Algestone acetophenide

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Algestone acetophenide
Algestone acetophenide.svg
Clinical data
Trade names Deladroxate, others
Synonyms Dihydroxyprogesterone acetophenide; DHPA; 16α,17α-Dihydroxyprogesterone acetophenide; 16α,17α-Dihydroxypregn-4-ene-3,20-dione cyclic acetal with acetophenone; (R)-16α,17-[(1-Phenylethylidene)dioxy]pregn-4-ene-3,20-dione; Alfasone acetophenide; Alphasone acetophenide
Routes of
Intramuscular injection
Drug class Progestin; Progestogen
ATC code
  • None
CAS Number
PubChem CID
ECHA InfoCard 100.041.981 Edit this at Wikidata
Chemical and physical data
Formula C29H36O4
Molar mass 448.603 g/mol
3D model (JSmol)

Algestone acetophenide, also known as dihydroxyprogesterone acetophenide (DHPA) and sold under the brand name Deladroxate among others, is a progestin medication which is used in combination with an estrogen as a form of long-lasting injectable birth control.[1][2][3] It has also been used to a much lesser extent alone.[4] The medication is not effective by mouth and must be given by injection into muscle, typically once per month.[1][2][3]

Side effects of algestone acetophenide are similar to those of other progestins. Algestone acetophenide is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[5][6][7] It has no other important hormonal activity.[5][6][7]

Algestone acetophenide was discovered in 1958 and was introduced for medical use in the 1960s.[8][9][10] It was not introduced in the United States, but it is marketed widely throughout Latin America, as well as in Spain and Italy.[11][12][4][10]

Medical uses[edit]

Algestone acetophenide is used in combination with estradiol enanthate as a once-monthly combined injectable contraceptive for women in Latin America and Spain.[1][2][3] It has also been marketed for use alone in Italy.[4]

Available forms[edit]

The following forms of algestone acetophenide in combination with an estrogen are available:[2]

  • 150 mg algestone acetophenide and 10 mg estradiol enanthate (brand names Deladroxate, Perlutan, Topasel)
  • 75 mg algestone acetophenide and 5 mg estradiol enanthate (brand names Anafertin, Yectames)

Side effects[edit]

Side effects of algestone acetophenide are similar to those of other progestins.[citation needed]



Algestone acetophenide is a progestogen, or an agonist of the progesterone receptor.[5][6][7] It is said to be both more potent and longer-acting than the related progestogen hydroxyprogesterone caproate.[13] The medication has no androgenic, antiandrogenic, estrogenic, glucocorticoid, or antimineralocorticoid activities.[5][6][7]


Algestone acetophenide, also known as 16α,17α-dihydroxyprogesterone acetophenide, as well as 16α,17α-dihydroxypregn-4-ene-3,20-dione cyclic acetal with acetophenone or as (R)-16α,17-[(1-phenylethylidene)dioxy]pregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone.[14][4][15] It is specifically a derivative of 17α-hydroxyprogesterone with an additional hydroxyl group at the C17α position, or of algestone (16α,17α-dihydroxyprogesterone), and with the two hydroxyl groups cyclized into an acetophenide moiety (a cyclic acetal with acetophenone).[14][4][15] Analogues of algestone acetophenide include other 17α-hydroxyprogesterone derivatives such as algestone acetonide, chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate, and segesterone acetate.[14][4]


Algestone acetophenide was first described in the literature in 1958 and was patented in 1960.[8][9] It was developed in combination with estradiol enanthate as a long-lasting combined injectable contraceptive under the tentative brand name Deladroxate by Squibb and was studied in women starting in 1964.[16][17][18] Development was discontinued by Squibb in the United States in the late 1960s due to concerns of toxicological findings in animals, including mammary gland tumors in beagle dogs and pituitary hyperplasia in rats, as well as possible accumulation of estradiol enanthate in the body with continued use.[11][10] Subsequent research has shed doubt that these animal findings are applicable to humans and that the dosages required for contraception would pose any risks.[11] Although the medication was not marketed in the United States, its development was continued elsewhere and it went on to be introduced and widely used in Latin America and Spain.[12][4][10] A standalone version of algestone acetophenide was introduced in Italy in 1982 under the brand names Neolutin Depo and Neolutin Depositum.[15][4]

Society and culture[edit]

Generic names[edit]

Algestone acetophenide is the generic name of the drug and its USAN.[14][19] It is also known as dihydroxyprogesterone acetophenide (DHPA).[14][4][19]

Brand names[edit]

Algestone acetophenide is or has been marketed, mostly in combination with estradiol enanthate, under the brand names Agurin, Algestonam, Bovitrol, Ciclovular, Decadroxone, Deladroxone, Deproxone, Dexadroxate, Droxone, Exuna, Horprotal, Neolutin, Nomagest, Novular, Patector, Patectro, Perludil, Perlutal, Perlutan, Soluna, Topasel, Uno-Ciclo, and Yectames.[14][4][15][19][12][10]


Algestone acetophenide has been marketed widely throughout Latin America, including in Argentina, Belize, Brazil, the Dominican Republic, El Salvador, Guatemala, Honduras, Mexico, Nicaragua, Panama, and Peru among others.[4][15][19][12] It has also been marketed in Spain and Italy.[12][4][10]


  1. ^ a b c Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". J Obstet Gynaecol (Lahore). 4 Suppl 1: S1–34. doi:10.3109/01443619409027641. PMID 12290848. 
  2. ^ a b c d Bagade, O., Pawar, V., Patel, R., Patel, B., Awasarkar, V., & Diwate, S. (2014). Increasing Use of Long-Acting Reversible Contraception: Safe, Reliable, and Cost-Effective Birth Control.
  3. ^ a b c Rowlands, S (2009). "New technologies in contraception". BJOG: An International Journal of Obstetrics & Gynaecology. 116 (2): 230–239. doi:10.1111/j.1471-0528.2008.01985.x. ISSN 1470-0328. 
  4. ^ a b c d e f g h i j k l Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 26–. ISBN 978-3-88763-075-1. 
  5. ^ a b c d Lerner LJ, Brennan DM, Borman A (1961). "Biological activities of 16 alpha, 17 alpha dihydroxyprogesterone derivatives". Proc. Soc. Exp. Biol. Med. 106: 231–4. doi:10.3181/00379727-106-26296. PMID 13761080. 
  6. ^ a b c d Lerner, L. J., Brennan, D. M., DePhillipo, M., & Yiacas, E. (1961). Comparison of biological activities of progesterone, norethisterone and the acetophenone derivatives of 16 alpha, 17 alpha-dihydroxyprogesterone.(Abstr.). In Federation Proceedings (Vol. 20, p. 200).
  7. ^ a b c d Kurihara N, Tadokoro S, Ogawa H (1972). "Studies on hormonal actions of dihydroxyprogesterone acetophenide, estradiol enanthate and their mixtures". Jpn. J. Pharmacol. 22 (1): 43–58. doi:10.1254/jjp.22.43. PMID 4537624. 
  8. ^ a b Fried, J. (1960). U.S. Patent No. 2,941,997. Washington, DC: U.S. Patent and Trademark Office.
  9. ^ a b Fried J, Borman A (1958). "Synthetic derivatives of cortical hormones". Vitam. Horm. 16: 303–74. PMID 13625604. 
  10. ^ a b c d e f Thomas Rabe; Benno Runnebaum (6 December 2012). Fertility Control — Update and Trends: Update and Trends. Springer Science & Business Media. pp. 183–. ISBN 978-3-642-86696-8. Two additional monthly, combined injectable methods warrant mention. Deladroxate (commercially labelled as Perlutan, Topasel, Agurin, Horprotal and Uno-Ciclo in various countries), is a combination of 150 mg dihydroxyprogesterone acetophenide and 10 mg estradiol enanthate, and is available in many Latin American countries and Spain. The method is highly effective, without a single pregnancy reported in large clinical trials (Koetsawang 1994). Although available since the 1960s, the method has not been studied as extensively as Cyclofem or Mesigyna. The original manufacturer withdrew support due to toxicological concerns with dihydroxyprogesterone acetophenide, and clinical evaluations continue to be published. A recent dose-finding trial compared the standard available dose of 150/10 with a lower dose of 90/6, and concluded the lower dose was equally effective (Coutinho et al., 1997). 
  11. ^ a b c Population Reports: Injectables and implants. Department of Medical and Public Affairs, George Washington University. 1987. p. K-75. In the US, Squibb Pharmaceutical Company withdrew Deladroxate from clinical testing in the late 1960s because of concerns over (1) breast tumors in beagle dogs, (2) pituitary hyperplasia in rats, and (3) possible accumulation of estradiol enanthate in the body with continued use (89, 98, 243). Subsequently, however, questions have been raised about whether such animal findings are applicable to humans. Research suggests that the adverse effects of Deladroxate on animals may occur only with doses higher than the equivalent of a contraceptive dose (2, 62, 82, 121, 272). 
  12. ^ a b c d e Pramilla Senanayake; Malcolm Potts (14 April 2008). Atlas of Contraception, Second Edition. CRC Press. pp. 50–. ISBN 978-0-203-34732-4. 
  13. ^ Kawakami M, Sawyer CH (1967). "Effects of sex hormones and antifertility steroids in brain thresholds in the rabbit". Endocrinology. 80 (5): 857–71. doi:10.1210/endo-80-5-857. PMID 4164655. 
  14. ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 27–. ISBN 978-1-4757-2085-3. 
  15. ^ a b c d e William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 153–. ISBN 978-0-8155-1856-3. 
  16. ^ Rutherford RN, Banks AL, Coburn WA (1964). "Deladroxate for the Prevention of Ovulation". Fertil. Steril. 15: 648–52. doi:10.1016/s0015-0282(16)35410-3. PMID 14236841. 
  17. ^ Taymor ML, Planck S, Yahia C (1964). "Ovulation Inhibition with a Long-Acting Parenteral Progestogen-Estrogen Combination". Fertil. Steril. 15: 653–60. doi:10.1016/s0015-0282(16)35411-5. PMID 14236842. 
  18. ^ Paolo Giovanni Artini; Andrea R. Genazzani; Felice Petraglia (11 December 2001). Advances in Gynecological Endocrinology. CRC Press. pp. 101–. ISBN 978-1-84214-071-0. Subseuqently another formulation of 150 mg of dihydroxyprogesterone acetophenide (DHPA) with 10 mg estradiol enanthate (E2-EN) was tested in the 1960s3-6. 
  19. ^ a b c d