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MedKoo Cat#: 414860 | Name: Perhexiline free base

Description:

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

Perhexiline is a prophylactic antianginal agent. Perhexiline is thought to act by inhibiting mitochondrial carnitine palmitoyltransferase-1. This shifts myocardial metabolism from fatty acid to glucose utilisation which results in increased ATP production for the same O2 consumption and consequently increases myocardial efficiency. Its clinical use has been limited by its narrow therapeutic index and high inter- and intra-individual pharmacokinetic variability.

Chemical Structure

Perhexiline free base
Perhexiline free base
CAS#6621-47-2 (free base)

Theoretical Analysis

MedKoo Cat#: 414860

Name: Perhexiline free base

CAS#: 6621-47-2 (free base)

Chemical Formula: C19H35N

Exact Mass: 277.2770

Molecular Weight: 277.49

Elemental Analysis: C, 82.24; H, 12.71; N, 5.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
6621-47-2 (free base) 6724-53-4 (maleate)
Synonym
Perhexiline free base;
IUPAC/Chemical Name
PerhexiPiperidine, 2-(2,2-dicyclohexylethyl)-line Free Base
InChi Key
CYXKNKQEMFBLER-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2
SMILES Code
C1(CC(C2CCCCC2)C3CCCCC3)NCCCC1
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
It was outlawed in many countries due to its adverse effects on poor metabolisers (PM). The product has been reintroduced for patients who have contraindications, or have not responded to other treatments for angina.

Preparing Stock Solutions

The following data is based on the product molecular weight 277.49 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: Jiang S, Fu W, Wang S, Zhu G, Wang J, Ma Y. Bacterial Outer Membrane Vesicles Loaded with Perhexiline Suppress Tumor Development by Regulating Tumor- Associated Macrophages Repolarization in a Synergistic Way. Int J Mol Sci. 2023 Jul 7;24(13):11222. doi: 10.3390/ijms241311222. PMID: 37446401; PMCID: PMC10342243. 2: Reyes-Castellanos G, Abdel Hadi N, Gallardo-Arriaga S, Masoud R, Garcia J, Lac S, El Kaoutari A, Gicquel T, Planque M, Fendt SM, Linares LK, Gayet O, Guillaumond F, Dusetti N, Iovanna J, Carrier A. Combining the antianginal drug perhexiline with chemotherapy induces complete pancreatic cancer regression in vivo. iScience. 2023 May 19;26(6):106899. doi: 10.1016/j.isci.2023.106899. PMID: 37305702; PMCID: PMC10250830. 3: Dhakal B, Tomita Y, Drew P, Price T, Maddern G, Smith E, Fenix K. Perhexiline: Old Drug, New Tricks? A Summary of Its Anti-Cancer Effects. Molecules. 2023 Apr 21;28(8):3624. doi: 10.3390/molecules28083624. PMID: 37110858; PMCID: PMC10145508. 4: Dhakal B, Li CMY, Ramezanpour M, Houtak G, Li R, Bouras G, Collela A, Chegeni N, Chataway TK, Drew P, Sallustio BC, Vreugde S, Smith E, Maddern G, Licari G, Fenix K. Proteomic characterisation of perhexiline treatment on THP-1 M1 macrophage differentiation. Front Immunol. 2023 Mar 13;14:1054588. doi: 10.3389/fimmu.2023.1054588. PMID: 36993962; PMCID: PMC10040681. 5: Chong CR, Liu S, Imam H, Heresztyn T, Sallustio BC, Chirkov YY, Horowitz JD. Perhexiline Therapy in Patients with Type 2 Diabetes: Incremental Insulin Resistance despite Potentiation of Nitric Oxide Signaling. Biomedicines. 2022 Sep 23;10(10):2381. doi: 10.3390/biomedicines10102381. PMID: 36289640; PMCID: PMC9598312. 6: Ren Z, Chen S, Qin X, Li F, Guo L. Study of the roles of cytochrome P450 (CYPs) in the metabolism and cytotoxicity of perhexiline. Arch Toxicol. 2022 Dec;96(12):3219-3231. doi: 10.1007/s00204-022-03369-0. Epub 2022 Sep 9. PMID: 36083301; PMCID: PMC10395006. 7: Dhakal B, Li CMY, Li R, Yeo K, Wright JA, Gieniec KA, Vrbanac L, Sammour T, Lawrence M, Thomas M, Lewis M, Perry J, Worthley DL, Woods SL, Drew P, Sallustio BC, Smith E, Horowitz JD, Maddern GJ, Licari G, Fenix K. The Antianginal Drug Perhexiline Displays Cytotoxicity against Colorectal Cancer Cells In Vitro: A Potential for Drug Repurposing. Cancers (Basel). 2022 Feb 18;14(4):1043. doi: 10.3390/cancers14041043. PMID: 35205791; PMCID: PMC8869789. 8: Midei MG, Darpo B, Ayers G, Brown R, Couderc JP, Daly W, Ferber G, Sager PT, Camm AJ. Electrophysiological and ECG Effects of Perhexiline, a Mixed Cardiac Ion Channel Inhibitor, Evaluated in Nonclinical Assays and in Healthy Subjects. J Clin Pharmacol. 2021 Dec;61(12):1606-1617. doi: 10.1002/jcph.1934. Epub 2021 Jul 20. PMID: 34214210. 9: Ananthakrishna R, Lee SL, Foote J, Sallustio BC, Binda G, Mangoni AA, Woodman R, Semsarian C, Horowitz JD, Selvanayagam JB. Randomized controlled trial of perhexiline on regression of left ventricular hypertrophy in patients with symptomatic hypertrophic cardiomyopathy (RESOLVE-HCM trial). Am Heart J. 2021 Oct;240:101-113. doi: 10.1016/j.ahj.2021.06.010. Epub 2021 Jun 25. PMID: 34175315. 10: Pfeffer TJ, List M, Müller JH, Scherr M, Bauersachs J, Hilfiker-Kleiner D, Ricke-Hoch M. Perhexiline treatment improves toxic effects of β-adrenergic receptor stimulation in experimental peripartum cardiomyopathy. ESC Heart Fail. 2021 Aug;8(4):3375-3381. doi: 10.1002/ehf2.13412. Epub 2021 May 17. PMID: 34002539; PMCID: PMC8318439. 11: Tan Y, Sia P, Simon S. Optic neuropathy secondary to perhexiline and amiodarone. BMJ Case Rep. 2021 Jan 27;14(1):e237727. doi: 10.1136/bcr-2020-237727. PMID: 33504523; PMCID: PMC7843302. 12: Ren Z, Chen S, Pak S, Guo L. A mechanism of perhexiline's cytotoxicity in hepatic cells involves endoplasmic reticulum stress and p38 signaling pathway. Chem Biol Interact. 2021 Jan 25;334:109353. doi: 10.1016/j.cbi.2020.109353. Epub 2020 Dec 9. PMID: 33309543; PMCID: PMC7982969. 13: Ren Z, Chen S, Seo JE, Guo X, Li D, Ning B, Guo L. Mitochondrial dysfunction and apoptosis underlie the hepatotoxicity of perhexiline. Toxicol In Vitro. 2020 Dec;69:104987. doi: 10.1016/j.tiv.2020.104987. Epub 2020 Aug 28. PMID: 32861758; PMCID: PMC7938330. 14: Guidi A, Prasanth Saraswati A, Relitti N, Gimmelli R, Saccoccia F, Sirignano C, Taglialatela-Scafati O, Campiani G, Ruberti G, Gemma S. (+)-(R)- and (-)-(S)-Perhexiline maleate: Enantioselective synthesis and functional studies on Schistosoma mansoni larval and adult stages. Bioorg Chem. 2020 Sep;102:104067. doi: 10.1016/j.bioorg.2020.104067. Epub 2020 Jun 30. PMID: 32663671. 15: Kant S, Kesarwani P, Guastella AR, Kumar P, Graham SF, Buelow KL, Nakano I, Chinnaiyan P. Perhexiline Demonstrates FYN-mediated Antitumor Activity in Glioblastoma. Mol Cancer Ther. 2020 Jul;19(7):1415-1422. doi: 10.1158/1535-7163.MCT-19-1047. Epub 2020 May 19. PMID: 32430486; PMCID: PMC7335329. 16: Licari G, Milne RW, Somogyi AA, Sallustio BC. Enantioselectivity in the tissue distribution of perhexiline contributes to different effects on hepatic histology and peripheral neural function in rats. Pharmacol Res Perspect. 2018 Jun;6(3):e00406. doi: 10.1002/prp2.406. Epub 2018 May 22. PMID: 29864243; PMCID: PMC5980244. 17: Camilleri P, Zhang D, Midei M, Daly W, Copp J, Flinn C, Luongo C, Shamszad P. The validation of an LC-MS/MS assay for perhexiline and major hydroxy metabolites, and its application to therapeutic monitoring in patient plasma. Bioanalysis. 2017 Jul;9(13):1011-1025. doi: 10.4155/bio-2017-0068. Epub 2017 Jul 10. PMID: 28692346. 18: Tseng CC, Noordali H, Sani M, Madhani M, Grant DM, Frenneaux MP, Zanda M, Greig IR. Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy. J Med Chem. 2017 Apr 13;60(7):2780-2789. doi: 10.1021/acs.jmedchem.6b01592. Epub 2017 Mar 21. PMID: 28277663. 19: Liu PP, Liu J, Jiang WQ, Carew JS, Ogasawara MA, Pelicano H, Croce CM, Estrov Z, Xu RH, Keating MJ, Huang P. Elimination of chronic lymphocytic leukemia cells in stromal microenvironment by targeting CPT with an antiangina drug perhexiline. Oncogene. 2016 Oct 27;35(43):5663-5673. doi: 10.1038/onc.2016.103. Epub 2016 Apr 11. PMID: 27065330; PMCID: PMC5064824. 20: Guidi A, Lalli C, Perlas E, Bolasco G, Nibbio M, Monteagudo E, Bresciani A, Ruberti G. Discovery and Characterization of Novel Anti-schistosomal Properties of the Anti-anginal Drug, Perhexiline and Its Impact on Schistosoma mansoni Male and Female Reproductive Systems. PLoS Negl Trop Dis. 2016 Aug 12;10(8):e0004928. doi: 10.1371/journal.pntd.0004928. PMID: 27518281; PMCID: PMC4982595.

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