NAV

Inecalcitol

Identification

Generic Name
Inecalcitol
DrugBank Accession Number
DB04796
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
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
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Pharmacology

Indication

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

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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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interactions in your software
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.
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 / 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)
Affected organisms
Not Available

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
[H][C@@]1(CC[C@]2([H])\C(CCC[C@]12C)=C\C=C1C[C@@H](O)C[C@H](O)C1)[C@H](C)CC#CC(C)(C)O

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. [Article]
  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. [Article]
  3. Link [Link]
PubChem Compound
6915835
PubChem Substance
46504586
ChemSpider
5291648
ChEMBL
CHEMBL2105107
ZINC
ZINC000012504514
PDBe Ligand
TX5

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentAcute Myeloid Leukemia1
2Unknown StatusTreatmentChronic Phase Chronic Myeloid Leukemia1

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/MSsplash10-001i-0129000000-d9e997772db2346a5b1c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-0da7ba40e756d2f71634
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1009000000-fcdfda816d9d0f22f48d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-4579200000-34e3b795ae9158254901
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000y-2439000000-1db0a0d195d6f711110c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-3798000000-eaf4ba82285f146736bf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.41844
predicted
DeepCCS 1.0 (2019)
[M+H]+216.31387
predicted
DeepCCS 1.0 (2019)
[M+Na]+222.13469
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Vitamin D3 receptor
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. [Article]

Drug created at September 11, 2007 17:49 / Updated at January 14, 2023 19:02