Basic information
- Standard SMILES
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1- InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N- Molecular formula
- C21H21NO2S
- Average molar mass
- 351.5 g/mol
- Monoisotopic mass
- 351.12929991
Overview
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.
Names & identifiers
- Preferred name
- Tazarotene
- IUPAC
- ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
- English name
- Tazarotene
- Molecular formula
- C21H21NO2S
- Molecular weight
- 351.46
Names & synonyms
Show more names
Database identifiers
- CAS
118292-40-3- PubChem CID
- 5381
- DTXSID
DTXSID5046691- ChEMBL
CHEMBL1657- ChEBI
CHEBI:32184- UNII
- 81BDR9Y8PS
- Nikkaji
- J679.813F
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 64.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 547
Experimental & physicochemical properties
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
Physicochemical properties
- Melting point
- 95 · 95-98°C
- Boiling point
- 499.8 · 499.8±45.0 °C(Predicted)
- Density
- 1.22 · 1.22±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 15 mg/mL · DMSO: >15mg/mL
- pka
- 0.04 · 0.04±0.29(Predicted)
- form
- powder
- color
- white to very faintly yellow
- Merck
- 14 · 14,9081
- Cosmetics Ingredients Functions
- 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 DataBase Reference
- 118292 · 118292-40-3(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- Avage; tazarotene; Tazorac
- FDA UNII
- 81 BDR9Y8PS · 81BDR9Y8PS
- NCI Drug Dictionary
- Avage
- ATC code
- 5 AX05 · D05AX05
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 361 d · H361d
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- WGK Germany
- 3 · 3
- RTECS
- 5675100 · US5675100
- HS Code
- 2934.99 · 2934.99.3000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Repr. 2
Safety & regulation
Toxicology
Safety data
- wgk
- 3
- rtecs
- US5675100
- hs_code
- 2934.99.3000
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361d
- Hazard Classifications
- Repr. 2
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
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.
Applications
DescriptionTazarotene belongs to a third generation prescription topical retinoid. It is marketed in different forms including cream (brand name: Avage), foam (brand name: Fabuir) and gel (brand name: Tazorac). It is mainly used for the treatment of psoriasis, acne, and sun damaged skin. The detailed mechanisms of action of Tazarotene are still unclear. It is converted to its active form, the cognate carboxylic acid of tazarotene (AGN 190299) in vivo through rapid de-esterification in animals and man. AGN 190299 is capable of binding to all the three members of the retinoic acid receptor (RAR) family: RARα, RARβ, and RARγ with relative selectivity for RARβ, and RARγ. This process may further modify gene expression. However, it is unclear whether this is related to its mode of action. Common side effects associated with it include worsening of acne, desquamation, burning/stinging, erythema and pruritus increased sensitivity to sunlight, dry skin, itchiness, redness, skin pain rash and skin discoloration. In most cases, these side effects are mild and can remarkable decrease after the first 2–4 weeks. Tazarotene should not be used in the following cases: patients are allergic to it; patients are pregnant; patients have a sunburn; patients are taking photo-sensitive drugs such as thiazides and tetracycline.
UsesTazarotene 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
UsesUsed to treat psoriasis, acne and sun damaged skin.
Usesanticholelithic
UsesAn acetylenic retinoid prodrug converted to the active metabolite, Tazarotenic acid, with selective affinity for retinoic acid receptors RARand RAR. Antiacne; antipsoriatic. Used in treatment of photodamaged skin
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
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.
Related reactions
Linked notes
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