MHP/HPS/EML/2021.02.
  10. ^ a b c d "Valoid Tablets by Amdipharm". Electronic Medicines Compendium. Datapharm. Archived from the original on 4 March 2016. Retrieved 1 October 2011.
  11. ^ "Diconal Tablets by Amdipharm". Electronic Medicines Compendium. Datapharm. Archived from the original on 1 April 2008. Retrieved 5 August 2008.
  12. ^ "Conversion Factors for Controlled Substances". DEA Diversion Control Division. Retrieved 26 March 2020.
  13. ^ a b Sneader W (2005). Drug discovery: a history. John Wiley & Sons. p. 404.
    ISBN 0-471-89979-8. Archived
    from the original on 10 September 2017.
  14. ^ Sittig M (1988). Pharmaceutical manufacturing encyclopedia. William Andrew. p. 406.
    ISBN 0-8155-1144-2. Archived
    from the original on 10 September 2017.
  15. ^ Rajoo SG. "Introduction". In Lobo M (ed.). Anti-emetics - Metoclopramide, Domperidone, Ondansetron, Cyclizine. Archived from the original on 2 April 2015. Retrieved 9 March 2015. {{cite book}}: |work= ignored (help)
  16. PMID 2775912
    .
  17. PMID 8765114
    .
  18. ^ Conor Ryan for The Independent. June 20, 2013 IGB left with €250k bill after dog doping case Archived 2016-03-04 at the Wayback Machine
  19. ^ "Bonine for Kids". Insight Pharmaceuticals. Archived from the original on 17 September 2010.
  20. ISBN 978-1-60913-345-0
    .

External links

  • "Cyclizine". Drug Information Portal. U.S. National Library of Medicine.