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
Weitere Namen anzeigen
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
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
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)
- Aggregatzustand
- powder
- Farbe
- white to very faintly yellow
- Merck
- 14 · 14,9081
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONING
- 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 Datenbank
- 118292 · 118292-40-3(CAS DataBase Reference)
Sicherheit und Regulatorisches
Toxikologische Informationen
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
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.
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
TAZAROTENE
Established Pharmacologic Class [EPC] - Retinoid
Chemical Structure [CS] - Retinoids
Tazarotene is a Retinoid.
TAZAROTENE
MeSH Pharmacological Classification
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
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.
Anwendungen
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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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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