D-3263 free base

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

MedKoo CAT#: 205653

CAS#: 947257-66-1 (free base); 1008763-54-9 (HCl salt)

Description: D-3263 is a TRPM8 agonist ( transient receptor potential melastatin member 8) with potential antineoplastic activity. The active ingredient in enteric-coated TRPM8 agonist D-3263 hydrochloride binds to and activates TRPM8, which may result in an increase in calcium and sodium entry; the disruption of calcium and sodium homeostasis; and the induction of cell death in TRPM8-expressing tumor cells.

Chemical Structure

D-3263 free base
CAS# 947257-66-1 (free base); 1008763-54-9 (HCl salt)

Theoretical Analysis

MedKoo Cat#: 205653
Name: D-3263 free base
CAS#: 947257-66-1 (free base); 1008763-54-9 (HCl salt)
Chemical Formula: C21H31N3O3
Exact Mass: 373.2365
Molecular Weight: 373.497
Elemental Analysis: C, 67.53; H, 8.37; N, 11.25; O, 12.85

Price and Availability

Size Price Availability Quantity
50.0mg USD 1950.0 2 Weeks
100.0mg USD 2650.0 2 Weeks
200.0mg USD 3950.0 2 Weeks
500.0mg USD 5950.0 2 Weeks
1.0g USD 7950.0 2 Weeks
2.0g USD 14650.0 2 Weeks
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Synonym: D3263; D 3263; D-3263; D-3263 HCl;

IUPAC/Chemical Name: 3-(2-aminoethyl)-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carbonyl)-5-methoxy-1,3-dihydro-2H-benzo[d]imidazol-2-one


InChi Code: InChI=1S/C21H31N3O3/c1-13(2)16-7-5-14(3)11-17(16)20(25)24-18-8-6-15(27-4)12-19(18)23(10-9-22)21(24)26/h6,8,12-14,16-17H,5,7,9-11,22H2,1-4H3/t14-,16+,17-/m1/s1

SMILES Code: O=C1N(C([C@H]2[C@H](C(C)C)CC[C@@H](C)C2)=O)C3=CC=C(OC)C=C3N1CCN

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 soluble 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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 373.497 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

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1. 5-Benzyloxytryptamine as an antagonist of TRPM8 By DeFalco, Jeff; Steiger, Daniel; Dourado, Michelle; Emerling, Daniel; Duncton, Matthew A. J. From Bioorganic & Medicinal Chemistry Letters (2010), 20(23), 7076-7079.

2. Small-molecule modulators of Trp-p8 activity By Moreno, Ofir; Natarajan, Sateesh; Duncan, David F. From PCT Int. Appl. (2009), WO 2009067410 A1 20090528.

3. Small-molecule modulators of Trp-p8 activity By Moreno, Ofir; Natarajan, Sateesh; Duncan, David F. From U.S. Pat. Appl. Publ. (2008), US 20080255185 A1 20081016.

4. Preparation of menthylcarbonylbenzimidazolones and related compounds modulators of Trp-p8 (transient receptor potential-p8) activity By Moreno, Ofir; Natarajan, Sateesh; Duncan, David F. From PCT Int. Appl. (2007), WO 2007095340 A2 20070823.

Additional Information

 This agent may decrease dihydrotestosterone (DHT) levels, which may contribute to its inhibitory effects on prostate cancer and BPH. TRPM8 is a transmembrane calcium channel protein that is normally expressed in prostate cells and appears to be overexpressed in benign prostatic hyperplasia (BPH) and in prostate cancer.

TRPM8 (also known as TRPP8)  is an ion channel that is triggered by cold temperatures and small-molecule agonists and belongs to the melastatin subfamily - one of seven subfamilies of TRP proteins. In normal human tissues, TRPM8 is expressed predominantly in the prostate, a gland in the male reproductive system. It is over-expressed in prostate hyperplasia and multiple types of cancer including prostate cancer, breast cancer, colon cancer and lung cancer. In recent years, it has emerged that TRP channels play a diverse and key role in cell biology and in pathology. Dendreon has synthesized small molecule agonists including D3263 that activate the TRPM8 ion channel and induce cell death. ( source: http://www.dendreon.com/research-development/trpm8/).