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Identification
NameInecalcitol
Accession NumberDB04796
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
19-nor-14-epi-23-yne-1,25 dihydroxyvitamin D3
9,10-seco-14bh-19-norcholesta-5(z),7(e)-dien-1(r),3(r),25-triol-23-yne
External Identifiers
  • TX-522
  • TX522
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
CategoriesNot Available
UNII05FZV98342
CAS number163217-09-2
WeightAverage: 400.603
Monoisotopic: 400.297745148
Chemical FormulaC26H40O3
InChI KeyHHGRMHMXKPQNGF-WNSNRMDMSA-N
InChI
InChI=1S/C26H40O3/c1-18(7-5-13-25(2,3)29)23-11-12-24-20(8-6-14-26(23,24)4)10-9-19-15-21(27)17-22(28)16-19/h9-10,18,21-24,27-29H,6-8,11-12,14-17H2,1-4H3/b20-10+/t18-,21-,22-,23-,24-,26-/m1/s1
IUPAC Name
(1R,3R)-5-{2-[(1R,3aR,4E,7aR)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}cyclohexane-1,3-diol
SMILES
[H][C@@]1(CC[C@]2([H])\C(CCC[C@]12C)=C\C=C1C[C@@H](O)C[[email protected]](O)C1)[[email protected]](C)CC#CC(C)(C)O
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
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationInvestigated for use/treatment in prostate cancer, psoriasis and hyperparathyroidism.
PharmacodynamicsNot Available
Mechanism of actionInecalcitol is an analogue of calcitriol, the naturally active metabolite of vitamin D. Calcitriol and their analogues activate the vitamin D receptor (VDR). Vitamin D has a major role in regulating calcium absorption from the gut, storage in mineral form in the bones, and excretion by the kidney and effectively prevents rickets in infants. Vitamin D and calcitriol can cause hypercalcemia at high or frequently repeated doses; in turn, hypercalcemia can cause kidney toxicity by accumulation of calcium-containing micro-crystals and heart and muscle dysfunction by impairing contractions. [Hybrigenics Website] The mechanism of action is currently unknown, but it is proposed that inecalcitol exerts its superagonistic action through enhancing coactivator binding by the VDR.
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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9674
Blood Brain Barrier+0.8207
Caco-2 permeable+0.7691
P-glycoprotein substrateSubstrate0.7632
P-glycoprotein inhibitor INon-inhibitor0.6073
P-glycoprotein inhibitor IINon-inhibitor0.5706
Renal organic cation transporterNon-inhibitor0.8472
CYP450 2C9 substrateNon-substrate0.8131
CYP450 2D6 substrateNon-substrate0.9071
CYP450 3A4 substrateSubstrate0.7549
CYP450 1A2 substrateNon-inhibitor0.8627
CYP450 2C9 inhibitorNon-inhibitor0.809
CYP450 2D6 inhibitorNon-inhibitor0.9353
CYP450 2C19 inhibitorNon-inhibitor0.6117
CYP450 3A4 inhibitorNon-inhibitor0.6365
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5297
Ames testNon AMES toxic0.9107
CarcinogenicityNon-carcinogens0.8929
BiodegradationNot ready biodegradable1.0
Rat acute toxicity4.7066 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8707
hERG inhibition (predictor II)Non-inhibitor0.8772
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 Solubility0.00221 mg/mLALOGPS
logP4.97ALOGPS
logP4ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.67ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.57 m3·mol-1ChemAxon
Polarizability48.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Wong MS, Delansorne R, Man RY, Vanhoutte PM: Vitamin D derivatives acutely reduce endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am J Physiol Heart Circ Physiol. 2008 Jul;295(1):H289-96. doi: 10.1152/ajpheart.00116.2008. Epub 2008 May 16. [PubMed:18487433 ]
  2. Eelen G, Verlinden L, Van Camp M, Claessens F, De Clercq P, Vandewalle M, Bouillon R, Verstuyf A: Altered Vitamin D receptor-coactivator interactions reflect superagonism of Vitamin D analogs. J Steroid Biochem Mol Biol. 2005 Oct;97(1-2):65-8. Epub 2005 Jul 20. [PubMed:16039117 ]
  3. Link [Link]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24