Pizotifen malate | CAS#5189-11-7 |serotonin antagonist

MedKoo Cat#: 329471 | Name: Pizotifen malate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pizotifen, also known as Pizotyline, 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.

Chemical Structure

Pizotifen malate

CAS#5189-11-7 (malate)

Theoretical Analysis

MedKoo Cat#: 329471

Name: Pizotifen malate

CAS#: 5189-11-7 (malate)

Chemical Formula: C23H27NO5S

Exact Mass: 0.0000

Molecular Weight: 429.53

Elemental Analysis: C, 64.32; H, 6.34; N, 3.26; O, 18.62; S, 7.46

Price and Availability

Size	Price	Availability
500mg	USD 350.00	2 Weeks
1g	USD 750.00	2 Weeks
2g	USD 1,150.00	2 Weeks
5g	USD 1,650.00	2 Weeks

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Related CAS #

5189-11-7 (malate) 15574-96-6 (free base) 24359-22-6 (maleate) 73391-87-4 (HCl)

Synonym

Pizotyline malate; BC-105 malate; Litec malate; Pizotifen malate; Sanomtgran. BC-105; BC 105; BC105;

IUPAC/Chemical Name

4-(9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine malate

InChi Key

IWAWCPZVTXCFKD-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CN1CC/C(CC1)=C2C3=CC=CC=C3CCC4=C\2C=CS4.OC(CC(O)=O)C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Related CAS# 5189-11-7 (Pizotyline malate) 15574-96-6 (Pizotyline free base))

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pizotifen malate (Pizotyline malate) is a potent 5-HT2 receptor antagonist, with a high affinity for 5-HT1C binding site.

In vitro activity:

In the present study, it was found that pizotifen could inhibit the viability of gastric cancer cell lines MNK45 and AGS cells in a dose-dependent manner. Pizotifen treatment suppressed cell migration and invasion in MNK45 and AGS cells, whilst also inducing apoptosis. Western blot analysis demonstrated that pizotifen blocked the expression of Wnt3a, β-catenin and N-cadherin, whilst increasing E-cadherin expression. In addition, BML-284, a pharmacological Wnt signaling activator, partially reversed the changes in the expression levels of β-catenin, N-cadherin and E-cadherin in MNK45 and AGS cells induced by pizotifen. Reference: Exp Ther Med. 2020 Feb;19(2):817-824. https://pubmed.ncbi.nlm.nih.gov/32010241/

In vivo activity:

Intrathecal pizotifen attenuates neuropathic and inflammatory pain mainly due to elevated GABAergic synaptic inhibition. Neuropathic pain is induced by segmental spinal nerve ligation (SNL), and inflammatory pain is induced by intraplantar injection of complete Freund's adjuvant (CFA). Both in SNL and CFA mice, spinally administered pizotifen reduced mechanical and thermal hyperalgesia dose-dependently. Since the levels of GAD65/67 were increased, and the frequency of mIPSCs in the spinal dorsal horn was increased, together with the antinociceptive effect being reversed by both GABAAR and GAD blockade, this antinociceptive effect might be generated from strengthened GABAergic inhibition. Reference: Neurosci Lett. 2022 Apr 1;775:136545. https://pubmed.ncbi.nlm.nih.gov/35202750/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	46.56
	DMF:PBS (pH 7.2) (1:8)	0.1	0.26
	DMSO	18.0	41.91
	Ethanol	0.5	1.16

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 429.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jiang Y, Wang W, Wu X, Shi J. Pizotifen inhibits the proliferation and invasion of gastric cancer cells. Exp Ther Med. 2020 Feb;19(2):817-824. doi: 10.3892/etm.2019.8308. Epub 2019 Dec 9. PMID: 32010241; PMCID: PMC6966152. 2. Piao SS, Shang B. Pizotifen Inhibits the Proliferation and Migration of Colon Cancer HCT116 Cells by Down-regulating Wnt Signaling Pathway. Ann Clin Lab Sci. 2019 Mar;49(2):183-188. PMID: 31028062. 3. Li J, Zhang X, Xu C, Liu YX, Ge C, Zhao Z, Zhu YB, Bao HG. Intrathecally administered pizotifen alleviates neuropathic and inflammatory pain in mice by enhancing GABAergic inhibition. Neurosci Lett. 2022 Apr 1;775:136545. doi: 10.1016/j.neulet.2022.136545. Epub 2022 Feb 21. PMID: 35202750. 4. Sarantos MR, Papanikolaou T, Ellerby LM, Hughes RE. Pizotifen Activates ERK and Provides Neuroprotection in vitro and in vivo in Models of Huntington's Disease. J Huntingtons Dis. 2012;1(2):195-210. doi: 10.3233/JHD-120033. PMID: 23393546; PMCID: PMC3564659.

In vitro protocol:

In vivo protocol:

1. Li J, Zhang X, Xu C, Liu YX, Ge C, Zhao Z, Zhu YB, Bao HG. Intrathecally administered pizotifen alleviates neuropathic and inflammatory pain in mice by enhancing GABAergic inhibition. Neurosci Lett. 2022 Apr 1;775:136545. doi: 10.1016/j.neulet.2022.136545. Epub 2022 Feb 21. PMID: 35202750. 2. Sarantos MR, Papanikolaou T, Ellerby LM, Hughes RE. Pizotifen Activates ERK and Provides Neuroprotection in vitro and in vivo in Models of Huntington's Disease. J Huntingtons Dis. 2012;1(2):195-210. doi: 10.3233/JHD-120033. PMID: 23393546; PMCID: PMC3564659.

1: Leite ELL, Sheila de Queiroz Souza A, Riceli Vasconcelos Ribeiro P, de Cássia Alves Pereira R, Florêncio Martins N, Kueirislene Amâncio Ferreira M, Silva Alencar de Menezes JE, Silva Dos Santos H, Deusdênia Loiola Pessoa O, Marques Canuto K. Molecular Docking and GC/MS-Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model. Chem Biodivers. 2024 Mar;21(3):e202302122. doi: 10.1002/cbdv.202302122. Epub 2024 Feb 28. PMID: 38354224. 2: Tronvik E, Giri S, Young W. Preventive treatment of migraine: Non-specific oral agents. Handb Clin Neurol. 2024;199:67-86. doi: 10.1016/B978-0-12-823357-3.00009-4. PMID: 38307673. 3: Alzola-Andres M, Cerveny D, Domingo-Echaburu S, Lekube X, Ruiz-Sancho L, Brodin T, Orive G, Lertxundi U. Pharmaceutical residues in stranded dolphins in the Bay of Biscay. Sci Total Environ. 2024 Feb 20;912:168570. doi: 10.1016/j.scitotenv.2023.168570. Epub 2023 Nov 17. PMID: 37979850. 4: Adongo DW, Benneh CK, Tandoh A, Biney RP, Kukuia KKE, Mante PK, Harley BK, Oteng D, Appiah EA, Anorbor EC, Woode E. Anxiolytic-like effects of Pseudospondias microcarpa hydroethanolic leaf extract in zebrafish: Possible involvement of GABAergic and serotonergic pathways. Nat Prod Bioprospect. 2023 Oct 4;13(1):33. doi: 10.1007/s13659-023-00399-8. PMID: 37789217; PMCID: PMC10547670. 5: Cesário HPSF, Silva FCO, Ferreira MKA, de Menezes JESA, Dos Santos HS, Marques da Fonseca A, Nogueira CES, Marinho MM, Marinho ES, Teixeira AMR, Silveira ER, Pessoa ODL. Anxiolytic effects of N-(4,5-dihydro-5-oxo-1,2-d ithiolo-[4,3,b]-pyrrole-6-yl)-N-methylformamide, a pyrroloformamide isolated from a marine Streptomyces sp., in adult zebrafish by the 5-HT system. J Biomol Struct Dyn. 2024 Jan-Feb;42(1):445-460. doi: 10.1080/07391102.2023.2193988. Epub 2023 Apr 10. PMID: 37038661. 6: de Menezes JFS, Sá Pires Silva AM, Aparecida Faria de Almeida E, da Silva AF, Morais Bomfim De Lima J, da Silva AW, Ferreira MKA, de Menezes JESA, Dos Santos HS, Marinho ES, Marinho GS, Marques da Fonseca A. Synthesis and anxiolytic effect of europium metallic complex containing lapachol [Eu(DBM)3. LAP] in adult zebrafish through serotonergic neurotransmission: in vivo and in silico approach. J Biomol Struct Dyn. 2024 Feb- Mar;42(3):1280-1292. doi: 10.1080/07391102.2023.2199087. Epub 2023 Apr 8. PMID: 37029769. 7: He X, Zhou Y, Chen W, Zhao X, Duan L, Zhou H, Li M, Yu Y, Zhao J, Guo Y, Gu H, Jiang Y, Dong Z, Liu K. Repurposed pizotifen malate targeting NRF2 exhibits anti-tumor activity through inducing ferroptosis in esophageal squamous cell carcinoma. Oncogene. 2023 Apr;42(15):1209-1223. doi: 10.1038/s41388-023-02636-3. Epub 2023 Feb 25. PMID: 36841865. 8: Nakayama J, Makinoshima H, Gong Z. Gastrulation Screening to Identify Anti- metastasis Drugs in Zebrafish Embryos. Bio Protoc. 2022 Oct 5;12(19):e4525. doi: 10.21769/BioProtoc.4525. PMID: 36313195; PMCID: PMC9548519. 9: Santos PSF, Melhado EM, Kaup AO, Costa ATNMD, Roesler CAP, Piovesan ÉJ, Sarmento EM, Theotonio GOM, Campos HC, Fortini I, Souza JA, Júnior JAM, Segundo JBA, Carvalho JJF, Speziali JG, Calia LC, Barea LM, Queiroz LP, Souza MNP, Figueiredo MRCF, Costa MENM, Peres MFP, Jurno ME, Peixoto PM, Kowacs PA, Rocha- Filho PAS, Filho PFM, Silva-Neto RP, Fragoso YD. Consensus of the Brazilian Headache Society (SBCe) for prophylactic treatment of episodic migraine: part II. Arq Neuropsiquiatr. 2022 Sep;80(9):953-969. doi: 10.1055/s-0042-1755320. Epub 2022 Oct 18. PMID: 36257618; PMCID: PMC10658446. 10: Al Lawati TT, Saadah OI, Al Riyami R, Al Yarubi Z. Prophylactic Therapy Response in Children with Abdominal Migraine: A Single Centre Experience in Oman. Pediatr Gastroenterol Hepatol Nutr. 2022 Mar;25(2):121-128. doi: 10.5223/pghn.2022.25.2.121. Epub 2022 Mar 10. PMID: 35360376; PMCID: PMC8958052. 11: Li J, Zhang X, Xu C, Liu YX, Ge C, Zhao Z, Zhu YB, Bao HG. Intrathecally administered pizotifen alleviates neuropathic and inflammatory pain in mice by enhancing GABAergic inhibition. Neurosci Lett. 2022 Apr 1;775:136545. doi: 10.1016/j.neulet.2022.136545. Epub 2022 Feb 21. PMID: 35202750. 12: Loh NR, Whitehouse WP, Howells R. What is new in migraine management in children and young people? Arch Dis Child. 2022 Dec;107(12):1067-1072. doi: 10.1136/archdischild-2021-322373. Epub 2022 Feb 21. PMID: 35190383. 13: Kemet C, Hill E, Feng H. Fishing for drugs. Elife. 2022 Feb 8;11:e76632. doi: 10.7554/eLife.76632. PMID: 35133278; PMCID: PMC8824469. 14: Nakayama J, Tan L, Li Y, Goh BC, Wang S, Makinoshima H, Gong Z. A zebrafish embryo screen utilizing gastrulation identifies the HTR2C inhibitor pizotifen as a suppressor of EMT-mediated metastasis. Elife. 2021 Dec 17;10:e70151. doi: 10.7554/eLife.70151. PMID: 34919051; PMCID: PMC8824480. 15: Lam T, Ranjan R, Newark K, Surana S, Bhangu N, Lazenbury A, Childs AM, Abbey I, Gibbon F, Thomas G, Singh J, Prabhakar P, Kaminska M, Lascelles K, Hacohen Y, Brown K, Lim M. A recent surge of fulminant and early onset subacute sclerosing panencephalitis (SSPE) in the United Kingdom: An emergence in a time of measles. Eur J Paediatr Neurol. 2021 Sep;34:43-49. doi: 10.1016/j.ejpn.2021.07.006. Epub 2021 Jul 16. PMID: 34388650. 16: da Silva AW, Ferreira MKA, Rebouças EL, Mendes FRS, Dos S Moura AL, de Menezes JESA, Marinho MM, Marinho ES, Santos HS, Teixeira AMR. Anxiolytic-like effect of natural product 2-hydroxy-3,4,6-trimethoxyacetophenone isolated from Croton anisodontus in adult zebrafish via serotonergic neuromodulation involvement of the 5-HT system. Naunyn Schmiedebergs Arch Pharmacol. 2021 Oct;394(10):2023-2032. doi: 10.1007/s00210-021-02116-z. Epub 2021 Jul 12. PMID: 34251503. 17: Pompilio G, Migliore A, Integlia D. Systematic literature review and Bayesian network meta-analysis of episodic cluster headache drugs. Eur Rev Med Pharmacol Sci. 2021 Feb;25(3):1631-1640. doi: 10.26355/eurrev_202102_24874. PMID: 33629333. 18: Araújo JRC, Campos AR, Ferreira MKA, Santos SAAR, de Barros Mamede Vidal Damasceno M, Magalhães FEA, de Azevedo Moreira R, de Oliveira Monteiro-Moreira AC. Dioclea Altissima Seed Lectin (DAL) Prevents Anxiety-like Behavioral Responses in Adult Zebrafish (Danio Rerio): Involvement of GABAergic and 5-HT Systems. CNS Neurol Disord Drug Targets. 2022;21(1):95-103. doi: 10.2174/1871527320666210212112651. PMID: 33583388. 19: Orlando V, Mucherino S, Monetti VM, Trama U, Menditto E. Treatment patterns and medication adherence among newly diagnosed patients with migraine: a drug utilisation study. 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