EBB was first described in 1938.[7] It was developed for use as a form of birth control in the 1970s[8][1] and was introduced for medical use for this indication by the 1980s.[9][10] The medication is used in combination with DHPA as a combined injectable contraceptive in Peru and Singapore.[11][12]
The combination of EBB and DHPA contains 10 mg estradiol benzoate butyrate (EBB), an estrogen, and 150 mgalgestone acetophenide (dihydroxyprogesterone acetophenide; DHPA), a progestin.[11][12]
The combination of EBB and DHPA is said to be associated with poor control of menstrual bleeding when used as a once-a-month combined injectable contraceptive.[1][14]
The estrogenic potencyoforalethinylestradiol is approximately 30-fold higher than that of parenteral EBB.[1] In accordance, 50 μg/day oral ethinylestradiol has been reported to be about 3 times stronger in estrogenic effect than once-a-month injections of 10 mg EBB.[1]
EBB is a syntheticestranesteroid and the C3 benzoate (benzenecarboxylate) and C17β butyrate (butanoate) diesterofestradiol.[17] It is also known as estradiol 3-benzoate 17β-n-butyrate or as estra-1,3,5(10)-triene-3,17β-diol 3-benzoate 17β-n-butyrate.[17]
EBB, along with a variety of other estradiol esters, was first described in 1938 by Karl Miescher and colleagues of CibainBasel, Switzerland.[7][19][20][21] It was developed in combination with DHPA as a combined injectable contraceptive in the 1970s.[8][1][22][23][24][25] The combination was marketed for use as a combined injectable contraceptive in Peru by 1987.[9][10]
EBB is marketed in combination with DHPA under the brand names Neolutin N, Redimen, Soluna, and Unijab.[1][11][12][26][27][28] It was originally developed under the tentative brand name Unimens, but ultimately was not marketed under this particular brand name.[1][2][13][8][29]
^ abcdefKuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. 261–322. doi:10.1007/978-3-642-60107-1_15. ISBN978-3-642-60107-1. Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.
^ abcNewton 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. doi:10.3109/01443619409027641. PMID12290848.
^ abBonnema J, Dalebout JA (February 1992). "The abuse of high dose estrogen/progestin combination drugs in delay of menstruation: the assumptions and practices of doctors, midwives and pharmacists in a Peruvian city". Social Science & Medicine. 34 (3): 281–289. doi:10.1016/0277-9536(92)90270-Z. PMID1557669.
^ abThomas DB, Molina R, Rodriguez Cuevas H, Ray RM, Riotton G, Dabancens A, et al. (August 1989). "Monthly injectable steroid contraceptives and cervical carcinoma". American Journal of Epidemiology. 130 (2): 237–247. doi:10.1093/oxfordjournals.aje.a115330. PMID2665476.
^Emmens CW, Martin L (5 December 2016). "Estrogens". In Dorfman RI (ed.). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 36–. ISBN978-1-4832-7299-3.
^Ferin J (January 1952). "Relative duration of action of natural and synthetic estrogens administered parenterally in women with estrogen deficiency". The Journal of Clinical Endocrinology and Metabolism. 12 (1): 28–35. doi:10.1210/jcem-12-1-28. PMID14907837.
^Lockyer NS (1938). Nature. Macmillan Journals Limited. p. 292. The oestradiol benzoate butyrate and dipropionate were supplied by Dr. Miescher (of Ciba Ltd.) who recently described their prolonged effects in rats8.
^American journal of cancer. 1940. Note: Our thanks are due to Doctor Karl Miescher of Messrs. Ciba in Basel, Switzerland, for a liberal supply of different esters of estradiol used in this work.
^Minucci D, Arreghini G, Rabasso A (1973). "[Modification of the endometrium during combined therapy with dihydroxyprogesterone acetophenide and estradiol-3-benzoate-17-n-butyrate]" [Modification of the endometrium during combined therapy with dihydroxyprogesterone acetophenide and estradiol-3-benzoate-17-n-butyrate]. Rivista di Ostetricia Ginecologia Pratica e Medicina Perinatale (in Italian). 54 (10): 497–505. PMID4807299.
^Cittadini E, Catalano G (1973). "[Use of a new combination: dihydroxyprogesterone acetophenide and estradiol-3-benzoate-17 isobutyrate in gynecology]" [Use of a new combination: dihydroxyprogesterone acetophenide and estradiol-3-benzoate-17 isobutyrate in gynecology]. Rivista di Ostetricia Ginecologia Pratica e Medicina Perinatale (in Italian). 54 (10): 506–512. PMID4620236.
^Selvaggi L, Putignano G (December 1975). "[Response of peripheral receptors to the parenteral administration of an association of dihydroxyprogesterone acetophenide and estradiol-3 benzoate-17-n-butyrate. Preliminary note]" [Response of peripheral receptors to the parenteral administration of an association of dihydroxyprogesterone acetophenide and estradiol-3 benzoate-17-n-butyrate. Preliminary note]. Minerva Ginecologica (in Italian). 27 (12): 961–963. PMID778679.
^Cappello F (December 1975). "[Use of a parenteral estroprogestin as an inhibitor of ovulation in a single monthly administration]" [Use of a parenteral estroprogestin as an inhibitor of ovulation in a single monthly administration]. Minerva Ginecologica (in Italian). 27 (12): 964–968. PMID778680.
