SR13668

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

MedKoo CAT#: 205672

CAS#: 637774-61-9

Description: SR13668 is an Akt inhibitor, is also a n orally bioavailable indole-3-carbinol (I3C) analogue inhibitor of the serine/threonine protein kinase Akt (protein kinase B) with potential antineoplastic and antiangiogenic activities. Akt inhibitor SR13668 binds to and inhibits the activity of Akt, which may result in inhibition of the PI3K/Akt signaling pathway and tumor cell proliferation, and the induction of tumor cell apoptosis. Activation of the PI3K/Akt signaling pathway is frequently associated with tumorigenesis and dysregulated PI3K/Akt signaling may contribute to tumor resistance to a variety of antineoplastic agents.


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Optional 3: SR13668 , purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205672
Name: SR13668
CAS#: 637774-61-9
Chemical Formula: C25H22N2O5
Exact Mass: 430.15287
Molecular Weight: 430.45258
Elemental Analysis: C, 69.76; H, 5.15; N, 6.51; O, 18.58


Synonym: SR13668; SR 13668; SR13668; CHEMBL245030; LS190469; 210dicarbethoxy6methoxy57dihydroindolo23b carbazole

IUPAC/Chemical Name: diethyl 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylate

SMILES Code: O=C(C1=CC2=C(NC3=C2C=C4C(NC5=C4C=C(C(OCC)=O)C=C5)=C3OC)C=C1)OCC


Technical Data

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, not in water

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

SR13668 , a bis-indole with potent activity in vitro and in vivo against various cancers and promising cancer chemopreventive activity, was found to have very low oral bioavailability, <1%, in rats during pilot pharmacokinetic studies.
 
 
 


References

1: Reid JM, Walden CA, Qin R, Ziegler KL, Haslam JL, Rajewski RA, Warndahl R, Fitting CL, Boring D, Szabo E, Crowell J, Perloff M, Jong L, Bauer BA, Mandrekar SJ, Ames MM, Limburg PJ; Cancer Prevention Network. Phase 0 clinical chemoprevention trial of the Akt inhibitor SR13668. Cancer Prev Res (Phila). 2011 Mar;4(3):347-53. PubMed PMID: 21372034; PubMed Central PMCID: PMC3061470.

2: Cohen EE, Schilsky RL. The next phase of chemoprevention research. Cancer Prev Res (Phila). 2011 Mar;4(3):293-5. PubMed PMID: 21372026.

3: Green CE, Swezey R, Bakke J, Shinn W, Furimsky A, Bejugam N, Shankar GN, Jong L, Kapetanovic IM. Improved oral bioavailability in rats of SR13668, a novel anti-cancer agent. Cancer Chemother Pharmacol. 2011 May;67(5):995-1006. Epub 2010 Jul 10. PubMed PMID: 20623225; PubMed Central PMCID: PMC3061244.

4: Kapetanovic IM, Muzzio M, Hu SC, Crowell JA, Rajewski RA, Haslam JL, Jong L, McCormick DL. Pharmacokinetics and enhanced bioavailability of candidate cancer preventative agent, SR13668 in dogs and monkeys. Cancer Chemother Pharmacol. 2010 May;65(6):1109-16. Epub 2009 Sep 16. PubMed PMID: 19756605.

5: Jackson JP, Kabirov KK, Kapetanovic IM, Lyubimov A. In vitro assessment of P450 induction potential of novel chemopreventive agents SR13668, 9-cis-UAB30, and pentamethychromanol in primary cultures of human hepatocytes. Chem Biol Interact. 2009 May 15;179(2-3):263-72. Epub 2008 Dec 16. PubMed PMID: 19135037.

6: Chao WR, Yean D, Amin K, Green C, Jong L. Computer-aided rational drug design: a novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling. J Med Chem. 2007 Jul 26;50(15):3412-5. Epub 2007 Jun 29. PubMed PMID: 17602463.

7: Doppalapudi RS, Riccio ES, Rausch LL, Shimon JA, Lee PS, Mortelmans KE, Kapetanovic IM, Crowell JA, Mirsalis JC. Evaluation of chemopreventive agents for genotoxic activity. Mutat Res. 2007 May 18;629(2):148-60. Epub 2007 Feb 25. PubMed PMID: 17387038.

8: He H, Cho HT, Li W, Kawakita T, Jong L, Tseng SC. Signaling-transduction pathways required for ex vivo expansion of human limbal explants on intact amniotic membrane. Invest Ophthalmol Vis Sci. 2006 Jan;47(1):151-7. PubMed PMID: 16384957; PubMed Central PMCID: PMC1579252.