CEP-9722

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

MedKoo CAT#: 204910

CAS#: 916574-83-9

Description: CEP-9722 is a small-molecule prodrug of CEP-8983, a novel 4-methoxy-carbazole inhibitor of the nuclear enzymes poly(ADP-ribose) polymerase (PARP) 1 and 2, with potential antineoplastic activity. Upon administration and conversion from CEP-9722, CEP-8983 selectively binds to PARP 1 and 2, preventing repair of damaged DNA via base excision repair (BER). This agent enhances the accumulation of DNA strand breaks and promotes genomic instability and apoptosis. CEP-8983 may potentiate the cytotoxicity of DNA-damaging agents and reverse tumor cell chemo- and radioresistance.


Price and Availability

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Price

1g
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Size
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2g
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Size
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5g
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CEP-9722 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 204910
Name: CEP-9722
CAS#: 916574-83-9
Chemical Formula: C24H26N4O3
Exact Mass: 418.20049
Molecular Weight: 418.497
Elemental Analysis: C, 68.88; H, 6.26; N, 13.39; O, 11.47


Synonym: CEP-9722; CEP 9722; CEP9722

IUPAC/Chemical Name: 11-methoxy-2-((4-methylpiperazin-1-yl)methyl)-4,5,6,7-tetrahydro-1H-cyclopenta[a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione

InChi Key: CTLOSZHDGZLOQE-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H26N4O3/c1-26-9-11-27(12-10-26)13-28-23(29)18-14-5-3-6-15(14)22-20(21(18)24(28)30)19-16(25-22)7-4-8-17(19)31-2/h4,7-8,25H,3,5-6,9-13H2,1-2H3

SMILES Code: O=C1N(CN2CCN(C)CC2)C(C3=C1C4=C(C5=C3CCC5)NC6=C4C(OC)=CC=C6)=O


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:
2934990300


Additional Information

It was demonstrated that CEP-8983 sensitized carcinoma cells to the growth-inhibitory effects of temozolomide and/or SN38 increased the fraction of and/or lengthened duration of time tumor cells accumulated in chemotherapy-induced G(2)-M arrest and sensitized tumor cells to chemotherapy-induced DNA damage and apoptosis. A granulocyte-macrophage colony-forming unit colony formation assay showed that coincubation of CEP-8983 with temozolomide or topotecan did not potentiate chemotherapy-associated myelotoxicity. CEP-9722 (136 mg/kg) administered with temozolomide (68 mg/kg for 5 days) or irinotecan (10 mg/kg for 5 days) inhibited significantly the growth of RG2 tumors (60%) or HT29 tumors (80%) compared with temozolomide or irinotecan monotherapy, respectively. In addition, CEP-9722 showed "stand alone" antitumor efficacy in these preclinical xenografts. In vivo biochemical efficacy studies showed that CEP-9722 attenuated PAR accumulation in glioma xenografts in a dose- and time-related manner. These data indicate that CEP-8983 and its prodrug are effective chemosensitizing agents when administered in combination with select chemotherapeutic agents against chemoresistant tumors. (Source: Mol Cancer Ther. 2007 Aug;6(8):2290-302. http://mct.aacrjournals.org/content/6/8/2290.long).
 
11-methoxy-4,5,6,7-tetrahydro-1H-cyclopenta[a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione
(CEP-8983)
 
 


References

1: Penning TD. Small-molecule PARP modulators--current status and future therapeutic potential. Curr Opin Drug Discov Devel. 2010 Sep;13(5):577-86. Review. PubMed PMID: 20812149.