BAY 38-7271

BAY 38-7271
Legal status
Legal status	CA: Schedule II;
Identifiers
	IUPAC name (−)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluorobutyl-1-sulfonate;
CAS Number	212188-60-8 ;
PubChem CID	9845561;
ChemSpider	8021275 ;
UNII	SRX4T6TMUS;
ChEMBL	ChEMBL1668508 ;
CompTox Dashboard (EPA)	DTXSID701010009 ;
Chemical and physical data
Formula	C20H21F3O5S
Molar mass	430.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)CCCS(=O)(=O)Oc3cccc(Oc1cccc2c1C[C@@H](C2)CO)c3;
	InChI 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 ; Key:XJURALZPEJKKOV-CQSZACIVSA-N ;
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Originally synthesized by chemist Wayne E. Kenney, BAY 38-7271 (KN 38-7271) is a drug which is a cannabinoid receptor agonist developed by Bayer AG. It has analgesic and neuroprotective effects and is used in scientific research, with proposed uses in the treatment of traumatic brain injury.^[1]^[2] It is a full agonist with around the same potency as CP 55,940 in animal studies, and has fairly high affinity for both CB₁ and CB₂ receptors, with K_i values of 2.91nM at CB₁ and 4.24nM at CB₂.^[3]^[4] It has been licensed to KeyNeurotek Pharmaceuticals for clinical development,^[5] and was in Phase II trials in 2008^[6] but its development appears to have stopped.

References

^ Mauler F, Horváth E, De Vry J, Jäger R, Schwarz T, Sandmann S, et al. (2003). "BAY 38-7271: a novel highly selective and highly potent cannabinoid receptor agonist for the treatment of traumatic brain injury". CNS Drug Reviews. 9 (4): 343–58. doi:10.1111/j.1527-3458.2003.tb00259.x. PMC 6741701. PMID 14647528.
^ Mauler F, Hinz V, Augstein KH, Fassbender M, Horváth E (October 2003). "Neuroprotective and brain edema-reducing efficacy of the novel cannabinoid receptor agonist BAY 38-7271". Brain Research. 989 (1): 99–111. doi:10.1016/s0006-8993(03)03376-6. PMID 14519516. S2CID 20422282.
^ Mauler F, Mittendorf J, Horváth E, De Vry J (July 2002). "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". The Journal of Pharmacology and Experimental Therapeutics. 302 (1): 359–68. doi:10.1124/jpet.302.1.359. PMID 12065738.
^ De Vry J, Rüdiger Jentzsch K (December 2002). "Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist". European Journal of Pharmacology. 457 (2–3): 147–52. doi:10.1016/s0014-2999(02)02697-3. PMID 12464360.
^ Pipeline
^ KeyNeurotek Pharmaceuticals AG Reports Positive Phase I Data of Its Cannabinoid Receptor-Agonist

[1] Mauler F, Horváth E, De Vry J, Jäger R, Schwarz T, Sandmann S, et al. (2003). "BAY 38-7271: a novel highly selective and highly potent cannabinoid receptor agonist for the treatment of traumatic brain injury". CNS Drug Reviews. 9 (4): 343–58. doi:10.1111/j.1527-3458.2003.tb00259.x. PMC 6741701. PMID 14647528.

[2] Mauler F, Hinz V, Augstein KH, Fassbender M, Horváth E (October 2003). "Neuroprotective and brain edema-reducing efficacy of the novel cannabinoid receptor agonist BAY 38-7271". Brain Research. 989 (1): 99–111. doi:10.1016/s0006-8993(03)03376-6. PMID 14519516. S2CID 20422282.

[3] Mauler F, Mittendorf J, Horváth E, De Vry J (July 2002). "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". The Journal of Pharmacology and Experimental Therapeutics. 302 (1): 359–68. doi:10.1124/jpet.302.1.359. PMID 12065738.

[4] De Vry J, Rüdiger Jentzsch K (December 2002). "Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist". European Journal of Pharmacology. 457 (2–3): 147–52. doi:10.1016/s0014-2999(02)02697-3. PMID 12464360.

[5] Pipeline

[6] KeyNeurotek Pharmaceuticals AG Reports Positive Phase I Data of Its Cannabinoid Receptor-Agonist

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Legal status

Legal status	CA: Schedule II
Identifiers
IUPAC name (−)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluorobutyl-1-sulfonate
CAS Number	212188-60-8^Y
PubChem CID	9845561
ChemSpider	8021275^Y
UNII	SRX4T6TMUS
ChEMBL	ChEMBL1668508^N
CompTox Dashboard (EPA)	DTXSID701010009
Chemical and physical data
Formula	C₂₀H₂₁F₃O₅S
Molar mass	430.44 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)CCCS(=O)(=O)Oc3cccc(Oc1cccc2c1C[C@@H](C2)CO)c3
InChI 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^Y Key:XJURALZPEJKKOV-CQSZACIVSA-N^Y
^NY (what is this?) (verify)