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Tazarotene

CAT: 0804-HY-15388-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-15388-01Size:5 mg
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Description
Tazarotene (AGN 190168) is a selective retinoic acid receptor (RAR) agonist for the treatment of plaque psoriasis and acne vulgaris. Tazarotene is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
CAS Number
118292-40-3
Product Name Alternative
AGN 190168
UNSPSC
12352005
Hazard Statement
H361
Target
Autophagy; RAR/RXR
Type
Reference compound
Related Pathways
Autophagy; Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology; Cancer
Assay Protocol
https://www.medchemexpress.com/Tazarotene.html
Purity
99.17
Solubility
DMSO : 50 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL
Smiles
O=C(C1=CC=C(C#CC2=CC=C3C(C(C)(C)CCS3)=C2)N=C1)OCC
Molecular Formula
C21H21NO2S
Molecular Weight
351.46
Precautions
H361
References & Citations
[1]Talpur R, et al. Efficacy and safety of topical tazarotene: a review. Expert Opin Drug Metab Toxicol. 2009 Feb;5 (2) :195-210.|[2]Nagpal S, et al. Negative regulation of two hyperproliferative keratinocyte differentiation markers by a retinoic acidreceptor-specific retinoid: insight into the mechanism of retinoid action in psoriasis. Cell Growth Differ. 1996 Dec;7 (12) :1783-91.|[3]Tang-Liu DD, et al. Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis. Clin Pharmacokinet. 1999 Oct;37 (4) :273-87.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Tazarotene

Tazarotene is the ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin. It has a role as a keratolytic drug, a prodrug and a teratogenic agent. It is an ethyl ester, a member of pyridines, a retinoid, a thiochromane and an acetylenic compound. It is functionally related to a tazarotenic acid.

CAS Number118292-40-3
PubChem CID5381
IUPAC Nameethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
Molecular FormulaC21H21NO2S
Molecular Weight351.5
XLogP4.9
Topological Polar Surface Area64.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Heavy Atom Count25
Formal Charge0
Complexity547
SMILES
CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C
InChI
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Tazarotene
CAS: 118292-40-3
CID: 5381
Formula: C21H21NO2S
MW: 351.5
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight351.5
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass351.12930009
Monoisotopic Mass351.12930009
Topological Polar Surface Area64.5 Ų
Heavy Atom Count25
Formal Charge0
Complexity547
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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