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8,9-Dehydroestrone

February 15, 2024

8,9-Dehydroestrone, or Δ8-estrone, also known as estra-1,3,5(10),8-tetraen-3-ol-17-one, is a naturally occurring estrogen found in horses which is closely related to equilin, equilenin, and estrone, and, as the 3-sulfate ester sodium salt, is a minor constituent (3.5%) of conjugated estrogens (Premarin).[1][2][3][4] It produces 8,9-dehydro-17β-estradiol as an important active metabolite, analogously to conversion of estrone or estrone sulfate into estradiol.[2][4][5][3] The compound was first described in 1997.[6][3] In addition to 8,9-dehydroestrone and 8,9-dehydro-17β-estradiol, 8,9-dehydro-17α-estradiol is likely also to be present in conjugated estrogens, but has not been identified at this time.[2]

8,9-Dehydroestrone
Clinical data
Other namesΔ8-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of
administration		By mouth
Drug classEstrogen
Identifiers
  • (13S,14S)-3-Hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
CAS Number
  • 474-87-3
PubChem CID
  • 6451472
ChemSpider
  • 4953937
UNII
  • 7C1N8RKG9F
CompTox Dashboard (EPA)
  • DTXSID40197125
Chemical and physical data
FormulaC18H20O2
Molar mass268.356 g·mol−1
3D model (JSmol)
  • Interactive image
  • C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
  • InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1
  • Key:OUGSRCWSHMWPQE-WMZOPIPTSA-N

See also edit

References edit

  1. ^ Fritz MA, Speroff L (28 March 2012). "Postmenopausal Hormone Therapy". Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
  2. ^ a b c Bhavnani BR (January 1998). "Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism". Proceedings of the Society for Experimental Biology and Medicine. 217 (1): 6–16. doi:10.3181/00379727-217-44199. PMID 9421201. S2CID 45177839.
  3. ^ a b c Bhavnani BR, Cecutti A, Gerulath A (October 1998). "Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men". The Journal of Steroid Biochemistry and Molecular Biology. 67 (2): 119–131. doi:10.1016/s0960-0760(98)00082-x. PMID 9877212. S2CID 54352249.
  4. ^ a b Baracat E, Haidar M, Lopez FJ, Pickar J, Dey M, Negro-Vilar A (June 1999). "Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women". The Journal of Clinical Endocrinology and Metabolism. 84 (6): 2020–2027. doi:10.1210/jcem.84.6.5800. PMID 10372704.
  5. ^ Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  6. ^ Bhavnani BR, Cecutti A, Dey MS (1997). "Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin". Journal Society Gynecologic Investigation. 4 (1 (Suppl): 392.


 

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February 15, 2024
dehydroestrone, estrone, also, known, estra, tetraen, naturally, occurring, estrogen, found, horses, which, closely, related, equilin, equilenin, estrone, sulfate, ester, sodium, salt, minor, constituent, conjugated, estrogens, premarin, produces, dehydro, 17β. 8 9 Dehydroestrone or D8 estrone also known as estra 1 3 5 10 8 tetraen 3 ol 17 one is a naturally occurring estrogen found in horses which is closely related to equilin equilenin and estrone and as the 3 sulfate ester sodium salt is a minor constituent 3 5 of conjugated estrogens Premarin 1 2 3 4 It produces 8 9 dehydro 17b estradiol as an important active metabolite analogously to conversion of estrone or estrone sulfate into estradiol 2 4 5 3 The compound was first described in 1997 6 3 In addition to 8 9 dehydroestrone and 8 9 dehydro 17b estradiol 8 9 dehydro 17a estradiol is likely also to be present in conjugated estrogens but has not been identified at this time 2 8 9 DehydroestroneClinical dataOther namesD8 Estrone Estra 1 3 5 10 8 tetraen 3 ol 17 oneRoutes ofadministrationBy mouthDrug classEstrogenIdentifiersIUPAC name 13S 14S 3 Hydroxy 13 methyl 7 11 12 14 15 16 hexahydro 6H cyclopenta a phenanthren 17 oneCAS Number474 87 3PubChem CID6451472ChemSpider4953937UNII7C1N8RKG9FCompTox Dashboard EPA DTXSID40197125Chemical and physical dataFormulaC 18H 20O 2Molar mass268 356 g mol 13D model JSmol Interactive imageSMILES C C 12CCC3 C C H 1CCC2 O CCC4 C3C CC C4 OInChI InChI 1S C18H20O2 c1 18 9 8 14 13 5 3 12 19 10 11 13 2 4 15 14 16 18 6 7 17 18 20 h3 5 10 16 19H 2 4 6 9H2 1H3 t16 18 m0 s1Key OUGSRCWSHMWPQE WMZOPIPTSA NSee also editList of estrogens Equine estrogensReferences edit Fritz MA Speroff L 28 March 2012 Postmenopausal Hormone Therapy Clinical Gynecologic Endocrinology and Infertility Lippincott Williams amp Wilkins pp 751 ISBN 978 1 4511 4847 3 a b c Bhavnani BR January 1998 Pharmacokinetics and pharmacodynamics of conjugated equine estrogens chemistry and metabolism Proceedings of the Society for Experimental Biology and Medicine 217 1 6 16 doi 10 3181 00379727 217 44199 PMID 9421201 S2CID 45177839 a b c Bhavnani BR Cecutti A Gerulath A October 1998 Pharmacokinetics and pharmacodynamics of a novel estrogen delta8 estrone in postmenopausal women and men The Journal of Steroid Biochemistry and Molecular Biology 67 2 119 131 doi 10 1016 s0960 0760 98 00082 x PMID 9877212 S2CID 54352249 a b Baracat E Haidar M Lopez FJ Pickar J Dey M Negro Vilar A June 1999 Estrogen activity and novel tissue selectivity of delta8 9 dehydroestrone sulfate in postmenopausal women The Journal of Clinical Endocrinology and Metabolism 84 6 2020 2027 doi 10 1210 jcem 84 6 5800 PMID 10372704 Kuhl H August 2005 Pharmacology of estrogens and progestogens influence of different routes of administration Climacteric 8 Suppl 1 3 63 doi 10 1080 13697130500148875 PMID 16112947 S2CID 24616324 Bhavnani BR Cecutti A Dey MS 1997 Effects in postmenopausal women of delta 8 estrone sulfate A novel estrogen component of Premarin Journal Society Gynecologic Investigation 4 1 Suppl 392 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 8 9 Dehydroestrone amp oldid 1199142838, wikipedia, wiki, book, books, library,

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