Tazarotene

HCID 5381CAS 118292-40-3

Grundinformationen

Standard-SMILES
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
Summenformel
C21H21NO2S
Durchschnittliche Molmasse
351,5 g/mol
Monoisotopische Masse
351,12929991

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Tazarotene
IUPAC
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
Englischer Name
Tazarotene
Summenformel
C21H21NO2S
Molmasse
351.46

Namen und Synonyme

tazarotene118292-40-3TazoracEthyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinateZoracAvageAGN-190168FabiortazarotenotazarotenumDTXSID5046691Idp-123
Weitere Namen anzeigen
azaroteneTazorac/zoracTazarotene(Avage)Tazarotene, >=98%Tazarotene 99% Min
81BDR9Y8PSAGN190168ARAZLODUOBRII COMPONENT TAZAROTENEethyl 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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,9
Polarare Oberfläche (TPSA)
64,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 Einträge

5.6

5.6

Solubility · 2 Einträge

Soluble

7.50e-04 g/L

Human Drugs · 3 Einträge

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
95 · 95-98°C
Siedepunkt
499.8 · 499.8±45.0 °C(Predicted)
Dichte
1.22 · 1.22±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
15 mg/mL · DMSO: >15mg/mL
pka
0.04 · 0.04±0.29(Predicted)

Sicherheit und Regulatorisches

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
hs_code
2934.99.3000
RTECS-Nr.
US5675100
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Repr. 2

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

D - Dermatologicals

QD - Dermatologicals

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

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 Eintrag

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 Eintrag

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.

Anwendungen · 1 Eintrag

VerwendenTazarotene 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

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北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Ergänzende Hinweise

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

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