Explore a selection of our essential drug information below, or:
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
Structure for Androstenediol (DB01524)
- 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
- External IDs
- HE2100
- NSC-12163
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Hormone deficiency Combination Product in combination with: Thyroid, porcine (DB09100), Estrone (DB00655), Androstenedione (DB01536), Testosterone (DB00624), Pregnenolone (DB02789) •••••••••••• ••••••• ••••••• •••••• Used in combination for symptomatic treatment of Ovarian function insufficiency Combination Product in combination with: Testosterone (DB00624), Pregnenolone (DB02789), Estrone (DB00655), Thyroid, porcine (DB09100), Androstenedione (DB01536) •••••••••••• ••••••• ••••••• •••••• Used in combination for symptomatic treatment of Ovarian atrophy Combination Product in combination with: Thyroid, porcine (DB09100), Estrone (DB00655), Androstenedione (DB01536), Pregnenolone (DB02789), Testosterone (DB00624) •••••••••••• ••••••• ••••••• •••••• Used in combination for symptomatic treatment of Hypoestrogenism Combination Product in combination with: Thyroid, porcine (DB09100), Testosterone (DB00624), Androstenedione (DB01536), Estrone (DB00655), Pregnenolone (DB02789) •••••••••••• ••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism AEstrogen receptor inhibitorHumans AEstrogen receptor beta inhibitorHumans - 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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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 Androstenediol is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone phosphate. Budesonide The risk or severity of edema formation can be increased when Androstenediol is combined with Budesonide. Ciclesonide The risk or severity of edema formation can be increased when Androstenediol is combined with Ciclesonide. - Food Interactions
- Not Available
Products
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- 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
- External Links
- 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
- Androstenediol
- PDB Entries
- 3klp
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.055 mg/mL ALOGPS logP 3.42 ALOGPS logP 2.8 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 18.2 Chemaxon pKa (Strongest Basic) -0.77 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 85.48 m3·mol-1 Chemaxon Polarizability 34.87 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9451 Caco-2 permeable + 0.8918 P-glycoprotein substrate Substrate 0.6937 P-glycoprotein inhibitor I Non-inhibitor 0.6917 P-glycoprotein inhibitor II Non-inhibitor 0.9113 Renal organic cation transporter Non-inhibitor 0.7501 CYP450 2C9 substrate Non-substrate 0.8402 CYP450 2D6 substrate Non-substrate 0.8948 CYP450 3A4 substrate Substrate 0.7593 CYP450 1A2 substrate Non-inhibitor 0.7389 CYP450 2C9 inhibitor Non-inhibitor 0.9327 CYP450 2D6 inhibitor Non-inhibitor 0.9268 CYP450 2C19 inhibitor Non-inhibitor 0.7832 CYP450 3A4 inhibitor Non-inhibitor 0.8505 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7223 Ames test Non AMES toxic 0.9194 Carcinogenicity Non-carcinogens 0.937 Biodegradation Not ready biodegradable 0.9606 Rat acute toxicity 2.2291 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8493 hERG inhibition (predictor II) Non-inhibitor 0.6626
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.2416681 predictedDarkChem Lite v0.1.0 [M-H]- 178.4214681 predictedDarkChem Lite v0.1.0 [M-H]- 176.3258681 predictedDarkChem Lite v0.1.0 [M-H]- 174.5291 predictedDeepCCS 1.0 (2019) [M+H]+ 177.2922681 predictedDarkChem Lite v0.1.0 [M+H]+ 176.7044681 predictedDarkChem Lite v0.1.0 [M+H]+ 176.3962681 predictedDarkChem Lite v0.1.0 [M+H]+ 176.43324 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.7272681 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.7034681 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.58171 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)
- Specific Function
- DNA binding
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at July 31, 2007 13:10 / Updated at August 26, 2024 19:22