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Chemistry

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Also known as: 83-44-3, Deoxycholate, Desoxycholic acid, Cholerebic, Cholorebic, Choleic acid

Molecular Formula

C₂₄H₄₀O₄

Molecular Weight

392.6 g/mol

InChI Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

FDA UNII

005990WHZZ

A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.

Deoxycholic acid is a Cytolytic Agent. The physiologic effect of deoxycholic acid is by means of Decreased Cell Membrane Integrity.

1 2D Structure

Deoxycholic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

2.1.3 InChI Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

2.1.4 Canonical SMILES

CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C

2.1.5 Isomeric SMILES

C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C

2.2 Other Identifiers

2.2.1 UNII

005990WHZZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 12beta-isomer Deoxycholic Acid

2. 3beta-isomer Deoxycholic Acid

3. 5alpha-isomer Deoxycholic Acid

4. Choleic Acid

5. Deoxycholate

6. Deoxycholate, Sodium

7. Deoxycholic Acid, 12beta Isomer

8. Deoxycholic Acid, 12beta-isomer

9. Deoxycholic Acid, 3beta Isomer

10. Deoxycholic Acid, 3beta-isomer

11. Deoxycholic Acid, 5alpha Isomer

12. Deoxycholic Acid, 5alpha-isomer

13. Deoxycholic Acid, Disodium Salt

14. Deoxycholic Acid, Magnesium (2:1) Salt

15. Deoxycholic Acid, Monoammonium Salt

16. Deoxycholic Acid, Monopotassium Salt

17. Deoxycholic Acid, Monosodium Salt

18. Deoxycholic Acid, Sodium Salt, 12beta-isomer

19. Desoxycholic Acid

20. Dihydroxycholanoic Acid

21. Kybella

22. Lagodeoxycholic Acid

23. Sodium Deoxycholate

2.3.2 Depositor-Supplied Synonyms

1. 83-44-3

2. Deoxycholate

3. Desoxycholic Acid

4. Cholerebic

5. Cholorebic

6. Choleic Acid

7. Degalol

8. Deoxycholatic Acid

9. Droxolan

10. Pyrochol

11. Septochol

12. Desoxycholsaeure

13. 7alpha-deoxycholic Acid

14. 3alpha,12alpha-dihydroxy-5beta-cholanic Acid

15. Cholic Acid, Deoxy-

16. Dihydroxycholanoic Acid

17. Atx-101

18. 7-deoxycholic Acid

19. Kybella

20. (3alpha,5beta,12alpha)-3,12-dihydroxycholan-24-oic Acid

21. 3,12-dihydroxycholanic Acid

22. Deoxy Cholic Acid

23. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic Acid

24. 5-beta-deoxycholic Acid

25. Desoxycholic Acid [nf]

26. Desoxycholsaeure [german]

27. Nsc8797

28. Nsc 8797

29. Nsc-8797

30. Mfcd00003673

31. (4r)-4-[(3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-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

32. (r)-4-((3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

33. 7.alpha.-deoxycholic Acid

34. 3.alpha.,12.alpha.-dihydroxycholanic Acid

35. Dwj211

36. Chebi:28834

37. Cholan-24-oic Acid, 3,12-dihydroxy-, (3alpha,5beta,12alpha)-

38. Dwj-211

39. 005990whzz

40. 3-alpha,12-alpha-dihydroxycholansaeure [german]

41. 3-alpha,12-alpha-dihydroxy-5-beta-cholanoic Acid

42. Atx-101 (deoxycholic Acid)

43. 5beta-cholan-24-oic Acid, 3alpha,12alpha-dihydroxy-

44. 3-alpha,12-alpha-dihydroxy-5-beta-cholan-24-oic Acid

45. Cholan-24-oic Acid, 3,12-dihydroxy-, (3a,5b,12a)-

46. Cholan-24-oic, 3,12-dihydroxy-(3alpha,5beta,12alpha)-

47. 3,12-dihydroxycholan-24-oic Acid, (3alpha,5beta,12alpha)-

48. 17-beta-(1-methyl-3-carboxypropyl)-etiocholane-3-alpha,12-alpha-diol

49. L7-beta-(1-methyl-3-carboxypropyl)-etiocholane-3-alpha,12-alpha-diol

50. 3.alpha.,12.alpha.-dihydroxy-5.beta.-cholanic Acid

51. 3.alpha.,12.alpha.-dihydroxy-5.beta.-cholanoic Acid

52. 3.alpha.,12.alpha.-dihydroxy-5.beta.-cholan-24-oic Acid

53. 5-beta-cholan-24-oic Acid, 3-alpha,12-alpha-dihydroxy-

54. Cholan-24-oic Acid, 3,12-dihydroxy-, (3-alpha,5-beta,12-alpha)-

55. 17.beta.-(1-methyl-3-carboxypropyl)-etiocholane-3.alpha.,12.alpha.-diol

56. Atx 101

57. Dxc

58. Smr000112166

59. Deoxycholatate

60. De-oxycholate

61. 3-hydroxy-polydeoxycholic Acid

62. Deoxy-cholate

63. Unii-005990whzz

64. 3alpha-hydroxy-polydeoxycholate

65. Deoxycholic Acid [usan:inn]

66. Deoxycholic-acid

67. Atx101

68. Ccris 1627

69. Hsdb 293

70. 5b-deoxycholate

71. 3alpha

72. 7-deoxycholate

73. Deoxy-cholic Acid

74. Einecs 201-478-5

75. Kybella (tn)

76. 5b-deoxycholic Acid

77. 7-desoxycholic Acid

78. 3-alpha,12-alpha-dihydroxycholansaeure

79. Brn 3219882

80. 1e3v

81. Deoxycholic Acid [inn]

82. Spectrum5_002007

83. Bmse000833

84. Schembl4300

85. Deoxycholic Acid (nf/inn)

86. Bidd:pxr0198

87. Gtpl610

88. 4-10-00-01608 (beilstein Handbook Reference)

89. Mls001066423

90. Mls001306460

91. Deoxycholic Acid [ii]

92. Deoxycholic Acid [mi]

93. Chembl406393

94. Deoxycholic Acid [hsdb]

95. Deoxycholic Acid [inci]

96. Deoxycholic Acid [usan]

97. Desoxycholic Acid [fcc]

98. 5b-cholanic Acid-3a,12a-diol

99. Dtxsid0042662

100. Desoxycholic Acid [vandf]

101. Deoxycholic Acid [usp-rs]

102. Deoxycholic Acid [who-dd]

103. Hms2270h22

104. Hy-n0593

105. Zinc3914810

106. Deoxycholic Acid, >=98% (hplc)

107. Bbl013877

108. Bdbm50375599

109. Deoxycholic Acid, >=99.0% (t)

110. Lmst04010040

111. S4689

112. Stk801948

113. Akos005622617

114. Deoxycholic Acid [ep Impurity]

115. Deoxycholic Acid [orange Book]

116. Ccg-268565

117. Cs-7613

118. Db03619

119. Deoxycholic Acid [usp Monograph]

120. As-13233

121. Bp-13275

122. Nci60_041946

123. 3-.alpha.,12-.alpha.-dihydroxycholansaeure

124. Deoxycholic Acid, Bioxtra, >=98% (hplc)

125. C04483

126. D10781

127. D85117

128. Q425680

129. Sr-01000765601

130. 5.beta.-cholan-24-oic Acid,12.alpha.-dihydroxy-

131. Sr-01000765601-2

132. 3i+/-,12i+/--dihydroxy-5i(2)-cholansa Currencyure

133. Ursodeoxycholic Acid Impurity E [ep Impurity]

134. Z1945707492

135. 5.beta.-cholan-24-oic Acid, 3.alpha.,12.alpha.-dihydroxy-

136. 3,12-dihydroxycholan-24-oic Acid, (3.alpha.,5.beta.,12.alpha.)- #

137. Cholan-24-oic Acid,12-dihydroxy-, (3.alpha.,5.beta.,12.alpha.)-

138. Deoxycholic Acid, 500 Mug/ml In Methanol, Certified Reference Material

139. (3alpha,5alpha,8alpha,12alpha,14beta,17alpha)-3,12-dihydroxycholan-24-oic Acid

140. Cholan-24-oic Acid, 3,12-dihydroxy-, (3-.alpha., 5-.beta.,12-.alpha.)-

141. Cholan-24-oic Acid, 3,12-dihydroxy-, (3alpha,5beta,12alpha)-, Homopolymer

142. Deoxycholic Acid (desoxycholic Acid), United States Pharmacopeia (usp) Reference Standard

143. L7-.beta.-(1-methyl-3-carboxypropyl)-etiocholane-3-.alpha.,12-.alpha.-diol

144. (4r)-4-((3r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

145. (4r)-4-[(1s,2s,5r,7r,10r,11s,14r,15r,16s)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic Acid

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₄₀O₄
Molecular Weight	392.6 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	392.29265975 g/mol
Monoisotopic Mass	392.29265975 g/mol
Topological Polar Surface Area	77.8 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	605
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
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 Therapeutic Uses

Cholagogues and Choleretics; Detergents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

The useful effects of exogenous bile acids result from their capacity to decrease the cholesterol content of the bile and promote dissolution of cholesterol gallstones. /Bile acids/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 935

VET USE: TO INCR VOL OF BILE WITHOUT SIGNIFICANTLY ALTERING PROPORTIONS OF ITS CONSTITUENTS. MOST EFFECTIVE BILE ACID IN AIDING ABSORPTION OF FATS & FAT-SOLUABLE VITAMINS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 154

4.2 Drug Indication

For improvement in appearance of moderate to severe fullness associated with submental fat in adults.

FDA Label

Investigated for use/treatment in solid tumors.

Treatment of localised fat deposits

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

DEOXYCHOLIC ACID

5.2.2 FDA UNII

005990WHZZ

5.2.3 Pharmacological Classes

Decreased Cell Membrane Integrity [PE]; Cytolytic Agent [EPC]

5.3 ATC Code

D - Dermatologicals

D11 - Other dermatological preparations

D11A - Other dermatological preparations

D11AX - Other dermatologicals

D11AX24 - Deoxycholic acid

5.4 Absorption, Distribution and Excretion

Absorption

Deoxycholic acid is rapidly absorbed after subcutaneous administration. After maximum recommended single treatment dose, 100mg, the post-treatment plasma levels returned to endogenous levels within 24 hours. With the proposed treatment guideline, no accumulation is expected.

Route of Elimination

The exogenous deoxycholic acid joins the endogenous bile acid pool in the enterohepatic circulation and is excreted unchanged in feces along with endogenous deoxycholic acid.

LIVER NORMALLY SECRETES APPROX 24 G OF BILE SALTS IN 700 TO 1000 ML OF BILE IN 24 HR. MOST OF BILE SALTS ARE REABSORBED IN LOWER SMALL INTESTINE & AGAIN BECOME AVAILABLE FOR SECRETION. ... POOL OF BILE SALTS IS APPROX 2 TO 5 G. /BILE SALTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 971

5.5 Metabolism/Metabolites

Deoxycholic acid is not metabolized to any significant extent under normal conditions.

5.6 Mechanism of Action

As a bile acid, deoxycholic acid emulsifies fat in the gut. Synthetically derived deoxycholic acid, when injected, stimulates a targeted breakdown of adipose cells by disrupting the cell membrane and causing adipocytolysis. This results in an inflammatory reaction and clearing of the adipose tissue remnants by macrophages. Deoxycholic acid's actions are reduced by albumin and tissue-associated proteins, therefore its effect is limited to protein-poor subcutaneous fat tissue. Protein-rich tissues like muscle and skin are unaffected by deoxycholic acid, contributing to its safety profile.

IN SOLN CONJUGATED BILE SALTS FORM MICELLES IN WHICH LIPID MATERIALS MAY BE ENTRAINED. ...ALSO PROMOTE DIGESTION OF FATS BY STIMULATING PANCREATIC SECRETION & BY ACTIVATING PANCREATIC LIPASE. ... DEOXYCHOLIC.../ACID/ PROMOTE/S/ NET EXCRETION OF NA, K, & WATER IN COLON...MAY BE...FACTORS REGULATING COLONIC ABSORPTION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 971

DEOXYCHOLATE ADMIN DECR ABSORPTION OF CHOLESTEROL FROM HUMAN INTESTINAL TRACT. IT APPEARED TO INFLUENCE INTESTINAL FLORA AS ASSESSED INDIRECTLY BY ANALYSIS OF TYPES OF NEUTRAL STEROLS ELIM WITH FECES.

PMID:377936 GALLO-TORRES ET AL; AM J CLIN NUTR 32 (7): 1363-1365 (1979)

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