Perphenazine-d4 | CAS#155593-75-2 | Perphenazine quantification internal standard

MedKoo Cat#: 463870 | Name: Perphenazine-d4

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Description:

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

Perphenazine-d4 is intended for use as an internal standard for the quantification of perphenazine by GC- or LC-MS. Perphenazine is a typical antipsychotic. It binds to dopamine D2, α1A-, α2A-, α2B-, and α2C-adrenergic, M3 muscarinic, and histamine H1 receptors, as well as the serotonin (5-HT) receptor subtypes 5-HT1A, 5-HT2A, 5-HT2C, 5-HT6, and 5-HT7. Perphenazine enhances morphine-induced analgesia in the tail-flick and hot plate tests in rats. It reduces cannibalism in female mice when administered at doses of 2 and 4 mg/kg. Formulations containing perphenazine have been used in the treatment of schizophrenia and psychosis.

Chemical Structure

Perphenazine-d4

CAS#155593-75-2

Theoretical Analysis

MedKoo Cat#: 463870

Name: Perphenazine-d4

CAS#: 155593-75-2

Chemical Formula: C21H22D4ClN3OS

Exact Mass: 407.1736

Molecular Weight: 407.99

Elemental Analysis: C, 61.82; H, 7.41; Cl, 8.69; N, 10.30; O, 3.92; S, 7.86

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1,100.00	2 Weeks

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Synonym

Perphenazine-d4; Perphenazine d4;

IUPAC/Chemical Name

2-(4-(3-(2-chloro-10H-phenothiazin-10-yl-1,3,7,9-d4)propyl)piperazin-1-yl)ethan-1-ol

InChi Key

RGCVKNLCSQQDEP-WNJORUDBSA-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/i2D,4D,6D,16D

SMILES Code

OCCN1CCN(CCCN2C3=C(C(Cl)=C(C=C3SC4=CC([2H])=CC([2H])=C42)[2H])[2H])CC1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Perphenazine-d4 is intended for use as an internal standard for the quantification of perphenazine by GC- or LC-MS.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 407.99 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. 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:

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: Madonna MC, Duer JE, Lee JV, Williams J, Avsaroglu B, Zhu C, Deutsch R, Wang R, Crouch BT, Hirschey MD, Goga A, Ramanujam N. In Vivo Optical Metabolic Imaging of Long-Chain Fatty Acid Uptake in Orthotopic Models of Triple-Negative Breast Cancer. Cancers (Basel). 2021 Jan 5;13(1):148. doi: 10.3390/cancers13010148. PMID: 33466329; PMCID: PMC7794847. 2: Williams BA, Holder-Murray JM, Esper SA, Subramaniam K, Skledar SJ, Kentor ML, Orebaugh SL, Mangione MP, Ibinson JW, Waters JH, Williams JP, Chelly JE. Oral Perphenazine 8 mg: A Low-Cost, Efficacious Antiemetic Option. Anesth Analg. 2021 Feb 1;132(2):e29-e31. doi: 10.1213/ANE.0000000000005279. PMID: 33449568; PMCID: PMC7785708. 3: 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. 4: Schlauersbach J, Hanio S, Lenz B, Vemulapalli SPB, Griesinger C, Pöppler AC, Harlacher C, Galli B, Meinel L. Leveraging bile solubilization of poorly water- soluble drugs by rational polymer selection. J Control Release. 2020 Dec 15;330:36-48. doi: 10.1016/j.jconrel.2020.12.016. Epub ahead of print. PMID: 33333120. 5: Mohammadi P, Mahjub R, Mohammadi M, Derakhshandeh K, Ghaleiha A, Mahboobian MM. Pharmacokinetics and brain distribution studies of perphenazine-loaded solid lipid nanoparticles. Drug Dev Ind Pharm. 2020 Dec 18:1-7. doi: 10.1080/03639045.2020.1862172. Epub ahead of print. PMID: 33307865. 6: Li X, Guo X, Fan X, Feng T, Wang C, Yao Z, Xu X, Chen Z, Wang H, Xie S, He J, Zhuo K, Xiang Q, Cen H, Wang J, Smith RC, Jin H, Keshavan MS, Marder SR, Davis JM, Jiang K, Xu Y, Liu D. Sequential Multiple-Assignment Randomized Trials to Compare Antipsychotic Treatments (SMART-CAT) in first-episode schizophrenia patients: Rationale and trial design. Schizophr Res. 2020 Dec 2:S0920-9964(20)30529-6. doi: 10.1016/j.schres.2020.11.010. Epub ahead of print. PMID: 33279374. 7: Xia Y, Xu F, Xiong M, Yang H, Lin W, Xie Y, Xi H, Xue Q, Ye T, Yu L. Repurposing of antipsychotic trifluoperazine for treating brain metastasis, lung metastasis and bone metastasis of melanoma by disrupting autophagy flux. Pharmacol Res. 2021 Jan;163:105295. doi: 10.1016/j.phrs.2020.105295. Epub 2020 Nov 8. PMID: 33176207. 8: Waade RB, Solhaug V, Høiseth G. Impact of CYP2D6 on serum concentrations of flupentixol, haloperidol, perphenazine and zuclopenthixol. Br J Clin Pharmacol. 2020 Oct 28. doi: 10.1111/bcp.14626. Epub ahead of print. PMID: 33118660. 9: Kast RE. Adding perphenazine to increase effectiveness of standard glioblastoma chemoirradiation. J BUON. 2020 Jul-Aug;25(4):1676-1686. PMID: 33099901. 10: Kishi T, Sakuma K, Okuya M, Iwata N. Association between discontinuation due to withdrawal of consent and use of long-acting injectable antipsychotics: A meta-analysis of randomized trials for schizophrenia. J Psychiatr Res. 2021 Jan;132:144-150. doi: 10.1016/j.jpsychires.2020.10.009. Epub 2020 Oct 16. PMID: 33096355. 11: Dai M, Wu Y, Tang Y, Yue W, Yan H, Zhang Y, Tan L, Deng W, Chen Q, Yang G, Lu T, Wang L, Yang F, Zhang F, Yang J, Li K, Lv L, Tan Q, Zhang H, Ma X, Li L, Wang C, Ma X, Zhang D, Yu H, Zhao L, Ren H, Wang Y, Hu X, Zhang G, Du X, Wang Q, Li T; Chinese Antipsychotics Pharmacogenomics Consortium. Longitudinal trajectory analysis of antipsychotic response in patients with schizophrenia: 6-week, randomised, open-label, multicentre clinical trial. BJPsych Open. 2020 Oct 22;6(6):e126. doi: 10.1192/bjo.2020.105. PMID: 33090091; PMCID: PMC7745240. 12: Chokhawala K, Stevens L. Antipsychotic Medications. 2020 Oct 23. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 30137788. 13: Weibel S, Rücker G, Eberhart LH, Pace NL, Hartl HM, Jordan OL, Mayer D, Riemer M, Schaefer MS, Raj D, Backhaus I, Helf A, Schlesinger T, Kienbaum P, Kranke P. Drugs for preventing postoperative nausea and vomiting in adults after general anaesthesia: a network meta-analysis. Cochrane Database Syst Rev. 2020 Oct 19;10:CD012859. doi: 10.1002/14651858.CD012859.pub2. PMID: 33075160. 14: Otręba M, Kośmider L, Rzepecka-Stojko A. Antiviral activity of chlorpromazine, fluphenazine, perphenazine, prochlorperazine, and thioridazine towards RNA-viruses. A review. Eur J Pharmacol. 2020 Nov 15;887:173553. doi: 10.1016/j.ejphar.2020.173553. Epub 2020 Sep 16. PMID: 32949606; PMCID: PMC7493736. 15: Park S, Lim JG, Chang HJ, Oh E. What Shall We Do for the Patients with Shaky Leg Syndrome? A Review of 23 Patients. Neurodegener Dis. 2020;20(1):46-54. doi: 10.1159/000509411. Epub 2020 Sep 10. PMID: 32911473. 16: Rohilla S, Bansal R, Chauhan P, Kachler S, Klotz KN. A New Series Of 1,3-Dimethylxanthine Based Adenosine A2a Receptor Antagonists As A Non- Dopaminergic Treatment Of Parkinson's Disease. Curr Drug Discov Technol. 2020 Aug 27. doi: 10.2174/1570163817666200827112252. Epub ahead of print. PMID: 32860362. 17: Otręba M, Kośmider L. In vitro anticancer activity of fluphenazine, perphenazine and prochlorperazine. A review. J Appl Toxicol. 2021 Jan;41(1):82-94. doi: 10.1002/jat.4046. Epub 2020 Aug 27. PMID: 32852120. 18: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Perphenazine. 2020 Jul 1. PMID: 31643687. 19: Chen Y, Cui Y, Sun X, Wu H, Ou M, Tang Y, Ni S, Li X, Zhu J, Mao F, Wang Y, Li J. Repurposing of antipsychotics perphenazine for the treatment of endometrial cancer. Bioorg Med Chem Lett. 2020 Jul 15;30(14):127239. doi: 10.1016/j.bmcl.2020.127239. Epub 2020 May 4. PMID: 32527541. 20: 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.