WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 203091
CAS#: 128-13-2 (free acid)
Description: Ursodiol, also known as Ursodeoxycholic acid, is a synthetically-derived form of ursodiol, a bile acid produced by the liver and secreted and stored in the gallbladder. Also produced by the Chinese black bear liver, ursodiol has been used in the treatment of liver disease for centuries. This agent dissolves or prevents cholesterol gallstones by blocking hepatic cholesterol production and decreasing bile cholesterol. Ursodiol also reduces the absorption of cholesterol from the intestinal tract.
MedKoo Cat#: 203091
Name: Ursodiol
CAS#: 128-13-2 (free acid)
Chemical Formula: C24H40O4
Exact Mass: 392.29266
Molecular Weight: 392.57
Elemental Analysis: C, 73.43; H, 10.27; O, 16.30
Related CAS #: 128-13-2 (free acid) 2898-95-5 (sodium)
Synonym: Ursodiol, Ursodeoxycholic acid, Actigall, URSO, Deursil, Ursosan, Ursofalk, Urso Forte
IUPAC/Chemical Name: (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
InChi Key: RUDATBOHQWOJDD-UZVSRGJWSA-N
InChi Code: 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
SMILES Code: C[C@@H]([C@H]1CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)CCC(O)=O
Appearance: White 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, not in water
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
The following data is based on the product molecular weight 392.57 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 |
1: Hansen JD, Kumar S, Lo WK, Poulsen DM, Halai UA, Tater KC. Ursodiol and colorectal cancer or dysplasia risk in primary sclerosing cholangitis and inflammatory bowel disease: a meta-analysis. Dig Dis Sci. 2013 Nov;58(11):3079-87. doi: 10.1007/s10620-013-2772-0. Epub 2013 Jul 30. Review. PubMed PMID: 23896754.
2: San Luis VA, Btaiche IF. Ursodiol in patients with parenteral nutrition-associated cholestasis. Ann Pharmacother. 2007 Nov;41(11):1867-72. Epub 2007 Oct 2. Review. PubMed PMID: 17911205.
3: Brentnall TA. Ursodiol: good drug makes good. Gastroenterology. 2003 Apr;124(4):1139-40. Review. PubMed PMID: 12671906.
4: Comcowich SA, Spitzer TR, Tsunoda SM. Ursodiol to prevent hepatic venoocclusive disease. Ann Pharmacother. 1997 Oct;31(10):1249-52. Review. PubMed PMID: 9337452.
5: O'Brien CB, Shields DS, Saul SH, Reddy KR. Drug-induced vanishing bile duct syndrome: response to ursodiol. Am J Gastroenterol. 1996 Jul;91(7):1456-7. Review. PubMed PMID: 8678017.
6: Rubin RA, Kowalski TE, Khandelwal M, Malet PF. Ursodiol for hepatobiliary disorders. Ann Intern Med. 1994 Aug 1;121(3):207-18. Review. PubMed PMID: 8017748.
7: Vondracek TG, Seifert CF. Use of ursodiol in a patient with biliary cirrhosis. Clin Pharm. 1992 Aug;11(8):672-3. Review. PubMed PMID: 1511539.
8: Rosenbaum CL, Cluxton RJ Jr. Ursodiol: a cholesterol gallstone solubilizing agent. Drug Intell Clin Pharm. 1988 Dec;22(12):941-5. Review. PubMed PMID: 3072172.
Ursodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria.
Ursodeoxycholic acid goes by the trade names Actigall, Ursosan, Ursofalk, Urso, and Urso Forte. In Italy and Switzerland, it is marketed under the name Deursil. Ursodeoxycholic acid can be chemically synthesized and was brought to market by the Montreal-based Axcan Pharma in 1998, which continues to market the drug. The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery. The drug is very expensive, however, and if the patient stops taking it, the gallstones tend to recur if the condition that gave rise to their formation does not change. For these reasons, it has not supplanted surgical treatment by cholecystectomy. It is the only FDA approved drug to treat primary biliary cirrhosis. See: http://en.wikipedia.org/wiki/Ursodiol .
