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=C2C=CC=C4)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
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 |
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Primary | Sandomigran Approved UseUnknown |
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Primary | Sandomigran Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The role of the central serotonergic system in pilocarpine-induced seizures: receptor mechanisms. | 1989 Nov |
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Pharmacological interventions for recurrent abdominal pain (RAP) in childhood. | 2002 |
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Cyclic vomiting syndrome in Thai children. | 2002 Aug |
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Paroxysmal hemicrania and cluster headache: two discrete entities or is there an overlap? | 2002 Dec |
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Migraine and Raynaud phenomenon: possible late complications of Kawasaki disease. | 2002 Mar |
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Hypotension caused by extracorporeal circulation: serotonin from pump-activated platelets triggers nitric oxide release. | 2002 Nov 12 |
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Systematic review of treatments for recurrent abdominal pain. | 2003 Jan |
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Hypoxic initiation of pulmonary hypertension is mediated by serotonin secretion from neuroepithelial bodies in chemodenervated dogs. | 2003 Mar 31 |
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Agomelatine(S 20098) antagonizes the penile erections induced by the stimulation of 5-HT2C receptors in Wistar rats. | 2003 Oct |
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Raynaud phenomena and migraine in two children: inclusion within a family of related disorders. | 2005 Dec |
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Cyclic Vomiting Syndrome in 41 adults: the illness, the patients, and problems of management. | 2005 Dec 21 |
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The Effect of Paroxetine on the Reduction of Migraine Frequency is Independent of Its Anxiolytic Effect. | 2006 Dec |
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Adult abdominal migraine: a new syndrome or sporadic feature of migraine headache? A case report. | 2006 Jan |
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Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat. | 2006 Mar 27 |
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Which therapy for which patient? | 2006 May |
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Evaluation of guided imagery as treatment for recurrent abdominal pain in children: a randomized controlled trial. | 2006 Nov 8 |
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Anatomical alterations of the visual motion processing network in migraine with and without aura. | 2006 Oct |
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Migraine associated vertigo. | 2007 Sep |
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Cluster headache. | 2008 Feb 15 |
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Cluster headache. | 2008 Jul 23 |
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Pizotifen relieves acute migraine symptoms. | 2008 Mar 1 |
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What happens to new-onset headache in children that present to primary care? A case-cohort study using electronic primary care records. | 2009 Dec |
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Treatment of primary headache in children: a multicenter hospital-based study in France. | 2009 Dec |
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Potential contribution of prescription practices to the emergence and spread of chloroquine resistance in south-west Nigeria: caution in the use of artemisinin combination therapy. | 2009 Dec 30 |
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Migraine headache in children. | 2009 Jan 13 |
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5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials. | 2009 Jun |
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Recent concepts on cyclic vomiting syndrome in children. | 2010 Apr |
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Prophylaxis of migraine headache. | 2010 Apr 20 |
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New methods for diagnosis and treatment of vestibular diseases. | 2010 Aug 9 |
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Cluster headache. | 2010 Feb 9 |
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Fulminant hepatitis possibly related to pizotifen therapy. | 2010 Jul-Aug |
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P3MC: a double blind parallel group randomised placebo controlled trial of Propranolol and Pizotifen in preventing migraine in children. | 2010 Jun 16 |
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Prescribing for migraine with the focus on selective 5HT1-receptor agonists: a pharmacy database analysis. | 2010 May |
|
Validation and application of reversed phase high-performance liquid chromatographic method for quantification of pizotifen malate in pharmaceutical solid dosage formulations. | 2010 Oct |
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.
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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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93
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100000092611
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DB06153
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50213
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27400
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8373
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C87214
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2220
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PIZOTIFEN
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DTXSID6023490
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50212
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15574-96-6
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239-632-9
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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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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)