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Trifarotene

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Also known as: 895542-09-3, Cd5789, Cd-5789, 0j8rn2w0hk, 4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(2-hydroxyethoxy)phenyl]benzoic acid, 3''-(tert-butyl)-4'-(2-hydroxyethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid

Molecular Formula

C₂₉H₃₃NO₄

Molecular Weight

459.6 g/mol

InChI Key

MFBCDACCJCDGBA-UHFFFAOYSA-N

FDA UNII

0J8RN2W0HK

Trifarotene is a selective retinoic acid receptor gamma (RAR gamma) agonist that can be used in the treatment of acne vulgaris. Upon topical application, trifarotene selectively binds to the RAR gamma receptor, thereby altering the expression of certain genes that are involved in inflammation and cellular differentiation.

1 2D Structure

Trifarotene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(2-hydroxyethoxy)phenyl]benzoic acid

2.1.2 InChI

InChI=1S/C29H33NO4/c1-29(2,3)25-19-23(10-12-26(25)30-14-4-5-15-30)24-18-22(11-13-27(24)34-17-16-31)20-6-8-21(9-7-20)28(32)33/h6-13,18-19,31H,4-5,14-17H2,1-3H3,(H,32,33)

2.1.3 InChI Key

MFBCDACCJCDGBA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)C1=C(C=CC(=C1)C2=C(C=CC(=C2)C3=CC=C(C=C3)C(=O)O)OCCO)N4CCCC4

2.2 Other Identifiers

2.2.1 UNII

0J8RN2W0HK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aklief

2. Cd5789

2.3.2 Depositor-Supplied Synonyms

1. 895542-09-3

2. Cd5789

3. Cd-5789

4. 0j8rn2w0hk

5. 4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(2-hydroxyethoxy)phenyl]benzoic Acid

6. 3''-(tert-butyl)-4'-(2-hydroxyethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic Acid

7. 3''-tert-butyl-4'-(2-hydroxyethoxy)-4''-(pyrrolidin-1-yl)(1,1':3',1'')terphenyl-4-carboxylic Acid

8. Aklief

9. Trifarotene [inn]

10. Trifarotene [usan:inn]

11. Unii-0j8rn2w0hk

12. (1,1':3',1''-terphenyl)-4-carboxylic Acid, 3''-(1,1-dimethylethyl)-4'-(2-hydroxyethoxy)-4''-(1-pyrrolidinyl)-

13. [1,1':3',1''-terphenyl]-4-carboxylic Acid, 3''-(1,1-dimethylethyl)-4'-(2-hydroxyethoxy)-4''-(1-pyrrolidinyl)-

14. Aklief (tn)

15. Cd 5789

16. Trifarotene [mi]

17. Trifarotene (usan/inn)

18. Trifarotene [usan]

19. Trifarotene [who-dd]

20. Schembl381493

21. Gtpl9962

22. Chembl3707313

23. Dtxsid30237781

24. Trifarotene [orange Book]

25. Bcp31392

26. Ex-a2704

27. Bdbm50457548

28. Akos037649283

29. At10456

30. Db12808

31. Compound 15b [pmid: 29706423]

32. Bs-17812

33. Bt166038

34. Hy-100256

35. Cs-0018407

36. D11225

37. Cd5789; Cd-5789; Cd 5789

38. Q27236856

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₃NO₄
Molecular Weight	459.6 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	459.24095853 g/mol
Monoisotopic Mass	459.24095853 g/mol
Topological Polar Surface Area	70 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	647
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Trifarotene is indicated for the topical treatment of acne vulgaris in patients 9 years of age and older.

Treatment of ichthyoses

Treatment of acne

5 Pharmacology and Biochemistry

5.1 Pharmacology

Trifarotene exerts its effects via agonism at retinoid receptors - these receptors function to alter DNA transcription, resulting in downstream modulation of the expression of various genes involved in acne pathogenesis. It may be associated with skin irritation and should not be applied to cuts, abrasions, or otherwise damaged skin. As trifarotene may result in photosensitivity, patients should be cautioned to avoid excess sun exposure and to use sunscreen and/or protective clothing if exposure is unavoidable.

5.2 MeSH Pharmacological Classification

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 ATC Code

D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AD - Retinoids for topical use in acne

D10AD06 - Trifarotene

5.4 Absorption, Distribution and Excretion

Absorption

Systemic absorption of trifarotene is minimal. In a pharmacokinetic study involving 19 subjects, systemic concentrations were only quantifiable in 7 - steady state C_max values ranged from undetectable (<5 pg/mL) to 10 pg/mL and AUC_0-24h ranged from 75 to 104 pg.h/mL.

Route of Elimination

Trifarotene is eliminated primarily in the feces.

5.5 Metabolism/Metabolites

Trifarotene is rapidly metabolized in human hepatocytes - its observed half-life in human keratinocytes is >24 hours, whereas half-life in human liver microsomes is approximately 5 minutes. Metabolism of trifarotene is catalyzed primarily by CYP2C9, CYP3A4, CYP2C8, and, to a lesser extent, CYP2B6.

5.6 Biological Half-Life

The terminal half-life of trifarotene is typically between 2 to 9 hours.

5.7 Mechanism of Action

Trifarotene is a potent and selective agonist of retinoic acid receptor- (RAR-). It has significantly less activity at RAR- and RAR- (16- and 65-fold lower than activity at RAR-, respectively), and has no activity at retinoid X receptors (RXRs). Agonism at retinoic acid receptors results in dimerization, and the resulting receptor-ligand dimer binds to specific DNA regulatory sequences (retinoic acid response elements, or RAREs) in the promotor regions of retinoid-responsible genes. Downstream alterations to gene expression induced by binding to these regions is the principle mechanism through which trifarotene exerts its comedolytic, anti-inflammatory, and depigmenting effects. Like other retinoids, trifarotene influences the expression of a number of genes involved in retinoid metabolism, epidermal differentiation/proliferation, and epidermal response to stress. In addition, trifarotene appears to modulate retinoid-mediated pathways involved in proteolysis, skin hydration, and cell adhesion - modulation of these additional pathways has not been observed with other retinoids and may therefore be unique to trifarotene.

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