Synonym
D3263; D 3263; D-3263;
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 Key
ZGTYTFYRCIRWBL-HYVNUMGLSA-N
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
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
More Info
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/).
Preparing Stock Solutions
The following data is based on the
product
molecular weight
373.50
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.
| 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. 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.
