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
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)
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 Date2005 |
|||
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 Date2005 |
|||
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 Date2005 |
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 |
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Cyclizine-induced chorea. Observations on the influence of cyclizine on dopamine-related movement disorders. | 1977 Mar |
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Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
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Postoperative nausea management and patient-controlled analgesia. | 2001 Jun 28-Jul 11 |
|
Standard treatment: the role of antihistamines. | 2001 Nov |
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Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol. | 2001 Nov-Dec |
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Subcutaneous cyclizine. | 2001 Sep |
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Simultaneous screening and quantitation of 18 antihistamine drugs in blood by liquid chromatography ionspray tandem mass spectrometry. | 2001 Sep 15 |
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Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. | 2002 Feb |
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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 |
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Comparison of intrathecal fentanyl and diamorphine in addition to bupivacaine for caesarean section under spinal anaesthesia. | 2002 Sep |
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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 |
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A comparison of cyclizine, ondansetron and placebo as prophylaxis against postoperative nausea and vomiting in children. | 2003 Jul |
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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 |
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Antihistamines in the treatment of dermatitis. | 2003 Nov-Dec |
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Dystonic reaction to cyclizine. | 2004 Apr |
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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 |
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Outcome and patient acceptance of outpatient laparoscopic cholecystectomy. | 2004 Jul-Sep |
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The Cyclimorph cough. | 2004 Jun |
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Early analgesic effects of parecoxib versus ketorolac following laparoscopic sterilization: a randomized controlled trial. | 2004 Jun |
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Chlorpheniramine maleate as an alternative to antiemetic cyclizine. | 2004 May |
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Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column. | 2005 Aug 12 |
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Transient paralysis after administration of a single dose of cyclizine. | 2005 Dec |
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Diluent choice for subcutaneous infusion: a survey of the literature and Australian practice. | 2005 Feb |
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Percutaneous absorption of cyclizine and its alkyl analogues. | 2005 Feb |
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An LC-MS-MS method for the determination of cyclizine in human serum. | 2005 Sep 25 |
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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 |
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Use of intravenous cyclizine in cardiac chest pain. | 2006 Jul |
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Drugs for preventing postoperative nausea and vomiting. | 2006 Jul 19 |
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A preliminary ecotoxicity study of pharmaceuticals in the marine environment. | 2006 Nov |
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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 |
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Management of Ménière's disease in general practice: adherence to the UK National Health Service 'Prodigy' guidelines. | 2008 Aug |
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Chemotherapy-and cancer-related nausea and vomiting. | 2008 Jan |
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The misuse/abuse of antihistamine antiemetic medication (cyclizine) by cancer patients. | 2008 Oct |
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Morphine-induced hallucinations - resolution with switching to oxycodone: a case report and review of the literature. | 2009 Dec 23 |
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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
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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NCI_THESAURUS |
C267
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CHEMBL648
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C65357
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SUB01517MIG
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DBSALT001182
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DTXSID10974465
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91071
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861R00J986
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100000087986
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71473
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5897-19-8
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ACTIVE MOIETY
SUBSTANCE RECORD