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Identification
- Generic Name
- Eldecalcitol
- DrugBank Accession Number
- DB05295
- Background
Eldecalcitol (ED-71), a vitamin D analog, is a more potent inhibitor of bone resorption than alfacalcidol in an estrogen-deficient rat model of osteoporosis. Eldecalcitol, effectively and safely increased lumbar and hip bone mineral density (BMD) in osteoporotic patients who also received vitamin D3 supplementation.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Eldecalcitol (DB05295)
- Weight
- Average: 490.725
Monoisotopic: 490.36582471 - Chemical Formula
- C30H50O5
- Synonyms
- 1α,25-dihydroxy-2β-(3-hydroxypropoxy)cholecalciferol
- Eldecalcitol
- External IDs
- ED-71
Pharmacology
- Indication
Investigated for use/treatment in osteoporosis.
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Not Available
- Mechanism of action
Eldecalcitol [1a,25-DIHYDROXY-2ß-(3-hydroxypropoxy)vitamin D3] is an analog of 1a,25-dihydroxyvitamin D3 [1,25(OH)2D3], bearing a hydroxypropoxy residue at the 2b position. Eldecalcitol is also effective in increasing bone mass and was able to enhance bone strength in rodents. It binds to the vitamin D receptor (VDR) with less affinity but binds to vitamin D-binding protein with higher affinity than 1,25(OH)2D, showing a long half-life in plasma.
Target Actions Organism UVitamin D3 receptor 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
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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 softwareAcetyldigitoxin The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Eldecalcitol is combined with Acetyldigitoxin. Alfacalcidol The risk or severity of adverse effects can be increased when Alfacalcidol is combined with Eldecalcitol. Aluminum hydroxide The serum concentration of Aluminum hydroxide can be increased when it is combined with Eldecalcitol. Beclomethasone dipropionate The therapeutic efficacy of Eldecalcitol can be decreased when used in combination with Beclomethasone dipropionate. Bendroflumethiazide The risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Eldecalcitol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Vitamin D and derivatives
- Direct Parent
- Vitamin D and derivatives
- Alternative Parents
- Triterpenoids / Cyclitols and derivatives / Tertiary alcohols / Secondary alcohols / Dialkyl ethers / Primary alcohols / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Cyclitol or derivatives / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- tetrol, D3 vitamins, hydroxycalciol (CHEBI:73927) / Vitamin D3 and derivatives (LMST03020477)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- I2JP8UE90H
- CAS number
- 104121-92-8
- InChI Key
- FZEXGDDBXLBRTD-AYIMTCTASA-N
- InChI
- InChI=1S/C30H50O5/c1-20(9-6-15-29(3,4)34)24-13-14-25-22(10-7-16-30(24,25)5)11-12-23-19-26(32)28(27(33)21(23)2)35-18-8-17-31/h11-12,20,24-28,31-34H,2,6-10,13-19H2,1,3-5H3/b22-11+,23-12-/t20-,24-,25+,26-,27-,28-,30-/m1/s1
- IUPAC Name
- (1R,2R,3R,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol
- SMILES
- [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)[C@@H](OCCCO)[C@H](O)C1=C)[C@H](C)CCCC(C)(C)O
References
- General References
- Matsumoto T, Miki T, Hagino H, Sugimoto T, Okamoto S, Hirota T, Tanigawara Y, Hayashi Y, Fukunaga M, Shiraki M, Nakamura T: A new active vitamin D, ED-71, increases bone mass in osteoporotic patients under vitamin D supplementation: a randomized, double-blind, placebo-controlled clinical trial. J Clin Endocrinol Metab. 2005 Sep;90(9):5031-6. Epub 2005 Jun 21. [Article]
- External Links
- PubChem Compound
- 6918141
- PubChem Substance
- 175426970
- ChemSpider
- 5293354
- ChEBI
- 73927
- ZINC
- ZINC000003934328
- PDBe Ligand
- ED9
- Wikipedia
- Eldecalcitol
- PDB Entries
- 3wgp
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Not Yet Recruiting Not Available Postmenopausal Osteoporosis 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Osteoporosis 1 somestatus stop reason just information to hide 4 Not Yet Recruiting Treatment Osteopenia (Disorder) / Osteoporosis / Rheumatoid Arthritis 1 somestatus stop reason just information to hide 4 Recruiting Treatment Decreased bone mineral density / Postmenopausal Osteoporosis 1 somestatus stop reason just information to hide 4 Recruiting Treatment Postmenopausal Osteoporosis 1 somestatus stop reason just information to hide
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 0.0105 mg/mL ALOGPS logP 5.04 ALOGPS logP 3.67 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 13.38 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 90.15 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 143.54 m3·mol-1 Chemaxon Polarizability 59.7 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.962 Blood Brain Barrier + 0.8035 Caco-2 permeable - 0.5609 P-glycoprotein substrate Substrate 0.8469 P-glycoprotein inhibitor I Inhibitor 0.7612 P-glycoprotein inhibitor II Inhibitor 0.5476 Renal organic cation transporter Non-inhibitor 0.7485 CYP450 2C9 substrate Non-substrate 0.8635 CYP450 2D6 substrate Non-substrate 0.8666 CYP450 3A4 substrate Substrate 0.7426 CYP450 1A2 substrate Non-inhibitor 0.9083 CYP450 2C9 inhibitor Non-inhibitor 0.7833 CYP450 2D6 inhibitor Non-inhibitor 0.934 CYP450 2C19 inhibitor Non-inhibitor 0.8324 CYP450 3A4 inhibitor Non-inhibitor 0.8989 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8498 Ames test Non AMES toxic 0.926 Carcinogenicity Non-carcinogens 0.9245 Biodegradation Not ready biodegradable 0.9862 Rat acute toxicity 3.3673 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9273 hERG inhibition (predictor II) Non-inhibitor 0.5437
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00kb-0115900000-50fe360b006d3b452099 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0000900000-0092024fc1d1eca50951 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-2004900000-c13c6ff941d1ad59c308 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-9125700000-6c9dfbc1e5f0dd01baa4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-066s-6408900000-14a6dc9d5db3e1691375 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01ox-9547300000-9a05f1f1926ad79dc669 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 232.03362 predictedDeepCCS 1.0 (2019) [M+H]+ 233.929 predictedDeepCCS 1.0 (2019) [M+Na]+ 239.68314 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor for calcitriol, the active form of vitamin D3 which mediates the action of this vitamin on cells (PubMed:10678179, PubMed:15728261, PubMed:16913708, PubMed:28698609, PubMed:37478846). Enters the nucleus upon vitamin D3 binding where it forms heterodimers with the retinoid X receptor/RXR (PubMed:28698609). The VDR-RXR heterodimers bind to specific response elements on DNA and activate the transcription of vitamin D3-responsive target genes (PubMed:28698609). Plays a central role in calcium homeostasis (By similarity). Also functions as a receptor for the secondary bile acid lithocholic acid (LCA) and its metabolites (PubMed:12016314, PubMed:32354638)
- Specific Function
- bile acid nuclear receptor activity
- Gene Name
- VDR
- Uniprot ID
- P11473
- Uniprot Name
- Vitamin D3 receptor
- Molecular Weight
- 48288.64 Da
Drug created at November 18, 2007 18:23 / Updated at February 21, 2021 18:51