Identification

Name
1-Testosterone
Accession Number
DB01481
Type
Small Molecule
Groups
Experimental, Illicit, Investigational
Description

1-Testosterone 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.

Structure
Thumb
Synonyms
  • 1-T
  • 1-Testo
  • 17beta-hydroxy-5alpha-androst-1-en-3-one
  • Androstendolone
  • delta1-Dihydrotestosterone
External IDs
J108.132B
Categories
UNII
Y984BV1Q0G
CAS number
65-06-5
Weight
Average: 288.4244
Monoisotopic: 288.20893014
Chemical Formula
C19H28O2
InChI Key
OKJCFMUGMSVJBG-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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics

Delta1-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 action

Delta1-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.

TargetActionsOrganism
AAndrogen receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  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:16621347]
External Links
KEGG Compound
C15377
PubChem Compound
236666
PubChem Substance
46507716
ChemSpider
206590
ChEBI
59714

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableUnknown StatusTreatmentRestless Legs Syndrome (RLS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0128 mg/mLALOGPS
logP3.38ALOGPS
logP3.41ChemAxon
logS-4.4ALOGPS
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
Refractivity84.7 m3·mol-1ChemAxon
Polarizability34.06 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9835
Caco-2 permeable+0.8943
P-glycoprotein substrateSubstrate0.6036
P-glycoprotein inhibitor INon-inhibitor0.5133
P-glycoprotein inhibitor IINon-inhibitor0.8114
Renal organic cation transporterNon-inhibitor0.791
CYP450 2C9 substrateNon-substrate0.7459
CYP450 2D6 substrateNon-substrate0.9292
CYP450 3A4 substrateSubstrate0.7431
CYP450 1A2 substrateNon-inhibitor0.7338
CYP450 2C9 inhibitorNon-inhibitor0.9397
CYP450 2D6 inhibitorNon-inhibitor0.9672
CYP450 2C19 inhibitorNon-inhibitor0.8086
CYP450 3A4 inhibitorNon-inhibitor0.8474
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.933
Ames testNon AMES toxic0.9268
CarcinogenicityNon-carcinogens0.9287
BiodegradationNot ready biodegradable0.983
Rat acute toxicity2.0714 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9314
hERG inhibition (predictor II)Non-inhibitor0.6661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo-5-alpha-steroids / 3-oxo delta-1-steroids / 17-hydroxysteroids / Delta-1-steroids / Cyclohexenones / Secondary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxo-delta-1-steroid / 3-oxosteroid / 3-oxo-5-alpha-steroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-1-steroid / Cyclohexenone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
17beta-hydroxy steroid, 3-oxo Delta(1)-steroid, anabolic androgenic steroid (CHEBI:59714)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
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:17139284]
  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:17016423]
  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:16621347]

Drug created on July 31, 2007 07:09 / Updated on January 13, 2018 14:56