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    Chemistry

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    Also known as: 118292-40-3, Tazorac, Zorac, Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate, Avage, Agn-190168
    Molecular Formula
    C21H21NO2S
    Molecular Weight
    351.5  g/mol
    InChI Key
    OGQICQVSFDPSEI-UHFFFAOYSA-N
    FDA UNII
    81BDR9Y8PS
    Tazarotene
    Tazarotene is a synthetic, topical retinoid. Tazarotene induces the expression of tazarotene-induced gene 3 (TIG3), a tumor suppressor gene. In psoriasis, tazarotene normalizes abnormal keratinocyte differentiation and reduces their hyperproliferation. (NCI04)
    Tazarotene is a Retinoid.
    1 2D Structure

    Tazarotene

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
    2.1.2 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
    2.1.3 InChI Key
    OGQICQVSFDPSEI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    81BDR9Y8PS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Agn 190168

    2. Agn-190168

    3. Ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate

    4. Tazorac

    2.3.2 Depositor-Supplied Synonyms

    1. 118292-40-3

    2. Tazorac

    3. Zorac

    4. Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate

    5. Avage

    6. Agn-190168

    7. Fabior

    8. Agn 190168

    9. Tazarotene (avage)

    10. Idp-123

    11. 81bdr9y8ps

    12. Chembl1657

    13. Ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate

    14. 3-pyridinecarboxylic Acid, 6-((3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-yl)ethynyl)-, Ethyl Ester

    15. Chebi:32184

    16. Ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2h-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate

    17. Ncgc00167525-01

    18. Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2h-thiochromen-6-yl)ethynyl]nicotinate

    19. Dsstox_cid_26691

    20. Dsstox_rid_81825

    21. Dsstox_gsid_46691

    22. Tazaroteno

    23. Tazarotenum

    24. Suretin

    25. Tazoral

    26. Zora

    27. 6-(4,4-dimethyl-thiochroman-6-ylethynyl)-nicotinic Acid Ethyl Ester

    28. Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate;6-(4,4-dimethyl-thiochroman-6-ylethynyl)-nicotinic Acid Ethyl Ester

    29. Tazorac (tn)

    30. Avage (tn)

    31. Cas-118292-40-3

    32. Unii-81bdr9y8ps

    33. Acnitaz

    34. Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]pyridine-3-carboxylate

    35. Ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)-ethynyl)nicotinate

    36. Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)-ethynyl]nicotinate

    37. Tazarotene (jan/usan/inn)

    38. Tazarotene [usan:inn:ban]

    39. Tazarotene,(s)

    40. Tazarotene- Bio-x

    41. Fabior (tn)

    42. Arazlo

    43. Tazarotene [mi]

    44. Tazarotene [inn]

    45. Tazarotene [jan]

    46. Tazarotene [inci]

    47. Tazarotene [usan]

    48. Tazarotene [vandf]

    49. Schembl3134

    50. Tazarotene [mart.]

    51. Tazarotene [who-dd]

    52. Mls003915630

    53. Bidd:gt0293

    54. Gtpl6952

    55. Dtxsid5046691

    56. Tazarotene [orange Book]

    57. Hms3655k05

    58. Hms3747c19

    59. Hms3747e19

    60. Duobrii Component Tazarotene

    61. Act06773

    62. Amy31169

    63. Bcp22966

    64. Zinc1542199

    65. Tox21 112522

    66. Tox21_112522

    67. Ac-755

    68. Bdbm50265951

    69. Mfcd00867628

    70. S1569

    71. Idp-118 Component Tazarotene

    72. Akos015902872

    73. Tazarotene Component Of Duobrii

    74. Tox21_112522_1

    75. Bs-1012

    76. Ccg-268046

    77. Cs-1029

    78. Db00799

    79. Ncgc00167525-02

    80. Ncgc00167525-03

    81. Bt164442

    82. Hy-15388

    83. Smr002096194

    84. Bcp0726000163

    85. Db-014992

    86. Ft-0652578

    87. Sw220026-1

    88. T3108

    89. Agn190168, Agn-190168

    90. D01132

    91. Ab01274801-01

    92. Ab01274801_02

    93. 292t403

    94. A846572

    95. Sr-01000931253

    96. Q-102516

    97. Q3981685

    98. Sr-01000931253-2

    99. Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinate

    100. 6-(4,4-dimethylthiochroman-6-ylethynyl) Nicotinic Acid Ethyl Ester

    101. (+/-)octahydrocyclopenta[b]pyrrole-2-carboxylicacidhydrochloride

    102. 6-(2-(4,4-dimethyl-thiochroman-6yl)ethynyl)-nicotinic Acid Ethyl Ester

    103. Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2h-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate

    104. 6-[2-(3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-yl)ethynyl]- 3-pyridinecarboxylic Acid Ethyl Ester

    105. 6-[2-(3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic Acid Ethyl Ester

    106. 6-[2-(3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylicacidethylester

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 351.5 g/mol
    Molecular Formula C21H21NO2S
    XLogP34.9
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass351.12930009 g/mol
    Monoisotopic Mass351.12930009 g/mol
    Topological Polar Surface Area64.5 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity547
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameAvage
    PubMed HealthTazarotene (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelAVAGE Cream is a white cream and contains the compound tazarotene; this formulation of tazarotene cream is also marketed for the treatment of plaque psoriasis and acne vulgaris as TAZORAC (tazarotene) Cream, 0.1%. Tazarotene is a member of the ac...
    Active IngredientTazarotene
    Dosage FormCream
    RouteTopical
    Strength0.1%
    Market StatusPrescription
    CompanyAllergan

    2 of 6  
    Drug NameFabior
    PubMed HealthTazarotene (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelFABIOR (tazarotene) Foam, 0.1% contains the compound tazarotene, a member of the acetylenic class of retinoids. It is for topical use only.Chemically, tazarotene is ethyl 6-[(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinate. The structural formula is...
    Active IngredientTazarotene
    Dosage FormAerosol, foam
    RouteTopical
    Strength0.1%
    Market StatusPrescription
    CompanyStiefel Labs

    3 of 6  
    Drug NameTazorac
    Drug LabelTAZORAC Gel is a translucent, aqueous gel and contains the compound tazarotene, a member of the acetylenic class of retinoids. It is for topical dermatologic use only. The active ingredient is represented by the following structural formula: Formul...
    Active IngredientTazarotene
    Dosage FormCream; Gel
    RouteTopical
    Strength0.05%; 0.1%
    Market StatusPrescription
    CompanyAllergan

    4 of 6  
    Drug NameAvage
    PubMed HealthTazarotene (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelAVAGE Cream is a white cream and contains the compound tazarotene; this formulation of tazarotene cream is also marketed for the treatment of plaque psoriasis and acne vulgaris as TAZORAC (tazarotene) Cream, 0.1%. Tazarotene is a member of the ac...
    Active IngredientTazarotene
    Dosage FormCream
    RouteTopical
    Strength0.1%
    Market StatusPrescription
    CompanyAllergan

    5 of 6  
    Drug NameFabior
    PubMed HealthTazarotene (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelFABIOR (tazarotene) Foam, 0.1% contains the compound tazarotene, a member of the acetylenic class of retinoids. It is for topical use only.Chemically, tazarotene is ethyl 6-[(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinate. The structural formula is...
    Active IngredientTazarotene
    Dosage FormAerosol, foam
    RouteTopical
    Strength0.1%
    Market StatusPrescription
    CompanyStiefel Labs

    6 of 6  
    Drug NameTazorac
    Drug LabelTAZORAC Gel is a translucent, aqueous gel and contains the compound tazarotene, a member of the acetylenic class of retinoids. It is for topical dermatologic use only. The active ingredient is represented by the following structural formula: Formul...
    Active IngredientTazarotene
    Dosage FormCream; Gel
    RouteTopical
    Strength0.05%; 0.1%
    Market StatusPrescription
    CompanyAllergan

    4.2 Drug Indication

    Used to treat psoriasis, acne and sun damaged skin (photodamage).

    FDA Label

    Treatment of lamellar ichthyosis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Keratolytic Agents

    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. (See all compounds classified as Keratolytic Agents.)

    Teratogens

    An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TAZAROTENE
    5.3.2 FDA UNII
    81BDR9Y8PS
    5.3.3 Pharmacological Classes
    Retinoids [CS]; Retinoid [EPC]
    5.4 ATC Code

    D - Dermatologicals

    D05 - Antipsoriatics

    D05A - Antipsoriatics for topical use

    D05AX - Other antipsoriatics for topical use

    D05AX05 - Tazarotene

    5.5 Absorption, Distribution and Excretion

    Absorption

    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.

    Route of Elimination

    Tazarotene and tazarotenic acid were metabolized to sulfoxides, sulfones and other polar metabolites which were eliminated through urinary and fecal pathways.

    5.6 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.

    5.7 Biological Half-Life

    The half-life of the active form of the drug, tazarotenic acid, is approximately 18 hours in normal and psoriatic patients.

    5.8 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.

    API Reference Price

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    19-Feb-2021
    29-Aug-2024
    KGS
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    DOSAGE - AEROSOL, FOAM;TOPICAL - 0.1%

    USFDA APPLICATION NUMBER - 202428

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    DOSAGE - CREAM;TOPICAL - 0.05%

    USFDA APPLICATION NUMBER - 21184

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    DOSAGE - CREAM;TOPICAL - 0.1%

    USFDA APPLICATION NUMBER - 21184

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    ABOUT THIS PAGE

    Tazarotene Manufacturers

    A Tazarotene manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Tazarotene, including repackagers and relabelers. The FDA regulates Tazarotene manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Tazarotene API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Tazarotene manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Tazarotene Suppliers

    A Tazarotene supplier is an individual or a company that provides Tazarotene active pharmaceutical ingredient (API) or Tazarotene finished formulations upon request. The Tazarotene suppliers may include Tazarotene API manufacturers, exporters, distributors and traders.

    click here to find a list of Tazarotene suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Tazarotene USDMF

    A Tazarotene DMF (Drug Master File) is a document detailing the whole manufacturing process of Tazarotene active pharmaceutical ingredient (API) in detail. Different forms of Tazarotene DMFs exist exist since differing nations have different regulations, such as Tazarotene USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Tazarotene DMF submitted to regulatory agencies in the US is known as a USDMF. Tazarotene USDMF includes data on Tazarotene's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Tazarotene USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Tazarotene suppliers with USDMF on PharmaCompass.

    Tazarotene WC

    A Tazarotene written confirmation (Tazarotene WC) is an official document issued by a regulatory agency to a Tazarotene manufacturer, verifying that the manufacturing facility of a Tazarotene active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Tazarotene APIs or Tazarotene finished pharmaceutical products to another nation, regulatory agencies frequently require a Tazarotene WC (written confirmation) as part of the regulatory process.

    click here to find a list of Tazarotene suppliers with Written Confirmation (WC) on PharmaCompass.

    Tazarotene NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Tazarotene as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Tazarotene API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Tazarotene as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Tazarotene and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Tazarotene NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Tazarotene suppliers with NDC on PharmaCompass.

    Tazarotene GMP

    Tazarotene Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Tazarotene GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Tazarotene GMP manufacturer or Tazarotene GMP API supplier for your needs.

    Tazarotene CoA

    A Tazarotene CoA (Certificate of Analysis) is a formal document that attests to Tazarotene's compliance with Tazarotene specifications and serves as a tool for batch-level quality control.

    Tazarotene CoA mostly includes findings from lab analyses of a specific batch. For each Tazarotene CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Tazarotene may be tested according to a variety of international standards, such as European Pharmacopoeia (Tazarotene EP), Tazarotene JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Tazarotene USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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