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

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    Deoxycholic Acid

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    2D Structure
    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

    2D Structure

    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 Weight 392.6 g/mol
    Molecular Formula C24H40O4
    XLogP34.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass392.29265975 g/mol
    Monoisotopic Mass392.29265975 g/mol
    Topological Polar Surface Area77.8 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity605
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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