Equilin

Short description: Chemical compound

Equilin

Clinical data
Other names| Δ7-Estrone; 7-Dehydroestrone; Estra-1,3,5(10),7-tetraen-3-ol-17-one
Routes of
administration| By mouth
Drug class| Estrogen
Identifiers

IUPAC name

* (9S,13S,14S)-3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

CAS Number|

* 474-86-2 Y

PubChem CID|

* 223368

DrugBank|

* DB02187 Y

ChemSpider|

* 193995 Y

UNII|

* 08O86EX0J4

KEGG|

* D04041 Y

ChEBI|

* CHEBI:42309 Y

ChEMBL|

* ChEMBL323533 Y

Chemical and physical data
Formula| C18H20O2
Molar mass| 268.356 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* O=C3CC[C@H]4C/2=C/Cc1c(ccc(O)c1)[C@H]\2CC[C@]34C

InChI

* 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/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1 Y

* Key:WKRLQDKEXYKHJB-HFTRVMKXSA-N Y

(verify)

Equilin is a naturally occurring estrogen sex hormone found in horses as well as a medication.[1][2][3] It is one of the estrogens present in the estrogen combination drug preparations known as conjugated estrogens (CEEs; e.g. Premarin) and esterified estrogens (EEs; e.g. Estratab, Menest).[2][3] CEEs is the most commonly used form of estrogen medications in hormone replacement therapy (HRT) for menopausal symptoms in the United States .[3] Estrone sulfate is the major estrogen in CEEs (about 50%) while equilin sulfate is the second major estrogen in the formulation, present as about 25% of the total.[2][3]

## Contents

* 1 Pharmacology
* 1.1 Pharmacodynamics
* 1.2 Pharmacokinetics
* 2 Chemistry
* 3 References

## Pharmacology

### Pharmacodynamics

Equilin is an estrogen, or an agonist of the estrogen receptors (ERs), the ERα and ERβ.[2] In terms of relative binding affinity for the ERs, equilin has about 13% and 49% of that of estradiol for the ERα and ERβ, respectively.[2] Analogously to the reversible transformation of estrone into estradiol by 17β-hydroxysteroid dehydrogenase, equilin can be converted into the more potent estrogen 17β-dihydroequilin in the body.[2][3] This estrogen has about 113% and 108% of the relative binding affinities of estradiol for the ERα and ERβ, respectively.[2][3] Equilin is present in CEEs in the form of equilin sulfate, which itself is inactive and acts as a prodrug of equilin via steroid sulfatase.[2][3]

Similarly to synthetic estrogens like ethinylestradiol, equilin and CEEs have disproportionate effects in certain tissues such as the liver and uterus relative to bioidentical human estrogens like estradiol and estrone.[2] Because of their disproportionate potency in the liver, equilin and CEEs have relatively increased effects on liver protein synthesis compared to estradiol.[2]

A dosage of 0.25 mg/day equilin sulfate is equivalent to 0.625 mg/day CEEs in terms of relief from hot flashes.[2] At a dosage of 0.625 mg/day equilin sulfate, the increases in circulating levels of sex hormone-binding globulin (SHBG), corticosteroid-binding globulin, and angiotensinogen were 1.5 to 8 times those observed with estrone sulfate.[2] Equilin has about 42% of the relative potency of CEEs in the vagina and 80% of the relative potency of CEEs in the uterus, while its more active form, 17β-dihydroequilin, has about 83% of the relative potency of CEEs in the vagina and 200% of the relative potency of CEEs in the uterus.[2]

### Pharmacokinetics

Equilin has about 8% of the relative binding affinity of testosterone for SHBG, relative to 12% in the case of estrone.[2] In terms of plasma protein binding, it is bound 26% to SHBG and 13% to albumin.[2] The metabolic clearance rates of equilin and equilin sulfate are 2,640 L/day/m2 and 175 L/day/m2, respectively.[2] In accordance, the biological half-life of equilin sulfate is substantially longer than that of equilin.[2] Equilin is converted into 17β-dihydroequilin in the liver and in other tissues.[2][3] Equilin and 17β-dihydroequilin can also be transformed into equilenin and 17β-dihydroequilenin.[2][3] Equilin is excreted in the form of glucuronide conjugates.[2]

## Chemistry

Equilin, also known as δ7-estrone or as 7-dehydroestrone, as well as estra-1,3,5(10),7-tetraen-3-ol-17-one, is a naturally occurring estrane steroid and an analogue of estrone.[2][3] In terms of chemical structure and pharmacology, equilin is to 17β-dihydroequilin (δ7-17β-estradiol) as estrone is to estradiol.[2][3]

## References

1. ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 495. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA298.
2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 2.12 2.13 2.14 2.15 2.16 2.17 2.18 2.19 2.20 2.21 "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. http://hormonebalance.org/images/documents/Kuhl 05 Pharm Estro Progest Climacteric_1313155660.pdf.
3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 "Pharmacology of conjugated equine estrogens: efficacy, safety and mechanism of action". J. Steroid Biochem. Mol. Biol. 142: 16–29. July 2014. doi:10.1016/j.jsbmb.2013.10.011. PMID 24176763.

* v
* t
* e

Estrogens and antiestrogens

Estrogens|

| ER 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, [[Chemistry:Estradiol estradiol valerate, Polyestradiol phosphate|polyestradiol phosphate]], estradiol ester mixtures (Climacteron))
* Estramustine phosphate
* Estriol
* Estriol esters (e.g., estriol succinate, polyestriol phosphate)
* Estrone
* Estrone esters
* Estrone sulfate
* Estropipate (piperazine estrone sulfate)
* Ethinylestradiol#
* Ethinylestradiol sulfonate
* Hydroxyestrone diacetate
* Mestranol
* Methylestradiol
* Moxestrol
* Nilestriol
* Prasterone (dehydroepiandrosterone; DHEA)
* Prasterone enanthate
* Prasterone sulfate
* Promestriene
* Quinestradol
* Quinestrol

* Nonsteroidal: Benzestrol
* Bifluranol
* Chlorotrianisene
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol (stilbestrol)
* Diethylstilbestrol esters/ethers
* Dimestrol (diethylstilbestrol dimethyl ether)
* Fosfestrol (diethylstilbestrol diphosphate)
* Mestilbol (diethylstilbestrol monomethyl ether)
* Doisynoestrol (fenocycline)
* Hexestrol
* Hexestrol esters
* Methallenestril
* Methestrol dipropionate (promethestrol dipropionate)
* Paroxypropione
* Quadrosilan
* Triphenylbromoethylene
* Triphenylchloroethylene
* Zeranol

|

Progonadotropins|

* Antiandrogens (e.g., bicalutamide)
* GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
* Gonadotropins (e.g., FSH, LH)

Antiestrogens|

| ER antagonists
(incl. SERMs/SERDs)|

* Acolbifene†
* Anordrin
* Bazedoxifene
* Broparestrol
* Clomifene#
* Cyclofenil
* Enclomifene†
* Epitiostanol
* Lasofoxifene
* Mepitiostane
* Ormeloxifene
* Ospemifene
* Raloxifene
* Tamoxifen#
* Toremifene

* Exclusively antagonistic: Fulvestrant

|

Aromatase inhibitors|

* First-generation: Aminoglutethimide
* Testolactone

* Second-generation: Fadrozole
* Formestane

* Third-generation: Anastrozole
* Exemestane
* Letrozole

Antigonadotropins|

* Androgens/Anabolic steroid|Anabolic steroid|Anabolic steroid]]]]s (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone)
* D2 receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
* GnRH agonists (e.g., leuprorelin, goserelin)
* GnRH antagonists (e.g., cetrorelix, elagolix)
* Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

Others|

* Mixed mechanism of action: Danazol
* Gestrinone

* Androstenedione immunogens: Androvax (androstenedione albumin)
* Ovandrotone albumin (Fecundin)

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

See also
Estrogen receptor modulators
Androgens and antiandrogens
Progestogens and antiprogestogens
List of estrogens

* v
* t
* e

Estrogen receptor modulators

ER|

| 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-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)
* 16α-Fluoroestradiol
* 16α-Hydroxy-DHEA
* 16α-Hydroxyestrone
* 16α-Iodoestradiol
* 16α-LE2
* 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
* 17α-Estradiol (alfatradiol)
* 17α-Dihydroequilenin
* 17α-Dihydroequilin
* 17α-Epiestriol (16α-hydroxy-17α-estradiol)
* 17β-Dihydroequilenin
* 17β-Dihydroequilin
* 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
* Cloxestradiol acetate
* Conjugated estriol
* Conjugated estrogens
* Cyclodiol
* Cyclotriol
* DHEA
* DHEA-S
* Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
* Epimestrol
* Equilenin
* Equilin
* ERA-63 (ORG-37663)
* Esterified estrogens
* Estetrol
* Estradiol
* Estradiol esters
* Lipoidal estradiol
* Polyestradiol phosphate
* Estramustine
* Estramustine phosphate
* Estrapronicate
* Estrazinol
* Estriol
* Estriol esters
* Polyestriol phosphate
* Estrofurate
* Estromustine
* Estrone
* Estrone esters
* Estrone methyl ether
* Estropipate
* Etamestrol (eptamestrol)
* Ethinylestradiol
* Ethinylestradiol 3-benzoate
* Ethinylestradiol sulfonate
* 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

* Nonsteroidal: (R,R)-THC
* (S,S)-THC
* 2,8-DHHHC
* β-LGND1
* β-LGND2 (GTx-878)
* AC-186
* Allenestrol
* Allenolic acid
* Benzestrol
* Bifluranol
* Bisdehydrodoisynolic acid
* Carbestrol
* D-15414
* DCW234
* Diarylpropionitrile
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol
* Diethylstilbestrol esters
* Dimestrol (dianisylhexene)
* Doisynoestrol (fenocycline)
* Doisynolic acid
* Efavirenz
* ERB-196 (WAY-202196)
* Erteberel (SERBA-1, LY-500307)
* Estrobin (DBE)
* Fenestrel
* FERb 033
* Fosfestrol (diethylstilbestrol diphosphate)
* Furostilbestrol (diethylstilbestrol difuroate)
* GTx-758
* Hexestrol
* Hexestrol esters
* ICI-85966 (Stilbostat)
* Mestilbol
* Methallenestril
* Methestrol
* Methestrol dipropionate
* Paroxypropione
* Pentafluranol
* Phenestrol
* Prinaberel (ERB-041, WAY-202041)
* Propylpyrazoletriol
* Quadrosilan
* SC-4289
* SERBA-2
* SKF-82,958
* Terfluranol
* Triphenylbromoethylene
* Triphenylchloroethylene
* Triphenyliodoethylene
* Triphenylmethylethylene (triphenylpropene)
* WAY-166818
* WAY-169916
* WAY-200070
* WAY-204688 (SIM-688)
* WAY-214156

* Unknown/unsorted: ERB-26
* ERA-45
* ERB-79
* ZK-283197

* 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, [[Chemistry:Epicateepicatechin, Chemistry:Equol|equol]], formononetin, glabrene, glabridin, Genistein|genistein]], genistin, glycitein, kaempferol, Chemistry:Liquiritigenin

|

Mixed
(SERMs)|

* 2-Phenylbenzofuran
* 2-Phenylbenzothiophene
* 4'-Hydroxynorendoxifen
* 27-Hydroxycholesterol
* Acefluranol
* Acolbifene
* Afimoxifene
* Anordiol
* Anordrin
* Arzoxifene
* Bazedoxifene
* Brilanestrant
* Broparestrol
* Chlorotrianisene
* Clomifene
* Clomifenoxide
* Cyclofenil
* D-15413
* Droloxifene
* Elacestrant
* Enclomifene
* Endoxifen
* Etacstil (GW-5638, DPC-974)
* Ethamoxytriphetol (MER-25)
* Femarelle
* Fispemifene
* GW-7604
* ICI-55548
* Idoxifene
* Lasofoxifene
* Levormeloxifene
* LN-1643
* LN-2299
* LY-117018
* Menerba
* Miproxifene
* Miproxifene phosphate
* Nafoxidine
* Nitromifene
* NNC 45-0095
* NNC 45-0320
* NNC 45-0781
* NNC 45-1506
* Ormeloxifene
* Ospemifene
* Panomifene
* Pipendoxifene
* Promensil
* Raloxifene
* Rimostil (P-081)
* Spironolactone
* SS1010
* Tamoxifen
* TAS-108 (SR-16234)
* Toremifene
* Trioxifene
* TZE-5323
* Y-134
* Zindoxifene
* Zuclomifene

Antagonists|

* (R,R)-THC
* 7β-Hydroxy-DHEA
* Chloroindazole
* Cytestrol acetate
* EM-800
* Epitiostanol
* ERA-90
* ERB-88
* Fulvestrant (ICI-182780)
* Glyceollins (I, II, III, IV)
* ICI-164384
* Mepitiostane
* Methylepitiostanol
* Methylpiperidinopyrazole
* MIBE
* Oxabicycloheptene sulfonate
* Phenytoin
* PHTPP
* Prochloraz
* RU-58668
* SS1020
* TAS-108 (SR-16234)
* ZB716
* ZK-164015
* ZK-191703

* Coregulator-binding modulators: ERX-11

GPER|

| Agonists|

* 2-Methoxyestradiol
* 7β-Hydroxyepiandrosterone
* Afimoxifene (4-hydroxytamoxifen)
* Atrazine
* Bisphenol A
* Daidzein
* DDT (p,p'-DDT, o',p'-DDE)
* Equol
* Estradiol
* Ethinylestradiol
* Fulvestrant (ICI-182780)
* G-1
* Genistein
* GPER-L1
* GPER-L2
* Hydroxytyrosol
* Kepone
* Niacin
* Nicotinamide
* Nonylphenol
* Oleuropein
* PCBs (2,2',5'-PCB-4-OH)
* Propylpyrazoletriol
* Quercetin
* Raloxifene
* Resveratrol
* Tamoxifen
* Tectoridin
* Zearalanone
* Zearalenol
* Zearalenone
* Zeranol (zearalanol))

|

Antagonists|

* CCL18
* Estriol
* G-15
* G-36
* MIBE

See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens

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*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ER]: Estrogen receptor
*[GnRH]: gonadotropin-releasing hormone
*[FSH]: follicle-stimulating hormone
*[LH]: luteinizing hormone
*[SERMs]: Selective estrogen receptor modulators
*[SERDs]: selective estrogen receptor downregulators
*[GPER]: G protein-coupled estrogen receptor