You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDelta1-dihydrotestosterone
Accession NumberDB01481
Typesmall molecule
Groupsexperimental, illicit
Description

Delta1-dihydrotestosterone is an anabolic steroid that differs from testosterone by having a 1,2-double bond instead of 4,5-double bond in its A ring. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-TNot AvailableNot Available
1-TestoNot AvailableNot Available
1-testosteroneNot AvailableNot Available
17beta-hydroxy-5alpha-androst-1-en-3-oneNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number65-06-5
WeightAverage: 288.4244
Monoisotopic: 288.20893014
Chemical FormulaC19H28O2
InChI KeyOKJCFMUGMSVJBG-ABEVXSGRSA-N
InChI
InChI=1S/C19H28O2/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/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C=C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassAndrogens and Derivatives
Direct parentAndrogens and Derivatives
Alternative parentsKetosteroids; Hydroxysteroids; Secondary Alcohols; Ketones; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclic alcohol; ketone; secondary alcohol; 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
PharmacodynamicsDelta1-dihydrotestosterone binds to the androgen receptor, a nuclear receptor which binds the androgenic hormones testosterone and dihydrotestosterone. Once bound, the receptor/ligand complex localizes to the nucleus and acts as a DNA binding transcription factor, regulating gene expression. In animals, Delta1-dihydrotestosterone stimulates the growth of the prostate as well as the seminal vesicles.
Mechanism of actionDelta1-dihydrotestosterone binds to the androgen receptor, a nuclear receptor which binds the androgenic hormones testosterone and dihydrotestosterone. Once bound, the receptor/ligand complex localizes to the nucleus and acts as a DNA binding transcription factor, regulating gene expression.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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 + 0.9835
Caco-2 permeable + 0.8943
P-glycoprotein substrate Substrate 0.6036
P-glycoprotein inhibitor I Non-inhibitor 0.5133
P-glycoprotein inhibitor II Non-inhibitor 0.8114
Renal organic cation transporter Non-inhibitor 0.791
CYP450 2C9 substrate Non-substrate 0.7459
CYP450 2D6 substrate Non-substrate 0.9292
CYP450 3A4 substrate Substrate 0.7431
CYP450 1A2 substrate Non-inhibitor 0.7338
CYP450 2C9 substrate Non-inhibitor 0.9397
CYP450 2D6 substrate Non-inhibitor 0.9672
CYP450 2C19 substrate Non-inhibitor 0.8086
CYP450 3A4 substrate Non-inhibitor 0.8474
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.933
Ames test Non AMES toxic 0.9268
Carcinogenicity Non-carcinogens 0.9287
Biodegradation Not ready biodegradable 0.983
Rat acute toxicity 2.0714 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9314
hERG inhibition (predictor II) Non-inhibitor 0.6661
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.28e-02 g/lALOGPS
logP3.38ALOGPS
logP3.41ChemAxon
logS-4.3ALOGPS
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
refractivity84.7ChemAxon
polarizability34.06ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. Pubmed
External Links
ResourceLink
KEGG CompoundC15377
PubChem Compound236666
PubChem Substance46507716
ChemSpider206590
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. Pubmed

Comments
comments powered by Disqus
Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14