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Identification
NameEldecalcitol
Accession NumberDB05295
TypeSmall Molecule
GroupsInvestigational
DescriptionEldecalcitol (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 Identifiers
  • ED-71
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIII2JP8UE90H
CAS number104121-92-8
WeightAverage: 490.725
Monoisotopic: 490.36582471
Chemical FormulaC30H50O5
InChI KeyFZEXGDDBXLBRTD-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)[[email protected]](O)C1=C)[[email protected]](C)CCCC(C)(C)O
Pharmacology
IndicationInvestigated for use/treatment in osteoporosis.
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionEldecalcitol [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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin D3 receptorProteinunknownNot AvailableHumanP11473 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclitol or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

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/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
Gene Name:
VDR
Uniprot ID:
P11473
Molecular Weight:
48288.64 Da
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Drug created on November 18, 2007 11:23 / Updated on August 17, 2016 12:24