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MedKoo Cat#: 145003 | Name: CEP-751

Description:

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

CEP-751, also known as KT-6587, is an potent Trk inhibitor. CEP-751 had a significant growth-inhibitory effect on the MBL line D283 (on day 39, P = 0.031). CEP-751 showed a modest growth-inhibitory effect on IMR5 (P = 0.062) and CHP-134 (P = 0.049). CEP-751 induced apoptosis in the treated CHP-134 tumors. CEP-751 may be a useful therapeutic agent for NBL or MBL. CEP-751 at 100 nM inhibits the receptor tyrosine kinase activity of the neurotrophin receptors trkA, trkB and trkC. CEP-751 exhibited anti-tumor efficacy against tumors derived from NIH3T3 cells transfected with trkA.

Chemical Structure

CEP-751
CAS#156177-59-2

Theoretical Analysis

MedKoo Cat#: 145003

Name: CEP-751

CAS#: 156177-59-2

Chemical Formula: C27H23N3O4

Exact Mass: 453.1689

Molecular Weight: 453.50

Elemental Analysis: C, 71.51; H, 5.11; N, 9.27; O, 14.11

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 #
No Data
Synonym
CEP-751; CEP 751; CEP751; KT-6587; KT 6587; KT6587;
IUPAC/Chemical Name
(5S,6S,8R)-6-(hydroxymethyl)-6-methoxy-5-methyl-5,6,7,8,14,15-hexahydro-13H-16-oxa-4b,8a,14-triaza-5,8-methanodibenzo[b,h]cycloocta[jkl]cyclopenta[e]-as-indacen-13-one
InChi Key
NMMGUHANGUWNBN-VHEIIQRDSA-N
InChi Code
1S/C27H23N3O4/c1-26-27(13-31,33-2)11-19(34-26)29-17-9-5-3-7-14(17)21-22-16(12-28-25(22)32)20-15-8-4-6-10-18(15)30(26)24(20)23(21)29/h3-10,19,31H,11-13H2,1-2H3,(H,28,32)/t19-,26+,27+/m1/s1
SMILES Code
[H][C@]12C[C@@](CO)(OC)[C@](C)(O1)N3C4=C(C=CC=C4)C5=C3C6=C(C7=C(C=CC=C7)N26)C8=C5CNC8=O
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 453.50 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: Camoratto AM, Jani JP, Angeles TS, Maroney AC, Sanders CY, Murakata C, Neff NT, Vaught JL, Isaacs JT, Dionne CA. CEP-751 inhibits TRK receptor tyrosine kinase activity in vitro exhibits anti-tumor activity. Int J Cancer. 1997 Aug 7;72(4):673-9. doi: 10.1002/(sici)1097-0215(19970807)72:4<673::aid- ijc20>3.0.co;2-b. PMID: 9259409. 2: George DJ, Dionne CA, Jani J, Angeles T, Murakata C, Lamb J, Isaacs JT. Sustained in vivo regression of Dunning H rat prostate cancers treated with combinations of androgen ablation and Trk tyrosine kinase inhibitors, CEP-751 (KT-6587) or CEP-701 (KT-5555). Cancer Res. 1999 May 15;59(10):2395-401. PMID: 10344749. 3: Evans AE, Kisselbach KD, Liu X, Eggert A, Ikegaki N, Camoratto AM, Dionne C, Brodeur GM. Effect of CEP-751 (KT-6587) on neuroblastoma xenografts expressing TrkB. Med Pediatr Oncol. 2001 Jan;36(1):181-4. doi: 10.1002/1096-911X(20010101)36:1<181::AID-MPO1043>3.0.CO;2-Q. PMID: 11464878. 4: Evans AE, Kisselbach KD, Yamashiro DJ, Ikegaki N, Camoratto AM, Dionne CA, Brodeur GM. Antitumor activity of CEP-751 (KT-6587) on human neuroblastoma and medulloblastoma xenografts. Clin Cancer Res. 1999 Nov;5(11):3594-602. PMID: 10589776. 5: Strock CJ, Park JI, Rosen M, Dionne C, Ruggeri B, Jones-Bolin S, Denmeade SR, Ball DW, Nelkin BD. CEP-701 and CEP-751 inhibit constitutively activated RET tyrosine kinase activity and block medullary thyroid carcinoma cell growth. Cancer Res. 2003 Sep 1;63(17):5559-63. PMID: 14500395. 6: Strock CJ, Park JI, Rosen DM, Ruggeri B, Denmeade SR, Ball DW, Nelkin BD. Activity of irinotecan and the tyrosine kinase inhibitor CEP-751 in medullary thyroid cancer. J Clin Endocrinol Metab. 2006 Jan;91(1):79-84. doi: 10.1210/jc.2005-1882. Epub 2005 Nov 1. PMID: 16263812. 7: Undevia SD, Vogelzang NJ, Mauer AM, Janisch L, Mani S, Ratain MJ. Phase I clinical trial of CEP-2563 dihydrochloride, a receptor tyrosine kinase inhibitor, in patients with refractory solid tumors. Invest New Drugs. 2004 Nov;22(4):449-58. doi: 10.1023/B:DRUG.0000036687.26604.8c. PMID: 15292715. 8: Dionne CA, Camoratto AM, Jani JP, Emerson E, Neff N, Vaught JL, Murakata C, Djakiew D, Lamb J, Bova S, George D, Isaacs JT. Cell cycle-independent death of prostate adenocarcinoma is induced by the trk tyrosine kinase inhibitor CEP-751 (KT6587). Clin Cancer Res. 1998 Aug;4(8):1887-98. PMID: 9717816. 9: Hudkins RL, Iqbal M, Park CH, Goldstein J, Herman JL, Shek E, Murakata C, Mallamo JP. Prodrug esters of the indolocarbazole CEP-751 (KT-6587). Bioorg Med Chem Lett. 1998 Jul 21;8(14):1873-6. doi: 10.1016/s0960-894x(98)00328-x. PMID: 9873450. 10: Akinaga S, Sugiyama K, Akiyama T. UCN-01 (7-hydroxystaurosporine) and other indolocarbazole compounds: a new generation of anti-cancer agents for the new century? Anticancer Drug Des. 2000 Feb;15(1):43-52. PMID: 10888035. 11: Pinski J, Weeraratna A, Uzgare AR, Arnold JT, Denmeade SR, Isaacs JT. Trk receptor inhibition induces apoptosis of proliferating but not quiescent human osteoblasts. Cancer Res. 2002 Feb 15;62(4):986-9. PMID: 11861369. 12: Weeraratna AT, Arnold JT, George DJ, DeMarzo A, Isaacs JT. Rational basis for Trk inhibition therapy for prostate cancer. Prostate. 2000 Oct 1;45(2):140-8. doi: 10.1002/1097-0045(20001001)45:2<140::aid-pros8>3.0.co;2-#. PMID: 11027413. 13: Miknyoczki SJ, Dionne CA, Klein-Szanto AJ, Ruggeri BA. The novel Trk receptor tyrosine kinase inhibitor CEP-701 (KT-5555) exhibits antitumor efficacy against human pancreatic carcinoma (Panc1) xenograft growth and in vivo invasiveness. Ann N Y Acad Sci. 1999 Jun 30;880:252-62. doi: 10.1111/j.1749-6632.1999.tb09530.x. PMID: 10415871. 14: Lavelle F. American Association for Cancer Research 1997: progress and new hope in the fight against cancer. Expert Opin Investig Drugs. 1997 Jun;6(6):771-5. doi: 10.1517/13543784.6.6.771. PMID: 15989640.