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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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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/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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