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MedKoo Cat#: 318474 | Name: Perphenazine
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Description:

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

Perphenazine is a phenothiazine derivative and a dopamine antagonist with antiemetic and antipsychotic properties. Perphenazine blocks postsynaptic dopamine 2(D2) receptors in the mesolimbic and medullary chemoreceptor trigger zone (CTZ), thereby preventing the excess of dopamine in the brain. This leads to reduction in psychotic symptoms, such as hallucinations and delusions.

Chemical Structure

Perphenazine
CAS#58-39-9

Theoretical Analysis

MedKoo Cat#: 318474

Name: Perphenazine

CAS#: 58-39-9

Chemical Formula: C21H26ClN3OS

Exact Mass: 403.1485

Molecular Weight: 403.97

Elemental Analysis: C, 62.44; H, 6.49; Cl, 8.78; N, 10.40; O, 3.96; S, 7.94

Price and Availability

Size Price Availability Quantity
1g USD 150.00
2g USD 250.00
5g USD 450.00
10g USD 750.00
20g USD 1,250.00
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Related CAS #
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Synonym
Perphenazine; Trilafon; Perphenazin; Perfenazine; Etaperazine; Chlorpiprazine
IUPAC/Chemical Name
2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol
InChi Key
RGCVKNLCSQQDEP-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
SMILES Code
C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl)CCO
Appearance
White to off-white crystalline 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Perphenazine is an orally active dopamine receptor and histamine-1 receptor antagonist, with Ki values of 0.56 nM (D2), 0.43 nM (D3), 6 nM (5-HT2A), respectively.
In vitro activity:
The present study investigated the molecular mechanism underling the antitumor effects of PPZ in the neuroblastoma rat sarcoma oncogene (NRAS)-mutated Sezary syndrome cell line, HUT78. The results of the present study demonstrated that PPZ induced the dephosphorylation of Akt and ERK1/2, and triggered apoptosis in HUT78 cells. Reference: Oncol Lett. 2021 Feb;21(2):113. https://pubmed.ncbi.nlm.nih.gov/33376545/
In vivo activity:
This study used perphenazine, an FDA-approved dopamine receptor antagonist to determine the therapeutic effect. Two different animal models including 12-o-tetradecanoylphorbol-13-acetate (TPA) and oxazolone (OXA)-induced dermatitis were employed. TPA and OXA-mediated ear swelling was attenuated by perphenazine. Moreover, perphenazine inhibited infiltrated mast cells into lesion area. This study found levels of serum IgE, histamine and cytokines are decreased in mice cotreated with perphenazine and OXA compared to OXA-treated mice. Reference: Int J Mol Sci. 2020 May 3;21(9):3241. https://pubmed.ncbi.nlm.nih.gov/32375285/
Solvent mg/mL mM comments
Solubility
DMSO 87.0 215.36
Ethanol 74.0 183.18
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 403.97 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:
1. Tao L, Qing Y, Cui Y, Shi D, Liu W, Chen L, Cao Y, Dai Z, Ge X, Zhang L. Lysosomal membrane permeabilization mediated apoptosis involve in perphenazine-induced hepatotoxicity in vitro and in vivo. Toxicol Lett. 2022 Aug 15;367:76-87. doi: 10.1016/j.toxlet.2022.07.814. Epub 2022 Jul 29. PMID: 35914675. 2. Tsuji S, Kohyanagi N, Mizuno T, Ohama T, Sato K. Perphenazine exerts antitumor effects on HUT78 cells through Akt dephosphorylation by protein phosphatase 2A. Oncol Lett. 2021 Feb;21(2):113. doi: 10.3892/ol.2020.12374. Epub 2020 Dec 15. PMID: 33376545; PMCID: PMC7751355. 3. Heo MJ, Choi SY, Lee C, Choi YM, An IS, Bae S, An S, Jung JH. Perphenazine Attenuates the Pro-Inflammatory Responses in Mouse Models of Th2-Type Allergic Dermatitis. Int J Mol Sci. 2020 May 3;21(9):3241. doi: 10.3390/ijms21093241. PMID: 32375285; PMCID: PMC7247351. 4. Ozdemir E, Bagcivan I, Gursoy S. Role of D₁/D₂ dopamin receptors antagonist perphenazine in morphine analgesia and tolerance in rats. Bosn J Basic Med Sci. 2013 May;13(2):119-25. doi: 10.17305/bjbms.2013.2394. PMID: 23725509; PMCID: PMC4333934.
In vitro protocol:
1. Tao L, Qing Y, Cui Y, Shi D, Liu W, Chen L, Cao Y, Dai Z, Ge X, Zhang L. Lysosomal membrane permeabilization mediated apoptosis involve in perphenazine-induced hepatotoxicity in vitro and in vivo. Toxicol Lett. 2022 Aug 15;367:76-87. doi: 10.1016/j.toxlet.2022.07.814. Epub 2022 Jul 29. PMID: 35914675. 2. Tsuji S, Kohyanagi N, Mizuno T, Ohama T, Sato K. Perphenazine exerts antitumor effects on HUT78 cells through Akt dephosphorylation by protein phosphatase 2A. Oncol Lett. 2021 Feb;21(2):113. doi: 10.3892/ol.2020.12374. Epub 2020 Dec 15. PMID: 33376545; PMCID: PMC7751355.
In vivo protocol:
1. Heo MJ, Choi SY, Lee C, Choi YM, An IS, Bae S, An S, Jung JH. Perphenazine Attenuates the Pro-Inflammatory Responses in Mouse Models of Th2-Type Allergic Dermatitis. Int J Mol Sci. 2020 May 3;21(9):3241. doi: 10.3390/ijms21093241. PMID: 32375285; PMCID: PMC7247351. 2. Ozdemir E, Bagcivan I, Gursoy S. Role of D₁/D₂ dopamin receptors antagonist perphenazine in morphine analgesia and tolerance in rats. Bosn J Basic Med Sci. 2013 May;13(2):119-25. doi: 10.17305/bjbms.2013.2394. PMID: 23725509; PMCID: PMC4333934.
1: Slawson MH, Johnson-Davis KL. Quantitation of Haloperidol, Fluphenazine, Perphenazine, and Thiothixene in Serum or Plasma Using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). Methods Mol Biol. 2016;1383:49-57. doi: 10.1007/978-1-4939-3252-8_6. PubMed PMID: 26660173. 2: Maust MS, Muramatsu RS, Egan K, Ahmed I. Perphenazine-Associated Hyperosmolar Hyperglycemic State. J Clin Psychopharmacol. 2015 Aug;35(4):485-6. doi: 10.1097/JCP.0000000000000359. PubMed PMID: 26120945. 3: Hartung B, Sampson S, Leucht S. Perphenazine for schizophrenia. Cochrane Database Syst Rev. 2015 Mar 6;3:CD003443. doi: 10.1002/14651858.CD003443.pub3. Review. PubMed PMID: 25749632. 4: Halayqa M, Domańska U. PLGA biodegradable nanoparticles containing perphenazine or chlorpromazine hydrochloride: effect of formulation and release. Int J Mol Sci. 2014 Dec 22;15(12):23909-23. doi: 10.3390/ijms151223909. PubMed PMID: 25535080; PubMed Central PMCID: PMC4284797. 5: Tardy M, Huhn M, Engel RR, Leucht S. Perphenazine versus low-potency first-generation antipsychotic drugs for schizophrenia. Cochrane Database Syst Rev. 2014 Oct 7;10:CD009369. doi: 10.1002/14651858.CD009369.pub2. Review. PubMed PMID: 25290157. 6: Takeuchi H, Fervaha G, Uchida H, Suzuki T, Bies RR, Grönte D, Remington G. Impact of once- versus twice-daily perphenazine dosing on clinical outcomes: an analysis of the CATIE data. J Clin Psychiatry. 2014 May;75(5):506-11. doi: 10.4088/JCP.13m08695. PubMed PMID: 24569099. 7: Henao JP, Peperzak KA, Lichvar AB, Orebaugh SL, Skledar SJ, Pippi MA, Williams BA. Extrapyramidal symptoms following administration of oral perphenazine 4 or 8 mg: an 11-year retrospective analysis. Eur J Anaesthesiol. 2014 Apr;31(4):231-5. doi: 10.1097/EJA.0000000000000048. PubMed PMID: 24503705; PubMed Central PMCID: PMC4365999. 8: Activation of PP2A by perphenazine induces apoptosis in T-ALL. Cancer Discov. 2014 Mar;4(3):OF14. doi: 10.1158/2159-8290.CD-RW2014-017. Epub 2014 Jan 23. PubMed PMID: 24596208. 9: Turunen E, Korhonen O, Lehto VP, Kauppinen A, Ahtiainen H, Järvinen K, Jarho P. Effect of storage on the dissolution rate of a fast-dissolving perphenazine/β-cyclodextrin complex. J Pharm Pharmacol. 2014 Mar;66(3):367-77. doi: 10.1111/jphp.12174. Epub 2013 Nov 10. PubMed PMID: 24206258. 10: Xu L, Li L, Huang J, You T. Analysis of perphenazine and fluphenazine by capillary electrophoresis coupled with tris (2,2'-bipyridyl) ruthenium (II) electrochemiluminescence detection. Talanta. 2014 Jan;118:1-6. doi: 10.1016/j.talanta.2013.09.048. Epub 2013 Oct 5. PubMed PMID: 24274263. 11: Kast RE, Ellingson BM, Marosi C, Halatsch ME. Glioblastoma treatment using perphenazine to block the subventricular zone's tumor trophic functions. J Neurooncol. 2014 Jan;116(2):207-12. doi: 10.1007/s11060-013-1308-y. Epub 2013 Nov 17. Review. PubMed PMID: 24242756. 12: Rosenheck R, Lin H. Noninferiority of perphenazine vs. three second-generation antipsychotics in chronic schizophrenia. J Nerv Ment Dis. 2014 Jan;202(1):18-24. doi: 10.1097/NMD.0000000000000065. PubMed PMID: 24375207; PubMed Central PMCID: PMC4635461. 13: Marco I, Cabezón O, Mentaberre G, Fernández-Sirera L, Casas-Díaz E, Fernandez-Aguilar X, López-Olvera JR, Serrano E, Navarro-Gonzalez N, Lavín S, Manteca X. Effect of perphenazine enanthate in Pyrenean chamois (Rupicapra pyrenaica). J Zoo Wildl Med. 2013 Dec;44(4):1083-5. PubMed PMID: 24450074. 14: Wang L, Xiao YY, Chen ML, Zeng F, Zong L. Pharmacokinetics of orally disintegrating tablets of perphenazine/hydroxypropyl-beta-cyclodextrin inclusion complex in rabbits. Pharmazie. 2013 Oct;68(10):800-4. PubMed PMID: 24273883. 15: Zheng ZY, Cui ML, Zhang LH, Jiang SL, Jiao L, Lin X, Lin SQ, Liu JM. Catalytic solid substrate-room temperature phosphorimetry for the determination of residual perphenazine based on the electronic effect of rhodamine 6G. Luminescence. 2013 Sep-Oct;28(5):634-40. doi: 10.1002/bio.2408. Epub 2012 Oct 1. PubMed PMID: 23023763. 16: Wang L, Zeng F, Zong L. Development of orally disintegrating tablets of Perphenazine/hydroxypropyl-β-cyclodextrin inclusion complex. Pharm Dev Technol. 2013 Sep-Oct;18(5):1101-10. doi: 10.3109/10837450.2012.700932. Epub 2012 Jul 3. PubMed PMID: 22759202. 17: Juenke JM, Brown PI, Urry FM, Johnson-Davis KL, McMillin GA. Simultaneous UPLC-MS/MS assay for the detection of the traditional antipsychotics haloperidol, fluphenazine, perphenazine, and thiothixene in serum and plasma. Clin Chim Acta. 2013 Aug 23;423:32-4. doi: 10.1016/j.cca.2013.04.014. Epub 2013 Apr 23. PubMed PMID: 23618971. 18: Ozdemir E, Bagcivan I, Gursoy S. Role of D₁/D₂ dopamin receptors antagonist perphenazine in morphine analgesia and tolerance in rats. Bosn J Basic Med Sci. 2013 May;13(2):119-25. PubMed PMID: 23725509; PubMed Central PMCID: PMC4333934. 19: Retraction. Anti-emetic efficacy of prophylactic granisetron compared with perphenazine for the prevention of post-operative vomiting in children. Eur J Anaesthesiol. 2013 May;30(5):263. doi: 10.1097/01.EJA.0000429564.55393.82. PubMed PMID: 23571441. 20: Preoperative oral antiemetics for reducing postoperative vomiting after tonsillectomy in children: granisetron versus perphenazine. Anesth Analg 1999;88:1298-301. Retraction. Anesth Analg. 2013 Mar;116(3):744. doi: 10.1213/ANE.0b013e31828ac38a. PubMed PMID: 23439825.