WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200823
Description: Devimistat, also known as CPI-613, is a racemic mixture of the enantiomers of a synthetic alpha-lipoic lipoic acid analogue with potential chemopreventive and antineoplastic activities. Although the exact mechanism of action is unknown, alpha-lipoic acid analogue CPI-613 has been shown to inhibit metabolic and regulatory processes required for cell growth in solid tumors. Both enantiomers in the racemic mixture exhibit antineoplastic activity. The mechanism-of-action of CPI-613 appears distinct from the current classes of anti-cancer agents used in the clinic. CPI-613 demonstrates both in vitro and in vivo anti-tumor activity. CPI-613 was known to strongly disrupt tumor mitochondrial metabolism.
MedKoo Cat#: 200823
Chemical Formula: C22H28O2S2
Exact Mass: 388.15307
Molecular Weight: 388.59
Elemental Analysis: C, 68.00; H, 7.26; O, 8.23; S, 16.50
Related CAS #: 95809-78-2
Synonym: CPI613; CPI-613; CPI 613; Devimistat
IUPAC/Chemical Name: 6,8-bis(benzylthio)octanoic acid
InChi Key: ZYRLHJIMTROTBO-UHFFFAOYSA-N
InChi Code: InChI=1S/C22H28O2S2/c23-22(24)14-8-7-13-21(26-18-20-11-5-2-6-12-20)15-16-25-17-19-9-3-1-4-10-19/h1-6,9-12,21H,7-8,13-18H2,(H,23,24)
SMILES Code: O=C(O)CCCCC(SCC1=CC=CC=C1)CCSCC2=CC=CC=C2
Appearance: White 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
The following data is based on the product molecular weight 388.59 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|
1: Pardee TS, Lee K, Luddy J, Maturo C, Rodriguez R, Isom S, Miller LD, Stadelman KM, Levitan D, Hurd D, Ellis LR, Harrelson R, Manuel M, Dralle S, Lyerly S, Powell BL. A Phase I Study of the First-in-Class Antimitochondrial Metabolism Agent, CPI-613, in Patients with Advanced Hematologic Malignancies. Clin Cancer Res. 2014 Oct 15;20(20):5255-64. doi: 10.1158/1078-0432.CCR-14-1019. Epub 2014 Aug 27. PubMed PMID: 25165100; PubMed Central PMCID: PMC4199870.
2: Stuart SD, Schauble A, Gupta S, Kennedy AD, Keppler BR, Bingham PM, Zachar Z. A strategically designed small molecule attacks alpha-ketoglutarate dehydrogenase in tumor cells through a redox process. Cancer Metab. 2014 Mar 10;2(1):4. doi: 10.1186/2049-3002-2-4. PubMed PMID: 24612826; PubMed Central PMCID: PMC4108059.
3: Zachar Z, Marecek J, Maturo C, Gupta S, Stuart SD, Howell K, Schauble A, Lem J, Piramzadian A, Karnik S, Lee K, Rodriguez R, Shorr R, Bingham PM. Non-redox-active lipoate derivates disrupt cancer cell mitochondrial metabolism and are potent anticancer agents in vivo. J Mol Med (Berl). 2011 Nov;89(11):1137-48. doi: 10.1007/s00109-011-0785-8. Epub 2011 Jul 19. PubMed PMID: 21769686.
4: Lee KC, Shorr R, Rodriguez R, Maturo C, Boteju LW, Sheldon A. Formation and anti-tumor activity of uncommon in vitro and in vivo metabolites of CPI-613, a novel anti-tumor compound that selectively alters tumor energy metabolism. Drug Metab Lett. 2011 Aug;5(3):163-82. PubMed PMID: 21722089.
CPI-613 disruption of tumor mitochondrial metabolism is followed by efficient commitment to cell death by multiple, apparently redundant pathways, including apoptosis, in all tested cancer cell lines. Further, CPI-613 shows strong antitumor activity in vivo against human non-small cell lung and pancreatic cancers in xenograft models with low side-effect toxicity.