Tazarotene

HCID 5381CAS 118292-40-3

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

tazarotene118292-40-3TazoracEthyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinateZoracAvageAGN-190168FabiortazarotenotazarotenumDTXSID5046691Idp-123
Show more names
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

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

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 items

5.6

5.6

Solubility · 2 items

Soluble

7.50e-04 g/L

Human Drugs · 3 items

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

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)

Safety & regulation

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
US5675100
hs_code
2934.99.3000
Signal word
Warning
Symbol(GHS)
GHS08
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

ATC Code · 2 items

D - Dermatologicals

QD - Dermatologicals

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

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 item

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 item

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.

Applications · 5 items

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

Suppliers50 total

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]

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

16 records

Linked notes

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