TRIFAROTENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C29H33NO4
Molecular Weight	459.5766
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)(C)C1=CC(=CC=C1N2CCCC2)C3=CC(=CC=C3OCCO)C4=CC=C(C=C4)C(O)=O

InChI

InChIKey=MFBCDACCJCDGBA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C29H33NO4
Molecular Weight	459.5766
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Trifarotene is a novel first-in-class fourth-generation topical retinoid. It is a potent and selective RAR gamma-agonist. In multiple mouse models, trifarotene exhibited superior comedolytic, anti-inflammatory and depigmenting activity compared with other topical retinoids. In this 52-week study, trifarotene was safe, well-tolerated and effective in moderate facial and truncal acne. Trifarotene is in phase II clinical trial for the treatment of ichthyosis.

Originator

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
10.8 pg/mL	200 mg 1 times / day steady-state, topical		TRIFAROTENE plasma	Homo sapiens
12 pg/mL	200 mg 1 times / day steady-state, topical		TRIFAROTENE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
118 pg × h/mL	200 mg 1 times / day steady-state, topical		TRIFAROTENE plasma	Homo sapiens
137 pg × h/mL	200 mg 1 times / day steady-state, topical		TRIFAROTENE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h	200 mg 1 times / day steady-state, topical		TRIFAROTENE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 15 years (range: 12-17 years)	DLT: Skin irritation... Other AEs: Skin exfoliation, Erythema...
0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 20 years (range: 18-34 years)	Other AEs: Erythema...
0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 20 years (range: 18-34 years)	Other AEs: Skin irritation...
2 g 1 times / day multiple, topical Recommended	unhealthy, >= 9 years	Other AEs: Application site irritation, Application site pruritus...
2 g 1 times / day multiple, topical Recommended	unhealthy, >= 9 years	Disc. AE: Application site irritation, Application site erosion...

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AEs

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AE	Significance	Dose	Population
Erythema	all grades, 4 patients	0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 15 years (range: 12-17 years)
Skin exfoliation	all grades, 4 patients	0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 15 years (range: 12-17 years)
Skin irritation	all grades, 8 patients DLT	0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 15 years (range: 12-17 years)
Erythema	88.9%	0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 20 years (range: 18-34 years)
Skin irritation	88.9%	0.01 % 1 times / day multiple, topical Studied dose	unhealthy, 20 years (range: 18-34 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	substrate 1,037 inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 CYP1A2 1,524 CYP2B6 810 CYP2C19 1,478 OAT 4 BCRP 699 P-gp 1,461 BSEP 402 MRP 7	CYP2C8 693 CYP2B6 664 P-gp 1,537 BCRP 561 OATP1B1/3 11 BSEP 52 MRP2 205 UGT 192	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity
BSEP 403	inhibitor 3,277	no
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2B6 1,001	inducer 1,573	no
CYP2B6 1,001	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP2C9 1,037	substrate 3,367	major	unlikely
CYP2B6 664	substrate 3,367	minor
CYP2C8 693	substrate 3,367	minor
UGT 192	substrate 3,367	minor
CYP3A4 1,737	substrate 3,367	minor	unlikely

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Ambeed	A298564	https://www.ambeed.com/products/895542-09-3.html
BioChemPartner	BCP31392	http://www.biochempartner.com/895542-09-3-BCP31392
BLD Pharm	BD00769386	http://www.bldpharm.com/products/895542-09-3.html
BOC Sciences	895542-09-3	https://www.bocsci.com/product/trifarotene-cas-895542-09-3-343568.html
Chem Scene	CS-0018407	http://www.chemscene.com/895542-09-3.html

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PubMed

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Title	Date	PubMed
Randomized phase 3 evaluation of trifarotene 50 μg/g cream treatment of moderate facial and truncal acne.	2019 Jun	30802558
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.	2020 Jan	31306527

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Patents

Substance Class	Chemical
Record UNII	0J8RN2W0HK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIFAROTENE

Official Name

English

TRIFAROTENE [ORANGE BOOK]

Common Name

English

CD-5789

Code

English

(1,1':3',1''-TERPHENYL)-4-CARBOXYLIC ACID, 3''-(1,1-DIMETHYLETHYL)-4'-(2-HYDROXYETHOXY)-4''-(1-PYRROLIDINYL)-

Systematic Name

English

Trifarotene [WHO-DD]

Common Name

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

431014

Retinoids for topical use in acne

WHO-ATC

D10AD06

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Code System

Code

Type

Description

CAS

895542-09-3

PRIMARY

NCI_THESAURUS

C118577

PRIMARY

FDA UNII

0J8RN2W0HK

PRIMARY

MERCK INDEX

m12163

PRIMARY

INN

9582

PRIMARY

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Related Record

Type

Details


					L9DP834D1P

CYTOCHROME P450 2C9

METABOLIC ENZYME -> SUBSTRATE

Qualification:

IC50

Amount:

3.9 MICROMOLAR (average)


					OSD7UB9MEE

Retinoic acid receptor gamma

TARGET -> AGONIST

Amount:


					L9DP834D1P

CYTOCHROME P450 2C9

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR

Amount:


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> SUBSTRATE

Amount:


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

REVERSIBLE

Qualification:

IC50

Amount:

7.8 MICROMOLAR (average)

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Related Record

Type

Details


					0J8RN2W0HK

TRIFAROTENE

ACTIVE MOIETY

Amount:

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SMILES

InChI

Originator

Approval Year

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

C_max

T_1/2

Drug as perpetrator