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Identification
NameDihydrotestosterone
Accession NumberDB02901  (EXPT01199)
TypeSmall Molecule
GroupsIllicit
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
(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
External Identifiers Not 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
UNII08J2K08A3Y
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[8.7.0.0²,⁷.0¹¹,¹⁵]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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.971
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 ReferencesNot Available
External Links
ATC CodesA14AA01G03BB02
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (111 KB)
Interactions
Drug Interactions
Drug
AcarboseDihydrotestosterone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolDihydrotestosterone may increase the anticoagulant activities of Acenocoumarol.
AlbiglutideDihydrotestosterone may increase the hypoglycemic activities of Albiglutide.
AlogliptinDihydrotestosterone may increase the hypoglycemic activities of Alogliptin.
BetamethasoneBetamethasone may increase the fluid retaining activities of Dihydrotestosterone.
BromocriptineDihydrotestosterone may increase the hypoglycemic activities of Bromocriptine.
CanagliflozinDihydrotestosterone may increase the hypoglycemic activities of Canagliflozin.
ChlorpropamideDihydrotestosterone may increase the hypoglycemic activities of Chlorpropamide.
CorticotropinCorticotropin may increase the fluid retaining activities of Dihydrotestosterone.
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Dihydrotestosterone.
CyclosporineDihydrotestosterone may increase the hepatotoxic activities of Cyclosporine.
DapagliflozinDihydrotestosterone may increase the hypoglycemic activities of Dapagliflozin.
DexamethasoneDexamethasone may increase the fluid retaining activities of Dihydrotestosterone.
DisopyramideDihydrotestosterone may increase the hypoglycemic activities of Disopyramide.
DulaglutideDihydrotestosterone may increase the hypoglycemic activities of Dulaglutide.
EmpagliflozinDihydrotestosterone may increase the hypoglycemic activities of Empagliflozin.
ErythromycinDihydrotestosterone may increase the hypoglycemic activities of Erythromycin.
ExenatideDihydrotestosterone may increase the hypoglycemic activities of Exenatide.
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Dihydrotestosterone.
GliclazideDihydrotestosterone may increase the hypoglycemic activities of Gliclazide.
GlimepirideDihydrotestosterone may increase the hypoglycemic activities of Glimepiride.
GlipizideDihydrotestosterone may increase the hypoglycemic activities of Glipizide.
GlyburideDihydrotestosterone may increase the hypoglycemic activities of Glyburide.
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Dihydrotestosterone.
inhaled insulinDihydrotestosterone may increase the hypoglycemic activities of inhaled insulin.
Insulin AspartDihydrotestosterone may increase the hypoglycemic activities of Insulin Aspart.
Insulin degludecDihydrotestosterone may increase the hypoglycemic activities of Insulin degludec.
Insulin DetemirDihydrotestosterone may increase the hypoglycemic activities of Insulin Detemir.
Insulin GlargineDihydrotestosterone may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineDihydrotestosterone may increase the hypoglycemic activities of Insulin Glulisine.
Insulin LisproDihydrotestosterone may increase the hypoglycemic activities of Insulin Lispro.
Insulin RegularDihydrotestosterone may increase the hypoglycemic activities of Insulin Regular.
LanreotideDihydrotestosterone may increase the hypoglycemic activities of Lanreotide.
LiraglutideDihydrotestosterone may increase the hypoglycemic activities of Liraglutide.
MecaserminDihydrotestosterone may increase the hypoglycemic activities of Mecasermin.
MetforminDihydrotestosterone may increase the hypoglycemic activities of Metformin.
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Dihydrotestosterone.
MifepristoneDihydrotestosterone may increase the hypoglycemic activities of Mifepristone.
MiglitolDihydrotestosterone may increase the hypoglycemic activities of Miglitol.
NateglinideDihydrotestosterone may increase the hypoglycemic activities of Nateglinide.
OctreotideDihydrotestosterone may increase the hypoglycemic activities of Octreotide.
PasireotideDihydrotestosterone may increase the hypoglycemic activities of Pasireotide.
PentamidineDihydrotestosterone may increase the hypoglycemic activities of Pentamidine.
PioglitazoneDihydrotestosterone may increase the hypoglycemic activities of Pioglitazone.
PramlintideDihydrotestosterone may increase the hypoglycemic activities of Pramlintide.
PrednisolonePrednisolone may increase the fluid retaining activities of Dihydrotestosterone.
PrednisonePrednisone may increase the fluid retaining activities of Dihydrotestosterone.
QuinineDihydrotestosterone may increase the hypoglycemic activities of Quinine.
RepaglinideDihydrotestosterone may increase the hypoglycemic activities of Repaglinide.
Repository corticotropinRepository corticotropin may increase the fluid retaining activities of Dihydrotestosterone.
RosiglitazoneDihydrotestosterone may increase the hypoglycemic activities of Rosiglitazone.
SaxagliptinDihydrotestosterone may increase the hypoglycemic activities of Saxagliptin.
SitagliptinDihydrotestosterone may increase the hypoglycemic activities of Sitagliptin.
SulfadiazineDihydrotestosterone may increase the hypoglycemic activities of Sulfadiazine.
SulfamethoxazoleDihydrotestosterone may increase the hypoglycemic activities of Sulfamethoxazole.
SulfisoxazoleDihydrotestosterone may increase the hypoglycemic activities of Sulfisoxazole.
SunitinibDihydrotestosterone may increase the hypoglycemic activities of Sunitinib.
TolazamideDihydrotestosterone may increase the hypoglycemic activities of Tolazamide.
TolbutamideDihydrotestosterone may increase the hypoglycemic activities of Tolbutamide.
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Dihydrotestosterone.
TrimethoprimDihydrotestosterone may increase the hypoglycemic activities of Trimethoprim.
WarfarinDihydrotestosterone may increase the anticoagulant activities of Warfarin.
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
Aromatase 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 December 08, 2015 14:33