Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H21NS.C4H6O5 |
Molecular Weight | 429.529 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CC(O)=O)C(O)=O.CN1CCC(CC1)=C2C3=C(CCC4=C2C=CC=C4)SC=C3
InChI
InChIKey=IWAWCPZVTXCFKD-UHFFFAOYSA-N
InChI=1S/C19H21NS.C4H6O5/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;5-2(4(8)9)1-3(6)7/h2-5,10,13H,6-9,11-12H2,1H3;2,5H,1H2,(H,6,7)(H,8,9)
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 |
PubMed
Title | Date | PubMed |
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Effects of chronic treatment with antidepressants on aggressiveness induced by clonidine in mice. | 1982 |
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The role of the central serotonergic system in pilocarpine-induced seizures: receptor mechanisms. | 1989 Nov |
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Solubility of solid dispersions of pizotifen malate and povidone. | 2001 Jul |
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Cluster headache: aetiology, diagnosis and management. | 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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Hypotension caused by extracorporeal circulation: serotonin from pump-activated platelets triggers nitric oxide release. | 2002 Nov 12 |
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[Current views on migraine and anti-migraine preparations]. | 2003 |
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Drugs for preventing migraine headaches in children. | 2003 |
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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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Practice parameter: pharmacological treatment of migraine headache in children and adolescents: report of the American Academy of Neurology Quality Standards Subcommittee and the Practice Committee of the Child Neurology Society. | 2004 Dec 28 |
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Determination of ketotifen in human plasma by LC-MS. | 2004 Jan 27 |
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Raynaud phenomena and migraine in two children: inclusion within a family of related disorders. | 2005 Dec |
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Use of intravenous midazolam and clonidine in cyclical vomiting syndrome: a case report. | 2005 Jan |
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Stability studies on some benzocycloheptane antihistaminic agents. | 2005 Jan 4 |
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Serotonin2C receptor blockade and thermoregulation during exercise in the heat. | 2005 Mar |
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Anticipatory nausea in cyclical vomiting. | 2005 Mar 24 |
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Pizotyline effectively attenuates the stimulus effects of N-methyl-3,4-methylenedioxyamphetamine (MDMA). | 2005 Oct |
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Weight variations in the prophylactic therapy of primary headaches: 6-month follow-up. | 2005 Sep |
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Topiramate for migraine prophylaxis. | 2006 Aug |
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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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Anatomical alterations of the visual motion processing network in migraine with and without aura. | 2006 Oct |
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Optimizing prophylactic treatment of migraine: Subtypes and patient matching. | 2008 Oct |
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Prophylaxis of migraine headache. | 2010 Apr 20 |
|
Cluster headache. | 2010 Feb 9 |
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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99O99YVR4C
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SUB20724
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100000090350
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758899
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50213
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168993
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DTXSID60966214
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m8899
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5189-11-7
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235747
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225-970-4
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ACTIVE MOIETY
SUBSTANCE RECORD