Synonym
VCP-746; VCP 746; VCP746;
IUPAC/Chemical Name
5-amino-4-benzoyl-N-(6-((9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-9H-purin-6-yl)amino)hexyl)-3-(3-(trifluoromethyl)phenyl)thiophene-2-carboxamide
InChi Key
BXNCSGUIWDCTBJ-QQLQPOFESA-N
InChi Code
InChI=1S/C35H36F3N7O6S/c36-35(37,38)21-12-8-11-20(15-21)23-24(26(47)19-9-4-3-5-10-19)30(39)52-29(23)33(50)41-14-7-2-1-6-13-40-31-25-32(43-17-42-31)45(18-44-25)34-28(49)27(48)22(16-46)51-34/h3-5,8-12,15,17-18,22,27-28,34,46,48-49H,1-2,6-7,13-14,16,39H2,(H,41,50)(H,40,42,43)/t22-,27-,28-,34-/m1/s1
SMILES Code
O=C(C1=C(C2=CC=CC(C(F)(F)F)=C2)C(C(C3=CC=CC=C3)=O)=C(N)S1)NCCCCCCNC4=C5N=CN([C@@H]6O[C@H](CO)[C@@H](O)[C@H]6O)C5=NC=N4
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
Shelf Life
>3 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
739.77
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: Vecchio EA, Chuo CH, Baltos JA, Ford L, Scammells PJ, Wang BH, Christopoulos
A, White PJ, May LT. The hybrid molecule, VCP746, is a potent adenosine A2B
receptor agonist that stimulates anti-fibrotic signalling. Biochem Pharmacol.
2016 Oct 1;117:46-56. doi: 10.1016/j.bcp.2016.08.007. Epub 2016 Aug 9. PubMed
PMID: 27520486.
2: Chuo CH, Devine SM, Scammells PJ, Krum H, Christopoulos A, May LT, White PJ,
Wang BH. VCP746, a novel A1 adenosine receptor biased agonist, reduces
hypertrophy in a rat neonatal cardiac myocyte model. Clin Exp Pharmacol Physiol.
2016 Oct;43(10):976-82. doi: 10.1111/1440-1681.12616. PubMed PMID: 27377874.
3: Baltos JA, Gregory KJ, White PJ, Sexton PM, Christopoulos A, May LT.
Quantification of adenosine A(1) receptor biased agonism: Implications for drug
discovery. Biochem Pharmacol. 2016 Jan 1;99:101-12. doi:
10.1016/j.bcp.2015.11.013. Epub 2015 Nov 12. PubMed PMID: 26581123.
4: Valant C, May LT, Aurelio L, Chuo CH, White PJ, Baltos JA, Sexton PM,
Scammells PJ, Christopoulos A. Separation of on-target efficacy from adverse
effects through rational design of a bitopic adenosine receptor agonist. Proc
Natl Acad Sci U S A. 2014 Mar 25;111(12):4614-9. doi: 10.1073/pnas.1320962111.
Epub 2014 Mar 11. PubMed PMID: 24619092; PubMed Central PMCID: PMC3970544.
