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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
17beta-Hydroxy-5alpha-androstan-3-one
17beta-Hydroxy-5alpha-androstane-3-one
17beta-Hydroxyandrostan-3-one
17β-hydroxy-3-oxo-5α-androstanone
17β-hydroxy-5α-androstan-3-one
4-Dihydrotestosterone
5alpha-Dihydrotestosterone
5α-DHT
Androstanolone
DHT
Dihydrotestosteron
Dihydrotestostérone
Stanolone
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnaboleenNot Available
AnabolexNot Available
AnaprotinNot Available
AndractimNot Available
AndroloneNot Available
Cristerona MBNot Available
NeodrolNot Available
ProteinaNot Available
ProtonaNot Available
StanaprolNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII08J2K08A3Y
CAS number521-18-6
WeightAverage: 290.4403
Monoisotopic: 290.224580204
Chemical FormulaC19H30O2
InChI KeyNVKAWKQGWWIWPM-ABEVXSGRSA-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/t12-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
[H][C@@]12CC[[email protected]](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
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
  • 3-oxo-5-alpha-steroid
  • 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
Related Articles
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
Polarizability34.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.2 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-000x-9870000000-f6d80b2a53942c9af50bView in MoNA
1D NMR13C NMR SpectrumNot 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.
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 HumanDihydrotestosterone may increase the hypoglycemic activities of Insulin Regular.
Insulin LisproDihydrotestosterone may increase the hypoglycemic activities of Insulin Lispro.
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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
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:17591767 ]
  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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Testosterone dehydrogenase (nad+) activity
Specific Function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular Weight:
34949.715 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid 17-alpha-monooxygenase activity
Specific Function:
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.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular Weight:
57369.995 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Androgen binding
Specific Function:
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.
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular Weight:
43778.755 Da
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:14622020 ]
  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:12957668 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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:14991868 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 06, 2016 14:22