ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

タザロテン

Tazarotene

HCID 5381
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
118292-40-3
標準SMILES
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
分子式
C21H21NO2S
平均分子量
351.5 g/mol
単同位体質量
351.12930009

概要

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.

名称と識別子

優先名称
Tazarotene
IUPAC
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
現地名
タザロテン
英語名
Tazarotene
分子式
C21H21NO2S
分子量
351.46

名称と別名

tazarotene118292-40-3TazoracEthyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinateZoracAvageFabiorAGN-190168tazarotenotazarotenumIdp-123ARAZLO
名称をさらに表示
6-[(3,4-ジヒドロ-4,4-ジメチル-2H-1-ベンゾチオピラン)-6-イル]ニコチン酸エチルタザロテン6-((4,4-ジメチルチオクロマン-6-イル)エチニル)ニコチン酸エチルタザロテン (JAN)エチル 6-(4,4-ジメチル-3,4-ジヒドロ-2H-1-ベンゾチオピラン-6-イル)ピリジン-3-カルボキシラートエチル 6-[2-(4,4-ジメチル-3,4-ジヒドロ-2H-1-ベンゾチオピラン-6-イル)エチニル]ピリジン-3-カルボキシラートゾラックタゾラック6-[[(3,4-ジヒドロ-4,4-ジメチル-2H-1-ベンゾチオピラン)-6-イル]エチニル]ピリジン-3-カルボン酸エチルazaroteneTazorac/zoracTazarotene(Avage)Tazarotene, >=98%Tazarotene 99% Min
DTXSID5046691DUOBRII COMPONENT TAZAROTENE81BDR9Y8PSAGN190168ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl esterDTXCID3026691CHEBI:32184

物性

構造計算による物性

XLogP
4.9
極性表面積
64.5 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
5
重原子数
25
形式電荷
0
複雑度
547

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 件

5.6

5.6

Solubility · 2 件

Soluble

7.50e-04 g/L

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Dermatologic Agents; Keratolytic Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

物理化学的性質

融点
95 · 95-98°C
沸点
499.8 · 499.8±45.0 °C(Predicted)
比重(密度)
1.22 · 1.22±0.1 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
15 mg/mL · DMSO：>15mg/mL
酸解離定数(Pka)
0.04 · 0.04±0.29(Predicted)
外見
粉
色
白色からわずかに黄色
Merck
14 · 14,9081
化粧品成分の機能

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
3
rtecs
US5675100
hs_code
2934.99.3000
Hazard Classifications
Repr. 2
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

D - Dermatologicals

QD - Dermatologicals

Protein BindingThe active form of the drug, tazarotenic acid, is highly bound to plasma proteins (>99%).
Pharmacodynamics · 1 件

Following topical application, tazarotene undergoes esterase hydrolysis to form its active metabolite, tazarotenic acid. When treating acne tazarotene may be taken in conjunction with an oral antibiotic. Tazarotene has been shown in peer-reviewed double blinded studies to reduce: mottling and hyperpigmentation, sallowness, fine wrinkling and coarse wrinkling in sun damaged skin. Histological studies have shown that long term (greater than 1 year) use of Tazarotene is associated with a significant reduction in atypical melanocytes and keratocytes - cells considered to be precursors of skin cancer. Some studies have shown long term use of Tazarotene to be associated with increased collagen production and better organization of skin collagen bundles.

Mechanism of Action · 1 件

Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors.

Biological Half-LifeThe half-life of the active form of the drug, tazarotenic acid, is approximately 18 hours in normal and psoriatic patients.
Metabolism/Metabolites · 1 件

Undergoes esterase hydrolysis in skin to form its active metabolite, tazarotenic acid. Tazarotenic acid is further metabolized in skin and, after systemic absorption, hepatically metabolized to sulfoxides, sulfones, and other polar products for elimination.

FDA Pharmacological Classification · 6 件

81BDR9Y8PS

TAZAROTENE

Established Pharmacologic Class [EPC] - Retinoid

関連反応

16 件
反応記録を作成
HRID 677043 の反応式
HRID 677043生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 820860 の反応式
HRID 820860反応物としてTest data from https://doi.org/10.1039/C8SC04228D
HRID 941672 の反応式
HRID 941672反応物としてValidation data from https://doi.org/10.1039/C8SC04228D
HRID 1062834 の反応式
HRID 1062834反応物としてuspto-grants-2005_11
HRID 1450232 の反応式
HRID 1450232生成物としてuspto-grants-1997_02
HRID 1450246 の反応式
HRID 1450246反応物としてuspto-grants-1997_02
HRID 1534510 の反応式
HRID 1534510生成物としてuspto-grants-1992_02
HRID 1534525 の反応式
HRID 1534525反応物としてuspto-grants-1992_02
1 / 2 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

データベース識別子

CAS
118292-40-3
PubChem CID
5381
DTXSID
DTXSID5046691
ChEMBL
CHEMBL1657
ChEBI
CHEBI:32184
UNII
81BDR9Y8PS
Nikkaji
J679.813F
スキンコンディショニング
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
SMILES
C1=NC(C#CC2C=C3C(=CC=2)SCCC3(C)C)=CC=C1C(OCC)=O
CAS データベース
118292 · 118292-40-3(CAS DataBase Reference)

化学的性質

化学的特性White Solid

Chemical Structure [CS] - Retinoids

Tazarotene is a Retinoid.

TAZAROTENE

MeSH Pharmacological Classification · 3 件

Drugs used to treat or prevent skin disorders or for the routine care of skin.

Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.

An agent that causes the production of physical defects in the developing embryo.

Absorption, Distribution and Excretion · 2 件

Minimal systemic absorption of tazarotene occurs due to its rapid metabolism in the skin to the active metabolite, tazarotenic acid, which can be systemically absorbed and further metabolized. Gender had no influence on the systemic bioavailability of tazarotenic acid.

Tazarotene and tazarotenic acid were metabolized to sulfoxides, sulfones and other polar metabolites which were eliminated through urinary and fecal pathways.

Cellular LocationsCytoplasm
応用分野 · 1 件

使用Tazarotene is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). It is commonly sold in two concentrations: 0.05% and 0.1%. In addition to tretinoin, wh

上流・下流製品情報

上流原料

864841-54-3864841-55-46-ブロモ-4,4-ジメチルチオクロマン6-[[(3,4-ジヒドロ-4,4-ジメチル-2H-1-ベンゾチオピラン)-6-イル]エチニル]ニコチン酸6-エチニル-4,4-ジメチルチオクロマントリフェニルホスフィンエタノール炭酸カリウム6-クロロニコチン酸エチルオルト酢酸トリエチル

補足説明

定義ChEBI: The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.