Norclostebol

{{Short description|Chemical compound}}

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| verifiedrevid = 444588255

| IUPAC_name = (8R,9S,10R,13S,14S,17S)-4-Chloro-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one

| image = Norclostebol.svg

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| image2 = Norclostebol molecule ball.png

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| tradename = Lentabol

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| CAS_number = 13583-21-6

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| PubChem = 166576

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

| ChemSpiderID = 145769

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| UNII = VI1001O2DI

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| synonyms = SKF-6611; CP-73; 4-Chloroestr-4-en-17β-ol-3-one

| C=18 | H=25 | Cl=1 | O=2

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

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| StdInChI = 1S/C18H25ClO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h10-12,14,16,21H,2-9H2,1H3/t10-,11-,12-,14+,16+,18+/m1/s1

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

| StdInChIKey = OZDDFAQVVGFDJP-YGRHGMIBSA-N

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Norclostebol ({{abbrlink|INN|International Nonproprietary Name}}; brand name Lentabol; former developmental code names SKF-6611, CP-73) is a synthetic androgen and anabolic steroid (AAS) that was derived from nandrolone.{{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=PA168|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=168–}}{{cite book| vauthors = Karch SB |title=Pathology, Toxicogenetics, and Criminalistics of Drug Abuse|url=https://books.google.com/books?id=bniSB1_pouYC&pg=PA67|date=9 October 2007|publisher=CRC Press|isbn=978-1-4200-5456-9|pages=67–}}{{cite book| vauthors = Wright JE |title=Anabolic Steroids and Sports: A Comprehensive, Up-to-date Summary and Discussion of the Scientific Findings about the Controversial Drugs Widely Used to Increase Muscle Size and Strength|url=https://books.google.com/books?id=PYNFAAAAYAAJ|year=1982|publisher=Sports Science Consultants|isbn=978-0-9609306-0-9}} It was described in the literature in 1957. Norclostebol is also used as an ester, norclostebol acetate (brand name Anabol 4-19).

Norclostebol is a 4-chloro derivative of testosterone. It works out to be significantly stronger than pure testosterone. It is approximately 6.6 times as anabolic while only 40% as androgenic. This may not be a particularly fair or valid comparison however. It is more appropriate to compare norclostebol to testosterone propionate due to the use of an ester. In this case they are fairly even in anabolic potency at 112% but only 20–25% as androgenic. In practice this means norclostebol is a potent anabolic compound with minimal tendency towards side effects.{{cite journal | vauthors = Le Bizec B, Van Hoof N, Courtheyn D, Gaudin I, Van De Wiele M, Bichon E, De Brabander H, André F | title = New anabolic steroid illegally used in cattle-structure elucidation of 19-norchlorotestosterone acetate metabolites in bovine urine | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 98 | issue = 1 | pages = 78–89 | date = January 2006 | pmid = 16216493 | doi = 10.1016/j.jsbmb.2005.07.008 }}