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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AnabolexNot Available
AnaprotinNot Available
AndractimNot Available
Cristerona MBNot Available
NeodrolNot Available
ProteinaNot Available
ProtonaNot Available
Brand mixturesNot Available
SaltsNot 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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
CC12CCC3C(CCC4CC(=O)CCC34C)C1CCC2O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • Cyclohexanone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9818
Caco-2 permeable+0.8846
P-glycoprotein substrateSubstrate0.57
P-glycoprotein inhibitor INon-inhibitor0.5631
P-glycoprotein inhibitor IINon-inhibitor0.846
Renal organic cation transporterNon-inhibitor0.7884
CYP450 2C9 substrateNon-substrate0.7715
CYP450 2D6 substrateNon-substrate0.93
CYP450 3A4 substrateSubstrate0.7314
CYP450 1A2 substrateNon-inhibitor0.6853
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.971
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9414
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity1.9757 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9444
hERG inhibition (predictor II)Non-inhibitor0.576
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 Solubility0.00998 mg/mLALOGPS
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 Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m3·mol-1ChemAxon
Polarizability34.17 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.2 KB)
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (111 KB)
Interactions
Drug Interactions
Drug
AcarboseMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
AcenocoumarolMay enhance the anticoagulant effect of Vitamin K Antagonists.
AlbiglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
AlogliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
BromocriptineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
C1 esterase inhibitorMay enhance the thrombogenic effect of C1 inhibitors.
CanagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
ChlorpropamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
CorticotropinCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
Cortisone acetateCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
DapagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
DisopyramideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
DulaglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
EmpagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
ExenatideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
FludrocortisoneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
GliclazideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlimepirideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlipizideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlyburideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
inhaled insulinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin AspartMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin DetemirMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin GlargineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin GlulisineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin LisproMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin RegularMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LanreotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LinagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LiraglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MecaserminMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MetforminMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MethylprednisoloneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
MifepristoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MiglitolMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
NateglinideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
OctreotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PasireotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PentamidineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PioglitazoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PramlintideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PrednisoneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
QuinineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
RepaglinideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
RosiglitazoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SaxagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SitagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfadiazineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfamethoxazoleMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfisoxazoleMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SunitinibMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TolazamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TolbutamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Food InteractionsNot Available

Targets

1. 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

2. Estradiol 17-beta-dehydrogenase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

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

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