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    Technical details about Prestwick3_000123, learn more about the structure, uses, toxicity, action, side effects and more

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    Prestwick3_000123

    APIs // Active Pharmaceutical Ingredients

    DOSSIERs // Finished Dosage Forms

    MARKET PLACE

    ANALYTICAL SOLUTION(s)

    PharmaCompass

    Phyton is a World Leader in Plant Cell Fermentation Technology and Commercial Manufacturing.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    1. Also known as: 81-23-2, Decholin, Dehystolin, Felacrinos, Sanocholen, Dilabil
    Molecular Formula
    C24H34O5
    Molecular Weight
    402.5  g/mol
    InChI Key
    OHXPGWPVLFPUSM-KLRNGDHRSA-N
    FDA UNII
    NH5000009I
    A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
    2.1.2 InChI
    InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
    2.1.3 InChI Key
    OHXPGWPVLFPUSM-KLRNGDHRSA-N
    2.1.4 Canonical SMILES
    CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
    2.1.5 Isomeric SMILES
    C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(C(=O)C[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CCC(=O)C4)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    NH5000009I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (5beta)-3,7,12-trioxocholan-24-oic Acid

    2. Atrocholin

    3. Cholan Hmb

    4. Cholan-hmb

    5. Cholanhmb

    6. Chologon

    7. Decholin

    8. Dehydrocholate

    9. Dehydrocholate, Sodium

    10. Dehydrocholic Acid, Lithium Salt

    11. Dehydrocholic Acid, Magnesium Salt

    12. Dehydrocholic Acid, Potassium Salt

    13. Dehydrocholic Acid, Sodium Salt

    14. Ketocholanic Acid

    15. Sodium Dehydrocholate

    16. Triketocholanic Acid

    17. Trioxocholate

    2.3.2 Depositor-Supplied Synonyms

    1. 81-23-2

    2. Decholin

    3. Dehystolin

    4. Felacrinos

    5. Sanocholen

    6. Dilabil

    7. Ketocholanic Acid

    8. Chologon

    9. Oxycholin

    10. Procholon

    11. Bilidren

    12. Bilostat

    13. Cholagon

    14. Cholimed

    15. Dehychol

    16. Didrocolo

    17. Drenobyl

    18. Novocolin

    19. Acolen

    20. Dehycon

    21. Didocol

    22. Erebile

    23. Hykolex

    24. Triketocholanic Acid

    25. Deidrocolico Vita

    26. Biochol

    27. Dehycol

    28. Ketochol

    29. Khologon

    30. Dehydrocholate

    31. Doxycholpotassium

    32. Cholan Dh

    33. Cholic Acid, Dehydro-

    34. Dee-co

    35. 3,7,12-trioxocholanic Acid

    36. 3,7,12-triketocholanic Acid

    37. 3,7,12-trioxo-5beta-cholanic Acid

    38. Dehydrocholsaeure

    39. 3,7,12-triketo-5beta-cholanoic Acid

    40. Acide Dehydrocholique

    41. 3,7,12-trioxo-5beta-cholan-24-oic Acid

    42. Hydrochol

    43. (4r)-4-[(5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic Acid

    44. (5beta)-3,7,12-trioxocholan-24-oic Acid

    45. Nsc-8796

    46. Cholan-24-oic Acid, 3,7,12-trioxo-, (5.beta.)-

    47. Mls000069501

    48. 81-23-2 (acid)

    49. Chebi:31459

    50. Cholan-24-oic Acid, 3,7,12-trioxo-, (5b)-

    51. Nh5000009i

    52. (r)-4-((5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

    53. Smr000058603

    54. Dsstox_cid_2888

    55. 3,7,12-trioxo-5.beta.-cholan-24-oic Acid

    56. Dsstox_rid_76775

    57. Dsstox_gsid_22888

    58. Atrocholin

    59. Cholepatin

    60. Dehydrocholsaeure [german]

    61. Acido Deidrocolico

    62. Acido Deidrocolico [dcit]

    63. Acido Dehidrocolico

    64. Acido Dehidrocolico [spanish]

    65. Acide Dehydrocholique [french]

    66. Acidum Dehydrocholicum [latin]

    67. Acidum Dehydrocholicum

    68. Acido Dehidrocolico [inn-spanish]

    69. Acide Dehydrocholique [inn-french]

    70. Acidum Dehydrocholicum [inn-latin]

    71. Nsc 8796

    72. Einecs 201-335-7

    73. Brn 3226734

    74. Cholan-24-oic Acid, 3,7,12-trioxo-, (5beta)-

    75. 5beta-cholanic Acid, 3,7,12-trioxo-

    76. Dilahil

    77. Dehydocholic Acid

    78. 3,7,12-trioxo-5-beta-cholan-24-oic Acid

    79. Unii-nh5000009i

    80. Dehydro-ca

    81. Dehydrocholate-acid

    82. Ncgc00095777-01

    83. Decholin (tn)

    84. Prestwick_498

    85. Cholan-24-oic Acid, 3,7,12-trioxo-, (5-beta)-

    86. Mfcd00066410

    87. Dehydrocholic Acid [usp:inn:ban:jan]

    88. 3,7,12-trioxo-5beta-cholan-24-oicacid

    89. Opera_id_1391

    90. Prestwick3_000123

    91. 3,12-trioxocholanic Acid

    92. 5beta-cholan-24-oic Acid, 3,7,12-trioxo-

    93. 3,12-triketocholanic Acid

    94. 5-beta-cholan-24-oic Acid, 3,7,12-trioxo-

    95. Schembl26391

    96. Bspbio_000166

    97. 4-10-00-03478 (beilstein Handbook Reference)

    98. Mls001076501

    99. Mls001424181

    100. Bpbio1_000184

    101. Chembl514446

    102. Dehydrocholic Acid [mi]

    103. Dehydrocholic Acid [inn]

    104. Dehydrocholic Acid [jan]

    105. Dtxsid2022888

    106. Nsc8796

    107. 3,7,12-trioxo-5-cholanic Acid

    108. Dehydrocholic Acid [vandf]

    109. Hms2052a11

    110. Hms2095i08

    111. Hms2235j07

    112. Hms3712i08

    113. Dehydrocholic Acid [mart.]

    114. Dehydrocholic Acid [usp-rs]

    115. Dehydrocholic Acid [who-dd]

    116. Hy-b1393

    117. Zinc3860869

    118. 3,7,12-trioxo-24-cholanic Acid

    119. Purified Dehydrocholic Acid (jp17)

    120. Tox21_111519

    121. Lmst04010106

    122. Pdsp2_000076

    123. S4562

    124. 3,12-trioxo-5.beta.-cholanic Acid

    125. Dehydrocholic Acid (jp17/usp/inn)

    126. Dehydrocholic Acid, >=99.0% (t)

    127. 3,12-triketo-5.beta.-cholanic Acid

    128. Akos024284359

    129. Tox21_111519_1

    130. 3,12-triketo-5.beta.-cholanoic Acid

    131. 5.beta.-cholanic Acid,7,12-trioxo-

    132. Ccg-101103

    133. Cs-4902

    134. Db11622

    135. Nc00353

    136. 3,7,12-trioxo-5.beta.-cholanic Acid

    137. 3,7,12-trioxocholan-24-oic Acid #

    138. 3,7,12-triketo-5.beta.-cholanic Acid

    139. Ncgc00024025-03

    140. Ncgc00024025-05

    141. 3,7,12-triketo-5.beta.-cholanoic Acid

    142. 4-((1s,2s,7s,11s,10r,14r,15r)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0<2, 7>.0<11,15>]heptadec-14-yl)pentanoic Acid

    143. Dehydrocholic Acid [usp Monograph]

    144. 5.beta.-cholanic Acid, 3,7,12-trioxo-

    145. 3,12-trioxo-5.beta.-cholan-24-oic Acid

    146. 5.beta.-cholan-24-oic Acid,7,12-trioxo-

    147. D0042

    148. D01693

    149. D94651

    150. 3,7,12-tri-keto-5.beta.-cholan-24-oic Acid

    151. 5.beta.-cholan-24-oic Acid, 3,7,12-trioxo-

    152. Cholan-24-oic Acid,7,12-trioxo-, (5.beta.)-

    153. Q903387

    154. Sr-01000003022

    155. Sr-01000003022-3

    156. W-104212

    157. Brd-k90976994-001-02-1

    158. 3,7,12-trioxo-5beta-cholanic Acid 5beta-cholanic Acid-3,5,12-trione

    159. Dehydrocholic Acid, United States Pharmacopeia (usp) Reference Standard

    160. (r)-4-((5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoicacid

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 402.5 g/mol
    Molecular Formula C24H34O5
    XLogP32.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass402.24062418 g/mol
    Monoisotopic Mass402.24062418 g/mol
    Topological Polar Surface Area88.5 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity756
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    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

    No approved therapeutic indications.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Following infusion of dehydrocholic acid (DHCA) in rats, the secretions of all the endogenous biliary bile acids were decreased within 30-60 minutes of infusion. Phospholipid secretion as well as cholesterol levels were also declined. The bile flow was increased after administration of dehydrocholic acid.

    5.2 MeSH Pharmacological Classification

    Cholagogues and Choleretics

    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.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    The duodenal experiment indicates that dehydrocholic acid is absorbed from the proximal small intestine.

    Route of Elimination

    Administered dehydrocholic acid is excreted rapidly in bile as glycine- and taurine-conjugated bile acids.

    Volume of Distribution

    No pharmacokinetic data available.

    Clearance

    No pharmacokinetic data available.

    5.4 Metabolism/Metabolites

    The major site of metabolism is proposed to be the liver. The major metabolite accounting for 70% of total detectable metabolites is dihydroxymonoketo bile acid (3,7-dihydroxy-12-keto-5-cholanoic acid). About 20% of metabolites is monohydroxydiketoacid (3-hydroxy-7,12-keto-5-cholanoic acid) and about 10% is cholic acid.

    5.5 Biological Half-Life

    No pharmacokinetic data available.

    5.6 Mechanism of Action

    It is proposed that dehydrocholic acid induces choleresis, which is associated with biliary lipid secretion and reduced secretion of endogenous and/or exogenous biliary components. Dehydrocholic acid may decrease bile phospholipid secretion due to a lack of micelle formation by dehydrocholic acid-produced bile. A study suggests that due to enhanced permeability of tight junctions in the canalicular membranes, dehydrocholic acid facilitates direct exchange between bile and plasma.

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