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MedKoo Cat#: 524843 | Name: CP-461 free base

Description:

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

CP-461, also known as OSI-461, is a PDE2A/5A inhibitor potentially for the treatment of renal cell carcinoma, prostate cancer, and Crohn's disease.

Chemical Structure

CP-461 free base
CP-461 free base
CAS#227619-92-3 (free base)

Theoretical Analysis

MedKoo Cat#: 524843

Name: CP-461 free base

CAS#: 227619-92-3 (free base)

Chemical Formula: C25H21FN2O

Exact Mass: 384.1638

Molecular Weight: 384.45

Elemental Analysis: C, 78.10; H, 5.51; F, 4.94; N, 7.29; O, 4.16

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 #
227619-96-7 (HCl)
Synonym
CP-461; OSI-461; UNII-824ZMS3BGL; CP-461; CEL031; CP461; OSI461; CEL 031; CP 461; OSI 461
IUPAC/Chemical Name
1H-Indene-3-acetamide, 5-fluoro-2-methyl-N-(phenylmethyl)-1-(4-pyridinylmethylene)-, (1Z)-
InChi Key
NVCAMOJXQVJSOM-XKZIYDEJSA-N
InChi Code
InChI=1S/C25H21FN2O/c1-17-22(13-18-9-11-27-12-10-18)21-8-7-20(26)14-24(21)23(17)15-25(29)28-16-19-5-3-2-4-6-19/h2-14H,15-16H2,1H3,(H,28,29)/b22-13-
SMILES Code
CC\1=C(c2cc(ccc2/C1=C\c3ccncc3)F)CC(=O)NCc4ccccc4
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 384.45 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: Singh R, Fröbel J, Cadeddu RP, Bruns I, Schroeder T, Brünnert D, Wilk CM, Zerbini LF, Haas R, Czibere A. The novel compound OSI-461 induces apoptosis and growth arrest in human acute myeloid leukemia cells. Ann Hematol. 2012 Feb;91(2):173-81. doi: 10.1007/s00277-011-1282-4. PubMed PMID: 21717102. 2: Resta LP, Pili R, Eisenberger MA, Spitz A, King S, Porter J, Franke A, Boinpally R, Carducci MA, Sweeney CJ. A phase I study of OSI-461 in combination with mitoxantrone in patients with advanced solid tumors potentially responsive to mitoxantrone. Cancer Chemother Pharmacol. 2011 Feb;67(2):431-8. doi: 10.1007/s00280-010-1328-7. PubMed PMID: 20445979; PubMed Central PMCID: PMC3028086. 3: O'Bryant CL, Lieu CH, Leong S, Boinpally R, Basche M, Gore L, Leonardi K, Schultz MK, Hariharan S, Chow L, Diab S, Gibbs A, Eckhardt SG. A dose-ranging study of the pharmacokinetics and pharmacodynamics of the selective apoptotic antineoplastic drug (SAAND), OSI-461, in patients with advanced cancer, in the fasted and fed state. Cancer Chemother Pharmacol. 2009 Feb;63(3):477-89. doi: 10.1007/s00280-008-0761-3. PubMed PMID: 18509645; PubMed Central PMCID: PMC2814254. 4: Xiao D, Deguchi A, Gundersen GG, Oehlen B, Arnold L, Weinstein IB. The sulindac derivatives OSI-461, OSIP486823, and OSIP487703 arrest colon cancer cells in mitosis by causing microtubule depolymerization. Mol Cancer Ther. 2006 Jan;5(1):60-7. PubMed PMID: 16432163. 5: Galmarini CM. OSI-461 (OSI). Curr Opin Investig Drugs. 2004 Jun;5(6):648-56. Review. PubMed PMID: 15242254. 6: Shimizu M, Suzui M, Deguchi A, Lim JT, Xiao D, Hayes JH, Papadopoulos KP, Weinstein IB. Synergistic effects of acyclic retinoid and OSI-461 on growth inhibition and gene expression in human hepatoma cells. Clin Cancer Res. 2004 Oct 1;10(19):6710-21. PubMed PMID: 15475462. 7: Deguchi A, Xing SW, Shureiqi I, Yang P, Newman RA, Lippman SM, Feinmark SJ, Oehlen B, Weinstein IB. Activation of protein kinase G up-regulates expression of 15-lipoxygenase-1 in human colon cancer cells. Cancer Res. 2005 Sep 15;65(18):8442-7. PubMed PMID: 16166323. 8: Lim JT, Piazza GA, Pamukcu R, Thompson WJ, Weinstein IB. Exisulind and related compounds inhibit expression and function of the androgen receptor in human prostate cancer cells. Clin Cancer Res. 2003 Oct 15;9(13):4972-82. PubMed PMID: 14581372. 9: Li H, Liu L, David ML, Whitehead CM, Chen M, Fetter JR, Sperl GJ, Pamukcu R, Thompson WJ. Pro-apoptotic actions of exisulind and CP461 in SW480 colon tumor cells involve beta-catenin and cyclin D1 down-regulation. Biochem Pharmacol. 2002 Nov 1;64(9):1325-36. PubMed PMID: 12392815. 10: Deguchi A, Soh JW, Li H, Pamukcu R, Thompson WJ, Weinstein IB. Vasodilator-stimulated phosphoprotein (VASP) phosphorylation provides a biomarker for the action of exisulind and related agents that activate protein kinase G. Mol Cancer Ther. 2002 Aug;1(10):803-9. PubMed PMID: 12492113. 11: Moon EY, Lerner A. Benzylamide sulindac analogues induce changes in cell shape, loss of microtubules and G(2)-M arrest in a chronic lymphocytic leukemia (CLL) cell line and apoptosis in primary CLL cells. Cancer Res. 2002 Oct 15;62(20):5711-9. PubMed PMID: 12384529. 12: Sun W, Stevenson JP, Gallo JM, Redlinger M, Haller D, Algazy K, Giantonio B, Alila H, O'Dwyer PJ. Phase I and pharmacokinetic trial of the proapoptotic sulindac analog CP-461 in patients with advanced cancer. Clin Cancer Res. 2002 Oct;8(10):3100-4. PubMed PMID: 12374677. 13: Liu L, Li H, Underwood T, Lloyd M, David M, Sperl G, Pamukcu R, Thompson WJ. Cyclic GMP-dependent protein kinase activation and induction by exisulind and CP461 in colon tumor cells. J Pharmacol Exp Ther. 2001 Nov;299(2):583-92. PubMed PMID: 11602670. 14: Yoon JT, Palazzo AF, Xiao D, Delohery TM, Warburton PE, Bruce JN, Thompson WJ, Sperl G, Whitehead C, Fetter J, Pamukcu R, Gundersen GG, Weinstein IB. CP248, a derivative of exisulind, causes growth inhibition, mitotic arrest, and abnormalities in microtubule polymerization in glioma cells. Mol Cancer Ther. 2002 Apr;1(6):393-404. PubMed PMID: 12477052.

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