Cyclizine

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Cyclizine
Cyclizine2DCSD.svg
Cyclizine 3d balls.png
Systematic (IUPAC) name
1-benzhydryl-4-methyl-piperazine
Clinical data
Trade names Marezine, Valoid, Nausicalm
AHFS/Drugs.com Consumer Drug Information
Pregnancy
category
  • AU: A
  • US: B (No risk in non-human studies)
Legal status
  • AU: S3 (Pharmacist only)
  • UK: POM (Prescription only)
  • US: OTC
  • OTC (Netherlands)
Routes of
administration		 Oral, IM, IV
Pharmacokinetic data
Metabolism N-demethylated to inactive norcyclizine[1]
Biological half-life 20 hours
Identifiers
CAS Number 82-92-8 YesY
ATC code R06AE03 (WHO)
PubChem CID: 6726
IUPHAR/BPS 7151
DrugBank DB01176 YesY
ChemSpider 6470 YesY
UNII QRW9FCR9P2 YesY
KEGG D03621 YesY
ChEBI CHEBI:3994 YesY
ChEMBL CHEMBL648 YesY
Chemical data
Formula C18H22N2
Molecular mass 266.381 g/mol
  • 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 YesY
  • Key:UVKZSORBKUEBAZ-UHFFFAOYSA-N YesY
  (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.

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[2]

Medical uses

Nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operatively following administration of general anaesthesia and opioids. It is sometimes given in hyperemesis gravidarum, although the manufacturer advises that it be avoided in pregnancy. Off-licence 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.[3]

The drug Diconal is a combination of cyclizine with the opioid dipipanone.[4] Dipipanone is a schedule I controlled substance in the US, due to its high abuse potential.

Contraindications

Its antimuscarinic action warrants caution in patients with prostatic hypertrophy, urinary retention, or angle-closure glaucoma. Liver disease exacerbates its sedative effects.[3]

Adverse effects

Common (over 10%) — Drowsiness, xerostomia (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 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.[3]

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.[5][6]

The substance received more credit when NASA chose it as a space antiemetic for the first occupied 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 very much studied.[5][7]

Society and culture

Some people using methadone recreationally combine cyclizine with their methadone dose, a combination that is known to produce strong psychoactive effects.[8] It has also been used recreationally for its anticholinergic effects to induce hallucinations.[9]

It has also been used illegally in greyhound racing to sabotage a dog's performance.[10]

Names

As cyclizine hydrochloride tablets and cyclizine lactate solution for intramuscular or intravenous injection (brand names: Valoid[3] in UK and Marezine, Marzine and Emoquil in US). Cyclizine is marketed as Bonine for Kids in the US.[11]

Cyclizine derivatives

Structural comparison of cyclizine
and related H1 antagonists[12]
Cyclizine derivatives backbone.svg
Compound R1 R2
Cyclizine H CH3
Chlorcyclizine Cl CH3
Meclizine Cl Meclizine R2.svg
Buclizine Cl Buclizine R2.svg
Oxatomide H Oxatomide R2.svg
Hydroxyzine Cl Hydroxyzine R2.svg
Cetirizine Cl Cetirizine R2.svg

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 3.2 3.3 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ http://www.drugs.smd.qmul.ac.uk/drugs/html5/Anti-emetics/AN-FEF54A37-6289-402B-E208-9284E183608A.html
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Conor Ryan for The Independent. June 20, 2013 IGB left with €250k bill after dog doping case
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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