{"ATC Code":"A - Alimentary tract and metabolism","Abbreviation":"DHT","Aliases":["STANOLONE","Androstanolone","Andractim","Anabolex","Androlone","Neodrol","4-Dihydrotestosterone","5alpha-Dihydrotestosterone","Anaboleen","Stanaprol"],"CAS":"521-18-6","CanonicalSMILES":"CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C","ChEBI":"CHEBI:16330","ChEMBL":"CHEMBL27769","ChemicalClasses":["steroid"],"Dosing Info":[],"DrugClasses":[],"European Community (EC) Number":"208-307-3","Human Drugs":"Pharmaceuticals","IUPACName":"(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one","InChI":"InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1","InChIKey":"NVKAWKQGWWIWPM-ABEVXSGRSA-N","MeSH Pharmacological Classification":"Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)","Melting Point":"181 °C","MolecularFormula":"C\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"290.4 g/mol","Physical Description":"Solid","PubChemId":10635,"Record Description":["17beta-hydroxy-5alpha-androstan-3-one is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a 17beta-hydroxy steroid, a 17beta-hydroxyandrostan-3-one and a 3-oxo-5alpha-steroid. It derives from a hydride of a 5alpha-androstane.","A potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.","Androstanolone has been reported in Homo sapiens, Aeromonas veronii, and Daphnia magna with data available.","Therapeutic Androstanolone is a therapeutic anabolic steroid hormone identical to endogenous dihydrotestosterone.  Androstanolone binds to and activates specific nuclear receptors.  This agent may be used for testosterone replacement therapy in hypogonadal men, in HIV-wasting syndrome, and in other conditions in order to increase nitrogen retention and fat-free muscle mass. (NCI04)","Dihydrotestosterone is the most potent androgen, required for sex development. Dihydrotestosterone is synthesized from testosterone in the prostate gland, testes, hair follicles and adrenal glands by 5-alpha reductase. Dihydrotestosterone exerts its action similar to testosterone, which binds to and activates specific nuclear androgen receptors.  After translocation into the nucleus, the activated hormone-receptor complex binds to the androgen response elements on the DNA and activates gene expressions that are required for sex development. Dihydrotestosterone is responsible for the formation of male primary sex characteristics and most male secondary sex characteristics during puberty, such as muscular growth, facial and body hair growth, and deepening of the voice.","STANOLONE is a small molecule drug with a maximum clinical trial phase of II and has 1 investigational indication.","Dihydrotestosterone is a potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid. -- Pubchem; Dihydrotestosterone (DHT) (INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5-alpha-reductase by means of reducing the alpha 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent than testosterone because of increased affinity to the androgen receptor. -- Wikipedia.","A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.","17beta-hydroxy-5alpha-androstan-3-one is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a 17beta-hydroxy steroid, a 17beta-hydroxyandrostan-3-one and a 3-oxo-5alpha-steroid. It derives from a hydride of a 5alpha-androstane."],"References":[{"name":"Wikipedia","url":"https://en.wikipedia.org/wiki/Dihydrotestosterone"},{"name":"Wikidata","url":"https://www.wikidata.org/wiki/Q411054"},{"name":"DrugBank","url":"https://go.drugbank.com/drugs/DB02901"},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/compound/10635"},{"name":"ChemSpider","url":"https://www.chemspider.com/Chemical-Structure.10189.html"},{"name":"ChEMBL","url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL27769"},{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16330"},{"name":"Common Chemistry","url":"https://commonchemistry.cas.org/detail?cas_rn=521-18-6"},{"name":"HMDB","url":"https://hmdb.ca/metabolites/HMDB0002961"},{"name":"KEGG","url":"https://www.kegg.jp/entry/C03917"},{"name":"UNII","url":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/08J2K08A3Y"},{"name":"EPA DSSTox","url":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID9022364"}],"Solubility":"525 mg/mL at 25 °C","StructureBase64":"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