Synonym
BAY-38-7271; BAY387271; BAY 38-7271; (-)-Bay-38-7271; KN 387271; KN-387271; KN387271;
IUPAC/Chemical Name
1-Butanesulfonic acid, 4,4,4-trifluoro-, 3-(((2R)-2,3-dihydro-2-(hydroxymethyl)-1H-inden-4-yl)oxy)phenyl ester
InChi Key
XJURALZPEJKKOV-CQSZACIVSA-N
InChi Code
InChI=1S/C20H21F3O5S/c21-20(22,23)8-3-9-29(25,26)28-17-6-2-5-16(12-17)27-19-7-1-4-15-10-14(13-24)11-18(15)19/h1-2,4-7,12,14,24H,3,8-11,13H2/t14-/m1/s1
SMILES Code
c1cc(cc(c1)OS(=O)(=O)CCCC(F)(F)F)Oc2cccc3c2C[C@@H](C3)CO
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
430.44
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: Schmidt W, Schäfer F, Striggow V, Fröhlich K, Striggow F. Cannabinoid receptor subtypes 1 and 2 mediate long-lasting neuroprotection and improve motor behavior deficits after transient focal cerebral ischemia. Neuroscience. 2012 Dec 27;227:313-26. doi: 10.1016/j.neuroscience.2012.09.080. Epub 2012 Oct 13. PubMed PMID: 23069763.
2: Firsching R, Piek J, Skalej M, Rohde V, Schmidt U, Striggow F; KN38-7271 Study Group. Early survival of comatose patients after severe traumatic brain injury with the dual cannabinoid CB1/CB2 receptor agonist KN38-7271: a randomized, double-blind, placebo-controlled phase II trial. J Neurol Surg A Cent Eur Neurosurg. 2012 Aug;73(4):204-16. Epub 2012 Jun 13. PubMed PMID: 22696266.
3: De Vry J, Jentzsch KR. Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat. Eur J Pharmacol. 2004 Nov 28;505(1-3):127-33. PubMed PMID: 15556145.
4: De Vry J, Denzer D, Reissmueller E, Eijckenboom M, Heil M, Meier H, Mauler F. 3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): a novel cannabinoid Cb1/Cb2 receptor partial agonist with antihyperalgesic and antiallodynic effects. J Pharmacol Exp Ther. 2004 Aug;310(2):620-32. Epub 2004 May 12. PubMed PMID: 15140913.
5: Mauler F, Horváth E, De Vry J, Jäger R, Schwarz T, Sandmann S, Weinz C, Heinig R, Böttcher M. BAY 38-7271: a novel highly selective and highly potent cannabinoid receptor agonist for the treatment of traumatic brain injury. CNS Drug Rev. 2003 Winter;9(4):343-58. Review. PubMed PMID: 14647528.
6: Mauler F, Hinz V, Augstein KH, Fassbender M, Horváth E. Neuroprotective and brain edema-reducing efficacy of the novel cannabinoid receptor agonist BAY 38-7271. Brain Res. 2003 Oct 31;989(1):99-111. PubMed PMID: 14519516.
7: De Vry J, Rüdiger Jentzsch K. Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist. Eur J Pharmacol. 2002 Dec 20;457(2-3):147-52. PubMed PMID: 12464360.
8: Mauler F, Mittendorf J, Horváth E, De Vry J. Characterization of the diarylether sulfonylester (-)-(R)-3-(2-hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a potent cannabinoid receptor agonist with neuroprotective properties. J Pharmacol Exp Ther. 2002 Jul;302(1):359-68. PubMed PMID: 12065738.
