NAV

Talarozole

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Talarozole
DrugBank Accession Number
DB13083
Background

Talarozole has been investigated for the treatment of Psoriasis and Cutaneous Inflammation.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 377.51
Monoisotopic: 377.167416935
Chemical Formula
C21H23N5S
Synonyms
  • Talarozole
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Rambazole is a new generation all-trans retinoic acid metabolism blocking agent, highly specific against the retinoic acid 4-hydroxylase. The drug alleviates hyperproliferation and normalizes differentiation of the epidermis in animal models of psoriasis. All-trans-retinoic acid (RA) regulates epithelial differentiation and growth through activation of specific nuclear RA receptors (RARs). Rambazole acts by inhibiting the metabolic breakdown of the retinoid, increasing the biological efficacy of RA.

TargetActionsOrganism
UCytochrome P450 26A1Not 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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazoles
Sub Class
Not Available
Direct Parent
Benzothiazoles
Alternative Parents
Aniline and substituted anilines / 2-amino-1,3-thiazoles / Triazoles / Heteroaromatic compounds / Secondary amines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2,4-triazole / 1,3-benzothiazole / 1,3-thiazol-2-amine / Amine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Heteroaromatic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
XKD9N5CJ6W
CAS number
201410-53-9
InChI Key
SNFYYXUGUBUECJ-UHFFFAOYSA-N
InChI
InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)
IUPAC Name
N-{4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine
SMILES
CCC(CC)C(N1C=NC=N1)C1=CC=C(NC2=NC3=CC=CC=C3S2)C=C1

References

General References
  1. Stoppie P, Borgers M, Borghgraef P, Dillen L, Goossens J, Sanz G, Szel H, Van Hove C, Van Nyen G, Nobels G, Vanden Bossche H, Venet M, Willemsens G, Van Wauwe J: R115866 inhibits all-trans-retinoic acid metabolism and exerts retinoidal effects in rodents. J Pharmacol Exp Ther. 2000 Apr;293(1):304-12. [Article]
  2. Verfaille CJ, Thissen CA, Bovenschen HJ, Mertens J, Steijlen PM, van de Kerkhof PC: Oral R115866 in the treatment of moderate to severe plaque-type psoriasis. J Eur Acad Dermatol Venereol. 2007 Sep;21(8):1038-46. [Article]
PubChem Compound
9799888
PubChem Substance
347829208
ChemSpider
7975653
BindingDB
50253810
ChEBI
102167
ChEMBL
CHEMBL459505
Wikipedia
Talarozole

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAcne1
2CompletedTreatmentPsoriasis2
1CompletedNot AvailableCutaneous Inflammation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0145 mg/mLALOGPS
logP5.1ALOGPS
logP5.9Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)13.11Chemaxon
pKa (Strongest Basic)2.76Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area55.63 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity120.39 m3·mol-1Chemaxon
Polarizability41.78 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-b03a256932eff410b84e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0109000000-b8e2239b4410a8468c98
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0098000000-73aac7fda5bf35eba1dc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fvi-2149000000-5903ea610a0b17b92c13
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-8093000000-3b60e1be630c4d415d4e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00u2-1954000000-06a6db2e5c4fda1e7055
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]-189.28587
predicted
DeepCCS 1.0 (2019)
[M+H]+191.64386
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.76749
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cytochrome P450 26A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Retinoic acid binding
Specific Function
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
Gene Name
CYP26A1
Uniprot ID
O43174
Uniprot Name
Cytochrome P450 26A1
Molecular Weight
56198.11 Da
References
  1. Verfaille CJ, Thissen CA, Bovenschen HJ, Mertens J, Steijlen PM, van de Kerkhof PC: Oral R115866 in the treatment of moderate to severe plaque-type psoriasis. J Eur Acad Dermatol Venereol. 2007 Sep;21(8):1038-46. [Article]

Drug created at October 21, 2016 02:49 / Updated at February 21, 2021 18:54