Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21NS |
Molecular Weight | 295.442 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC(CC1)=C2C3=C(CCC4=CC=CC=C24)SC=C3
InChI
InChIKey=FIADGNVRKBPQEU-UHFFFAOYSA-N
InChI=1S/C19H21NS/c1-20-11-8-15(9-12-20)19-16-5-3-2-4-14(16)6-7-18-17(19)10-13-21-18/h2-5,10,13H,6-9,11-12H2,1H3
Molecular Formula | C19H21NS |
Molecular Weight | 295.442 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.medicines.org.uk/emc/medicine/24179Curator's Comment: description was created based on several sources, including
https://www.drugs.com/uk/sanomigran-1-5mg-tablets-leaflet.html | https://www.drugs.com/uk/pizotifen-0-5mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/24189186
Sources: https://www.medicines.org.uk/emc/medicine/24179
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/uk/sanomigran-1-5mg-tablets-leaflet.html | https://www.drugs.com/uk/pizotifen-0-5mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/24189186
Pizotifen (INN) or pizotyline (USAN), trade name Sandomigran, is a benzocycloheptene-based drug used as a medicine, primarily as a preventative to reduce the frequency of recurrent migraine headaches. Pizotifen is a serotonin antagonist acting mainly at the 5-HT2A and 5HT2C receptors. It also has some activity as an antihistamine as well as some anticholinergic activity. The main medical use for pizotifen is for the prevention of vascular headache including migraine and cluster headache. Pizotifen is one of a range of medications used for this purpose, other options include propranolol, topiramate, valproic acid and amitriptyline. While pizotifen is reasonably effective, its use is limited by side effects, principally drowsiness and weight gain, and it is usually not the first choice medicine for preventing migraines, instead being used as an alternative when other drugs have failed to be effective. It is not effective in relieving migraine attacks once in progress. Pizotifen has also been reported as highly effective in a severe case of erythromelalgia, a rare neurovascular disease that is sometimes refractory to the other drugs named above. Side effects include sedation, dry mouth, drowsiness, increased appetite and weight gain. Occasionally it may cause nausea, headaches, or dizziness. In rare cases, anxiety, aggression and depression may also occur. Pizotifen is well absorbed from the gastro-intestinal tract, peak plasma concentrations occurring approximately 5 hours after oral administration. The absorption of pizotifen is fast (absorption half life 0.5 to 0.8 hours) and nearly complete (80%). Over 90% is bound to plasma proteins. Pizotifen undergoes extensive metabolism. Over half of a dose is excreted in the urine, chiefly as metabolites; a significant proportion is excreted in the faeces. The primary metabolite of pizotifen (N-glucuronide conjugate) has a long elimination half-life of about 23 hours.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24189186 |
2.0 nM [Ki] | ||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24189186 |
1.4 nM [Ki] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24189186 |
7.5 nM [Ki] | ||
Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24189186 |
25.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Sandomigran Approved UseUnknown |
|||
Primary | Sandomigran Approved UseUnknown |
|||
Primary | Sandomigran Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIZOTYLINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14 ng/mL |
1 mg 3 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIZOTYLINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23 h |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIZOTYLINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9% |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIZOTYLINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 mg 3 times / day multiple, oral Studied dose Dose: 0.5 mg, 3 times / day Route: oral Route: multiple Dose: 0.5 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Weight gain, Sleepiness... AEs leading to discontinuation/dose reduction: Weight gain Sources: Sleepiness |
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Weight gain, Depression... AEs leading to discontinuation/dose reduction: Weight gain (11.1%) Sources: Depression (7.4%) Hunger abnormal (3.7%) Confusion (3.7%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Sleepiness | Disc. AE | 0.5 mg 3 times / day multiple, oral Studied dose Dose: 0.5 mg, 3 times / day Route: oral Route: multiple Dose: 0.5 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Weight gain | Disc. AE | 0.5 mg 3 times / day multiple, oral Studied dose Dose: 0.5 mg, 3 times / day Route: oral Route: multiple Dose: 0.5 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Weight gain | 11.1% Disc. AE |
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Confusion | 3.7% Disc. AE |
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Hunger abnormal | 3.7% Disc. AE |
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Depression | 7.4% Disc. AE |
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
Page: 102.0 |
no | |||
Page: 26.0 |
yes [Activation 28.1838 uM] | |||
yes [IC50 1.2589 uM] | ||||
yes [IC50 3.9811 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 16 | 146 |
inconclusive | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 11.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice. | 1982 |
|
Arterial complications of migraine treatment with methysergide and parenteral ergotamine. | 1982 Jul 24 |
|
Agonist activity of antimigraine drugs at recombinant human 5-HT1A receptors: potential implications for prophylactic and acute therapy. | 1997 Jun |
|
Solubility of solid dispersions of pizotifen malate and povidone. | 2001 Jul |
|
[Effectiveness of tolfenamic acid in the prevention of migraine]. | 2002 |
|
Central pathways for cough in man--unanswered questions. | 2002 |
|
Pharmacological interventions for recurrent abdominal pain (RAP) in childhood. | 2002 |
|
Abdominal migraine: evidence for existence and treatment options. | 2002 |
|
Cluster headache: aetiology, diagnosis and management. | 2002 |
|
Cyclic vomiting syndrome in Thai children. | 2002 Aug |
|
Paroxysmal hemicrania and cluster headache: two discrete entities or is there an overlap? | 2002 Dec |
|
[Critical ischaemia of the limbs and localized livedo in a case of ergotism]. | 2002 Jan 25 |
|
Migraine and Raynaud phenomenon: possible late complications of Kawasaki disease. | 2002 Mar |
|
Hypotension caused by extracorporeal circulation: serotonin from pump-activated platelets triggers nitric oxide release. | 2002 Nov 12 |
|
[Current views on migraine and anti-migraine preparations]. | 2003 |
|
Systematic review of treatments for recurrent abdominal pain. | 2003 Jan |
|
French guidelines for the diagnosis and management of migraine in adults and children. | 2004 Aug |
|
Determination of ketotifen in human plasma by LC-MS. | 2004 Jan 27 |
|
Do pizotifen or propranolol reduce the frequency of migraine headache? | 2004 Jul |
|
Topiramate in migraine prevention: evidence-based medicine from clinical trials. | 2004 Oct |
|
Raynaud phenomena and migraine in two children: inclusion within a family of related disorders. | 2005 Dec |
|
Cyclic Vomiting Syndrome in 41 adults: the illness, the patients, and problems of management. | 2005 Dec 21 |
|
Stability studies on some benzocycloheptane antihistaminic agents. | 2005 Jan 4 |
|
Serotonin2C receptor blockade and thermoregulation during exercise in the heat. | 2005 Mar |
|
Pizotyline effectively attenuates the stimulus effects of N-methyl-3,4-methylenedioxyamphetamine (MDMA). | 2005 Oct |
|
Weight variations in the prophylactic therapy of primary headaches: 6-month follow-up. | 2005 Sep |
|
The Effect of Paroxetine on the Reduction of Migraine Frequency is Independent of Its Anxiolytic Effect. | 2006 Dec |
|
Evaluation of guided imagery as treatment for recurrent abdominal pain in children: a randomized controlled trial. | 2006 Nov 8 |
|
Cluster headache. | 2008 Feb 15 |
|
Pharmacological interventions for recurrent abdominal pain (RAP) and irritable bowel syndrome (IBS) in childhood. | 2008 Jan 23 |
|
Prophylaxis of migraine headache. | 2010 Apr 20 |
|
Fulminant hepatitis possibly related to pizotifen therapy. | 2010 Jul-Aug |
|
Prescribing for migraine with the focus on selective 5HT1-receptor agonists: a pharmacy database analysis. | 2010 May |
Patents
Sample Use Guides
1.5mg daily (one 1.5mg tablet at night or 0.5mg tablets three times daily).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24189186
HEK293-EBNA cell was used as the gene transferring cell. Cultured HEK293-EBNA cells expressing human 5-HT2B receptor were washed with PBS(-). The cells were scraped in the presence of PBS(-), and the cells were recovered by centrifugation (1000 rpm, 10 min, 4 OC). They were homogenized using Polytron (PTA 10-TS) in the presence of 5 mM Tris-HCl (pH 7.4) buffer and centrifuged (40,000 xg. 10 min, 4 OC). They were suspended using a homogenizer in the presence of 50 mM Tris–HCl (pH 7.4) buffer. They were subjected to centrifugation (40,000 xg, 10 min, 4 OC), suspended in 50 mM Tris–HCl (pH 7.4) and stored at 80 0C. A total volume of 500 mkL containing 50 mM Tris–HCl–4 mM CaCl2 (pH 7.4) buffer, the human 5-HT2B receptor expressing HEK293-EBNA cell membrane preparation and a radio ligand [3H] Mesulergine (3.1 TBq/mmol) was incubated at 25 OC for 1 h. The Pizotifen was dissolved in 100% DMSO and diluted to respective concentrations.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:40:14 GMT 2025
by
admin
on
Mon Mar 31 18:40:14 GMT 2025
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Record UNII |
0BY8440V3N
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
N02CX01
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NCI_THESAURUS |
C66885
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WHO-VATC |
QN02CX01
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C87214
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2220
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PIZOTIFEN
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SUB09954MIG
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2693
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m8899
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0BY8440V3N
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CHEMBL294951
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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ACTIVE MOIETY |