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Chemical compound
Hippulin Other names Δ8 -14-Isoestrone; 8-Dehydro-14-isoestrone; 14-Isoestra-1,3,5(10),8-tetraen-3-ol-17-one Routes of By mouth Drug class Estrogen
(13S ,14R )-3-hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H -cyclopenta[a ]phenanthren-17-one
CAS Number PubChem CID ChemSpider UNII Formula C 18 H 20 O 2 Molar mass −1 3D model (JSmol )
C[C@]12CCC3=C([C@@H]1CCC2=O)CCc4c3ccc(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
Hippulin , also known as Δ8 -14-isoestrone , as well as 14-isoestra-1,3,5(10),8-tetraen-3-ol-17-one , is a naturally occurring estrogen found in horses and an isomer of equilin .[ 1] [ 2] [ 3] [ 4] sodium sulfate form, is a component of conjugated estrogens (Premarin), a pharmaceutical extract of the urine of pregnant mares ,[ 1] [ 2] [ 3] [ 5] [ 3] [ 4] [ 3]
^ a b C. W. Emmens (22 October 2013). Hormone Assay ISBN 978-1-4832-7286-3 ^ a b H.J. Buchsbaum (6 December 2012). The Menopause ISBN 978-1-4612-5525-3 ^ a b c d Banes D, Carol J, Haenni EO (1950). "The resolution of isoequilin A and the identification of compound 3" (PDF) . J. Biol. Chem . 187 (2): 557–70. doi :10.1016/S0021-9258(18)56200-1 PMID 14803438 . ^ a b Girard, H., Sandulesco, G., Fridenson, A., Gaudefroy, C., & Rutgers, J. J. (1932). Sur les Hormones Sexuelles Cristallisées Retirées de l'Urine des Juments Gravides. Compt. Rend. Acad. Sci, 194, 1020.
^ Wintersteiner, O. (1937). "Estrogenic Diols from the Urine of Pregnant Mares". Cold Spring Harbor Symposia on Quantitative Biology . 5 : 25–33. doi :10.1101/SQB.1937.005.01.003 . ISSN 0091-7451 . S2CID 81202266 .
Estrogens
ER Tooltip Estrogen receptor agonists
Steroidal: Alfatradiol Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate , tibolone )
Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , estradiol valerate , polyestradiol phosphate , estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g., estriol succinate , polyestriol phosphate )Estrogenic substances Estrone Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA)
Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins
Androgens /anabolic steroids (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )D2 receptor antagonists (prolactin releasers) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )GnRH agonistsleuprorelin , goserelin )GnRH antagonistscetrorelix , elagolix )Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , medroxyprogesterone acetate , megestrol acetate ) Others
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )Coumestans (e.g., coumestrol , psoralidin )Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )Lavender oil Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )Metalloestrogens (e.g., cadmium )Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )Steroid -like (e.g., deoxymiroestrol , miroestrol )Stilbenoids (e.g., resveratrol , rhaponticin )Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )Others (e.g., agnuside , rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
