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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 KeyNVKAWKQGWWIWPM-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
Not Available
11-Oxo-androsterone glucuronideDetails
Dihydrotestosterone
Not Available
3-alpha-Androstanediol glucuronideDetails
Dihydrotestosterone
Not Available
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

Targets

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

Enzymes

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

Carriers

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

Transporters

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

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