CAS 128-13-2|Deursil|Litursol|Ursodeoxycholic acid|Chenodeoxycholic acid|PMS-ursodiol c|3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid|Ursobilin|Arsacol|Ursochol|Ursolvan|3-alpha,7-beta-Dioxycholan...

General Information

Structure

Molecular Formula

C₂₄H₄₀O₄

Molecular Mass

392.572

Exact Mass

392.29265976

Charge

0

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

InChIKey

RUDATBOHQWOJDD-UZVSRGJWSA-N

Canonic Smiles

O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C

Isomeric Smiles

O[C@@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCC(=O)O)C)(CC[C@@H]2[C@@]2([C@H](C1)C[C@H](O)CC2)C)C

Calculated Properties

JChem

LogD (pH = 7.4)

0.98

LogD (pH = 5.5)

2.76

Log P

3.71

Rotatable Bonds

4

H Donor

3

H Acceptors

4

Lipinski's Rule of Five

true

Acid pKa

4.60

Polar Surface Area

77.76

Polarizability

46.34

Molar Refractivity

109.27

LOG S

-5.08

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

DeursilLitursolPMS-ursodiol cUrsobilinArsacolUrsocholUrsolvanAntigallActigallLyetonUrso forteUrsofalkDelursanDom-ursodiol cUrsoUrso DSCholit-ursanUrsacolPHL-ursodiol cSolutratUrso 250DestolitPeptaromUrsodamor

Synonyms

Ursodeoxycholic acidChenodeoxycholic acid3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid3-alpha,7-beta-Dioxycholanic acid7beta-Hydroxylithocholic acidAcide ursodesoxycholique [inn-french](3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid5beta-Cholan-24-oic acid-3alpha,7beta-diol3-alpha,7-beta-Dihydroxycholanic acidAcidum ursodeoxycholicum [inn-latin]Ursodesoxycholic acidUrsodiol3,7-Dihydroxycholan-24-oic acidUDCSAcido ursodeossicolico [italian]Acido ursodeoxicolico [inn-spanish]3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acidIso-ursodeoxycholic acid7-beta-Hydroxylithocholic acid7 β-Hydroxylithocholic acid5 β-Cholan-24-oic acid-3α,7 β-diol3α,7 β-Dihydroxy-5 β-cholan-24-oic acidUrsodeoxycholic acidUrsodiolUDCAUrsofalkUrsosanURSODESOXYCHOLIC ACID(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid7β-Hydroxylithocholic acid3α,7β-Dihydroxy-5β-cholan-24-oic acid5β-Cholan-24-oic acid-3α,7β-diolUrsodeoxycholic acid17β-(1-Methyl-3-carboxypropyl)etiocholane-3α,7β-diolDeursil3α,7β-Dihydroxy-5β-cholanic AcidDestolit7β-Dihydroxy-5β-cholan-24-oic acidAdursalDesocolUrsodamor(3α,5β,7β)-3,7-Dihydroxycholan-24-oic AcidDesolCholit-UrsanActigallArsacolDelursanUrsodeoxycholic acidursodeoxycholic acid(3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acidActigallUrsodiolUrsodeoxycholate3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid

IUPAC name

(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid (4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

IUPAC Traditional name

ursodeoxycholic acid

API Name

Ursodeoxycholic acid

Names and Identifiers

Registration numbers

CAS Number

128-13-2

PubChem CID

31401

PubChem SID

465087952490065116096482414718187

Beilstein Number

EC Number

MDL Number

DrugBank ID

BindingDB Database

LINCS Database

BKMS React Database

74685363122178492673428823149

BRENDA Ligand Database

26733631221784974685428823149

BRENDA Database

1.1.1.2701.1.1.1493.5.1.742.4.1.B71.1.1.2133.5.1.241.1.1.501.1.1.212.8.2.341.3.1.31.3.1.202.4.1.171.1.1.3571.1.1.1592.8.2.142.3.1.651.1.1.201

Patent number

US2007265187EP1321463WO2007103687US2007253934US2007190140EP1886685US2008076829WO2007096431US2008076828US2008057068EP1652913US2007197485US2006122391US2003104360

SABIO-RK Database

UniProt Database

Reaxys Registry

KEGG ID

CHEMBL

PubMed Citation Links

248167271498905017489439

Wikipedia Title

SureChEMBL Database

ACToR Database

CHEBI ID

LIPID MAPS Instance

Drug Central Database

CompTox Database

HMDB Database

KEGG DRUG Database

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S1643

Research Area: Metabolic Disease
Biological Activity:
Ursodiol reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones. (IC50=0.22 µM) It is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. [1] A hit rate of around 0.4% was observed with a Z’ factor of 0.6 ± 0.2. Two confirmed hits are bile acids, chenodiol and ursodiol with an IC50 of 2.4 and 0.22 µM, respectively. [2]

MP Biomedicals

02158252

Purity: 99%

05219738

MP Biomedicals Rare Chemical collection

DrugBank

DB01586

Drug Groups

approved; investigational

Description

Ursodeoxycholic acid is an epimer of chenodeoxycholic acid (DB06777). It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]

Indication

The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.

Pharmacology

Ursodiol (also known as ursodeoxycholic acid) is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the colon, primary bile acids can be metabolized into secondary bile acids by intestinal bacteria. Primary and secondary bile acids help the body digest fats. Ursodeoxycholic acid helps regulate cholesterol by reducing the rate at which the intestine absorbs cholesterol molecules while breaking up micelles containing cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.

Toxicity

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.

Affected Organisms

Humans and other mammals

Elimination

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.

References

• Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. [Pubmed]

• Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. [Pubmed]

• Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. [Pubmed]

External Links

• [Wikipedia]

Sigma Aldrich

U5127

包装
1, 5, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. U5127.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

U850000

Used as an anticholelithogenic. Epimer with Chenodiol with respect to the hydroxyl group at C7.

ChEBI

CHEBI:9907

A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.

Molecule Details

References

PubChem Literature

From Data Sources

• Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. Pubmed

• Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. Pubmed

• Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. Pubmed

• Zhou W et al. J Biomol Screen. 2010 Jun;15(5)

• Poupon, R.E, et al.: N. Engl. J. Med., 324, 1548 (1986)

• Tint, G.S., et al.: Gastroenterology, 91, 1007 (1986)

• MacKenzie, P., et al.: J. Biol. Chem., 283, 36205 (1986)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:1364