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Identification
Name Dihydrotestosterone
Accession Number DB02901 (EXPT01199)
Type small molecule
Groups illicit, experimental
Description

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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(5a,17b)-17-Hydroxyandrostan-3-one
(5alpha,17beta)-17-hydroxyandrostan-3-one
17beta-Hydroxy-5alpha-androstan-3-one
17beta-Hydroxy-5alpha-androstane-3-one
17beta-Hydroxyandrostan-3-one
4-Dihydrotestosterone
5.alpha.-Dihydrotestosterone
5a-Dihydrotestosterone
5alpha dihydrotestosterone
5alpha-Dihydrotestosterone
Anaboleen
Androlone
Androstan-17b-ol-3-one
Androstan-17beta-ol-3-one
Androstanolone
Stanaprol
Stanolone
First Prev Next Last
Salts Not Available
Brand names
Name Company
Anabolex
Anaprotin
Andractim
Cristerona MB
Neodrol
Proteina
Protona
Brand mixtures Not Available
Categories
  • Androgens
  • Steroidal
CAS number 521-18-6
Weight Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula C19H30O2
InChI Key InChIKey=NVKAWKQGWWIWPM-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
SMILES
CC12CCC3C(CCC4CC(=O)CCC34C)C1CCC2O
Plain Text
Mass Spec show (11.2 KB)
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Bicyclohexanes
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Bioavailability is very low (0-2%) following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Dihydrotestosterone
    		11-Oxo-androsterone glucuronide Details
    Dihydrotestosterone
      		3-alpha-Androstanediol glucuronide Details
      Dihydrotestosterone
        		11-beta-Hydroxyandrosterone-3-glucuronide Details
        Route of elimination Not Available
        Half life Not Available
        Clearance Not Available
        Toxicity Oral LD50 in rat is 7060 mg/kg. Oral LD50 in mouse is 3450 mg/kg.
        Affected organisms
        • Humans and other mammals
        Pathways Not Available
        Pharmacoeconomics
        Manufacturers Not Available
        Packagers Not Available
        Dosage forms Not Available
        Prices Not Available
        Patents Not Available
        Properties
        State solid
        Experimental Properties
        Property Value Source
        melting point 181 °C PhysProp
        water solubility 5.25E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
        logP 3.55 HANSCH,C ET AL. (1995)
        Predicted Properties
        Property Value Source
        water solubility 9.98e-03 g/l ALOGPS
        logP 3.37 ALOGPS
        logP 3.41 ChemAxon
        logS -4.5 ALOGPS
        pKa (strongest acidic) 19.38 ChemAxon
        pKa (strongest basic) -0.88 ChemAxon
        physiological charge 0 ChemAxon
        hydrogen acceptor count 2 ChemAxon
        hydrogen donor count 1 ChemAxon
        polar surface area 37.3 ChemAxon
        rotatable bond count 0 ChemAxon
        refractivity 83.6 ChemAxon
        polarizability 34.17 ChemAxon
        References
        Synthesis Reference Not Available
        General Reference Not Available
        External Links
        Resource Link
        KEGG Compound C03917 Link_out
        PubChem Compound 15 Link_out
        PubChem Substance 46506828 Link_out
        ChemSpider 14 Link_out
        BindingDB 18161 Link_out
        ChEBI 16330 Link_out
        ChEMBL 16330 Link_out
        HET DHT Link_out
        Wikipedia http://en.wikipedia.org/wiki/Dihydrotestosterone Link_out
        ATC Codes
        • A14AA01
        • G03BB02
        AHFS Codes Not Available
        PDB Entries
        FDA label Not Available
        MSDS show (111 KB)
        Interactions
        Drug Interactions Not Available
        Food Interactions Not Available
        Targets

        1. Estradiol 17-beta-dehydrogenase 1

        Pharmacological action: unknown

        Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH

        Organism class: human
        UniProt ID: P14061 Link_out
        Gene: HSD17B1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        2. Androgen receptor

        Pharmacological action: unknown

        The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

        Organism class: human
        UniProt ID: P10275 Link_out
        Gene: AR Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Askew EB, Gampe RT Jr, Stanley TB, Faggart JL, Wilson EM: Modulation of androgen receptor activation function 2 by testosterone and dihydrotestosterone. J Biol Chem. 2007 Aug 31;282(35):25801-16. Epub 2007 Jun 25. Pubmed
        2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
        Enzymes

        1. Cholesterol side-chain cleavage enzyme, mitochondrial

        Actions: substrate

        Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone

        UniProt ID: P05108 Link_out
        Gene: CYP11A1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        2. Cytochrome P450 17A1

        Actions: substrate

        Conversion of pregnenolone and progesterone to their 17- alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty

        UniProt ID: P05093 Link_out
        Gene: CYP17A1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        3. Cytochrome P450 19A1

        Actions: substrate

        Catalyzes the formation of aromatic C18 estrogens from C19 androgens

        UniProt ID: P11511 Link_out
        Gene: CYP19A1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
        Transporters

        1. Multidrug resistance protein 1

        Actions: substrate

        Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

        UniProt ID: P08183 Link_out
        Gene: ABCB1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Fedoruk MN, Gimenez-Bonafe P, Guns ES, Mayer LD, Nelson CC: P-glycoprotein increases the efflux of the androgen dihydrotestosterone and reduces androgen responsive gene activity in prostate tumor cells. Prostate. 2004 Apr 1;59(1):77-90. Pubmed
        Carriers

        1. Sex hormone-binding globulin

        Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration

        UniProt ID: P04278 Link_out
        Gene: SHBG Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        SNPs: SNPJam Report Link_out

        References:
        1. Metzger J, Schnitzbauer A, Meyer M, Soder M, Cuilleron CY, Hauptmann H, Huber E, Luppa PB: Binding analysis of 1alpha- and 17alpha-dihydrotestosterone derivatives to homodimeric sex hormone-binding globulin. Biochemistry. 2003 Nov 25;42(46):13735-45. Pubmed
        2. Hauptmann H, Metzger J, Schnitzbauer A, Cuilleron CY, Mappus E, Luppa PB: Syntheses and ligand-binding studies of 1 alpha- and 17 alpha-aminoalkyl dihydrotestosterone derivatives to human sex hormone-binding globulin. Steroids. 2003 Sep;68(7-8):629-39. Pubmed
        Comments
        Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:21