Eldecalcitol

Identification

Name
Eldecalcitol
Accession Number
DB05295
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
  • 1α,25-dihydroxy-2β-(3-hydroxypropoxy)cholecalciferol
External IDs
ED-71
Categories
UNII
I2JP8UE90H
CAS number
104121-92-8
Weight
Average: 490.725
Monoisotopic: 490.36582471
Chemical Formula
C30H50O5
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][[email protected]@]1(CC[[email protected]@]2([H])\C(CCC[[email protected]]12C)=C\C=C1\C[[email protected]@H](O)[[email protected]@H](OCCCO)[[email protected]](O)C1=C)[[email protected]](C)CCCC(C)(C)O

Pharmacology

Indication

Investigated for use/treatment in osteoporosis.

Structured Indications
Not Available
Pharmacodynamics
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.

TargetActionsOrganism
UVitamin D3 receptorNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:15972580]
External Links
PubChem Compound
6918141
PubChem Substance
175426970
ChemSpider
5293354
ChEBI
73927
HET
ED9
PDB Entries
3wgp

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingTreatmentBone destruction1
3CompletedTreatmentBone destruction1
Not AvailableRecruitingTreatmentBone destruction1

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 Solubility0.0105 mg/mLALOGPS
logP5.04ALOGPS
logP3.67ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.54 m3·mol-1ChemAxon
Polarizability59.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.962
Blood Brain Barrier+0.8035
Caco-2 permeable-0.5609
P-glycoprotein substrateSubstrate0.8469
P-glycoprotein inhibitor IInhibitor0.7612
P-glycoprotein inhibitor IIInhibitor0.5476
Renal organic cation transporterNon-inhibitor0.7485
CYP450 2C9 substrateNon-substrate0.8635
CYP450 2D6 substrateNon-substrate0.8666
CYP450 3A4 substrateSubstrate0.7426
CYP450 1A2 substrateNon-inhibitor0.9083
CYP450 2C9 inhibitorNon-inhibitor0.7833
CYP450 2D6 inhibitorNon-inhibitor0.934
CYP450 2C19 inhibitorNon-inhibitor0.8324
CYP450 3A4 inhibitorNon-inhibitor0.8989
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8498
Ames testNon AMES toxic0.926
CarcinogenicityNon-carcinogens0.9245
BiodegradationNot ready biodegradable0.9862
Rat acute toxicity3.3673 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9273
hERG inhibition (predictor II)Non-inhibitor0.5437
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Triterpenoid / Cyclitol or derivatives / Tertiary alcohol / Cyclic alcohol / Secondary alcohol / Ether / Dialkyl ether / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
tetrol, D3 vitamins, hydroxycalciol (CHEBI:73927) / Vitamin D3 and derivatives (LMST03020477)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da

Drug created on November 18, 2007 11:23 / Updated on December 01, 2017 15:35