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MedKoo Cat#: 330178 | Name: Fluphenazine dimaleate

Description:

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

Fluphenazine is a antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia. Fluphenazine exerts its actions by blocking postsynaptic dopamine D2 receptors in the limbic, cortical system and basal ganglia. This prevents the actions of dopamine, thereby reducing the hallucinations and delusions that are associated with schizophrenia. It is given by mouth, injection into a muscle, or just under the skin.

Chemical Structure

Fluphenazine dimaleate
Fluphenazine dimaleate
CAS#3093-66-1 (dimaleate)

Theoretical Analysis

MedKoo Cat#: 330178

Name: Fluphenazine dimaleate

CAS#: 3093-66-1 (dimaleate)

Chemical Formula: C30H34F3N3O9S

Exact Mass: 0.0000

Molecular Weight: 669.67

Elemental Analysis: C, 53.81; H, 5.12; F, 8.51; N, 6.27; O, 21.50; S, 4.79

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Synonym
69-23-8 (free base), 146-56-5 (HCl), 3093-66-1 (dimaleate),
IUPAC/Chemical Name
2-[4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol dimaleate
InChi Key
GTJLCONXCUYJOF-SPIKMXEPSA-N
InChi Code
InChI=1S/C22H26F3N3OS.2C4H4O4/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29;2*5-3(6)1-2-4(7)8/h1-2,4-7,16,29H,3,8-15H2;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-
SMILES Code
FC(C(C=C1N2CCCN3CCN(CCO)CC3)=CC=C1SC4=C2C=CC=C4)(F)F.O=C(O)/C=C\C(O)=O.O=C(O)/C=C\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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 669.67 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.

Recalculate based on batch purity %
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
1: Xu F, Xia Y, Feng Z, Lin W, Xue Q, Jiang J, Yu X, Peng C, Luo M, Yang Y, Wei Y, Yu L. Repositioning antipsychotic fluphenazine hydrochloride for treating triple negative breast cancer with brain metastases and lung metastases. Am J Cancer Res. 2019 Mar 1;9(3):459-478. eCollection 2019. PubMed PMID: 30949404; PubMed Central PMCID: PMC6448056. 2: Menilli L, García-Argáez AN, Dalla Via L, Miolo G. The neuroleptic drug fluphenazine induces a significant UVA-mediated cytotoxic effect on three human cancer cell lines through apoptosis. Photochem Photobiol Sci. 2019 Mar 12. doi: 10.1039/c9pp00023b. [Epub ahead of print] PubMed PMID: 30860541. 3: Otręba M, Beberok A, Wrześniok D, Buszman E. In vitro melanogenesis inhibition by fluphenazine and prochlorperazine in normal human melanocytes lightly pigmented. Daru. 2018 Sep;26(1):85-89. doi: 10.1007/s40199-018-0206-4. Epub 2018 Jul 24. PubMed PMID: 30159761; PubMed Central PMCID: PMC6154481. 4: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500732/ PubMed PMID: 29999791. 5: Matar HE, Almerie MQ, Sampson SJ. Fluphenazine (oral) versus placebo for schizophrenia. Cochrane Database Syst Rev. 2018 Jun 12;6:CD006352. doi: 10.1002/14651858.CD006352.pub3. Review. PubMed PMID: 29893410. 6: Siragusa S, Saadabadi A. Fluphenazine. 2018 Oct 27. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2019 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK459194/ PubMed PMID: 29083807. 7: Sobczak A, Teżyk A, Szyndlarewicz J, Ziarniak J, Świątek P, Malinka W. New fluphenazine analogue with antimutagenic and anti-multidrug resistance activity-degradation profile and stability-indicating method. Med Chem Res. 2017;26(10):2443-2451. doi: 10.1007/s00044-017-1944-4. Epub 2017 Jun 15. PubMed PMID: 29051697; PubMed Central PMCID: PMC5628186. 8: Umino M, Kobayashi R, Nisijima K, Suda S. Late-Onset Rhabdomyolysis Associated With an Intramuscular Injection of Fluphenazine Decanoate. Prim Care Companion CNS Disord. 2017 Sep 28;19(5). pii: 16l02078. doi: 10.4088/PCC.16l02078. PubMed PMID: 28972705. 9: Zanker J, Ferraro A. Consequences of market withdrawal of fluphenazine and trifluoperazine: Letter to the editor and case series. Aust N Z J Psychiatry. 2017 Dec;51(12):1256. doi: 10.1177/0004867417730418. Epub 2017 Sep 9. PubMed PMID: 28891312. 10: Strinic D, Belosic Halle Z, Luetic K, Nedic A, Petrovic I, Sucic M, Zivanovic Posilovic G, Balenovic D, Strbe S, Udovicic M, Drmic D, Stupnisek M, Lovric Bencic M, Seiwerth S, Sikiric P. BPC 157 counteracts QTc prolongation induced by haloperidol, fluphenazine, clozapine, olanzapine, quetiapine, sulpiride, and metoclopramide in rats. Life Sci. 2017 Oct 1;186:66-79. doi: 10.1016/j.lfs.2017.08.006. Epub 2017 Aug 7. PubMed PMID: 28797793. 11: Busanello A, Leal CQ, Peroza LR, Röpke J, de Moraes Reis E, de Freitas CM, Libardoni M, de Vargas Barbosa NB, Fachinetto R. Resveratrol Protects Against Vacuous Chewing Movements Induced by Chronic Treatment with Fluphenazine. Neurochem Res. 2017 Nov;42(11):3033-3040. doi: 10.1007/s11064-017-2335-4. Epub 2017 Jul 25. PubMed PMID: 28744755. 12: Omi T, Mitsui Y, Matsunaga H. Long-acting formulation leading to severe long-term adverse effects: a case report of fluphenazine and persistent extrapyramidal symptoms. J Clin Pharm Ther. 2018 Feb;43(1):117-120. doi: 10.1111/jcpt.12589. Epub 2017 Jul 17. PubMed PMID: 28718220. 13: Cieślik-Boczula K. The PPII-to-α-helix transition of poly-l-lysine in methanol/water solvent mixtures accompanied by fibrillar self-aggregation: An influence of fluphenazine molecules. Biophys Chem. 2017 Aug;227:14-20. doi: 10.1016/j.bpc.2017.05.012. Epub 2017 May 24. PubMed PMID: 28558910. 14: Jing JJ, Liu B, Wang X, Wang X, He LL, Guo XY, Xu ML, Li QY, Gao B, Dong BY. Binding of fluphenazine with human serum albumin in the presence of rutin and quercetin: An evaluation of food-drug interaction by spectroscopic techniques. Luminescence. 2017 Sep;32(6):1056-1065. doi: 10.1002/bio.3291. Epub 2017 Apr 4. PubMed PMID: 28374530. 15: Klutzny S, Lesche R, Keck M, Kaulfuss S, Schlicker A, Christian S, Sperl C, Neuhaus R, Mowat J, Steckel M, Riefke B, Prechtl S, Parczyk K, Steigemann P. Functional inhibition of acid sphingomyelinase by Fluphenazine triggers hypoxia-specific tumor cell death. Cell Death Dis. 2017 Mar 30;8(3):e2709. doi: 10.1038/cddis.2017.130. PubMed PMID: 28358364; PubMed Central PMCID: PMC5386533. 16: Saraei M, Ghaderi Y, Mosavi T, Shahnazi M, Nassiri-Asl M, Jahanihashemi H. The Effect of Fluphenazine and Thioridazine on Toxoplasma gondii In Vivo. Iran J Parasitol. 2016 Apr-Jun;11(2):226-231. PubMed PMID: 28096857; PubMed Central PMCID: PMC5236100. 17: Cheon JH, Lee BM, Kim HS, Yoon S. Highly Halaven-resistant KBV20C Cancer Cells Can Be Sensitized by Co-treatment with Fluphenazine. Anticancer Res. 2016 Nov;36(11):5867-5874. PubMed PMID: 27793910. 18: Sampford JR, Sampson S, Li BG, Zhao S, Xia J, Furtado VA. Fluphenazine (oral) versus atypical antipsychotics for schizophrenia. Cochrane Database Syst Rev. 2016 Jul 2;7:CD010832. doi: 10.1002/14651858.CD010832.pub2. Review. PubMed PMID: 27370402; PubMed Central PMCID: PMC6474115. 19: Otreba M, Wrześniok D, Beberok A, Rok J, Buszman E. FLUPHENAZINE AND PERPHENAZINE IMPACT ON MELANOGENESIS AND ANTIOXIDANT ENZYMES ACTIVITY IN NORMAL HUMAN MELANOCYTES. Acta Pol Pharm. 2016 Jul;73(4):903-911. PubMed PMID: 29648716. 20: Thummar KN, Ghava DJ, Mistry A, Vachhani A, Sheth NR. Forced Degradation Behaviour of Fluphenazine Hydrochloride by LC and Characterization of its Oxidative Degradation Product by LC-MS/MS. Sci Pharm. 2014 Dec 22;83(2):297-309. doi: 10.3797/scipharm.1411-04. Print 2015 Apr-Jun. PubMed PMID: 26839816; PubMed Central PMCID: PMC4727772.