NAV

Becocalcidiol

Identification

Generic Name
Becocalcidiol
DrugBank Accession Number
DB04891
Background

Becocalcidiol is a vitamin D(3) analogue which has not caused hypercalcaemia or significant irritation in preclinical trials.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 344.5307
Monoisotopic: 344.271530396
Chemical Formula
C23H36O2
Synonyms
  • Becocalcidiol
External IDs
  • 2MBISP
  • DP-006
  • QRX 101
  • QRX-101
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Pharmacology

Indication

For topical treatment of psoriasis and psoriatic disorders.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Becocalcidiol (formerly QRX-101) is a novel vitamin D analogue for the treatment of mild to moderate psoriasis. In clinical and preclinical studies, becocalcidiol has been well tolerated with a low incidence of skin irritation. Based on the completed Phase IIb study, becocalcidiol was statistically superior to placebo in reducing plaque and did not result in excessive blood calcium levels, a side effect of existing calcitriol topical treatments for psoriasis.

Mechanism of action

The mechanism of action of becocalcidiol in the treatment of psoriasis is accounted for by an antiproliferative activity for keratinocytes and the stimulation of epidermal cell differentiation.

TargetActionsOrganism
UMediator of RNA polymerase II transcription subunit 1Not AvailableHumans
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
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
Integrate drug-drug
interactions in your software
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Becocalcidiol is combined with Acetyldigitoxin.
AlfacalcidolThe risk or severity of adverse effects can be increased when Alfacalcidol is combined with Becocalcidiol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Becocalcidiol.
Beclomethasone dipropionateThe therapeutic efficacy of Becocalcidiol can be decreased when used in combination with Beclomethasone dipropionate.
BendroflumethiazideThe risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Becocalcidiol.
Food Interactions
Not Available

Products

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International/Other Brands
Asord (QuatRx)

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 / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Polycyclic triterpenoid / Secondary alcohol / Triterpenoid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Vitamin D3 and derivatives (LMST03020650)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
N75R59YD0F
CAS number
524067-21-8
InChI Key
QSLUXQQUPXBIHH-YHSKWIAJSA-N
InChI
InChI=1S/C23H36O2/c1-5-15(2)19-10-11-20-18(7-6-12-23(19,20)4)9-8-17-13-21(24)16(3)22(25)14-17/h8-9,15,19-22,24-25H,3,5-7,10-14H2,1-2,4H3/b18-9+/t15-,19+,20-,21+,22+,23+/m0/s1
IUPAC Name
(1R,3R)-5-{2-[(1R,3aS,4E,7aR)-1-[(2S)-butan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-2-methylidenecyclohexane-1,3-diol
SMILES
CC[C@@](C)([H])[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1/C[C@](O)([H])C(=C)[C@]([H])(O)C1

References

General References
  1. Helfrich YR, Kang S, Hamilton TA, Voorhees JJ: Topical becocalcidiol for the treatment of psoriasis vulgaris: a randomized, placebo-controlled, double-blind, multicentre study. Br J Dermatol. 2007 Aug;157(2):369-74. Epub 2007 Jun 26. [Article]
PubChem Compound
5289547
PubChem Substance
175426893
ChemSpider
4451487
ChEMBL
CHEMBL2104955
ZINC
ZINC000013975113
PDBe Ligand
VD1
PDB Entries
1rkg

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPsoriasis1

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 Solubility0.0097 mg/mLALOGPS
logP5.35ALOGPS
logP4.43Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.19Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity106.23 m3·mol-1Chemaxon
Polarizability42.79 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9927
Blood Brain Barrier+0.9405
Caco-2 permeable+0.7532
P-glycoprotein substrateSubstrate0.7521
P-glycoprotein inhibitor INon-inhibitor0.5739
P-glycoprotein inhibitor IINon-inhibitor0.5415
Renal organic cation transporterNon-inhibitor0.8229
CYP450 2C9 substrateNon-substrate0.8415
CYP450 2D6 substrateNon-substrate0.8915
CYP450 3A4 substrateSubstrate0.7371
CYP450 1A2 substrateNon-inhibitor0.7897
CYP450 2C9 inhibitorNon-inhibitor0.8704
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.7437
CYP450 3A4 inhibitorNon-inhibitor0.7088
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5566
Ames testNon AMES toxic0.9311
CarcinogenicityNon-carcinogens0.8824
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity3.9749 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7631
hERG inhibition (predictor II)Non-inhibitor0.7225
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, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-6c701e4bafc2d3dce780
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-06dj-0259000000-f49a94bcdb650ac0298e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0149000000-0ed6e063febb4ef53cc7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-1019000000-d0b19ad5aff752b1467f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4u-4469000000-b250a0c7d55006421c35
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-9554000000-7b21bf90c1c9d86b3ab8
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]-192.949254
predicted
DarkChem Lite v0.1.0
[M-H]-184.92923
predicted
DeepCCS 1.0 (2019)
[M+H]+193.065854
predicted
DarkChem Lite v0.1.0
[M+H]+187.04732
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.425854
predicted
DarkChem Lite v0.1.0
[M+Na]+192.95985
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Mediator of RNA polymerase II transcription subunit 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin d receptor binding
Specific Function
Component of the Mediator complex, a coactivator involved in the regulated transcription of nearly all RNA polymerase II-dependent genes. Mediator functions as a bridge to convey information from g...
Gene Name
MED1
Uniprot ID
Q15648
Uniprot Name
Mediator of RNA polymerase II transcription subunit 1
Molecular Weight
168476.57 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]
Details2. 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 October 21, 2007 17:09 / Updated at February 21, 2021 18:51