Estradiol Enanthate

• CAT Number: R021580
• CAS Number: 4956-37-0
• Molecular Formula: C25H36O3
• Molecular Weight: 384.56
• Purity: ≥95%
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Storage: Refrigerator
• IUPAC Name: [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] heptanoate
• 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
• InChIKey: RFWTZQAOOLFXAY-BZDYCCQFSA-N
• SMILES: CCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C

Estradiol enanthate (INN, USAN), or estradiol heptanoate, is a synthetic, steroidal estrogen and an estrogen ester – specifically, the 17β-enanthate ester of estradiol – which is used as a component of hormonal contraception. It acts as a prodrug of estradiol, and hence, is considered to be a natural, bioidentical form of estrogen. Estradiol enanthate is used in combination with the progestogen dihydroxyprogesterone acetophenide as a once-monthly combined injectable contraceptive in Spain and Latin America under brand names including Anafertin, Deladroxate, Perlutan, and Topasel. This combination has been marketed since the mid-1960s. Estradiol enanthate does not appear to be available as a standalone drug.

When estradiol enanthate is administered in oil via intramuscular injection, a depot effect occurs, and the drug has a very long duration of effect. A single 10 mg intramuscular dose of estradiol enanthate has been found to result in significantly elevated levels of estradiol for at least 31 days. The duration of estradiol enanthate is considerably longer than that of various other commonly used estradiol esters like estradiol valerate and estradiol cypionate.

Reference

1: Coutinho EM, Spinola P, Athayde C, Noronha CF, de Melo NR, Cabral ZA, Almeida
JA, da Silva BL, Neto JS, Rumi DO. Comparison of two regimens of a monthly
injectable contraceptive containing dihydroxyprogesterone acetophenide and
estradiol enanthate. Contraception. 2006 Mar;73(3):249-52. Epub 2005 Oct 20.
PubMed PMID: 16472564.

2: Coutinho EM, Spinola P, Tomaz G, Morais K, Nassar de Souza R, Sabino Pinho
Neto J, de Barros Leal W, Bomfim Hippolito S, D/’Aurea Abranches A. Efficacy,
acceptability, and clinical effects of a low-dose injectable contraceptive
combination of dihydroxyprogesterone acetophenide and estradiol enanthate.
Contraception. 2000 Apr;61(4):277-80. PubMed PMID: 10899484.

3: Martínez GH, Castañeda A, Correa JE. Vaginal bleeding patterns in users of
Perlutal, a once-a-month injectable contraceptive consisting of 10 mg estradiol
enanthate combined with 150 mg dihydroxyprogesterone acetophenide. A trial of
5462 woman-months. Contraception. 1998 Jul;58(1):21-7. PubMed PMID: 9743892.

4: Coutinho EM, Spinola P, Barbosa I, Gatto M, Tomaz G, Morais K, Yazlle ME, de
Souza RN, Pinho Neto JS, Leal Wde B, Leal C, Hippolito SB, Abranches AD.
Multicenter, double-blind, comparative clinical study on the efficacy and
acceptability of a monthly injectable contraceptive combination of 150 mg
dihydroxyprogesterone acetophenide and 10 mg estradiol enanthate compared to a
monthly injectable contraceptive combination of 90 mg dihydroxyprogesterone
acetophenide and 6 mg estradiol enanthate. Contraception. 1997 Mar;55(3):175-81.
PubMed PMID: 9115007.

5: Wiemeyer JC, Sagasta CL, Roncales Mateo JM, Lavarello AC, Angel de Toro LA,
Salas Diaz R. Multicentred clinical study of the metabolic effect of the monthly
injectable contraceptive containing dihydroxyprogesterone acetophenide 150 mg +
estradiol enanthate 10 mg. Contraception. 1990 Jul;42(1):13-28. Erratum in:
Contraception 1990 Dec;42(6):691. PubMed PMID: 2117515.

6: Recio R, Garza-Flores J, Schiavon R, Reyes A, Diaz-Sanchez V, Valles V, Luz de
la Cruz D, Oropeza G, Perez-Palacios G. Pharmacodynamic assessment of
dihydroxyprogesterone acetophenide plus estradiol enanthate as a monthly
injectable contraceptive. Contraception. 1986 Jun;33(6):579-89. PubMed PMID:
3769482.

7: Kurihara N, Tadokoro S, Ogawa H. Studies on hormonal actions of
dihydroxyprogesterone acetophenide, estradiol enanthate and their mixtures. Jpn J
Pharmacol. 1972 Feb;22(1):43-58. PubMed PMID: 4537624.