Enestebol

{{Short description|Chemical compound}}

{{Drugbox

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| verifiedrevid = 444396795

| IUPAC_name = (8R,9S,10R,13S,14S)-4,17-dihydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one

| image = Enestebol.png

| alt = Skeletal formula of the enestebol molecule

| width = 225px

| image2 = Enestebol 3D ball.png

| alt2 = Ball-and-stick model of the enestebol molecule

| width2 = 225px

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| routes_of_administration = By mouth

| class = Androgen; Anabolic steroid

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 2320-86-7

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| PubChem = 208919

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16736606

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

| UNII = LNS3MVH7NV

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104239

| synonyms = 4,17β-Dihydroxy-17α-methylandrosta-1,4-dien-3-one

| C=20 | H=28 | O=3

| SMILES=C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2(C)O)CCC4=C(C(=O)C=C[C@]34C)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C20H28O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,22-23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = XMPHGFYWQPUCAG-XMUHMHRVSA-N

}}

Enestebol ({{abbrlink|INN|International Nonproprietary Name}}), also known as 4-hydroxy-17α-methyl-δ¹-testosterone, as well as 4,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of testosterone which was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA417|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=417–}} It is closely related to oxymesterone (4-hydroxy-17α-methyltestosterone), as well as to chlorodehydromethyltestosterone (4-chloro-17α-methyl-δ¹-testosterone), methylclostebol (4-chloro-17α-methyltestosterone), and metandienone (17α-methyl-δ¹-testosterone).