NAV

Androstenediol

Identification

Generic Name
Androstenediol
DrugBank Accession Number
DB01524
Background

Androstenediol is an intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-hydroxysteroid dehydrogenases).

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
Synonyms
  • 5-andendiol
  • 5-androstenediol
  • androst-5-ene-3beta,17beta-diol
  • androst-5-enediol
  • Androstenediol
  • hermaphrodiol
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofHormone deficiencyCombination Product in combination with: Thyroid, porcine (DB09100), Estrone (DB00655), Androstenedione (DB01536), Testosterone (DB00624), Pregnenolone (DB02789)••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofOvarian function insufficiencyCombination Product in combination with: Testosterone (DB00624), Pregnenolone (DB02789), Estrone (DB00655), Thyroid, porcine (DB09100), Androstenedione (DB01536)••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofOvarian atrophyCombination Product in combination with: Thyroid, porcine (DB09100), Estrone (DB00655), Androstenedione (DB01536), Pregnenolone (DB02789), Testosterone (DB00624)••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofHypoestrogenismCombination Product in combination with: Thyroid, porcine (DB09100), Testosterone (DB00624), Androstenedione (DB01536), Estrone (DB00655), Pregnenolone (DB02789)••••••••••••••••••• ••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
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Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Androstenediol is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone phosphate.
BudesonideThe risk or severity of edema formation can be increased when Androstenediol is combined with Budesonide.
CiclesonideThe risk or severity of edema formation can be increased when Androstenediol is combined with Ciclesonide.
Food Interactions
Not Available

Products

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International/Other Brands
Tetrabol

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-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / 17-hydroxysteroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Cyclic alcohol / Delta-5-steroid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-hydroxy steroid, 17beta-hydroxy steroid (CHEBI:2710) / C19 steroids (androgens) and derivatives, Androstane and derivatives (C04295) / C19 steroids (androgens) and derivatives (LMST02020005)
Affected organisms
Not Available

Chemical Identifiers

UNII
95PS51EMXY
CAS number
521-17-5
InChI Key
QADHLRWLCPCEKT-LOVVWNRFSA-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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

References

General References
Not Available
Human Metabolome Database
HMDB0003818
KEGG Drug
D00179
KEGG Compound
C04295
PubChem Compound
10634
PubChem Substance
46507476
ChemSpider
10188
BindingDB
50223237
ChEBI
2710
ChEMBL
CHEMBL440283
ZINC
ZINC000003814414
PDBe Ligand
B81
Wikipedia
5-Androstenediol
PDB Entries
3klp

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 Solubility0.055 mg/mLALOGPS
logP3.42ALOGPS
logP2.8Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.2Chemaxon
pKa (Strongest Basic)-0.77Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity85.48 m3·mol-1Chemaxon
Polarizability34.87 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9451
Caco-2 permeable+0.8918
P-glycoprotein substrateSubstrate0.6937
P-glycoprotein inhibitor INon-inhibitor0.6917
P-glycoprotein inhibitor IINon-inhibitor0.9113
Renal organic cation transporterNon-inhibitor0.7501
CYP450 2C9 substrateNon-substrate0.8402
CYP450 2D6 substrateNon-substrate0.8948
CYP450 3A4 substrateSubstrate0.7593
CYP450 1A2 substrateNon-inhibitor0.7389
CYP450 2C9 inhibitorNon-inhibitor0.9327
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.7832
CYP450 3A4 inhibitorNon-inhibitor0.8505
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7223
Ames testNon AMES toxic0.9194
CarcinogenicityNon-carcinogens0.937
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity2.2291 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8493
hERG inhibition (predictor II)Non-inhibitor0.6626
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
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-004l-3920000000-6d05021a14366bfd40ba
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e5
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-3920000000-6d05021a14366bfd40ba
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0090000000-36380c5e6aee14deeb5e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-a795513fa4f735cb43e0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fu-0490000000-ed92688130cf06c81207
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-e2c5f5db6d9dba447283
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-9ca8a937c183b548c60e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-092i-0900000000-e11b9bfdf30a2386abe9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.2416681
predicted
DarkChem Lite v0.1.0
[M-H]-178.4214681
predicted
DarkChem Lite v0.1.0
[M-H]-176.3258681
predicted
DarkChem Lite v0.1.0
[M-H]-174.5291
predicted
DeepCCS 1.0 (2019)
[M+H]+177.2922681
predicted
DarkChem Lite v0.1.0
[M+H]+176.7044681
predicted
DarkChem Lite v0.1.0
[M+H]+176.3962681
predicted
DarkChem Lite v0.1.0
[M+H]+176.43324
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.7272681
predicted
DarkChem Lite v0.1.0
[M+Na]+176.7034681
predicted
DarkChem Lite v0.1.0
[M+Na]+182.58171
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51