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MedKoo product information:

 

CPI-613

  

Description of CPI-613: 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. 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

 

Current developer: Cornerstone Pharmaceuticals.

     

MedKoo Cat#: 200823

Name: CPI-613

CAS#: 95809-78-2

Synonym:   CPI-613; Octanoic acid, 6,8-bis[(phenylmethyl)thio]-

IUPAC/Chemical name: 

6,8-bis(benzylthio)octanoic acid

Chemical structure: Theoretical analysis

 

CPI-613

MedKoo Cat#: 200823
Name: CPI-613
CAS#: 95809-78-2

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

 

Availability and price:

CPI-613, >99%,  is in stock. Price reduced on 12/26/2013Same day ship out. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee:  $30.00 (USA); $45.00 (Canada); $70.00 (international)

10mg / $65.00

25mg / $95.00

50mg / $140.00

100mg / $180.00

200mg / $250.00

500mg / $450.00

1.0g / $650.00

2.0g / $950.00

5.0g / $1,950.00

Bulk available at low price.

   

  

Technical data

Product data sheet

View product data sheet

Appearance:

White solid powder

Purity:

>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

View current batch of CoA

QC data:

View NMR, View HPLC, View MS

Safety Data Sheet (MSDS):

View Material Safety Data Sheet (MSDS)

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).

Note: The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

 

Protocols from literature

In vitro protocol:

 in vitro and in vivo metabolites of CPI-613: 2011 Aug;5(3):163-82.

In vivo protocol:

 in vitro and in vivo metabolites of CPI-613: 2011 Aug;5(3):163-82.

disrupt cancer cell mitochondrial metabolism and are potent anticancer agents in vivo: 2011 Nov;89(11):1137-48.

 

Information about this agent

CPI-613, currently developed by Cornerstone Pharmaceuticals,  is the lead candidate from a new chemical class that, through a novel mechanism of action, targets metabolic changes considered to be common to many, if not all, cancer types. CPI-613 is currently being evaluated in several ongoing Phase I/II trials. CPI-613 was granted orphan drug status by the US FDA for pancreatic cancer, which has a poor prognosis, spreads rapidly and often goes undetected in its early stages.

 

Accoring to  Cornerstone Pharmaceuticals's website, in November of 2009, CPI-613 was named one of the “top most interesting oncology projects available for partnering” by Windhover Information, a leading provider of healthcare industry analysis.  CPI-613's key features found in preclinical tests include (1) active across a broad spectrum of cancer types (solid tumor and hematologic); (2) induces cancer cell death in animal models of human cancers with no toxic effect on normal cells at therapeutic levels; (3) demonstrates 100% efficacy against every human cancer type tested in cell culture.

 

  

 

References

1: 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. Epub 2011 Jul 19. PubMed PMID: 21769686.

 

2: 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.

 

3. Shorr, Robert; Rodriguez, Robert; Bingham, Paul; Boteju, Lakmal W.; Zachar, Zuzana. Pharmaceutical composition of lipoic acid derivatives. PCT Int. Appl. (2009), 76pp. CODEN: PIXXD2 WO 2009123597 A1 20091008 CAN 151:433859 AN 2009:1228415

4. Shorr, Robert; Rodriguez, Robert; Bhasin, Rajinder; Bingham, Paul; Boteju, Lakmal W.; Zachar, Zuzana. Modulation of enzymatic structure, activity, and/or expression level. PCT Int. Appl. (2009), 77pp. CODEN: PIXXD2 WO 2009110859 A1 20090911 CAN 151:328876 AN 2009:1108724

5. Shorr, Robert G.L.; Rodriguez, Robert J.; Bhasin, Rajinder. Pharmaceutical formulations containing lipoic acid derivatives such as bis(benzyl) lipoate, and ion pairing agent. U.S. Pat. Appl. Publ. (2008), 16 pp. CODEN: USXXCO US 2008262077 A1 20081023 CAN 149:478723 AN 2008:1278887

6. Schneiders, Joseph; Wenner, Gotthilf; Keller, Rudolf. Dialkyl iso- or terephthalates. Addn. to Ger. 1,085,146 (CA 55, 21058f). CAN 56:2230 AN 1962:2230

7. Holly, Frederick W.; Wagner, Arthur F. Intermediates for producing  -lipoic acid. Division of U.S. 2,853,497 (CA 53, 6088h). CAN 56:2229 AN 1962:2229

8. Reed, Lester J. Lipoic acid intermediates. (1961), US 2975198 19610314 CAN 55:118088 AN 1961:118088

9. Thomas, Walter M.; Groszos, Stephen J.; Day, Nancy E. Alkanolamine aluminates as ester redistribution catalysts. (1961), US 2985685 19610523 CAN 55:111736 AN 1961:111736

10. Reed, Lester J. 6,8-Dihalo octanoic esters. (1961), US 2980716 19610418 CAN 55:111735 AN 1961:111735

11. Schoberl, Alfons; Grafje, Heinz. Cyclic disulfides. II. The preparation and reactivities of cyclic disulfides with varying ring sizes. Justus Liebigs Annalen der Chemie (1958), 614 66-83. CODEN: JLACBF ISSN:0075-4617. CAN 52:113749 AN 1958:113749

12. Kameda, Yukio; Kimura, Yukio; Yamazoe, Hiroshi. Synthesis of dichloroacetyl derivatives of amines and amino acids. Ann. Rept. Fac. Pharm., Kanazawa Univ. (1956), 6 16-18. CAN 51:17087 AN 1957:17087

13. Nakano, Isamu.  -Lipoic acid and its related compounds. IV. Acetylation of ethyl dl-dihydro- -lipoate. Yakugaku Zasshi (1956), 76 1207-9. CODEN: YKKZAJ ISSN:0031-6903. CAN 51:17086 AN 1957:17086

14. Nakano, Isamu; Sano, Mitsuji.  -Lipoic acid and its related compounds. II. Synthesis of S-substituted DL-dihydro- -lipoic acid. Yakugaku Zasshi (1956), 76 943-7. CODEN: YKKZAJ ISSN:0031-6903. CAN 51:12472 AN 1957:12472

15. Nakano, Isamu; Sano, Mitsuji.  -Lipoic acid and its related compounds. I. Synthesis of DL- -lipoic acid. Yakugaku Zasshi (1955), 75 1296-8. CODEN: YKKZAJ ISSN:0031-6903. CAN 50:44528 AN 1956:44528

16. Reed, Lester J.; Niu, Ching-I. Syntheses of DL- -lipoic acid. Journal of the American Chemical Society (1955), 77 416-19. CODEN: JACSAT ISSN:0002-7863. CAN 49:27750 AN 1955:27750

17. Soper, Quentin F.; Buting, Walter E.; Cochran, James E., Jr.; Pohland, Albert. Syntheses of DL- -lipoic acid. Journal of the American Chemical Society (1954), 76 4109-12. CODEN: JACSAT ISSN:0002-7863. CAN 49:27749 AN 1955:27749.


 

 

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