Ursodeoxycholic acid

392.57200

392.57

204-879-3

724L30Y2QR

DTXSID6023731

C1818

A05AA02|A - Alimentary tract and metabolism

2918199090

77.76000

4.47790

Solid

1.128 g/cm3

203 °C

547.1ºC at 760mmHg

298.8ºC

1.543

ethanol: 50 mg/mL, clear

Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.

0mmHg at 25°C

208.98 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|198.7 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|200.9 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|198.3 Ų [M-H]- [CCS Type: DT, Method: single field calibrated]|186.8 Ų [M+H-2H2O]+ [CCS Type: DT, Method: single field calibrated]|200.2 Ų [M+HCOO]- [CCS Type: DT, Method: single field calibrated]|205.7 Ų [M+K-H+HCOO]- [CCS Type: DT, Method: single field calibrated]|199.4 Ų [M+Na-H+Cl]- [CCS Type: DT, Method: single field calibrated]|203.2 Ų [M+Na-H+HCOO]- [CCS Type: DT, Method: single field calibrated]

NONH for all modes of transport

2

R36/37/38

S24/25

FZ2000000

Xi

Stable under normal temperatures and pressures.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 98 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.

n multiple clinical trials in a variety of conditions, ursodiol has not been found to cause increases in serum enzyme elevations, worsening of underlying liver disease or clinically apparent liver injury. Nevertheless, there have been rare reports of clinical decompensation in patients with advanced liver disease and cirrhosis started on ursodiol, but the reason for such reactions is not known. In at least one instance, there was recurrence of jaundice on restarting ursodiol. Thus, ursodiol has beneficial effects on several forms of liver disease and has not been convincingly linked to cases of clinically apparent acute liver injury in patients without cirrhosis. There is some concern that ursodiol may be harmful in patients with advanced liver disease (Childs class B and C) and such patients probably should not receive ursodiol.

The drug decreases the absorption of cholesterol and is used to dissolve (cholesterol) gallstones in patients as an alternative to a surgical procedure to remove the gallstones.|FDA Label

Ursodeoxycholic acid or ursodiol is a naturally occurring bile acid that is used dissolve cholesterol gall stones and to treat cholestatic forms of liver diseases including primary biliary cirrhosis. Ursodiol has been linked to rare instances of transient and mild serum aminotransferase elevations during therapy and to rare instances of jaundice and worsening of liver disease in patients with preexisting cirrhosis.

Gastrointestinal Agents

Ursodiol (commonly known as ursodeoxycholic acid) is a product of metabolism of bacteria in the intestine. It is considered a secondary bile acid. The other type of bile acid, primary bile acids, are produced hepatically and subsequently stored in the gallbladder. When primary bile acids are secreted into the large intestine, they can be broken down into secondary bile acids by bacteria present in the intestine. Both types of bile acids assist in the metabolism of dietary fat. Ursodeoxycholic acid regulates cholesterol levels by slowing the rate at which the intestine is able to absorb cholesterol and also acts to break down micelles, which contain cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)

Only small quantities of ursodiol appear in the systemic circulation and very small amounts are excreted into urine. Eighty percent of lithocholic acid formed in the small bowel is excreted in the feces, but the 20% that is absorbed is sulfated at the 3-hydroxyl group in the liver to relatively insoluble lithocholyl conjugates which are excreted into bile and lost in feces.

Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells. The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution.

3 alpha,7 beta Dihydroxy 5 beta cholan 24 oic Acid

Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Lipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]