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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2
Molecular Weight 266.3813
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLIZINE

SMILES

CN1CCN(CC1)C(c2ccccc2)c3ccccc3

InChI

InChIKey=UVKZSORBKUEBAZ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003501

Cyclizine (cyclizine hydrochloride, Valoid®) is a histamine H1 antagonist of the piperazine class which is characterised by a low incidence of drowsiness. It possesses anticholinergic and antiemetic properties. The exact mechanism by which cyclizin (cyclizine hydrochloride, Valoid®) can prevent or suppress both nausea and vomiting from various causes is unknown. It increases lower oesophageal sphincter tone and reduces the sensitivity of the labyrinthine apparatus. It may inhibit the part of the midbrain known collectively as the emetic centre.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.42 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
VALOID

Approved Use

Valoid is indicated for the prevention and treatment of nausea and vomiting including: • Motion sickness. • Nausea and vomiting caused by narcotic analgesics and by general anaesthetics in the post-operative period. • Vomiting associated with radiotherapy, especially for breast cancer since cyclizine does not elevate prolactin levels. Valoid may be of value in relieving vomiting and attacks of vertigo associated with Meniere's disease and other forms of vestibular disturbance.

Launch Date

1.13365444E12
Preventing
VALOID

Approved Use

Valoid is indicated for the prevention and treatment of nausea and vomiting including: • Motion sickness. • Nausea and vomiting caused by narcotic analgesics and by general anaesthetics in the post-operative period. • Vomiting associated with radiotherapy, especially for breast cancer since cyclizine does not elevate prolactin levels. Valoid may be of value in relieving vomiting and attacks of vertigo associated with Meniere's disease and other forms of vestibular disturbance.

Launch Date

1.13365444E12
Preventing
VALOID

Approved Use

Valoid is indicated for the prevention and treatment of nausea and vomiting including: • Motion sickness. • Nausea and vomiting caused by narcotic analgesics and by general anaesthetics in the post-operative period. • Vomiting associated with radiotherapy, especially for breast cancer since cyclizine does not elevate prolactin levels. Valoid may be of value in relieving vomiting and attacks of vertigo associated with Meniere's disease and other forms of vestibular disturbance.

Launch Date

1.13365444E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
90 ng/mL
18.682 mg single, intravenous
dose: 18.682 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CYCLIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
273.53 ng × h/mL
18.682 mg single, intravenous
dose: 18.682 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CYCLIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.53 h
18.682 mg single, intravenous
dose: 18.682 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CYCLIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg single, intravenous
Recommended
Dose: 50 mg
Route: intravenous
Route: single
Dose: 50 mg
Co-administed with::
morphine(10 mg)
Sources:
healthy, 34 years
n = 1
Health Status: healthy
Condition: pregnancy
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
Other AEs: Dystonic reaction...
Other AEs:
Dystonic reaction (1 patient)
Sources:
80 mg/kg single, oral
Lethal dose
Dose: 80 mg/kg
Route: oral
Route: single
Dose: 80 mg/kg
Sources:
unhealthy, children and adults
Health Status: unhealthy
Condition: nausea and vomiting
Age Group: children and adults
Sex: unknown
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
5 mg/kg single, oral
Toxic dose
Dose: 5 mg/kg
Route: oral
Route: single
Dose: 5 mg/kg
Sources:
unhealthy, children and adults
n = 38
Health Status: unhealthy
Condition: nausea and vomiting
Age Group: children and adults
Sex: unknown
Population Size: 38
Sources:
Other AEs: Convulsions...
Other AEs:
Convulsions (38 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dystonic reaction 1 patient
50 mg single, intravenous
Recommended
Dose: 50 mg
Route: intravenous
Route: single
Dose: 50 mg
Co-administed with::
morphine(10 mg)
Sources:
healthy, 34 years
n = 1
Health Status: healthy
Condition: pregnancy
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
Death grade 5
Disc. AE
80 mg/kg single, oral
Lethal dose
Dose: 80 mg/kg
Route: oral
Route: single
Dose: 80 mg/kg
Sources:
unhealthy, children and adults
Health Status: unhealthy
Condition: nausea and vomiting
Age Group: children and adults
Sex: unknown
Sources:
Convulsions 38 patients
5 mg/kg single, oral
Toxic dose
Dose: 5 mg/kg
Route: oral
Route: single
Dose: 5 mg/kg
Sources:
unhealthy, children and adults
n = 38
Health Status: unhealthy
Condition: nausea and vomiting
Age Group: children and adults
Sex: unknown
Population Size: 38
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Cyclizine anaphylaxis, when administered with propanidid.
1969 Jan
Dimenhydrinate (Dramamine) abuse: hallucinogenic experiences with a proprietary antihistamine.
1972 Feb
Cyclizine-induced chorea. Observations on the influence of cyclizine on dopamine-related movement disorders.
1977 Mar
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity.
1991
Cyclizine and droperidol have comparable efficacy and side effects during patient-controlled analgesia.
2002 Jul-Sep
A comparison of cyclizine, ondansetron and placebo as prophylaxis against postoperative nausea and vomiting in children.
2003 Jul
A response to 'A comparison of cyclizine, ondansetron and placebo as prophylaxis against postoperative nausea and vomiting in children' O'Brien CM, Titley G, Whitehurst P, Anaesthesia 2003; 58: 707-11.
2003 Nov
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Dystonic reaction to cyclizine.
2003 Sep
Dystonic reaction to cyclizine.
2004 Apr
A capillary zone electrophoresis (CZE) method for the determination of cyclizine hydrochloride in tablets and suppositories.
2004 Apr 1
Is intraperitoneal levobupivacaine with epinephrine useful for analgesia following laparoscopic cholecystectomy? A randomized controlled trial.
2004 Aug
Improving the acceptability of the atrial defibrillator for the treatment of persistent atrial fibrillation: the atrial defibrillator sedation assessment study (ADSAS).
2004 Aug
The Cyclimorph cough.
2004 Jun
Early analgesic effects of parecoxib versus ketorolac following laparoscopic sterilization: a randomized controlled trial.
2004 Jun
Systematic review of the efficacy of antiemetics in the treatment of nausea in patients with far-advanced cancer.
2004 Jun
Chlorpheniramine maleate as an alternative to antiemetic cyclizine.
2004 May
Spectrophotometric and LC determination of two binary mixtures containing antihistamins.
2004 Sep
Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column.
2005 Aug 12
Transient paralysis after administration of a single dose of cyclizine.
2005 Dec
Diluent choice for subcutaneous infusion: a survey of the literature and Australian practice.
2005 Feb
An LC-MS-MS method for the determination of cyclizine in human serum.
2005 Sep 25
Acute eosinophilic pneumonia caused by calcium stearate, an additive agent for an oral antihistaminic medication.
2006
Prolonged extra-pyramidal side effects after discontinuation of haloperidol as an antiemetic.
2006 Apr
Systematic review on the recurrence of postoperative nausea and vomiting after a first episode in the recovery room - implications for the treatment of PONV and related clinical trials.
2006 Dec 13
Best evidence topic report. Use of intravenous cyclizine in cardiac chest pain.
2006 Jan
Use of intravenous cyclizine in cardiac chest pain.
2006 Jul
Drugs for preventing postoperative nausea and vomiting.
2006 Jul 19
A preliminary ecotoxicity study of pharmaceuticals in the marine environment.
2006 Nov
Akathisia and an unusual symptomatic treatment: a case report.
2007 Dec
Routine multimodal antiemesis including low-dose perphenazine in an ambulatory surgery unit of a university hospital: a 10-year history. Supplement to: Eliminating postoperative nausea and vomiting in outpatient surgery with multimodal strategies including low doses of nonsedating, off-patent antiemetics: is "zero tolerance" achievable?
2007 Jun 12
Eliminating postoperative nausea and vomiting in outpatient surgery with multimodal strategies including low doses of nonsedating, off-patent antiemetics: is "zero tolerance" achievable?
2007 Jun 12
Management of Ménière's disease in general practice: adherence to the UK National Health Service 'Prodigy' guidelines.
2008 Aug
Chemotherapy-and cancer-related nausea and vomiting.
2008 Jan
The misuse/abuse of antihistamine antiemetic medication (cyclizine) by cancer patients.
2008 Oct
Mechanistic investigation of N,N-diethyl-4-(phenyl-piperidin-4-ylidenemethyl)-benzamide-induced insulin depletion in the rat and RINm5F cells.
2008 Sep
A survey of post-craniotomy analgesia in British neurosurgical centres: time for perceptions and prescribing to change?
2009
Application of adsorptive voltammetry for the detection of sub-nano molar cyclizine in biological fluids and tablets using fast Fourier transform continuous cyclic voltammetry in a flowing system.
2009 Apr
Management of postoperative nausea and vomiting: focus on palonosetron.
2009 Feb
Effect of fluid preloading on postoperative nausea and vomiting following laparoscopic cholecystectomy.
2009 Jul
Synthesis and in vitro antiproliferative activity of novel 1-benzhydrylpiperazine derivatives against human cancer cell lines.
2009 Mar
The cautious use of cyclizine in a patient with myasthenia gravis.
2009 Oct
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Optimal management of nausea and vomiting of pregnancy.
2010 Aug 4
Delayed ethylene glycol poisoning presenting with abdominal pain and multiple cranial and peripheral neuropathies: a case report.
2010 Jul 21
Neuropharmacology of vestibular system disorders.
2010 Mar
Palliative management of malignant bowel obstruction in terminally ill patient.
2010 May
Prescribing for migraine with the focus on selective 5HT1-receptor agonists: a pharmacy database analysis.
2010 May
Boosting blood flow: intravenous cyclizine in microsurgery.
2010 Sep
Patents

Sample Use Guides

1 tablet (50 mg) orally, which may be repeated up to three times a day.
Route of Administration: Oral
In Vitro Use Guide
Cyclizine was tested for its effect on anti-IgE-induced histamine release from human lung fragments in vitro. IC50 value was 5.42 uM (0.14-20.44).
Name Type Language
CYCLIZINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
CYCLIZINE [MART.]
Common Name English
CYCLIZINE [HSDB]
Common Name English
CYCLIZINE [MI]
Common Name English
1-(DIPHENYLMETHYL)-4-METHYLPIPERAZINE
Systematic Name English
CYCLIZINE [INN]
Common Name English
CYCLIZINE [WHO-DD]
Common Name English
CYCLIZINE [VANDF]
Common Name English
PIPERAZINE, 1-(DIPHENYLMETHYL)-4-METHYL-
Systematic Name English
NSC-26608
Code English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
WHO-ATC R06AE53
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
WHO-VATC QR06AE53
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
NCI_THESAURUS C267
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
WHO-ATC R06AE03
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
WHO-VATC QR06AE03
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
LIVERTOX 246
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
201-445-5
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
WIKIPEDIA
CYCLIZINE
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
HSDB
3309
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
FDA UNII
QRW9FCR9P2
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
LACTMED
Cyclizine
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
INN
176
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
DRUG BANK
DB01176
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
NCI_THESAURUS
C65356
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
RXCUI
2977
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL648
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
MESH
D003501
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
EPA CompTox
82-92-8
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
CAS
82-92-8
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
DRUG CENTRAL
749
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
IUPHAR
7151
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
EVMPD
SUB06847MIG
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY
MERCK INDEX
M3973
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY Merck Index
PUBCHEM
6726
Created by admin on Sat Jun 26 02:05:39 UTC 2021 , Edited by admin on Sat Jun 26 02:05:39 UTC 2021
PRIMARY