MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 319722 | Name: Trifarotene
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Trifarotene is a gamma retinoic acid receptor agonist. Trifarotene is in development as a topical cream for the treatment of skin disorders, including acne vulgaris, cutaneous t-cell lymphoma and lamellar ichthyosis.

Chemical Structure

Trifarotene
Trifarotene
CAS#895542-09-3

Theoretical Analysis

MedKoo Cat#: 319722

Name: Trifarotene

CAS#: 895542-09-3

Chemical Formula: C29H33NO4

Exact Mass: 459.2410

Molecular Weight: 459.59

Elemental Analysis: C, 75.79; H, 7.24; N, 3.05; O, 13.92

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 185.00 Ready to ship
100mg USD 550.00 Ready to ship
200mg USD 950.00 Ready to ship
500mg USD 1,650.00 Ready to ship
1g USD 2,950.00 Ready to ship
2g USD 5,250.00 2 Weeks
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Trifarotene; CD5789; CD-5789; CD 5789. Aklief
IUPAC/Chemical Name
3''-(tert-butyl)-4'-(2-hydroxyethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid
InChi Key
MFBCDACCJCDGBA-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(C1=CC=C(C2=CC=C(OCCO)C(C3=CC=C(N4CCCC4)C(C(C)(C)C)=C3)=C2)C=C1)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Trifarotene (CD5789) is a selective RARγ agonist that shows ∼65-fold and ∼16-fold selectivitiy for the RARγ (EC50=7.7 nM) over RARα (EC50=500 nM) and RARβ (EC50=125 nM), respectively.
In vitro activity:
The objective of this study was to characterize the in vitro metabolism and pharmacology of the novel retinoid trifarotene. In vitro assays determined efficacy, potency and selectivity on RARs, as well as the activity on the expression of retinoid target genes in human keratinocytes. Trifarotene is a selective RARγ agonist with > 20-fold selectivity over RARα and RARβ. Trifarotene is active and stable in keratinocytes but rapidly metabolized by human hepatic microsomes, predicting improved safety. Reference: Br J Dermatol. 2018 Aug;179(2):442-456. https://pubmed.ncbi.nlm.nih.gov/29974453/
In vivo activity:
In vivo, trifarotene 0·01% applied topically is highly comedolytic and has anti-inflammatory and antipigmenting properties. Gene expression studies indicated potent activation of known retinoid-modulated processes (epidermal differentiation, proliferation, stress response, retinoic acid metabolism) and novel pathways (proteolysis, transport/skin hydration, cell adhesion) in ex vivo and in vivo models Reference: Br J Dermatol. 2018 Aug;179(2):442-456. https://pubmed.ncbi.nlm.nih.gov/29974453/
Solvent mg/mL mM
Solubility
DMSO 250.0 543.97
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 459.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Aubert J, Piwnica D, Bertino B, Blanchet-Réthoré S, Carlavan I, Déret S, Dreno B, Gamboa B, Jomard A, Luzy AP, Mauvais P, Mounier C, Pascau J, Pelisson I, Portal T, Rivier M, Rossio P, Thoreau E, Vial E, Voegel JJ. Nonclinical and human pharmacology of the potent and selective topical retinoic acid receptor-γ agonist trifarotene. Br J Dermatol. 2018 Aug;179(2):442-456. doi: 10.1111/bjd.16719. Epub 2018 Jul 4. PMID: 29974453.
In vitro protocol:
1. Aubert J, Piwnica D, Bertino B, Blanchet-Réthoré S, Carlavan I, Déret S, Dreno B, Gamboa B, Jomard A, Luzy AP, Mauvais P, Mounier C, Pascau J, Pelisson I, Portal T, Rivier M, Rossio P, Thoreau E, Vial E, Voegel JJ. Nonclinical and human pharmacology of the potent and selective topical retinoic acid receptor-γ agonist trifarotene. Br J Dermatol. 2018 Aug;179(2):442-456. doi: 10.1111/bjd.16719. Epub 2018 Jul 4. PMID: 29974453.
In vivo protocol:
1. Aubert J, Piwnica D, Bertino B, Blanchet-Réthoré S, Carlavan I, Déret S, Dreno B, Gamboa B, Jomard A, Luzy AP, Mauvais P, Mounier C, Pascau J, Pelisson I, Portal T, Rivier M, Rossio P, Thoreau E, Vial E, Voegel JJ. Nonclinical and human pharmacology of the potent and selective topical retinoic acid receptor-γ agonist trifarotene. Br J Dermatol. 2018 Aug;179(2):442-456. doi: 10.1111/bjd.16719. Epub 2018 Jul 4. PMID: 29974453.
1: Scott LJ. Trifarotene: First Approval. Drugs. 2019 Nov;79(17):1905-1909. doi: 10.1007/s40265-019-01218-6. Review. PubMed PMID: 31713811. 2: Blume-Peytavi U, Fowler J, Kemény L, Draelos Z, Cook-Bolden F, Dirschka T, Eichenfield L, Graeber M, Ahmad F, Alió Saenz A, Rich P, Tanghetti E. Long-term safety and efficacy of trifarotene 50 μg/g cream, a first-in-class RAR-γ selective topical retinoid, in patients with moderate facial and truncal acne. J Eur Acad Dermatol Venereol. 2019 Jul 15. doi: 10.1111/jdv.15794. [Epub ahead of print] PubMed PMID: 31306527. 3: Tan J, Thiboutot D, Popp G, Gooderham M, Lynde C, Del Rosso J, Weiss J, Blume-Peytavi U, Weglovska J, Johnson S, Parish L, Witkowska D, Sanchez Colon N, Alió Saenz A, Ahmad F, Graeber M, Stein Gold L. Randomized phase 3 evaluation of trifarotene 50 μg/g cream treatment of moderate facial and truncal acne. J Am Acad Dermatol. 2019 Jun;80(6):1691-1699. doi: 10.1016/j.jaad.2019.02.044. Epub 2019 Feb 22. PubMed PMID: 30802558. 4: Balak DMW. Topical trifarotene: a new retinoid. Br J Dermatol. 2018 Aug;179(2):231-232. doi: 10.1111/bjd.16733. PubMed PMID: 30141539. 5: Aubert J, Piwnica D, Bertino B, Blanchet-Réthoré S, Carlavan I, Déret S, Dreno B, Gamboa B, Jomard A, Luzy AP, Mauvais P, Mounier C, Pascau J, Pelisson I, Portal T, Rivier M, Rossio P, Thoreau E, Vial E, Voegel JJ. Nonclinical and human pharmacology of the potent and selective topical retinoic acid receptor-γ agonist trifarotene. Br J Dermatol. 2018 Aug;179(2):442-456. doi: 10.1111/bjd.16719. Epub 2018 Jul 4. PubMed PMID: 29974453. 6: Thoreau E, Arlabosse JM, Bouix-Peter C, Chambon S, Chantalat L, Daver S, Dumais L, Duvert G, Feret A, Ouvry G, Pascau J, Raffin C, Rodeville N, Soulet C, Tabet S, Talano S, Portal T. Structure-based design of Trifarotene (CD5789), a potent and selective RARγ agonist for the treatment of acne. Bioorg Med Chem Lett. 2018 Jun 1;28(10):1736-1741. doi: 10.1016/j.bmcl.2018.04.036. Epub 2018 Apr 15. PubMed PMID: 29706423.