Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H17NO2S |
| Molecular Weight | 323.409 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)CCSC2=CC=C(C=C12)C#CC3=CC=C(C=N3)C(O)=O
InChI
InChIKey=IQIBKLWBVJPOQO-UHFFFAOYSA-N
InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)
| Molecular Formula | C19H17NO2S |
| Molecular Weight | 323.409 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tazarotene a novel acetylenic retinoid is known to be effective in the topical treatment of psoriasis and acne. Tazarotene is rapidly and completely metabolized to its active metabolite tazarotenic acid. The exact mechanism of action of tazarotenic acid in the treatment of psoriasis and acne is not clearly defined. However, it is thought that the selective interaction of tazarotenic acid with the retinoic acid receptor (RAR) family (RARα, RARβ, and RARγ) and the subsequent induction of both positive and negative gene regulatory effects may be involved.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis. | 1997 Aug |
|
| Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways. | 2006 Feb 1 |
Patents
Sample Use Guides
In vitro enzyme kinetic parameters were determined for tazarotenic acid metabolite formation using 5 nM CYP26A1 or CYP26B1, 25 nM purified human reductase, and 0–10 μM tazarotenic acid. Incubations were carried out for 10 minutes at 37°C to ensure product linearity with regard to time and protein concentration. Additional experiments to determine the kinetic parameters for the sequential metabolism of tazarotenic acid metabolite sulfoxide used substrate concentrations ranging from 0 to 50 μM. Samples were prepared as described for in vitro metabolic profiling experiments.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 13:08:09 UTC 2019
by
admin
on
Tue Oct 22 13:08:09 UTC 2019
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| Record UNII |
85FDJ14553
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| Record Status |
Validated (UNII)
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| Record Version |
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118292-41-4
Created by
admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
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118292-41-4
Created by
admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
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147525
Created by
admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PRODRUG -> METABOLITE ACTIVE |
Esterase metabolism
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
