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MedKoo Cat#: 574118 | Name: Glyco-obeticholic acid
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Description:

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

Glyco-obeticholic acid is an active metabolite of obeticholic acid, which is a farnesoid X receptor (FXR) agonist and semisynthetic derivative of chenodeoxycholic acid. Glyco-obeticholic acid is formed from obeticholic acid by glycine conjugation in the liver but can be reconverted back to obeticholic acid by microorganism-mediated deconjugation in the ileum and colon. It has been used as a precursor in the synthesis of bile acid analogs as agonists of the farnesoid X receptor (FXR) and TGR5.

Chemical Structure

Glyco-obeticholic acid
Glyco-obeticholic acid
CAS#863239-60-5

Theoretical Analysis

MedKoo Cat#: 574118

Name: Glyco-obeticholic acid

CAS#: 863239-60-5

Chemical Formula: C28H47NO5

Exact Mass: 477.3454

Molecular Weight: 477.69

Elemental Analysis: C, 70.40; H, 9.92; N, 2.93; O, 16.75

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Glyco-obeticholic acid, Obeticholic Acid Glycine Conjugate
IUPAC/Chemical Name
((R)-4-((3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycine
InChi Key
MTLPUOZJBFHNSO-FCWTVGIUSA-N
InChi Code
InChI=1S/C28H47NO5/c1-5-18-22-14-17(30)10-12-28(22,4)21-11-13-27(3)19(7-8-20(27)25(21)26(18)34)16(2)6-9-23(31)29-15-24(32)33/h16-22,25-26,30,34H,5-15H2,1-4H3,(H,29,31)(H,32,33)/t16-,17-,18-,19-,20+,21+,22+,25+,26-,27-,28-/m1/s1
SMILES Code
CC[C@@H]1[C@]2([H])C[C@H](O)CC[C@]2(C)[C@]3([H])[C@@]([C@@](CC[C@]4([H])[C@@H](CCC(NCC(O)=O)=O)C)([H])[C@]4(C)CC3)([H])[C@@H]1O
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
>3 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
Product Data
Instruction
View handling instruction
Biological target:
Obeticholic acid is a farnesoid X receptor (FXR) agonist.
In vitro activity:
OCA (glyco-obeticholic acid) treatment enhanced brown adipogenesis, as evidenced by the increase in Oil Red cell staining (Fig. 1B) and by the upregulation of the late adipogenic marker PPARγ2 (Fig. 1C). In addition, OCA treatment upregulated the mRNA expression levels of the BAT-specific genes Ucp1, ELOVL fatty acid elongase 3 and PRDM16 (Fig. 1C). Reference: Exp Ther Med. 2021 Sep;22(3):991. https://pubmed.ncbi.nlm.nih.gov/34345273/
In vivo activity:
The effect of OCA (glyco-obeticholic acid) on kidney TNF-alpha and IL-6 levels was evaluated by ELISA. At the end of reperfusion, OCA administration caused a significant decrease in both TNF-alpha and IL-6 in the kidney cortex of OCA-treated I/R rats compared to I/R rats (Figure 4). Undetectable levels of TNF-alpha were found in the kidney medulla in all groups considered. Reference: Pharmaceuticals (Basel). 2022 Apr 24;15(5):524. https://pubmed.ncbi.nlm.nih.gov/35631351/

Preparing Stock Solutions

The following data is based on the product molecular weight 477.69 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. Zhang H, Dong M, Liu X. Obeticholic acid ameliorates obesity and hepatic steatosis by activating brown fat. Exp Ther Med. 2021 Sep;22(3):991. doi: 10.3892/etm.2021.10423. Epub 2021 Jul 14. PMID: 34345273; PMCID: PMC8311225. 2. New-Aaron M, Ganesan M, Dagur RS, Kharbanda KK, Poluektova LY, Osna NA. Obeticholic acid attenuates human immunodeficiency virus/alcohol metabolism-induced pro-fibrotic activation in liver cells. World J Hepatol. 2020 Nov 27;12(11):965-975. doi: 10.4254/wjh.v12.i11.965. PMID: 33312422; PMCID: PMC7701963. 3. Palladini G, Cagna M, Di Pasqua LG, Adorini L, Croce AC, Perlini S, Ferrigno A, Berardo C, Vairetti M. Obeticholic Acid Reduces Kidney Matrix Metalloproteinase Activation Following Partial Hepatic Ischemia/Reperfusion Injury in Rats. Pharmaceuticals (Basel). 2022 Apr 24;15(5):524. doi: 10.3390/ph15050524. PMID: 35631351; PMCID: PMC9145209. 4. Lin C, Yu B, Chen L, Zhang Z, Ye W, Zhong H, Bai W, Yang Y, Nie B. Obeticholic Acid Induces Hepatoxicity Via FXR in the NAFLD Mice. Front Pharmacol. 2022 May 9;13:880508. doi: 10.3389/fphar.2022.880508. PMID: 35614939; PMCID: PMC9124937.
In vitro protocol:
1. Zhang H, Dong M, Liu X. Obeticholic acid ameliorates obesity and hepatic steatosis by activating brown fat. Exp Ther Med. 2021 Sep;22(3):991. doi: 10.3892/etm.2021.10423. Epub 2021 Jul 14. PMID: 34345273; PMCID: PMC8311225. 2. New-Aaron M, Ganesan M, Dagur RS, Kharbanda KK, Poluektova LY, Osna NA. Obeticholic acid attenuates human immunodeficiency virus/alcohol metabolism-induced pro-fibrotic activation in liver cells. World J Hepatol. 2020 Nov 27;12(11):965-975. doi: 10.4254/wjh.v12.i11.965. PMID: 33312422; PMCID: PMC7701963.
In vivo protocol:
1. Palladini G, Cagna M, Di Pasqua LG, Adorini L, Croce AC, Perlini S, Ferrigno A, Berardo C, Vairetti M. Obeticholic Acid Reduces Kidney Matrix Metalloproteinase Activation Following Partial Hepatic Ischemia/Reperfusion Injury in Rats. Pharmaceuticals (Basel). 2022 Apr 24;15(5):524. doi: 10.3390/ph15050524. PMID: 35631351; PMCID: PMC9145209. 2. Lin C, Yu B, Chen L, Zhang Z, Ye W, Zhong H, Bai W, Yang Y, Nie B. Obeticholic Acid Induces Hepatoxicity Via FXR in the NAFLD Mice. Front Pharmacol. 2022 May 9;13:880508. doi: 10.3389/fphar.2022.880508. PMID: 35614939; PMCID: PMC9124937.
1. Markham, A., and Keam, S.J. Obeticholic Acid: First global approval. Drugs 76(12), 1221-1226 (2016). 2. Or, Y.S., Wang, G., Shen, R., et al. Bile acid analogs and FXR/TGR5 agonists and methods of use thereof. (2016).

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