Epitestosterone

Identification

Generic Name
Epitestosterone
DrugBank Accession Number
DB07768
Background

Epitestosterone is the 17-alpha isomer of testosterone, derived from pregnenolone via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 288.4244
Monoisotopic: 288.20893014
Chemical Formula
C19H28O2
Synonyms
  • (17-alpha)-17-Hydroxyandrost-4-en-3-one
  • 17-alpha-Hydroxyandrost-4-en-3-one
  • 17-alpha-Testosterone
  • 17-Epitestosterone
  • 17alpha-cis-Testosterone
  • cis-Testosterone
  • Isotestosterone
External IDs
  • NSC-26499

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAldo-keto reductase family 1 member C1Not AvailableHumans
UAldo-keto reductase family 1 member C2Not AvailableHumans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Epitestosterone is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when Epitestosterone is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when Epitestosterone is combined with Betamethasone phosphate.
BudesonideThe risk or severity of edema formation can be increased when Epitestosterone is combined with Budesonide.
CiclesonideThe risk or severity of edema formation can be increased when Epitestosterone is combined with Ciclesonide.
Clobetasol propionateThe risk or severity of edema formation can be increased when Epitestosterone is combined with Clobetasol propionate.
CorticotropinThe risk or severity of edema formation can be increased when Epitestosterone is combined with Corticotropin.
Cortisone acetateThe risk or severity of edema formation can be increased when Epitestosterone is combined with Cortisone acetate.
DeflazacortThe risk or severity of edema formation can be increased when Epitestosterone is combined with Deflazacort.
DesoximetasoneThe risk or severity of edema formation can be increased when Epitestosterone is combined with Desoximetasone.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Secondary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 17alpha-hydroxy steroid, androstanoid (CHEBI:42534) / C19 steroids (androgens) and derivatives (LMST02020051)
Affected organisms
Not Available

Chemical Identifiers

UNII
48L726977Z
CAS number
481-30-1
InChI Key
MUMGGOZAMZWBJJ-KZYORJDKSA-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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
[H][C@@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

References

General References
Not Available
Human Metabolome Database
HMDB0000628
PubChem Compound
10204
PubChem Substance
99444239
ChemSpider
9789
BindingDB
50410492
ChEBI
42534
ChEMBL
CHEMBL196228
ZINC
ZINC000004538008
PDBe Ligand
FFA
Wikipedia
Epitestosterone
PDB Entries
2ipf / 2ipg / 2ipj

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0333 mg/mLALOGPS
logP2.99ALOGPS
logP3.37ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.43 m3·mol-1ChemAxon
Polarizability33.76 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+0.973
Caco-2 permeable+0.8984
P-glycoprotein substrateSubstrate0.6498
P-glycoprotein inhibitor IInhibitor0.5489
P-glycoprotein inhibitor IINon-inhibitor0.8923
Renal organic cation transporterNon-inhibitor0.7324
CYP450 2C9 substrateNon-substrate0.8167
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7739
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.95
CYP450 2D6 inhibitorNon-inhibitor0.9452
CYP450 2C19 inhibitorNon-inhibitor0.6668
CYP450 3A4 inhibitorNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8683
Ames testNon AMES toxic0.9382
CarcinogenicityNon-carcinogens0.9483
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity1.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.7163
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-006t-1940000000-716f44b32e61cf34c7b4
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0090000000-e1af5f6bcaf571731a2b
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052b-7900000000-581eb9c19ccb29ebac52
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-052b-9300000000-37c235bd069ce0c93813
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
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0690-0190000000-d4814fdc14f2b2818eb2
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0fk9-1690000000-b39908a52b06c7853085
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
Gene Name
AKR1C1
Uniprot ID
Q04828
Uniprot Name
Aldo-keto reductase family 1 member C1
Molecular Weight
36788.02 Da
References
  1. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent...
Gene Name
AKR1C2
Uniprot ID
P52895
Uniprot Name
Aldo-keto reductase family 1 member C2
Molecular Weight
36734.97 Da
References
  1. 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. [Article]

Drug created on September 15, 2010 21:25 / Updated on June 12, 2020 16:52