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Chemistry

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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

Dehydrocholic Acid

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 Formula	C₂₄H₃₄O₅
Molecular Weight	402.5 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	402.24062418 g/mol
Monoisotopic Mass	402.24062418 g/mol
Topological Polar Surface Area	88.5 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	756
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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