Inecalcitol

Identification

Name
Inecalcitol
Accession Number
DB04796
Description
Not Available
Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 400.603
Monoisotopic: 400.297745148
Chemical Formula
C26H40O3
Synonyms
  • (7E)-19-Nor-9,10-seco-14beta-cholesta-5,7-dien-23-yne-1alpha,3beta,25-triol
  • Inecalcitol
External IDs
  • TX 522
  • TX-522
  • TX522

Pharmacology

Indication

Investigated for use/treatment in prostate cancer, psoriasis and hyperparathyroidism.

Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action

Inecalcitol 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.

TargetActionsOrganism
UVitamin D3 receptorNot AvailableHumans
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
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
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.
DrugInteraction
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Inecalcitol is combined with Acetyldigitoxin.
AlfacalcidolThe risk or severity of adverse effects can be increased when Alfacalcidol is combined with Inecalcitol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Inecalcitol.
Beclomethasone dipropionateThe therapeutic efficacy of Inecalcitol can be decreased when used in combination with Beclomethasone dipropionate.
BendroflumethiazideThe risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Inecalcitol.
BenzthiazideThe risk or severity of hypercalcemia can be increased when Benzthiazide is combined with Inecalcitol.
BetamethasoneThe therapeutic efficacy of Inecalcitol can be decreased when used in combination with Betamethasone.
Betamethasone phosphateThe therapeutic efficacy of Inecalcitol can be decreased when used in combination with Betamethasone phosphate.
BudesonideThe therapeutic efficacy of Inecalcitol can be decreased when used in combination with Budesonide.
CalcifediolThe risk or severity of adverse effects can be increased when Calcifediol is combined with Inecalcitol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

Products

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 / Ynones / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Tertiary alcohol / Triterpenoid / Ynone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Vitamin D3 and derivatives (LMST03020649)

Chemical Identifiers

UNII
05FZV98342
CAS number
163217-09-2
InChI Key
HHGRMHMXKPQNGF-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

References

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]
PubChem Compound
6915835
PubChem Substance
46504586
ChemSpider
5291648
ChEMBL
CHEMBL2105107
ZINC
ZINC000012504514
PDBe Ligand
TX5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentAcute Myeloid Leukemia (AML)1
2Unknown StatusTreatmentCML, Chronic Phase1

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 Solubility0.00221 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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

Targets

Kind
Protein
Organism
Humans
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
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]

Drug created on September 11, 2007 11:49 / Updated on June 12, 2020 10:52

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