Ursodeoxycholic acid

Ursodeoxycholic acid
Clinical data
Trade names	Actigall, Urso, others
Other names	Ursodiol
AHFS/Drugs.com	Monograph
MedlinePlus	a699047
License data	US DailyMed: Ursodiol;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
ATC code	A05AA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name 3α,7β-dihydroxy-5β-cholan-24-oic acid; OR; (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-; 10,13-dimethylhexadecahydro-; 1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid;
CAS Number	128-13-2 ;
PubChem CID	31401;
IUPHAR/BPS	7104;
DrugBank	DB01586 ;
ChemSpider	29131 ;
UNII	724L30Y2QR;
KEGG	D00734 ;
ChEBI	CHEBI:9907 ;
ChEMBL	ChEMBL1551 ;
PDB ligand	IU5 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6023731 ;
ECHA InfoCard	100.004.437
Chemical and physical data
Formula	C24H40O4
Molar mass	392.580 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	203 °C (397 °F)
	SMILES O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2[C@@H](O)C[C@@H]3C[C@H](O)CC[C@@]34C)C;
	InChI InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1 ; Key:RUDATBOHQWOJDD-UZVSRGJWSA-N ;
	(verify)

Ursodeoxycholic acid (UDCA), also known as ursodiol, is a secondary bile acid, produced in humans and most other species from metabolism by intestinal bacteria. It is synthesized in the liver in some species, and was first identified in bile of bears of genus Ursus, from which its name derived.^[8] In purified form, it has been used to treat or prevent several diseases of the liver or bile ducts.

It is available as a generic medication.^[9]^[10]

^ "Ursodiol, Heptiza 300/150 Use During Pregnancy". Drugs.com. 4 November 2019. Retrieved 20 February 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Product information". Health Canada. 3 August 2000. Retrieved 3 March 2024.
^ "Details for: Ursodiol C". Health Canada. 25 October 2021. Retrieved 3 March 2024.
^ "Ursodeoxycholic acid 300mg Tablets - Summary of Product Characteristics (SmPC)". (emc). 10 July 2019. Retrieved 29 April 2020.
^ "Actigall- ursodiol capsule". DailyMed. Retrieved 25 September 2021.
^ "Urso 250- ursodiol tablet, film coated Urso Forte- ursodiol tablet, film coated". DailyMed. Retrieved 25 September 2021.
^ Hagey LR, Crombie DL, Espinosa E, Carey MC, Igimi H, Hofmann AF (November 1993). "Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores". Journal of Lipid Research. 34 (11): 1911–1917. doi:10.1016/S0022-2275(20)35109-9. PMID 8263415.
^ "2020 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 23 February 2021. Retrieved 25 September 2021.
^ "Ursodiol: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 25 September 2021.

[Drugs.com_pregnancy-1] "Ursodiol, Heptiza 300/150 Use During Pregnancy". Drugs.com. 4 November 2019. Retrieved 20 February 2020.

[2] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[3] "Product information". Health Canada. 3 August 2000. Retrieved 3 March 2024.

[4] "Details for: Ursodiol C". Health Canada. 25 October 2021. Retrieved 3 March 2024.

[5] "Ursodeoxycholic acid 300mg Tablets - Summary of Product Characteristics (SmPC)". (emc). 10 July 2019. Retrieved 29 April 2020.

[Actigall_FDA_label-6] "Actigall- ursodiol capsule". DailyMed. Retrieved 25 September 2021.

[7] "Urso 250- ursodiol tablet, film coated Urso Forte- ursodiol tablet, film coated". DailyMed. Retrieved 25 September 2021.

[pmid8263415-8] Hagey LR, Crombie DL, Espinosa E, Carey MC, Igimi H, Hofmann AF (November 1993). "Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores". Journal of Lipid Research. 34 (11): 1911–1917. doi:10.1016/S0022-2275(20)35109-9. PMID 8263415.

[9] "2020 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 23 February 2021. Retrieved 25 September 2021.

[10] "Ursodiol: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 25 September 2021.

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Ursodeoxycholic acid

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