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Details

Stereochemistry RACEMIC
Molecular Formula C18H22N2.C3H6O3
Molecular Weight 356.4586
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLIZINE LACTATE

SMILES

CC(O)C(O)=O.CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=JOROEVAWQLGPFQ-UHFFFAOYSA-N
InChI=1S/C18H22N2.C3H6O3/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-2(4)3(5)6/h2-11,18H,12-15H2,1H3;2,4H,1H3,(H,5,6)

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

2005
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

2005
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

2005
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
Postoperative nausea management and patient-controlled analgesia.
2001 Jun 28-Jul 11
Standard treatment: the role of antihistamines.
2001 Nov
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.
2001 Nov-Dec
Subcutaneous cyclizine.
2001 Sep
Simultaneous screening and quantitation of 18 antihistamine drugs in blood by liquid chromatography ionspray tandem mass spectrometry.
2001 Sep 15
Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes.
2002 Feb
Comparison of cyclizine and ondansetron for the prevention of postoperative nausea and vomiting in laparoscopic day-case gynaecological surgery.
2002 Jan
Cyclizine and droperidol have comparable efficacy and side effects during patient-controlled analgesia.
2002 Jul-Sep
Comparison of intrathecal fentanyl and diamorphine in addition to bupivacaine for caesarean section under spinal anaesthesia.
2002 Sep
Biotransformation of cyclizine in greyhounds. 2: N(1)-dealkylation and identification of some neutral and phenolic metabolites in canine urine by gas chromatography-mass spectrometry.
2002 Sep
Biotransformation of cyclizine in greyhounds. 1: Identification and analysis of cyclizine and some basic metabolites in canine urine by gas chromatography-mass spectrometry.
2002 Sep
Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol.
2003 Apr
A comparison of cyclizine, ondansetron and placebo as prophylaxis against postoperative nausea and vomiting in children.
2003 Jul
Probable dystonic reaction after a single dose of cyclizine in a patient with a history of encephalitis.
2003 Mar
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.
2004 Apr
A capillary zone electrophoresis (CZE) method for the determination of cyclizine hydrochloride in tablets and suppositories.
2004 Apr 1
Improving the acceptability of the atrial defibrillator for the treatment of persistent atrial fibrillation: the atrial defibrillator sedation assessment study (ADSAS).
2004 Aug
Outcome and patient acceptance of outpatient laparoscopic cholecystectomy.
2004 Jul-Sep
The Cyclimorph cough.
2004 Jun
Early analgesic effects of parecoxib versus ketorolac following laparoscopic sterilization: a randomized controlled trial.
2004 Jun
Chlorpheniramine maleate as an alternative to antiemetic cyclizine.
2004 May
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
Percutaneous absorption of cyclizine and its alkyl analogues.
2005 Feb
An LC-MS-MS method for the determination of cyclizine in human serum.
2005 Sep 25
Prolonged extra-pyramidal side effects after discontinuation of haloperidol as an antiemetic.
2006 Apr
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
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
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
Morphine-induced hallucinations - resolution with switching to oxycodone: a case report and review of the literature.
2009 Dec 23
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
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
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 LACTATE
MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
CYCLIZINE LACTATE [VANDF]
Common Name English
PIPERAZINE, 1-(DIPHENYLMETHYL)-4-METHYL-, MONO(2-HYDROXYPROPANOATE)
Common Name English
Cyclizine lactate [WHO-DD]
Common Name English
1-(Diphenylmethyl)-4-methylpiperazine monolactate
Systematic Name English
CYCLIZINE LACTATE [MART.]
Common Name English
CYCLIZINE LACTATE [ORANGE BOOK]
Common Name English
MAREZINE
Brand Name English
CYCLIZINE LACTATE, (±)-
Common Name English
(±)-CYCLIZINE LACTATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL648
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
NCI_THESAURUS
C65357
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
EVMPD
SUB01517MIG
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
DRUG BANK
DBSALT001182
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID10974465
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
RXCUI
91071
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY RxNorm
FDA UNII
861R00J986
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
SMS_ID
100000087986
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
PUBCHEM
71473
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY
CAS
5897-19-8
Created by admin on Fri Dec 15 15:01:12 GMT 2023 , Edited by admin on Fri Dec 15 15:01:12 GMT 2023
PRIMARY