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Tazarotene

HCID 5381
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
118292-40-3
표준 SMILES
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
분자식
C21H21NO2S
평균 분자량
351.5 g/mol
단동위원소 질량
351.12930009

개요

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.

이름 및 식별자

우선 이름
Tazarotene
IUPAC
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
영어명
Tazarotene
분자식
C21H21NO2S
분자량
351.46

이름 및 동의어

tazarotene118292-40-3TazoracEthyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinateZoracAvageFabiorAGN-190168tazarotenotazarotenumIdp-123ARAZLO
이름 더 보기
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

데이터베이스 식별자

CAS
118292-40-3
PubChem CID
5381
DTXSID
DTXSID5046691
ChEMBL
CHEMBL1657
ChEBI
CHEBI:32184
UNII
81BDR9Y8PS
Nikkaji
J679.813F

물성

구조 계산 물성

XLogP
4.9
극성 표면적
64.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
25
형식 전하
0
복잡도
547

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2건

5.6

5.6

Solubility · 2건

Soluble

7.50e-04 g/L

Human Drugs · 3건

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

물리화학적 성질

녹는점
95 · 95-98°C
끓는 점
499.8 · 499.8±45.0 °C(Predicted)
밀도
1.22 · 1.22±0.1 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
15 mg/mL · DMSO: >15mg/mL
산도 계수 (pKa)
0.04 · 0.04±0.29(Predicted)
물리적 상태
가루
색상
흰색에서 아주 희미한 노란색
Merck
14 · 14,9081

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
US5675100
HS 번호
2934.99.3000
Hazard Classifications
Repr. 2
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 2건

D - Dermatologicals

QD - Dermatologicals

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

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 · 1건

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 · 1건

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 · 6건

81BDR9Y8PS

TAZAROTENE

Established Pharmacologic Class [EPC] - Retinoid

관련 반응

16건
반응 기록 만들기
HRID 677043 반응식
HRID 677043생성물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 820860 반응식
HRID 820860반응물로Test data from https://doi.org/10.1039/C8SC04228D
HRID 941672 반응식
HRID 941672반응물로Validation data from https://doi.org/10.1039/C8SC04228D
HRID 1062834 반응식
HRID 1062834반응물로uspto-grants-2005_11
HRID 1450232 반응식
HRID 1450232생성물로uspto-grants-1997_02
HRID 1450246 반응식
HRID 1450246반응물로uspto-grants-1997_02
HRID 1534510 반응식
HRID 1534510생성물로uspto-grants-1992_02
HRID 1534525 반응식
HRID 1534525반응물로uspto-grants-1992_02
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화장품 원료 기능
피부 컨디셔닝
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

화학적 성질

White Solid

Chemical Structure [CS] - Retinoids

Tazarotene is a Retinoid.

TAZAROTENE

MeSH Pharmacological Classification · 3건

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 · 2건

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
응용 분야 · 1건

용도Tazarotene 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

상·하류 제품 정보

상류 원료

864841-54-3864841-55-46-Bromo-3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyranAGN 1902996-에티닐-4,4-디메틸티오크로만트리페닐포스핀에틸알코올탄산 칼륨Ethyl 6-chloronicotinate오소초산에틸

추가 설명

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