Tazarotene
Grundinformationen
- CAS
118292-40-3- 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
- 351,12930009
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)nicotinateZoracAvageFabiorAGN-190168tazarotenotazarotenumIdp-123ARAZLO
Weitere Namen anzeigen
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
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
- Formalladung
- 0
- Komplexität
- 547
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP
5.6
5.6
Solubility
Soluble
7.50e-04 g/L
Human Drugs
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
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
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
D - Dermatologicals
QD - Dermatologicals
Protein BindingThe active form of the drug, tazarotenic acid, is highly bound to plasma proteins (>99%).
Pharmacodynamics
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
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
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
81BDR9Y8PS
Zugehörige Reaktionen
16
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