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
Structure for Epitestosterone (DB07768)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAldo-keto reductase family 1 member C1 Not Available Humans UAldo-keto reductase family 1 member C2 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareBeclomethasone dipropionate The risk or severity of edema formation can be increased when Epitestosterone is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when Epitestosterone is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when Epitestosterone is combined with Betamethasone phosphate. Budesonide The risk or severity of edema formation can be increased when Epitestosterone is combined with Budesonide. Ciclesonide The risk or severity of edema formation can be increased when Epitestosterone is combined with Ciclesonide. - 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
- (1R,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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
- External Links
- 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
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
Property Value Source Water Solubility 0.0333 mg/mL ALOGPS logP 2.99 ALOGPS logP 3.37 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 18.52 Chemaxon pKa (Strongest Basic) -0.88 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 84.43 m3·mol-1 Chemaxon Polarizability 33.93 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.973 Caco-2 permeable + 0.8984 P-glycoprotein substrate Substrate 0.6498 P-glycoprotein inhibitor I Inhibitor 0.5489 P-glycoprotein inhibitor II Non-inhibitor 0.8923 Renal organic cation transporter Non-inhibitor 0.7324 CYP450 2C9 substrate Non-substrate 0.8167 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7739 CYP450 1A2 substrate Non-inhibitor 0.9005 CYP450 2C9 inhibitor Non-inhibitor 0.95 CYP450 2D6 inhibitor Non-inhibitor 0.9452 CYP450 2C19 inhibitor Non-inhibitor 0.6668 CYP450 3A4 inhibitor Non-inhibitor 0.8812 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8683 Ames test Non AMES toxic 0.9382 Carcinogenicity Non-carcinogens 0.9483 Biodegradation Not ready biodegradable 0.9174 Rat acute toxicity 1.6259 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8938 hERG inhibition (predictor II) Non-inhibitor 0.7163
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.7418819 predictedDarkChem Lite v0.1.0 [M-H]- 177.2202819 predictedDarkChem Lite v0.1.0 [M-H]- 176.7911819 predictedDarkChem Lite v0.1.0 [M-H]- 171.18564 predictedDeepCCS 1.0 (2019) [M+H]+ 177.5820819 predictedDarkChem Lite v0.1.0 [M+H]+ 177.8082819 predictedDarkChem Lite v0.1.0 [M+H]+ 177.4380819 predictedDarkChem Lite v0.1.0 [M+H]+ 173.32147 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.1725819 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.5872819 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.34323 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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
- 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 at September 15, 2010 21:25 / Updated at June 12, 2020 16:52