Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H22N2 |
Molecular Weight | 266.3807 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68003501
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.medicines.org.uk/emc/medicine/14672 |
5.42 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | VALOID Approved UseValoid 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 Date1.13365444E12 |
|||
Preventing | VALOID Approved UseValoid 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 Date1.13365444E12 |
|||
Preventing | VALOID Approved UseValoid 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 Date1.13365444E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
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 |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/29691239/ |
yes | |||
Page: 38.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29691239/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | yes (pharmacogenomic study) Comment: The median overall metabolic ratio at steady state was 4.9 (3.8-9.2) and did vary with CYP2D6 genotype (P=0.02). Sources: https://pubmed.ncbi.nlm.nih.gov/22209223/ |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Comparison of intrathecal fentanyl and diamorphine in addition to bupivacaine for caesarean section under spinal anaesthesia. | 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 |
|
Quantitative enantiomeric analysis of chlorcyclizine, hydroxyzine, and meclizine by capillary electrophoresis. | 2003 Jul |
|
Dystonic reactions to cyclizine. | 2003 Jul |
|
Probable dystonic reaction after a single dose of cyclizine in a patient with a history of encephalitis. | 2003 Mar |
|
Cyclizine. | 2003 May |
|
Prevention of postoperative nausea and vomiting after spinal morphine for Caesarean section: comparison of cyclizine, dexamethasone and placebo. | 2003 May |
|
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 |
|
Screening and semi-quantitative analysis of post mortem blood for basic drugs using gas chromatography/ion trap mass spectrometry. | 2004 Dec 25 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Transient paralysis after administration of cyclizine. | 2006 Dec |
|
Use of intravenous cyclizine in cardiac chest pain. | 2006 Jul |
|
A comparison of cyclizine and granisetron alone and in combination for the prevention of postoperative nausea and vomiting. | 2006 Nov |
|
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 |
|
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 |
|
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 |
|
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 |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6159940
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).
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Classification Tree | Code System | Code | ||
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WHO-ESSENTIAL MEDICINES LIST |
8.4
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R06AE53
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QR06AE53
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NCI_THESAURUS |
C267
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R06AE03
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WHO-VATC |
QR06AE03
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LIVERTOX |
246
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201-445-5
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CYCLIZINE
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3309
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QRW9FCR9P2
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Cyclizine
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3994
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176
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DB01176
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C65356
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2977
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QRW9FCR9P2
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CHEMBL648
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D003501
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DTXSID4022864
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82-92-8
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749
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26608
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7151
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SUB06847MIG
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M3973
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6726
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)