Pregnanediol glucuronide, or 5β-pregnane-3α,20α-diol 3α-glucuronide, is the major metabolite of progesterone and the C3α glucuronide conjugate of pregnanediol (5β-pregnane-3α,20α-diol).[1][2] Approximately 15 to 30% of a parenteral dose of progesterone is metabolized into pregnanediol glucuronide.[1][2] While this specific isomer is referred to as pregnanediol glucuronide and is the most major form, there are actually many possible isomers of the metabolite.[3][4]
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| Names | |
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| IUPAC name
(20S)-20-Hydroxy-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid
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| Systematic IUPAC name
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-({(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-1-[(1S)-1-hydroxyethyl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl}oxy)oxane-2-carboxylic acid | |
| Other names
Pregnanediol 3α-glucuronide; 5β-Pregnane-3α,20α-diol 3α-glucuronide
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C27H44O8 | |
| Molar mass | 496.641 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References
edit- ^ a b Josimovich J (11 November 2013). Gynecologic Endocrinology. Springer Science & Business Media. p. 28. ISBN 978-1-4613-2157-6.
- ^ a b Etienne-Emile Baulieu; Paul A. Kelly (30 November 1990). Hormones: From Molecules to Disease. Springer Science & Business Media. pp. 401–. ISBN 978-0-412-02791-8.
- ^ Cupps PT (20 February 1991). Reproduction in Domestic Animals. Elsevier. pp. 101–. ISBN 978-0-08-057109-6.
- ^ R. Hobkirk (18 January 2018). Steroid Biochemistry. CRC Press. pp. 23–. ISBN 978-1-351-09380-4.
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