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Identification
NameDihydrotestosterone
Accession NumberDB02901  (EXPT01199)
Typesmall molecule
Groupsexperimental, illicit
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
Synonyms
SynonymLanguageCode
(5a,17b)-17-Hydroxyandrostan-3-oneNot AvailableNot Available
(5alpha,17beta)-17-hydroxyandrostan-3-oneNot AvailableNot Available
17beta-Hydroxy-5alpha-androstan-3-oneNot AvailableNot Available
17beta-Hydroxy-5alpha-androstane-3-oneNot AvailableNot Available
17beta-Hydroxyandrostan-3-oneNot AvailableNot Available
4-DihydrotestosteroneNot AvailableNot Available
5.alpha.-DihydrotestosteroneNot AvailableNot Available
5a-DihydrotestosteroneNot AvailableNot Available
5alpha dihydrotestosteroneNot AvailableNot Available
5alpha-DihydrotestosteroneNot AvailableNot Available
AnaboleenNot AvailableNot Available
AndroloneNot AvailableNot Available
Androstan-17b-ol-3-oneNot AvailableNot Available
Androstan-17beta-ol-3-oneNot AvailableNot Available
AndrostanoloneNot AvailableINN
StanaprolNot AvailableNot Available
StanoloneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AnabolexNot Available
AnaprotinNot Available
AndractimNot Available
Cristerona MBNot Available
NeodrolNot Available
ProteinaNot Available
ProtonaNot Available
Brand mixturesNot Available
Categories
CAS number521-18-6
WeightAverage: 290.4403
Monoisotopic: 290.224580204
Chemical FormulaC19H30O2
InChI KeyInChIKey=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
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
Mass Specshow(11.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassAndrogens and Derivatives
Direct parentAndrogens and Derivatives
Alternative parentsKetosteroids; Hydroxysteroids; Cyclohexanones; Secondary Alcohols; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclohexanone; cyclic alcohol; secondary alcohol; ketone; polyamine; alcohol; carbonyl group
Classification descriptionThis compound belongs to the androgens and derivatives. These are hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionBioavailability is very low (0-2%) following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Dihydrotestosterone
    11-Oxo-androsterone glucuronideDetails
    Dihydrotestosterone
      3-alpha-Androstanediol glucuronideDetails
      Dihydrotestosterone
        11-beta-Hydroxyandrosterone-3-glucuronideDetails
        Route of eliminationNot Available
        Half lifeNot Available
        ClearanceNot Available
        ToxicityOral LD50 in rat is 7060 mg/kg. Oral LD50 in mouse is 3450 mg/kg.
        Affected organisms
        • Humans and other mammals
        PathwaysNot Available
        SNP Mediated EffectsNot Available
        SNP Mediated Adverse Drug ReactionsNot Available
        ADMET
        Predicted ADMET features
        Property Value Probability
        Human Intestinal Absorption + 1.0
        Blood Brain Barrier + 0.9818
        Caco-2 permeable + 0.8846
        P-glycoprotein substrate Substrate 0.57
        P-glycoprotein inhibitor I Non-inhibitor 0.5631
        P-glycoprotein inhibitor II Non-inhibitor 0.846
        Renal organic cation transporter Non-inhibitor 0.7884
        CYP450 2C9 substrate Non-substrate 0.7715
        CYP450 2D6 substrate Non-substrate 0.93
        CYP450 3A4 substrate Substrate 0.7314
        CYP450 1A2 substrate Non-inhibitor 0.6853
        CYP450 2C9 substrate Non-inhibitor 0.9071
        CYP450 2D6 substrate Non-inhibitor 0.971
        CYP450 2C19 substrate Non-inhibitor 0.9025
        CYP450 3A4 substrate Non-inhibitor 0.8546
        CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9647
        Ames test Non AMES toxic 0.9414
        Carcinogenicity Non-carcinogens 0.9182
        Biodegradation Not ready biodegradable 0.9686
        Rat acute toxicity 1.9757 LD50, mol/kg Not applicable
        hERG inhibition (predictor I) Weak inhibitor 0.9444
        hERG inhibition (predictor II) Non-inhibitor 0.576
        Pharmacoeconomics
        ManufacturersNot Available
        PackagersNot Available
        Dosage formsNot Available
        PricesNot Available
        PatentsNot Available
        Properties
        Statesolid
        Experimental Properties
        PropertyValueSource
        melting point181 °CPhysProp
        water solubility5.25E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
        logP3.55HANSCH,C ET AL. (1995)
        Predicted Properties
        PropertyValueSource
        water solubility9.98e-03 g/lALOGPS
        logP3.37ALOGPS
        logP3.41ChemAxon
        logS-4.5ALOGPS
        pKa (strongest acidic)19.38ChemAxon
        pKa (strongest basic)-0.88ChemAxon
        physiological charge0ChemAxon
        hydrogen acceptor count2ChemAxon
        hydrogen donor count1ChemAxon
        polar surface area37.3ChemAxon
        rotatable bond count0ChemAxon
        refractivity83.6ChemAxon
        polarizability34.17ChemAxon
        number of rings4ChemAxon
        bioavailability1ChemAxon
        rule of fiveYesChemAxon
        Ghose filterYesChemAxon
        Veber's ruleYesChemAxon
        MDDR-like ruleNoChemAxon
        Spectra
        SpectraNot Available
        References
        Synthesis Reference

        A. Glenn Braswell, Aftab J. Ahmed, “Composition for inhibiting production of dihydrotestosterone to treat benign prostate hyperplasia.” U.S. Patent US6264996, issued October, 1996.

        US6264996
        General ReferenceNot Available
        External Links
        ResourceLink
        KEGG CompoundC03917
        PubChem Compound15
        PubChem Substance46506828
        ChemSpider14
        BindingDB18161
        ChEBI16330
        ChEMBL
        HETDHT
        WikipediaDihydrotestosterone
        ATC CodesA14AA01G03BB02
        AHFS CodesNot Available
        PDB Entries
        FDA labelNot Available
        MSDSshow(111 KB)
        Interactions
        Drug InteractionsNot Available
        Food InteractionsNot Available

        1. Estradiol 17-beta-dehydrogenase 1

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Components

        Name UniProt ID Details
        Estradiol 17-beta-dehydrogenase 1 P14061 Details

        2. Androgen receptor

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Components

        Name UniProt ID Details
        Androgen receptor P10275 Details

        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

        1. Cholesterol side-chain cleavage enzyme, mitochondrial

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cholesterol side-chain cleavage enzyme, mitochondrial P05108 Details

        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. Steroid 17-alpha-hydroxylase/17,20 lyase

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Steroid 17-alpha-hydroxylase/17,20 lyase P05093 Details

        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

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 19A1 P11511 Details

        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

        1. Sex hormone-binding globulin

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Components

        Name UniProt ID Details
        Sex hormone-binding globulin P04278 Details

        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

        1. Multidrug resistance protein 1

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Multidrug resistance protein 1 P08183 Details

        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

        Comments
        Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19