Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H22N2.2ClH |
| Molecular Weight | 339.303 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=CKLJCUGYMOMAEJ-UHFFFAOYSA-N
InChI=1S/C18H22N2.2ClH/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;2*1H
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 |
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 |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| 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). |
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 |
|
| Impact of an antiemetic protocol on postoperative nausea and vomiting in children. | 2001 Jan |
|
| Patterns of ergotamine and sumatriptan use in the Netherlands from 1991 to 1997. | 2001 Jun |
|
| Pre-emptive metoclopramide and ondansetron for nausea and vomiting associated with iloprost infusions. | 2001 Jun |
|
| Precipitation in Manchester: ketorolac/cyclizine. | 2001 May |
|
| 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 |
|
| 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 |
|
| Cyclizine. | 2003 May |
|
| Dystonic reaction to cyclizine. | 2003 Sep |
|
| Dystonic reaction to cyclizine. | 2004 Apr |
|
| 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 |
|
| The Cyclimorph cough. | 2004 Jun |
|
| Chlorpheniramine maleate as an alternative to antiemetic cyclizine. | 2004 May |
|
| Transient paralysis after administration of a single dose of cyclizine. | 2005 Dec |
|
| Percutaneous absorption of cyclizine and its alkyl analogues. | 2005 Feb |
|
| Acute eosinophilic pneumonia caused by calcium stearate, an additive agent for an oral antihistaminic medication. | 2006 |
|
| Transient paralysis after administration of cyclizine. | 2006 Dec |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Boosting blood flow: intravenous cyclizine in microsurgery. | 2010 Sep |
Patents
Sample Use Guides
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| Code System | Code | Type | Description | ||
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VF601QVZ67
Created by
admin on Sat Dec 16 01:58:01 GMT 2023 , Edited by admin on Sat Dec 16 01:58:01 GMT 2023
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PRIMARY | |||
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67533
Created by
admin on Sat Dec 16 01:58:01 GMT 2023 , Edited by admin on Sat Dec 16 01:58:01 GMT 2023
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PRIMARY | |||
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5897-18-7
Created by
admin on Sat Dec 16 01:58:01 GMT 2023 , Edited by admin on Sat Dec 16 01:58:01 GMT 2023
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PRIMARY |
SUBSTANCE RECORD
