BAR-502
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MedKoo CAT#: 530640

CAS#: 1612191-86-2

Description: BAR502 is a dual FXR and GPBAR1 agonist. BAR-502 promotes browning of white adipose tissue and reverses liver steatosis and fibrosis. BAR502 protects against liver damage caused by HFD by promoting the browning of adipose tissue.


Chemical Structure

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BAR-502
CAS# 1612191-86-2

Theoretical Analysis

MedKoo Cat#: 530640
Name: BAR-502
CAS#: 1612191-86-2
Chemical Formula: C25H44O3
Exact Mass: 392.33
Molecular Weight: 392.624
Elemental Analysis: C, 76.48; H, 11.30; O, 12.22

Price and Availability

Size Price Availability Quantity
100mg USD 850
200mg USD 1450
500mg USD 2250
1g USD 3250
2g USD 5450
5g USD 7650
Bulk inquiry

Synonym: BAR-502; BAR 502; BAR502.

IUPAC/Chemical Name: (3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-17-((R)-4-hydroxybutan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

InChi Key: HYCMOIGNYNCMRH-APIYUPOTSA-N

InChi Code: InChI=1S/C25H44O3/c1-5-17-21-14-16(27)8-11-25(21,4)20-9-12-24(3)18(15(2)10-13-26)6-7-19(24)22(20)23(17)28/h15-23,26-28H,5-14H2,1-4H3/t15-,16-,17-,18-,19+,20+,21+,22+,23-,24-,25-/m1/s1

SMILES Code: O[C@@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@@H](CCO)C)CC[C@@]4([H])[C@]3([H])[C@H](O)[C@H](CC)[C@]2([H])C1

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

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: Non-alcoholic steatohepatitis (NASH) is a highly prevalent chronic liver disease.

Product Data:
Biological target: BAR502 is a dual FXR and GPBAR1 agonist with IC50 values of 2 μM and 0.4 μM, respectively.
In vitro activity: TBD
In vivo activity: Whether BAR502, a non-bile acid, steroidal dual ligand for FXR and GPBAR1, reverses steato-hepatitis in mice fed a high fat diet (HFD) and fructose was investigated. After 9 week, mice on HFD gained ≈30% of b.w (P < 0.01 versus naïve) and were insulin resistant. These overweighting and insulin resistant mice were randomized to receive HFD or HFD in combination with BAR502. After 18 weeks, HFD mice developed NASH like features with severe steato-hepatitis and fibrosis, increased hepatic content of triacylglycerol and cholesterol and expression of SREPB1c, FAS, ApoC2, PPARα and γ, α-SMA, α1 collagen and MCP1 mRNAs. Treatment with BAR502 caused a ≈10% reduction of b.w., increased insulin sensitivity and circulating levels of HDL, while reduced steatosis, inflammatory and fibrosis scores and liver expression of SREPB1c, FAS, PPARγ, CD36 and CYP7A1 mRNA. BAR502 increased the expression of SHP and ABCG5 in the liver and SHP, FGF15 and GLP1 in intestine. BAR502 promoted the browning of epWAT and reduced liver fibrosis induced by CCl4. In summary, BAR502, a dual FXR and GPBAR1 agonist, protects against liver damage caused by HFD by promoting the browning of adipose tissue. Reference: Sci Rep. 2017 Feb 16;7:42801. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5311892/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.0 89.14
Ethanol 51.0 129.89

Preparing Stock Solutions

The following data is based on the product molecular weight 392.62 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. Carino A, Cipriani S, Marchianò S, Biagioli M, Santorelli C, Donini A, Zampella A, Monti MC, Fiorucci S. BAR502, a dual FXR and GPBAR1 agonist, promotes browning of white adipose tissue and reverses liver steatosis and fibrosis. Sci Rep. 2017 Feb 16;7:42801. doi: 10.1038/srep42801. PMID: 28202906; PMCID: PMC5311892. 2. Carino A, Marchianò S, Biagioli M, Fiorucci C, Zampella A, Monti MC, Morretta E, Bordoni M, Di Giorgio C, Roselli R, Ricci P, Distrutti E, Fiorucci S. Transcriptome Analysis of Dual FXR and GPBAR1 Agonism in Rodent Model of NASH Reveals Modulation of Lipid Droplets Formation. Nutrients. 2019 May 21;11(5):1132. doi: 10.3390/nu11051132. PMID: 31117231; PMCID: PMC6567134.
In vitro protocol: TBD
In vivo protocol: 1. Carino A, Cipriani S, Marchianò S, Biagioli M, Santorelli C, Donini A, Zampella A, Monti MC, Fiorucci S. BAR502, a dual FXR and GPBAR1 agonist, promotes browning of white adipose tissue and reverses liver steatosis and fibrosis. Sci Rep. 2017 Feb 16;7:42801. doi: 10.1038/srep42801. PMID: 28202906; PMCID: PMC5311892. 2. Carino A, Marchianò S, Biagioli M, Fiorucci C, Zampella A, Monti MC, Morretta E, Bordoni M, Di Giorgio C, Roselli R, Ricci P, Distrutti E, Fiorucci S. Transcriptome Analysis of Dual FXR and GPBAR1 Agonism in Rodent Model of NASH Reveals Modulation of Lipid Droplets Formation. Nutrients. 2019 May 21;11(5):1132. doi: 10.3390/nu11051132. PMID: 31117231; PMCID: PMC6567134.

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1: Carino A, Cipriani S, Marchianò S, Biagioli M, Santorelli C, Donini A,
Zampella A, Monti MC, Fiorucci S. BAR502, a dual FXR and GPBAR1 agonist, promotes
browning of white adipose tissue and reverses liver steatosis and fibrosis. Sci
Rep. 2017 Feb 16;7:42801. doi: 10.1038/srep42801. PubMed PMID: 28202906; PubMed
Central PMCID: PMC5311892.


2: Cipriani S, Renga B, D'Amore C, Simonetti M, De Tursi AA, Carino A, Monti MC,
Sepe V, Zampella A, Fiorucci S. Impaired Itching Perception in Murine Models of
Cholestasis Is Supported by Dysregulation of GPBAR1 Signaling. PLoS One. 2015 Jul
15;10(7):e0129866. doi: 10.1371/journal.pone.0129866. eCollection 2015. PubMed
PMID: 26177448; PubMed Central PMCID: PMC4503431.