Estradiol enanthate

Estradiol enanthate
Systematic (IUPAC) name

(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl heptanoate
Clinical data
Legal status	℞ (Prescription only)
Routes of administration	IM
Identifiers
CAS Registry Number	4956-37-0
ATC code	None
PubChem	CID 21070
ChemSpider	19815
Synonyms	17β-Estradiol-17-heptanoate
Chemical data
Formula	C₂₅H₃₆O₃
Molecular mass	384.552 g/mol
SMILES O=C(O[C@H]3CC[C@H]4[C@H]2[C@@H](c1ccc(O)cc1CC2)CC[C@]34C)CCCCCC
InChI InChI=1S/C25H36O3/c1-3-4-5-6-7-24(27)28-23-13-12-22-21-10-8-17-16-18(26)9-11-19(17)20(21)14-15-25(22,23)2/h9,11,16,20-23,26H,3-8,10,12-15H2,1-2H3/t20-,21-,22+,23+,25+/m1/s1 Key:RFWTZQAOOLFXAY-BZDYCCQFSA-N

Estradiol enanthate (INN, USAN), or estradiol enantate, is a synthetic ester, specifically the 17-heptanoyl ester, of the natural estrogen, estradiol.^[1]^[2] It is marketed under the brand names Anafertin, Deladroxate, Perlutan, and Topasel, which are combination formulations of estradiol enanthate and dihydroxyprogesterone acetophenide, as a once-monthly injectable hormonal contraceptive in Spain and Latin America,^[3]^[4] and has been used as such since at least the mid-1960s.^[5]

References

↑ A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. Retrieved 20 May 2012.
↑ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
↑ Zutshi (1 January 2005). Hormones in Obstetrics and Gynaecology. Jaypee Brothers Publishers. p. 138. ISBN 978-81-8061-427-9. Retrieved 20 May 2012.
↑ Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". Journal of Obstetrics and Gynaecology. 4 Suppl 1: S1–34. PMID 12290848.
↑ Rizkallah TH, Taymor ML (January 1966). "Ovulation inhibition with a log-acting injectable. II. The cycling effects of varying progestagen-estrogen combinations". American Journal of Obstetrics and Gynecology 94 (2): 161–4. PMID 5900652.

Estrogens and antiestrogens

Agonists

Steroidal	Diosgenin Estetrol Estradiol Estradiol acetate Estradiol benzoate Estradiol cypionate^# Estradiol dipropionate Estradiol enanthate Estradiol hemihydrate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estriol Estriol succinate Estrone Estrone sulfate Estriol Ethinylestradiol^# Mestranol Promestriene Equilenin Equilin

Nonsteroidal	Chlorotrianisene Dienestrol Fosfestrol Diethylstilbestrol Zeranol

Antiestrogens/
SERMs

Pure antagonists: Fulvestrant

Aromatase inhibitors

Nonselective: Aminoglutethimide; Testolactone

Selective: Anastrozole; Exemestane; Fadrozole; Formestane; Letrozole

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

Index of reproductive medicine

Description	Anatomy male female Physiology menstrual cycle Development sex determination and differentiation

Disease	Infections STD and STI Congenital male female Neoplasms and cancer male female gonadal germ cell Other male female Symptoms and signs eponymous

Treatment	Procedures male female Drugs benign prostatic hypertrophy erectile dysfunction and premature ejaculation sexual dysfunction infection STDs hormones androgens estrogens progestogens GnRH prolactin Assisted reproduction Birth control hormonal

Estrogenics

Receptor

ER (α, β)	Agonists: 5α-Androstane-3β,17β-diol 16α-Hydroxyestrone 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Benzestrol Bifluranol Broparestrol Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Chlorotrianisene Cloxestradiol Coumestans (e.g., coumestrol, psoralidin) DHEA Deoxymiroestrol Dienestrol Diethylstilbestrol Diethylstilbestrol diphosphate Diosgenin Doisynoestrol DPN DY-131 (GSK-9089) Epiestriol Epimestrol ERB-041 Etamestrol (eptamestrol) ERB-041 Equilenin Equilin Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol Ethinylestradiol Ethinylestradiol 3-isopropylsulfonate Etynodiol diacetate FERb 033 Fenestrel Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Miroestrol Moxestrol Nilestriol Orestrate Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate PPT Promestriene Promethoestrol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quinestradol Quinestrol Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenol A (BPA), DDT, parabens, PBBs, phthalates, PCBs) (R,R)-THC WAY-200070 Mixed (SERMs): 2-Hydroxyestrone (Z)-4-Hydroxytamoxifen Acolbifene Afimoxifene Arzoxifene Bazedoxifene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epimestrol Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Prinaberel Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene Antagonists: Fulvestrant ICI-164384 ICI-182780 MPP PHTPP RU-58668 SS1020 (R,R)-THC XCT-790 ZK-164015 ZK-191703

GPER	Agonists: Estradiol Fulvestrant G-1 Genistein ICI-182780 Quercetin Tamoxifen Tectoridin Antagonists: G-15

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones: Cholesterol
22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol
Pregnenolone
Pregnenolone sulfate
17-Hydroxypregnenolone
Progesterone
17-Hydroxyprogesterone
11-Deoxycortisol (cortodoxone)
DHEA
DHEA sulfate
16-Hydroxy-DHEA sulfate
5-Androstenediol
4-Androstenedione
16-Hydroxyandrostenedione
Testosterone

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
Calcitriol (vitamin D)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics