Algestone acetophenide

Not to be confused with Algestone acetonide.
Algestone acetophenide
Clinical data
Trade namesPerlutal, Topasel, Unalmes, Yectames, many others
Other namesDihydroxyprogesterone acetophenide; DHPA; Deladroxone; Droxone; Alfasone acetophenide; Alphasone acetophenide; SQ-15101; 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
Routes of
administration		Intramuscular injection
Drug classProgestogen; Progestin
ATC code
  • None
Pharmacokinetic data
Elimination half-lifeIMTooltip Intramuscular injection: 24 days[1][2]
ExcretionPreferentially feces[1][2]
Identifiers
IUPAC name
  • (4aR,4bS,6aS,6bS,8R,9aR,10aS,10bR)-6b-Acetyl-4a,6a,8-trimethyl-8-phenyl-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.981
Chemical and physical data
FormulaC29H36O4
Molar mass448.603 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C)[C@]25O[C@@](O[C@@H]5C[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@]3(/C(=C\C(=O)CC3)CC4)C)(c6ccccc6)C
InChI
  • InChI=1S/C29H36O4/c1-18(30)29-25(32-28(4,33-29)19-8-6-5-7-9-19)17-24-22-11-10-20-16-21(31)12-14-26(20,2)23(22)13-15-27(24,29)3/h5-9,16,22-25H,10-15,17H2,1-4H3/t22-,23+,24+,25-,26+,27+,28-,29-/m1/s1
  • Key:AHBKIEXBQNRDNL-FVCOMRFXSA-N

Algestone acetophenide, also known more commonly as dihydroxyprogesterone acetophenide (DHPA) and sold under the brand names Perlutal and Topasel among others, is a progestin medication which is used in combination with an estrogen as a form of long-lasting injectable birth control.[3][4][5][6] It has also been used alone, but is no longer available as a standalone medication.[7][8][9] DHPA is not active by mouth and is given once a month by injection into muscle.[4][5][6]

Side effects of DHPA are similar to those of other progestins. DHPA is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[10][11][12] It has no other important hormonal activity.[10][13][11][12]

DHPA was discovered in 1958 and was introduced for medical use in the 1960s.[14][15][16] It was not introduced in the United States, but it is marketed widely throughout Latin America.[17][18][7][16] It was also previously available alone in Italy and as a combined injectable contraceptive in Portugal and Spain, but has been discontinued in these countries.[8]

  1. ^ a b Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception. 49 (4): 361–385. doi:10.1016/0010-7824(94)90033-7. PMID 8013220.
  2. ^ a b "Bula do Algestona Acetofenida + Enantato de Estradiol". Consulta Remédios. Archived from the original on 2018-09-18. Retrieved 2018-09-18.
  3. ^ Jarquín González JD, Elda de Aguirre L, Rodríguez C, Abrego de Aguilar M, Carrillo F, León DA, et al. (September 1996). "Dihydroxyprogesterone acetophenide 150 mg + estradiol enantate 10 mg as monthly injectable contraceptives". Advances in Contraception. 12 (3): 213–225. doi:10.1007/BF01849664. PMID 8910663. S2CID 2522426.
  4. ^ a b 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. doi:10.3109/01443619409027641. PMID 12290848.
  5. ^ a b 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" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357. Archived from the original (PDF) on 2017-08-10. Retrieved 2016-08-24.
  6. ^ a b Rowlands S (January 2009). "New technologies in contraception" (PDF). BJOG. 116 (2): 230–239. doi:10.1111/j.1471-0528.2008.01985.x. PMID 19076955. S2CID 3415547.
  7. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  8. ^ a b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Martindale was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference pmid13761080 was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference LernerBrennan1961 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference pmid4537624 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid865726 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Fried1960 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid13625604 was invoked but never defined (see the help page).
  16. ^ a b Cite error: The named reference RabeRunnebaum2012 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference GWU1987 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference SenanayakePotts2008 was invoked but never defined (see the help page).
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