Talarozole

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

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Talarozole
Accession Number
DB13083  (DB05681)
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
  • Talarozole
Categories
UNII
XKD9N5CJ6W
CAS number
201410-53-9
Weight
Average: 377.51
Monoisotopic: 377.167416935
Chemical Formula
C21H23N5S
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

Pharmacology

Indication
Not Available
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
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.
Not Available
Food Interactions
Not Available

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. [PubMed:10734183]
  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. [PubMed:17714122]
External Links
PubChem Compound
9799888
PubChem Substance
347829208
ChemSpider
7975653
BindingDB
50253810
ChEBI
102167
ChEMBL
CHEMBL459505
Wikipedia
Talarozole

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableCutaneous Inflammation1
2CompletedTreatmentAcne1
2CompletedTreatmentPsoriasis2

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/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

Taxonomy

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
1,3-benzothiazole / Aniline or substituted anilines / Monocyclic benzene moiety / Benzenoid / 1,3-thiazol-2-amine / Azole / Thiazole / 1,2,4-triazole / Heteroaromatic compound / Secondary amine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:17714122]

Drug created on October 20, 2016 20:49 / Updated on September 02, 2019 19:52