Identification
- Generic Name
- Ergosterol
- DrugBank Accession Number
- DB04038
- Background
A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Ergosterol (DB04038)
- Weight
- Average: 396.659
Monoisotopic: 396.339216037 - Chemical Formula
- C28H44O
- Synonyms
- (22E,24S)-24-methylcholesta-5,7,22-trien-3β-ol
- Provitamin D2
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
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.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.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Zoo Chews Plus Iron Ergosterol (400 unit) + Ascorbic acid (50 mg) + Cyanocobalamin (4.5 mcg) + DL-alpha tocopheryl acetate (15 unit) + Ferrous fumarate (4 mg) + Folic acid (.3 mg) + Nicotinamide (13.5 mg) + Pyridoxine hydrochloride (1.05 mg) + Riboflavin (1.2 mg) + Sodium ascorbate (10 mg) + Thiamine mononitrate (1.05 mg) + Vitamin A acetate (2500 unit) Tablet Oral Hall Laboratories, Ltd. 1981-12-31 2003-09-11 Canada 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Ergostane steroids
- Direct Parent
- Ergosterols and derivatives
- Alternative Parents
- 3-hydroxy delta-7-steroids / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-7-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-5-steroid / Delta-7-steroid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3beta-sterol, ergostanoid, phytosterols (CHEBI:16933) / Ergosterols and C24-methyl derivatives, Vitamin D2 and derivatives, Ergostane and derivatives (C01694) / Ergosterols and C24-methyl derivatives (LMST01030093)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Z30RAY509F
- CAS number
- 57-87-4
- InChI Key
- DNVPQKQSNYMLRS-APGDWVJJSA-N
- InChI
- InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
- IUPAC Name
- (1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
- SMILES
- CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
References
- Synthesis Reference
Nina Vasilievna Tarasova, Elena Abramovna Obolnikova, Alexandr Dmitrievich Gololobov, Gleb Ivanovich Samokhvalov, Sergei Vladimirovich Chepigo, Galina Ivanovna Ivanova, Vladimir Vasilievich Imshenetsky, Vera Mikhailovna Kulikova, "Method for preparing ergosterol and ubiquinone-9 in a single process." U.S. Patent US3965130, issued October, 1961.
US3965130- General References
- Not Available
- External Links
- KEGG Compound
- C01694
- PubChem Compound
- 444679
- PubChem Substance
- 46505947
- ChemSpider
- 392539
- BindingDB
- 50378884
- ChEBI
- 16933
- ChEMBL
- CHEMBL1232562
- ZINC
- ZINC000004084618
- PDBe Ligand
- ERG
- Wikipedia
- Ergosterol
- PDB Entries
- 1bxm / 1zhz / 2aib / 5h2d / 5ys0 / 6cay / 6r4l / 6r4n / 6zzy / 7a4p … show 7 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 170 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000156 mg/mL ALOGPS logP 7.39 ALOGPS logP 6.63 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 18.27 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 127.13 m3·mol-1 Chemaxon Polarizability 51.01 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No 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 + 0.9642 Caco-2 permeable + 0.8165 P-glycoprotein substrate Substrate 0.6394 P-glycoprotein inhibitor I Inhibitor 0.6449 P-glycoprotein inhibitor II Non-inhibitor 0.8338 Renal organic cation transporter Non-inhibitor 0.7839 CYP450 2C9 substrate Non-substrate 0.8308 CYP450 2D6 substrate Non-substrate 0.8645 CYP450 3A4 substrate Substrate 0.7483 CYP450 1A2 substrate Non-inhibitor 0.914 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9478 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8916 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7895 Ames test Non AMES toxic 0.9231 Carcinogenicity Non-carcinogens 0.9287 Biodegradation Not ready biodegradable 0.9623 Rat acute toxicity 2.6528 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8502 hERG inhibition (predictor II) Non-inhibitor 0.7488
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS (1 TMS) GC-MS splash10-0536-2911000000-0f3a53ac2076470e08fd Mass Spectrum (Electron Ionization) MS splash10-07bg-6943000000-5fbc1f7b29d046df3944 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 13C NMR Spectrum 1D NMR Not Applicable 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52