BAR-501 | CAS#1632118-69-4 | UDCA-like GPBAR1 agonist

MedKoo Cat#: 530595 | Name: BAR-501

Description:

WARNING: This product is for research use only, not for human or veterinary use.

BAR-501 is a selective GPBAR1 agonist devoid of any FXR agonistic activity. BAR501 effectively reduced hepatic perfusion pressure and counteracted the vasoconstriction activity of norepinephrine. BAR501 rescues from endothelial dysfunction in rodent models of portal hypertension by exerting genomic and non-genomic effects on CSE, eNOS and ET-1 in liver sinusoidal cells.

Chemical Structure

BAR-501

CAS#1632118-69-4

Theoretical Analysis

MedKoo Cat#: 530595

Name: BAR-501

CAS#: 1632118-69-4

Chemical Formula: C26H46O3

Exact Mass: 406.3447

Molecular Weight: 406.65

Elemental Analysis: C, 76.79; H, 11.40; O, 11.80

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 650.00	2 Weeks
200mg	USD 1,050.00	2 Weeks
500mg	USD 1,950.00	2 Weeks
1g	USD 3,250.00	2 Weeks
2g	USD 4,650.00	2 Weeks
5g	USD 7,950.00	2 Weeks

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Related CAS #

No Data

Synonym

BAR-501; BAR 501; BAR501.

IUPAC/Chemical Name

(3R,5S,6S,7S,8S,9S,10S,13R,14S,17R)-6-ethyl-17-((R)-5-hydroxypentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

InChi Key

DQBAHTQWQZRMFH-CRPAWOMZSA-N

InChi Code

InChI=1S/C26H46O3/c1-5-18-22-15-17(28)10-12-26(22,4)21-11-13-25(3)19(16(2)7-6-14-27)8-9-20(25)23(21)24(18)29/h16-24,27-29H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21+,22+,23+,24+,25-,26-/m1/s1

SMILES Code

C[C@H](CCCO)[C@H]1CC[C@@]2([H])[C@]3([H])[C@@H](O)[C@@H](CC)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Appearance

Solid powder

Purity

>95% (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

>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

GPBAR1 is a bile acids activated receptor expressed in entero-hepatic tissues. In the liver expression of GPBAR1 is restricted to sinusoidal and Kuppfer cells. In the systemic circulation vasodilation caused by GPBAR1 agonists is abrogated by inhibition of cystathione-γ-liase (CSE), an enzyme essential to the generation of hydrogen sulfide (H2S), a vasodilatory agent.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

BAR501 is an agonist of GPBAR1 with an EC50 of 1 μM.

In vitro activity:

TBD

In vivo activity:

In naïve rats, BAR501 effectively reduced hepatic perfusion pressure and counteracted the vasoconstriction activity of norepinephrine. In the CCl4 model, 9 weeks treatment with BAR501 effectively protected against development of endothelial dysfunction by increasing liver CSE (cystathione-γ-liase) expression and activity and by reducing endothelin (ET)-1 gene expression. In mice feed methionine, treatment with BAR501 attenuated endothelial dysfunction and caused a GPBAR1-dependent regulation of CSE. Reference: PLoS One. 2015 Nov 5;10(11):e0141082. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4634759/

	Solvent	mg/mL	mM
Solubility
	DMSO	65.5	161.07
	DMF	20.0	49.18
	Ethanol	34.3	84.42

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 406.65 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

Formulation protocol:

1. Biagioli M, Carino A, Fiorucci C, Marchianò S, Di Giorgio C, Roselli R, Magro M, Distrutti E, Bereshchenko O, Scarpelli P, Zampella A, Fiorucci S. GPBAR1 Functions as Gatekeeper for Liver NKT Cells and provides Counterregulatory Signals in Mouse Models of Immune-Mediated Hepatitis. Cell Mol Gastroenterol Hepatol. 2019;8(3):447-473. doi: 10.1016/j.jcmgh.2019.06.003. Epub 2019 Jun 18. PMID: 31226434; PMCID: PMC6718949. 2. Renga B, Cipriani S, Carino A, Simonetti M, Zampella A, Fiorucci S. Reversal of Endothelial Dysfunction by GPBAR1 Agonism in Portal Hypertension Involves a AKT/FOXOA1 Dependent Regulation of H2S Generation and Endothelin-1. PLoS One. 2015 Nov 5;10(11):e0141082. doi: 10.1371/journal.pone.0141082. PMID: 26539823; PMCID: PMC4634759.

In vitro protocol:

TBD

In vivo protocol:

1: Renga B, Cipriani S, Carino A, Simonetti M, Zampella A, Fiorucci S. Reversal of Endothelial Dysfunction by GPBAR1 Agonism in Portal Hypertension Involves a AKT/FOXOA1 Dependent Regulation of H2S Generation and Endothelin-1. PLoS One. 2015 Nov 5;10(11):e0141082. doi: 10.1371/journal.pone.0141082. eCollection 2015. PubMed PMID: 26539823; PubMed Central PMCID: PMC4634759.