Identification
- Generic Name
- Androstenedione
- DrugBank Accession Number
- DB01536
- Background
A delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for Androstenedione (DB01536)
- Weight
- Average: 286.4085
Monoisotopic: 286.193280076 - Chemical Formula
- C19H26O2
- Synonyms
- 4-Androstene-3,17-dione
- 4-Androstenedione
- Androst-4-ene-3,17-dione
- Androstenedione
- delta-4-Androstenedione
- External IDs
- SKF 2170
Pharmacology
- Indication
Not Available
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- 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
4-androstenedione is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol.
Target Actions Organism AEstradiol 17-beta-dehydrogenase 1 inducerHumans A3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 positive allosteric modulatorHumans U6-deoxyerythronolide B hydroxylase inducerSaccharopolyspora erythraea (strain NRRL 23338) AAldo-keto reductase family 1 member C3 substrateinducerHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- 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
Pathway Category 17-beta Hydroxysteroid Dehydrogenase III Deficiency Disease Androstenedione Metabolism Metabolic Androgen and Estrogen Metabolism Metabolic Aromatase Deficiency Disease - 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 softwareAbametapir The serum concentration of Androstenedione can be increased when it is combined with Abametapir. Amiodarone The metabolism of Androstenedione can be decreased when combined with Amiodarone. Amprenavir The metabolism of Androstenedione can be decreased when combined with Amprenavir. Apalutamide The serum concentration of Androstenedione can be decreased when it is combined with Apalutamide. Aprepitant The metabolism of Androstenedione can be decreased when combined with Aprepitant. - Food Interactions
- Not Available
Categories
- Drug Categories
- 17-Ketosteroids
- Adrenal Cortex Hormones
- Androstanes
- Androstenes
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Ketosteroids
- Steroids
- Testosterone Congeners
- 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-oxosteroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic ketone / Cyclohexenone / Delta-4-steroid / Hydrocarbon derivative
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo Delta(4)-steroid, 17-oxo steroid, androstanoid (CHEBI:16422) / androstane, C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C00280) / C19 steroids (androgens) and derivatives (LMST02020007)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 409J2J96VR
- CAS number
- 63-05-8
- InChI Key
- AEMFNILZOJDQLW-QAGGRKNESA-N
- InChI
- InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
- IUPAC Name
- (3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
References
- Synthesis Reference
Angela M. H. Brodie, Harry J. Brodie, David A. Marsh, "Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis." U.S. Patent US4235893, issued October, 1962.
US4235893- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000053
- KEGG Drug
- D00051
- KEGG Compound
- C00280
- PubChem Compound
- 6128
- PubChem Substance
- 46508011
- ChemSpider
- 5898
- BindingDB
- 91713
- 784
- ChEBI
- 16422
- ChEMBL
- CHEMBL274826
- ZINC
- ZINC000004428526
- PDBe Ligand
- ASD
- Wikipedia
- Androstenedione
- PDB Entries
- 1eup / 1qyx / 1xf0 / 2vct / 2vcv / 3cas / 3eqm / 3iw1 / 3nbr / 3nhx … show 18 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Active Not Recruiting Treatment Estrogen Receptor and/or Progesterone Receptor Positive / HER2 negative / Stage IV Breast Cancer AJCC v6 and v7 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 158 °C PhysProp water solubility 57.8 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.75 HANSCH,C ET AL. (1995) logS -3.69 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.027 mg/mL ALOGPS logP 2.93 ALOGPS logP 3.93 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 18.52 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 83.61 m3·mol-1 Chemaxon Polarizability 33.21 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 + 0.9793 Caco-2 permeable + 0.8011 P-glycoprotein substrate Substrate 0.5526 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Non-inhibitor 0.6615 Renal organic cation transporter Non-inhibitor 0.6632 CYP450 2C9 substrate Non-substrate 0.8548 CYP450 2D6 substrate Non-substrate 0.9131 CYP450 3A4 substrate Substrate 0.7193 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9387 CYP450 2D6 inhibitor Non-inhibitor 0.9386 CYP450 2C19 inhibitor Non-inhibitor 0.8138 CYP450 3A4 inhibitor Non-inhibitor 0.8483 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8067 Ames test Non AMES toxic 0.9508 Carcinogenicity Non-carcinogens 0.9313 Biodegradation Not ready biodegradable 0.9343 Rat acute toxicity 1.5360 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7599 hERG inhibition (predictor II) Non-inhibitor 0.7469
Spectra
- Mass Spec (NIST)
- Download (11.2 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.5431327 predictedDarkChem Lite v0.1.0 [M-H]- 176.2939327 predictedDarkChem Lite v0.1.0 [M-H]- 176.7669327 predictedDarkChem Lite v0.1.0 [M-H]- 176.5377327 predictedDarkChem Lite v0.1.0 [M-H]- 176.3020327 predictedDarkChem Lite v0.1.0 [M-H]- 169.07628 predictedDeepCCS 1.0 (2019) [M+H]+ 176.9598327 predictedDarkChem Lite v0.1.0 [M+H]+ 167.4900336 predictedDarkChem Standard v0.1.0 [M+H]+ 177.4454327 predictedDarkChem Lite v0.1.0 [M+H]+ 177.2297327 predictedDarkChem Lite v0.1.0 [M+H]+ 177.1565327 predictedDarkChem Lite v0.1.0 [M+H]+ 171.34334 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.1647327 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.5575738 predictedDarkChem Standard v0.1.0 [M+Na]+ 176.9993327 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9557327 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.56035 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Testosterone dehydrogenase (nad+) activity
- Specific Function
- Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
- Gene Name
- HSD17B1
- Uniprot ID
- P14061
- Uniprot Name
- Estradiol 17-beta-dehydrogenase 1
- Molecular Weight
- 34949.715 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Steroid delta-isomerase activity
- Specific Function
- 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
- Gene Name
- HSD3B1
- Uniprot ID
- P14060
- Uniprot Name
- 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
- Molecular Weight
- 42251.25 Da
References
- Ishii-Ohba H, Inano H, Tamaoki B: Purification and properties of testicular 3 beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase. J Steroid Biochem. 1986 Oct;25(4):555-60. [Article]
- Kind
- Protein
- Organism
- Saccharopolyspora erythraea (strain NRRL 23338)
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
- Specific Function
- Catalyzes the NADPH-dependent conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB. Requires the participation of a ferredo...
- Gene Name
- eryF
- Uniprot ID
- Q00441
- Uniprot Name
- 6-deoxyerythronolide B hydroxylase
- Molecular Weight
- 45098.685 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- SubstrateInducer
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM: Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J Med Chem. 2016 Aug 25;59(16):7431-44. doi: 10.1021/acs.jmedchem.6b00160. Epub 2016 Aug 12. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Sevrioukova IF, Poulos TL: Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir. Proc Natl Acad Sci U S A. 2010 Oct 26;107(43):18422-7. doi: 10.1073/pnas.1010693107. Epub 2010 Oct 11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM: Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J Med Chem. 2016 Aug 25;59(16):7431-44. doi: 10.1021/acs.jmedchem.6b00160. Epub 2016 Aug 12. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 06, 2022 00:53