Allyltestosterone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-prop-2-enyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

| image = 17a-allyltestosterone_structure.png

| width = 250px

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 98169-58-5

| CAS_supplemental =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 54HM6O0YGK

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 22808244

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID = 58190189

| KEGG =

| ChEBI =

| ChEMBL =

| synonyms = 17α-Allyltestosterone; 17α-Allylandrost-4-en-17β-ol-3-one

| C=22 | H=32 | O=2

| SMILES = C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)CC=C

| StdInChI = 1S/C22H32O2/c1-4-10-22(24)13-9-19-17-6-5-15-14-16(23)7-11-20(15,2)18(17)8-12-21(19,22)3/h4,14,17-19,24H,1,5-13H2,2-3H3/t17-,18+,19+,20+,21+,22-/m1/s1

| StdInChIKey = DFRQHISHXQPKMU-VEYVBMQYSA-N

}}

Allyltestosterone, or 17α-allyltestosterone, also known as 17α-allylandrost-4-en-17β-ol-3-one, is a steroid derived from testosterone that was first synthesized in 1936 and was never marketed.{{cite book| chapter = Allyltestosterone | vauthors = Josephy E, Radt F |title=Elsevier's Encyclopaedia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds| chapter-url = https://books.google.com/books?id=HqHzCAAAQBAJ&pg=PA2653|date=1 December 2013|publisher=Springer|isbn=978-3-662-25863-7|pages=2653–}}{{cite book | vauthors = Ahluwalia GS | chapter = Management of unwanted hair | veditors = Ahluwalia G |title=Cosmetics Applications of Laser and Light-Based Systems| chapter-url = https://books.google.com/books?id=OvYSProMAiUC&pg=PA248|date=16 December 2008|publisher=William Andrew|isbn=978-0-8155-1967-6|pages=239–252 (248) }} Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor.{{cite patent | url = https://www.google.com/patents/US4885289 | country = US | number = 4885289 | title = Alteration of character of male beard growth | inventor = Breuer MM, Kaszynski EG, Shander D, Usdin VR, van der Lee H | assign1 = Gillette Co LLC | gdate = 5 December 1989 | postscript = . }} Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest.{{cite book| vauthors = Zeelen FJ |title=Medicinal chemistry of steroids|url=https://books.google.com/books?id=px9tAAAAMAAJ|year=1990|publisher=Elsevier Science Limited|isbn=978-0-444-88727-6|pages=108–109|quote=Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest.}} These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.{{cite journal | vauthors = Bergink EW, Loonen PB, Kloosterboer HJ | title = Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties | journal = Journal of Steroid Biochemistry | volume = 23 | issue = 2 | pages = 165–168 | date = August 1985 | pmid = 3928974 | doi = 10.1016/0022-4731(85)90232-8 }}{{cite journal | vauthors = Madjerek Z, De Visser J, Van Der Vies J, Overbeek GA | title = Allylestrenol, a pregnancy maintaining oral gestagen | journal = Acta Endocrinologica | volume = 35 | issue = I | pages = 8–19 | date = September 1960 | pmid = 13765069 | doi = 10.1530/acta.0.XXXV0008 }}{{cite book | vauthors = Bain FT | chapter = Infectious arthritis and osteomyelitis | veditors = McKinnon AO, Squires EL, Vaala WE, Varner DD |title=Equine Reproduction| chapter-url = https://books.google.com/books?id=QPJQT6-g-YMC&pg=PT4462 |date=5 July 2011|publisher=John Wiley & Sons|isbn=978-0-470-96187-2|pages= 457–462 }}{{cite book|author1=Committee to Review the Bureau of Land Management Wild Horse and Burro Management Program|author2=Board on Agriculture and Natural Resources|author3=Division on Earth and Life Studies|author4=National Research Council | chapter = Methods and Effects of Fertility Management |title=Using Science to Improve the BLM Wild Horse and Burro Program: A Way Forward| chapter-url = https://books.google.com/books?id=0T5eAgAAQBAJ&pg=PA120|date=4 October 2013|publisher=National Academies Press|isbn=978-0-309-26494-5|pages= 93–142 (120) }}