Trifluoperazine
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Hodoodo CAT#: H318906

CAS#: 117-89-5

Description: Trifluoperazine is a typical antipsychotic of the phenothiazine chemical class. The primary application of trifluoperazine is for schizophrenia. Other official indications may vary country by country, but generally it is also indicated for use in agitation and patients with behavioural problems, severe nausea and vomiting as well as severe anxiety. Trials have shown a moderate benefit of this drug in patients with borderline personality disorder.

Chemical Structure

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Trifluoperazine
CAS# 117-89-5
Instruction

Theoretical Analysis

Hodoodo Cat#: H318906
Name: Trifluoperazine
CAS#: 117-89-5
Chemical Formula: C21H24F3N3S
Exact Mass: 407.16
Molecular Weight: 407.496
Elemental Analysis: C, 61.90; H, 5.94; F, 13.99; N, 10.31; S, 7.87

Price and Availability

Size Price Availability Quantity
1mg USD 220 2 Weeks
5mg USD 450 2 Weeks
50mg USD 980 2 Weeks
100mg USD 1450 2 Weeks
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Synonym: Trifluoperazine, Trifluperazine, Trifluoroperazine, Trifluoperazina, Triflurin, Triperazine

IUPAC/Chemical Name: 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine

InChi Key: ZEWQUBUPAILYHI-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3

SMILES Code: FC(C(C=C1N2CCCN3CCN(C)CC3)=CC=C1SC4=C2C=CC=C4)(F)F

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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 407.50 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tse WS, Wong AS, Chan F, Pang AH, Bond AJ, Chan CK. Different mechanisms of risperidone result in improved interpersonal trust, social engagement and cooperative behavior in patients with schizophrenia compared to trifluoperazine. Psychiatry Clin Neurosci. 2016 May;70(5):218-26. doi: 10.1111/pcn.12382. Epub 2016 Apr 5. PubMed PMID: 26864920.

2: Abdülrezzak Ü, Erdoğan Z, Silov G, Özdal A, Turhal Ö. Effect of trifluoperazine on Tc-99m sestamibi uptake in patients with advanced nonsmall cell lung cancer. Indian J Nucl Med. 2016 Apr-Jun;31(2):103-7. doi: 10.4103/0972-3919.178256. PubMed PMID: 27095857; PubMed Central PMCID: PMC4815380.

3: Howland RH. Trifluoperazine: A Sprightly Old Drug. J Psychosoc Nurs Ment Health Serv. 2016 Jan 1;54(1):20-2. doi: 10.3928/02793695-20151223-01. PubMed PMID: 26760133.

4: Feldkamp MD, Gakhar L, Pandey N, Shea MA. Opposing orientations of the anti-psychotic drug trifluoperazine selected by alternate conformations of M144 in calmodulin. Proteins. 2015 May;83(5):989-96. doi: 10.1002/prot.24781. Epub 2015 Mar 25. PubMed PMID: 25694384; PubMed Central PMCID: PMC4400249.

5: Guo J, Ni C, Liu X, Liu T. Ganoderic acid B's influence towards the therapeutic window of trifluoperazine (TFP). Afr Health Sci. 2015 Mar;15(1):146-9. doi: 10.4314/ahs.v15i1.20. PubMed PMID: 25834543; PubMed Central PMCID: PMC4370157.

6: Rajesh P, Gunasekaran S, Gnanasambandan T, Seshadri S. Molecular structure and vibrational analysis of Trifluoperazine by FT-IR, FT-Raman and UV-Vis spectroscopies combined with DFT calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 25;137:1184-93. doi: 10.1016/j.saa.2014.08.100. Epub 2014 Sep 7. PubMed PMID: 25305610.

7: Pulkoski-Gross A, Li J, Zheng C, Li Y, Ouyang N, Rigas B, Zucker S, Cao J. Repurposing the antipsychotic trifluoperazine as an antimetastasis agent. Mol Pharmacol. 2015;87(3):501-12. doi: 10.1124/mol.114.096941. Epub 2014 Dec 31. PubMed PMID: 25552486; PubMed Central PMCID: PMC4419284.

8: Xiao JF, Liu XJ, Liu GW, Yang XY, Xiao P, Hou XM, Wang HT, Tang JJ, Zhang YT, Zhen C, Fang HH. The metabolism of trifluoperazine (TFP) exhibits atypical kinetic behavior in both human liver microsomes (HLMs) and monkey liver microsomes (MyLM). Eur J Drug Metab Pharmacokinet. 2014 Dec;39(4):335-7. doi: 10.1007/s13318-013-0163-8. Epub 2013 Dec 27. PubMed PMID: 24370939.

9: Brosius SN, Turk AN, Byer SJ, Longo JF, Kappes JC, Roth KA, Carroll SL. Combinatorial therapy with tamoxifen and trifluoperazine effectively inhibits malignant peripheral nerve sheath tumor growth by targeting complementary signaling cascades. J Neuropathol Exp Neurol. 2014 Nov;73(11):1078-90. doi: 10.1097/NEN.0000000000000126. PubMed PMID: 25289889; PubMed Central PMCID: PMC4458069.

10: Chae YJ, Choi BH, Choi JS, Hahn SJ. Block of Kv4.3 potassium channel by trifluoperazine independent of CaMKII. Neurosci Lett. 2014 Aug 22;578:159-64. doi: 10.1016/j.neulet.2014.06.045. Epub 2014 Jun 30. PubMed PMID: 24993295.

11: Attaran AM, Mohammadi N, Javanbakht M, Akbari-Adergani B. Molecularly imprinted solid-phase extraction for selective trace analysis of trifluoperazine. J Chromatogr Sci. 2014 Aug;52(7):730-8. doi: 10.1093/chromsci/bmt074. Epub 2013 Jun 19. PubMed PMID: 23788020.

12: Tardy M, Dold M, Engel RR, Leucht S. Trifluoperazine versus low-potency first-generation antipsychotic drugs for schizophrenia. Cochrane Database Syst Rev. 2014 Jul 8;7:CD009396. doi: 10.1002/14651858.CD009396.pub2. Review. PubMed PMID: 25003310.

13: Höllerhage M, Goebel JN, de Andrade A, Hildebrandt T, Dolga A, Culmsee C, Oertel WH, Hengerer B, Höglinger GU. Trifluoperazine rescues human dopaminergic cells from wild-type α-synuclein-induced toxicity. Neurobiol Aging. 2014 Jul;35(7):1700-11. doi: 10.1016/j.neurobiolaging.2014.01.027. Epub 2014 Jan 28. PubMed PMID: 24559643.

14: Osman M, Edwards D, Kilduff M. Trifluoperazine-induced angioedema. Case Rep Psychiatry. 2014;2014:140329. doi: 10.1155/2014/140329. Epub 2014 Aug 17. PubMed PMID: 25197603; PubMed Central PMCID: PMC4150501.

15: Koch K, Mansi K, Haynes E, Adams CE, Sampson S, Furtado VA. Trifluoperazine versus placebo for schizophrenia. Cochrane Database Syst Rev. 2014 Jan 11;1:CD010226. doi: 10.1002/14651858.CD010226.pub2. Review. PubMed PMID: 24414883.

16: Hong da H, Son YK, Li H, Jung ID, Park YM, Jung WK, Kim HS, Choi IW, Park WS. The calmodulin inhibitor and antipsychotic drug trifluoperazine inhibits voltage-dependent K+ channels in rabbit coronary arterial smooth muscle cells. Biochem Biophys Res Commun. 2014 Jan 3;443(1):321-5. doi: 10.1016/j.bbrc.2013.11.115. Epub 2013 Dec 6. PubMed PMID: 24316213.

17: Molokie RE, Wilkie DJ, Wittert H, Suarez ML, Yao Y, Zhao Z, He Y, Wang ZJ. Mechanism-driven phase I translational study of trifluoperazine in adults with sickle cell disease. Eur J Pharmacol. 2014 Jan 15;723:419-24. doi: 10.1016/j.ejphar.2013.10.062. Epub 2013 Nov 7. PubMed PMID: 24211787; PubMed Central PMCID: PMC3959657.

18: Hempel C, Nörenberg W, Sobottka H, Urban N, Nicke A, Fischer W, Schaefer M. The phenothiazine-class antipsychotic drugs prochlorperazine and trifluoperazine are potent allosteric modulators of the human P2X7 receptor. Neuropharmacology. 2013 Dec;75:365-79. doi: 10.1016/j.neuropharm.2013.07.027. Epub 2013 Aug 14. PubMed PMID: 23954492.

19: Yeh CT, Wu AT, Chang PM, Chen KY, Yang CN, Yang SC, Ho CC, Chen CC, Kuo YL, Lee PY, Liu YW, Yen CC, Hsiao M, Lu PJ, Lai JM, Wang LS, Wu CH, Chiou JF, Yang PC, Huang CY. Trifluoperazine, an antipsychotic agent, inhibits cancer stem cell growth and overcomes drug resistance of lung cancer. Am J Respir Crit Care Med. 2012 Dec 1;186(11):1180-8. doi: 10.1164/rccm.201207-1180OC. Epub 2012 Sep 28. PubMed PMID: 23024022.

20: Chaudhuri S, McCullough SS, Hennings L, Brown AT, Li SH, Simpson PM, Hinson JA, James LP. Effect of trifluoperazine on toxicity, HIF-1α induction and hepatocyte regeneration in acetaminophen toxicity in mice. Toxicol Appl Pharmacol. 2012 Oct 15;264(2):192-201. doi: 10.1016/j.taap.2012.08.001. Epub 2012 Aug 10. PubMed PMID: 22902588; PubMed Central PMCID: PMC3519387.