BAY-59-3074
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MedKoo CAT#: 524385

CAS#: 406205-74-1

Description: BAY-59-3074 is a novel cannabinoid CB1/CB2 receptor partial agonist with analgesic properties. It displays anti-hyperalgesic and antiallodynic properties in rat models of chronic neuropathic and inflammatory pain.


Chemical Structure

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BAY-59-3074
CAS# 406205-74-1

Theoretical Analysis

MedKoo Cat#: 524385
Name: BAY-59-3074
CAS#: 406205-74-1
Chemical Formula: C21H21FN8O
Exact Mass: 420.18
Molecular Weight: 420.440
Elemental Analysis: C, 59.99; H, 5.03; F, 4.52; N, 26.65; O, 3.81

Price and Availability

Size Price Availability Quantity
50mg USD 450
100mg USD 750
200mg USD 950
500mg USD 1650
1g USD 2850
2g USD 4650
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Synonym: BAY-59-3074; BAY 59-3074; BAY59-3074; BAY-593074; BAY 593074; BAY593074;

IUPAC/Chemical Name: 1-Butanesulfonic acid, 4,4,4-trifluoro-, 3-(2-cyano-3-(trifluoromethyl)phenoxy)phenyl ester

InChi Key: LWUSZIVDPJPVBW-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H13F6NO4S/c19-17(20,21)8-3-9-30(26,27)29-13-5-1-4-12(10-13)28-16-7-2-6-15(14(16)11-25)18(22,23)24/h1-2,4-7,10H,3,8-9H2

SMILES Code: O=S(CCCC(F)(F)F)(OC1=CC=CC(OC2=CC=CC(C(F)(F)F)=C2C#N)=C1)=O

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 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

More Info:

Product Data:
Biological target: Bay 59-3074 is a cannabinoid CB1/CB2 receptor partial agonist with Ki values of 48.3 and 45.5 nM at human CB1 and CB2 receptors, respectively.
In vitro activity: TBD
In vivo activity: BAY 59-3074 (0.3-3 mg/kg, p.o.) induced antihyperalgesic and antiallodynic effects against thermal or mechanical stimuli in rat models of chronic neuropathic (chronic constriction injury, spared nerve injury, tibial nerve injury, and spinal nerve ligation models) and inflammatory pain (carrageenan and complete Freund's adjuvant models). Antiallodynic efficacy of BAY 59-3074 (1 mg/kg, p.o.) in the spared nerve injury model was maintained after 2 weeks of daily administration. However, tolerance developed rapidly (within 5 days) for cannabinoid-related side effects, which occur at doses above 1 mg/kg (e.g., hypothermia). Uptitration from 1 to 32 mg/kg p.o. (doubling of daily dose every 4th day) prevented the occurrence of such side effects, whereas antihyperalgesic and antiallodynic efficacy was maintained/increased. No withdrawal symptoms were seen after abrupt withdrawal following 14 daily applications of 1 to 10 mg/kg p.o. It is concluded that BAY 59-3074 may offer a valuable therapeutic approach to treat diverse chronic pain conditions. Reference: J Pharmacol Exp Ther. 2004 Aug;310(2):620-32. https://jpet.aspetjournals.org/content/310/2/620.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 56.8 135.05
Ethanol 68.2 162.14

Preparing Stock Solutions

The following data is based on the product molecular weight 420.44 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.

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
Formulation protocol: 1. 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. doi: 10.1124/jpet.103.062836. Epub 2004 May 12. PMID: 15140913.
In vitro protocol: TBD
In vivo protocol: 1. 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. doi: 10.1124/jpet.103.062836. Epub 2004 May 12. PMID: 15140913.

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1: Teng H, Thakur GA, Makriyannis A. Conformationally constrained analogs of BAY 59-3074 as novel cannabinoid receptor ligands. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5999-6002. doi: 10.1016/j.bmcl.2011.07.017. Epub 2011 Jul 23. PubMed PMID: 21880487; PubMed Central PMCID: PMC3693451.

2: 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.

3: 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.