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    Chemistry

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    Also known as: 459789-99-2, 6-ecdca, Int-747, 6-ethylchenodeoxycholic acid, Ocaliva, Obetichloic acid
    Molecular Formula
    C26H44O4
    Molecular Weight
    420.6  g/mol
    InChI Key
    ZXERDUOLZKYMJM-ZWECCWDJSA-N
    FDA UNII
    0462Z4S4OZ
    Obeticholic Acid
    Obeticholic Acid is an orally bioavailable semi-synthetic bile acid derivative and an agonist of the nuclear bile acid receptor farnesoid X receptor (FXR) that may be used to lower hepatic exposure to bile acids. Upon oral administration, obeticholic acid targets and binds to FXR expressed in the liver and intestine, activating FXR-mediated bile acid, inflammatory, fibrotic, and metabolic pathways. This suppresses the production of bile acid in the hepatocytes and increases bile acid transport out of the hepatocytes, thereby reducing hepatic exposure to bile acids. FXR plays an important role in bile acid homeostasis and is involved in hepatic and intestinal inflammation and liver fibrosis.
    Obeticholic acid is a Farnesoid X Receptor Agonist. The mechanism of action of obeticholic acid is as a Farnesoid X Receptor Agonist.
    1 2D Structure

    Obeticholic Acid

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (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
    2.1.2 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
    2.1.3 InChI Key
    ZXERDUOLZKYMJM-ZWECCWDJSA-N
    2.1.4 Canonical SMILES
    CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)O
    2.1.5 Isomeric 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
    2.2 Other Identifiers
    2.2.1 UNII
    0462Z4S4OZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-ecdca

    2. 6-ethyl Chenodeoxycholic Acid

    3. 6-ethyl-3,7-dihydroxycholan-24-oic Acid

    4. 6-ethylchenodeoxycholic Acid

    5. 6alpha-ethyl-3alpha,7alpha-dihydroxy-5beta-cholan-24-oic Acid

    6. 6alpha-ethyl-chenodeoxycholic Acid

    7. 6ecdca

    8. Cholan-24-oic Acid, 6-ethyl-3,7-dihydroxy-, (3alpha,5beta,6alpha,7alpha)-

    9. Dsp-1747

    10. Dsp1747

    11. Int 747

    12. Int-747

    13. Int747

    14. Ocaliva

    2.3.2 Depositor-Supplied Synonyms

    1. 459789-99-2

    2. 6-ecdca

    3. Int-747

    4. 6-ethylchenodeoxycholic Acid

    5. Ocaliva

    6. Obetichloic Acid

    7. 6alpha-ethyl-chenodeoxycholic Acid

    8. Int747

    9. Int 747

    10. Dsp-1747

    11. 6-ethyl-cdca

    12. (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

    13. 6-ethyl-chenodeoxycholic Acid

    14. 6alpha-ethylchenodeoxycholic Acid

    15. 0462z4s4oz

    16. 6alpha-ethyl-3alpha,7alpha-dihydroxy-5beta-cholan-24-oic Acid

    17. 6ecdca

    18. (4r)-4-[(1s,2s,5r,7s,8r,9r,10s,11s,14r,15r)-8-ethyl-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic Acid

    19. Unii-0462z4s4oz

    20. 6-et Cdca

    21. Obeticholic Acid [usan]

    22. Obeticholic Acid [usan:inn]

    23. 1osv

    24. Dsp1747

    25. Ocaliva (tn)

    26. 6-ethyl-3,7-dihydroxycholan-24-oic Acid

    27. 6-ecdca; Obeticholic Acid

    28. Obeticholic Acid [mi]

    29. Schembl715823

    30. Obeticholic Acid (int-747)

    31. Obeticholic Acid [inn]

    32. Obeticholic Acid [jan]

    33. Chembl566315

    34. Gtpl3435

    35. (3alpha,5beta,6alpha,7alpha)-6-ethyl-3,7-dihydroxycholan-24-oic Acid

    36. Bdbm21675

    37. Chebi:43602

    38. Dtxsid20196671

    39. Ex-a387

    40. 6-alpha-ethylchenodeoxycholic Acid

    41. Obeticholic Acid [who-dd]

    42. Obeticholic Acid (jan/usan/inn)

    43. Amy16595

    44. Mfcd16621104

    45. Zinc14164617

    46. Akos024259126

    47. Cholan-24-oic Acid, 6-ethyl-3,7-dihydroxy-, (3alpha,5beta,6alpha,7alpha)-

    48. Obeticholic Acid [orange Book]

    49. Cs-3813

    50. Db05990

    51. Gs-6103

    52. Ncgc00480885-01

    53. Hy-12222

    54. D09360

    55. P16663

    56. A854341

    57. Q15708271

    58. 3a, 7a -dihydroxy-6a -ethyl-5b-cholan-24-oic Acid

    59. 3alpha,7alpha-dihydroxy-6alpha-ethyl-5beta-cholan-24-oic Acid

    60. (3alpha,5beta,6alpha,7alpha,8xi)-6-ethyl-3,7-dihydroxycholan-24-oic Acid

    61. (3beta,5beta,6alpha,7beta)-6-ethyl-3,7-dihydroxycholan-24-oic Acid

    62. (3.alpha.,5.beta.,6.alpha.,7.alpha.)-6-ethyl-3,7-dihydroxycholan-24-oic Acid

    63. (r)-4-((3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

    64. (r)-4-((3r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

    65. Cholan-24-oic Acid, 6-ethyl-3,7-dihydroxy-, (3.alpha.,5.beta.,6.alpha.,7.alpha.)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 420.6 g/mol
    Molecular Formula C26H44O4
    XLogP35.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass420.32395988 g/mol
    Monoisotopic Mass420.32395988 g/mol
    Topological Polar Surface Area77.8 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity649
    Isotope Atom Count0
    Defined Atom Stereocenter Count11
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Obeticholic acid is indicated for the treatment of primary biliary cholangitis in combination with ursodeoxycholic acid (UDCA) in adults with an inadequate response to UDCA. It is also used as a monotherapy in adults with PBC that are unable to tolerate UDCA. Obeticholic acid is currently being considered for FDA approval to treat fibrosis caused by non-alcoholic liver steatohepatitis (NASH), and is likely to be approved for this indication in 2020.

    FDA Label

    Ocaliva is indicated for the treatment of primary biliary cholangitis (also known as primary biliary cirrhosis) in combination with ursodeoxycholic acid (UDCA) in adults with an inadequate response to UDCA or as monotherapy in adults unable to tolerate UDCA.

    Treatment of non-alcoholic steatohepatitis (NASH)

    Treatment of biliary atresia, Treatment of primary biliary cirrhosis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The activation of the FXR by obeticholic acid acts to reduce the synthesis of bile acids, inflammation, and the resulting hepatic fibrosis. This may increase the survival of patients with PBC, but to date, an association between obeticholic acid and survival in PBC has not been established.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    OBETICHOLIC ACID
    5.2.2 FDA UNII
    0462Z4S4OZ
    5.2.3 Pharmacological Classes
    Farnesoid X Receptor Agonists [MoA]; Farnesoid X Receptor Agonist [EPC]
    5.3 ATC Code

    A05AA04

    A05AA04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    A - Alimentary tract and metabolism

    A05 - Bile and liver therapy

    A05A - Bile therapy

    A05AA - Bile acids and derivatives

    A05AA04 - Obeticholic acid

    5.4 Absorption, Distribution and Excretion

    Absorption

    Obeticholic acid is absorbed in the gastrointestinal tract. The Cmax of obeticholic acid occurs at approximately 1.5 hours after an oral dose and ranges from 28.8-53.7 ng/mL at doses of 5-10mg. The median Tmax for both the conjugates of obeticholic acid is about 10 hours. One product monograph reports a Tmax of 4.5h for both 5 and 10mg doses. The AUC ranged from 236.6-568.1 ng/h/mL with 5mg to 10 mg doses.

    Route of Elimination

    About 87% of an orally administered dose is accounted for in the feces. Less than 3% of the dose can be recovered in the urine.

    Volume of Distribution

    The volume of distribution of obeticholic acid is 618 L.

    Clearance

    Clearance information for obeticholic acid is not readily available in the literature.

    5.5 Metabolism/Metabolites

    The metabolism of obeticholic acid occurs in the liver. Obeticholic acid is conjugated with glycine or taurine, followed by secretion into bile. The conjugates are then absorbed in the small intestine and then re-enter the liver via enterohepatic circulation. The intestinal microbiota in the ileum converts conjugated obeticholic acid in a deconjugated form that may be either reabsorbed or eliminated. Glycine conjugates account for 13.8% of the metabolites and taurine conjugates account for 12.3%. Another metabolite, 3-glucuronide, may also be formed, but displays little pharmacological activity.

    5.6 Biological Half-Life

    The biological half-life of obeticholic acid is reported to be 24 hours.

    5.7 Mechanism of Action

    Primary biliary cirrhosis is an autoimmune process by which the bile ducts and liver are damaged progressively, leading to fibrosis and cirrhosis. Bile acids increase the risk of damage and fibrosis to the damaged bile ducts. Obeticholic acid is a potent agonist of the farnesoid X receptor, which serves to regulate the hepatic metabolism of bile and cholesterol. This drug acts by binding to the farnesoid X receptor (FXR), found in the nucleus of liver and intestinal cells, which in turn increases liver bile flow, suppressing its production and decreasing hepatocyte exposure to excess levels of bile with cholestasis. Cholestasis is a process that normally causes inflammation and cirrhosis of the liver.

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    21-May-2021
    20-May-2024
    KGS
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