User:Mr. Ibrahem/Obeticholic acid

Mr. Ibrahem/Obeticholic acid
Clinical data
Trade names	Ocaliva
Other names	6α-ethyl-chenodeoxycholic acid; INT-747
AHFS/Drugs.com	Monograph
MedlinePlus	a616033
License data	EU EMA: by INN; US DailyMed: Obeticholic_acid;
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
Drug class	Modified bile acid
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name (3α,5β,6α,7α)-6-Ethyl-3,7-dihydroxycholan-24-oic acid; OR; (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;
Chemical and physical data
Formula	C26H44O4
Molar mass	420.634 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	108–110 °C (226–230 °F)
	SMILES CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O;
	InChI InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1; Key:ZXERDUOLZKYMJM-ZWECCWDJSA-N;

Obeticholic acid (OCA), sold under the brand name Ocaliva, is a medication used to treat primary biliary cholangitis.^[3] It is generally used in addition to ursodeoxycholic acid when this is insufficiently effective.^[3] It is taken by mouth.^[3]

Common side effects include itching and tiredness.^[1] Other side effects may include liver problems.^[3] It is a modified form of bile acid and works by attaching to farnesoid X receptors and decreasing bile production by the liver.^[1]

Obeticholic acid was approved for medical use in the United States and Europe in 2016.^[4]^[1] In the United Kingdom it costs the NHS about £2,400 per month as of 2021.^[3] In the United States this amount costs about 8,000 USD.^[5]

References

^ ^a ^b ^c ^d ^e ^f "Ocaliva". Archived from the original on 8 November 2021. Retrieved 6 November 2021.
^ Gioiello, Antimo; Macchiarulo, Antonio; Carotti, Andrea; Filipponi, Paolo; Costantino, Gabriele; Rizzo, Giovanni; Adorini, Luciano; Pellicciari, Roberto (April 2011). "Extending SAR of bile acids as FXR ligands: Discovery of 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine". Bioorganic & Medicinal Chemistry. 19 (8): 2650–2658. doi:10.1016/j.bmc.2011.03.004. PMID 21459580.
^ ^a ^b ^c ^d ^e ^f ^g ^h BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 96. ISBN 978-0857114105.
^ "Obeticholic Acid Monograph for Professionals". Drugs.com. Archived from the original on 16 July 2017. Retrieved 6 November 2021.
^ "Ocaliva Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 23 April 2021. Retrieved 6 November 2021.

[EPAR2021-1] ^ ^a ^b ^c ^d ^e ^f "Ocaliva". Archived from the original on 8 November 2021. Retrieved 6 November 2021.

[2] Gioiello, Antimo; Macchiarulo, Antonio; Carotti, Andrea; Filipponi, Paolo; Costantino, Gabriele; Rizzo, Giovanni; Adorini, Luciano; Pellicciari, Roberto (April 2011). "Extending SAR of bile acids as FXR ligands: Discovery of 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine". Bioorganic & Medicinal Chemistry. 19 (8): 2650–2658. doi:10.1016/j.bmc.2011.03.004. PMID 21459580.

[BNF81-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 96. ISBN 978-0857114105.

[AHFS2021-4] "Obeticholic Acid Monograph for Professionals". Drugs.com. Archived from the original on 16 July 2017. Retrieved 6 November 2021.

[5] "Ocaliva Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 23 April 2021. Retrieved 6 November 2021.

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