[CAS NO. 106685-40-9] Adapalene

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PRODUCTS SPECIFICATIONS [106685-40-9]

Catalog

HY-B0091

Brand

MCE

CAS

106685-40-9

DESCRIPTION [106685-40-9]

Overview

MDL	MFCD03106112
Molecular Weight	412.52
Molecular Formula	C28H28O3
SMILES	COC1=C(C23CC4CC(C3)CC(C2)C4)C=C(C5=CC6=C(C=C(C(O)=O)C=C6)C=C5)C=C1

For research use only. We do not sell to patients.

4 Publications Citing Use of MCE

Summary

Adapalene (CD271), a third-generation synthetic retinoid, is widely used for the research of acne. Adapalene is a potent RAR agonist, with AC ₅₀ s of 2.3 nM, 9.3 nM, and 22 nM for RARβ , RARγ , RARα , respectively. Adapalene also inhibits the enzymatic activity of GOT1 in a non-competitive manner. Adapalene exhibits anti-tumor activity ^[1] ^[2] ^[3] .

IC50 & Target

AC50: 2.3 nM (RARβ), 9.3 nM (RARγ), and 22 nM (RARα) ^[1]

In Vitro

Adapalene (1-200 μM; 24 h) inhibits the viability of ES-2, HOV-7, MCF-7 , Hela, SW1990, HT1080, and MM-468 cells, with IC ₅₀ s of 10.36 μM, 10.81 μM, 12.00 μM, 19.08 μM, 19.52 μM, 21.70 μM, and 31.47 μM, respectively ^[2] .
Adapalene (10-40 μM; 24 h) induces ES-2 cells apoptosis and inhibits proliferation in vitro ^[2] .
Adapalene (3-30 μM; 6-24 h) significantly increases the G1-phase population in LoVo or DLD1 cells ^[3] .
Adapalene (1-200 μM) inhibits GOT1 activity, with an IC ₅₀ of 21.79 μM ^[2] .
Adapalene (10 ^-6 -10 ^-3 nM) inhibits the expression of plasma membrane-associated enzyme transglutaminase Type I, with an IC ₅₀ of 2.5 nM ^[1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay ^[2]

Cell Line:	Pancreatic cancer (SW1990, Aspc-1), breast cancer (mm-231, mm-468, MCF-7), liver cancer (Hep3B), cervical cancer (Hela), ovarian cancer (HOV-7, ES-2), normal cells (CHO, L929)
Concentration:	1-200 μM
Incubation Time:	24 hours
Result:	Inhibited the viability of cancer cells with higher GOT1 protein expression.

Apoptosis Analysis ^[2]

Cell Line:	ES-2 cells ^[2]
Concentration:	10, 20, 40 μM
Incubation Time:	24 hours
Result:	Showed a significant increase in apoptosis compared with the control group. Down regulated the expression of anti-apoptotic protein Bcl-2 and PARP.

Cell Cycle Analysis ^[3]

Cell Line:	LoVo or DLD1 cells
Concentration:	3, 10, 30 μM
Incubation Time:	6, 12, 24 hours
Result:	Caused cell cycle arrest in G1 phase in a dose- and time-dependent manner.

In Vivo

Adapalene (15-100 mg/kg; p.o. daily for 21 days) inhibits the growth of DLD1 cell-derived xenograft tumors in BALB/C nude mice ^[3] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Female BALB/C nude mice (15 g, 4-5 weeks) were injected with DLD1 cells ^[3]
Dosage:	15, 20, 65, 100 mg/kg
Administration:	P.o. daily for 21 days
Result:	Significantly reduced tumor weight and volume.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT03650361	Aleor Dermaceuticals Limited\|Catawba Research, LLC	Acne Vulgaris	September 17, 2018	Phase 3
NCT05582434	Wake Forest University Health Sciences\|Bausch Health Americas, Inc.	Acne	December 2022	Early Phase 1
NCT00599521	Galderma R&D	Acne Vulgaris	November 2007	Phase 3
NCT01182636	Teva Pharmaceuticals USA	Acne Vulgaris	July 2007	Phase 1
NCT03866447	Assiut University	Acne Vulgaris	October 1, 2019	Phase 4
NCT00719121	Stiefel, a GSK Company\|GlaxoSmithKline	Cutaneous Inflammation	November 2006	Phase 1
NCT03563365	Yardley Dermatology Associates\|Topix Pharmaceuticals, Inc	Acne Vulgaris	June 4, 2018	Phase 4
NCT01209949	Galderma R&D	Acne Vulgaris	October 2010	Phase 4
NCT01231334	Allergan	Acne Vulgaris	August 2010	Phase 4
NCT01213199	Galderma R&D	Acne Scars	March 2011	Phase 2
NCT04104685	Vyne Therapeutics Inc.	Acne Vulgaris	September 18, 2019	Phase 2
NCT00421993	Galderma R&D	Acne Vulgaris	October 2006	Phase 3
NCT00688064	Galderma R&D	Severe Acne Vulgaris	August 2008	Phase 3
NCT02338544	Galderma Laboratorium GmbH	Acne Vulgaris	January 2015
NCT02716090	Ache Laboratorios Farmaceuticos S.A.	Acne Vulgaris		Phase 3
NCT00919191	Bausch Health Americas, Inc.	Acne Vulgaris	April 2009	Phase 4
NCT01425320	Allergan	Acne Vulgaris	January 2013	Phase 1
NCT00647556	Galderma R&D	Photoaging	April 2008	Phase 3
NCT00907101	Galderma R&D	P Acnes Colonization	June 2009	Phase 4
NCT01046565	Galderma R&D	Skin Manifestations	January 2010	Phase 1
NCT00151541	Allergan	Acne Vulgaris	February 2005	Phase 3
NCT00671749	Galderma R&D	Acne Vulgaris	December 2007	Phase 4
NCT04329403	Aurobindo Pharma Ltd	Acne Vulgaris	July 2020	Phase 3
NCT02651220	Actavis Inc.	Acne	November 2015	Phase 3
NCT01742637	Taro Pharmaceuticals USA	Acne Vulgaris	October 2012	Phase 1
NCT00660985	Galderma R&D	Acne Vulgaris	May 2008	Phase 4
NCT02932267	Galderma R&D	Acne Vulgaris	February 2, 2017	Phase 3
NCT05536882	University of Oklahoma	Molluscum Contagiosum	February 2023	Phase 3
NCT03650881	NYU Langone Health	Acne	August 7, 2018	Not Applicable
NCT00441415	Galderma R&D	Acne Vulgaris	February 2007	Phase 3
NCT01095640	Actavis Mid-Atlantic LLC\|Actavis Inc.	Acne Vulgaris	March 2009	Not Applicable
NCT01406080	Galderma Brasil Ltda.	Photoaging\|Photodamage	January 2013	Phase 3
NCT00829049	Allergan	Acne Vulgaris	October 2007	Phase 4
NCT02173054	Mahidol University	Acne	July 2014	Phase 3
NCT01504204	Wake Forest University\|Galderma R&D\|Wake Forest University Health Sciences	Acne Vulgaris	December 2011	Phase 4
NCT00696449	Wake Forest University\|Wake Forest University Health Sciences	Acne Vulgaris	June 2006	Phase 4
NCT05096312	East Avenue Medical Center, Philippines	Acne Vulgaris	December 21, 2018	Phase 4
NCT02755545	Galderma R&D	Acne	May 1, 2016	Phase 4
NCT03393494	Padagis LLC	Acne Vulgaris	December 13, 2017	Phase 3
NCT00469755	Galderma R&D	Acne Vulgaris	February 2006	Phase 4
NCT02899000	Galderma R&D	Acne Vulgaris	July 29, 2016	Phase 4
NCT01618773	Galderma Laboratorium GmbH	Acne Vulgaris	June 2012
NCT00883233	Galderma R&D	Acne	April 2009	Phase 3
NCT02721173	All India Institute of Medical Sciences, Bhubaneswar	Acne Vulgaris	April 2016	Phase 4
NCT02411942	Taro Pharmaceuticals USA	Acne Vulgaris	August 2014	Phase 1
NCT01046396	Galderma R&D	Skin Manifestations	January 2010	Phase 1
NCT00714714	Bausch Health Americas, Inc.	Acne Vulgaris	January 2008	Phase 4
NCT01485367	Multispecialty Aesthetic Clinical Research Organization\|Galderma R&D	Senile Purpura	December 2011	Phase 2
NCT01501799	Actavis Mid-Atlantic LLC	Acne Vulgaris	July 2011	Not Applicable
NCT03615768	Lee´s Pharmaceutical Limited\|Zhaoke (Guangzhou) Ophthalmology Pharmaceutical Ltd.	Acne Vulgaris	August 14, 2018	Phase 3
NCT02525549	Padagis LLC	Acne	December 2011	Phase 3
NCT02593383	Lee´s Pharmaceutical Limited	Acne	March 1, 2015	Phase 1\|Phase 2
NCT03626298	Rumah Sakit Pusat Angkatan Darat Gatot Soebroto	Acne Vulgaris	August 1, 2016	Phase 4
NCT04823845	Jonathan M Towarnicki\|University of Louisville	Plantar Wart	May 1, 2022	Early Phase 1
NCT00887484	Stiefel, a GSK Company\|GlaxoSmithKline	Acne Vulgaris	February 2009	Phase 4
NCT02180425	University of California, Davis	Acne	November 2013
NCT00687908	Galderma R&D	Acne	November 2008	Phase 3
NCT05497323	Dr.dr.Irma Bernadette, SpKK (K)\|Indonesia University	Acne Vulgaris	August 1, 2022	Phase 1
NCT00964223	Stiefel, a GSK Company\|GlaxoSmithKline	Acne Vulgaris	July 2009	Phase 4
NCT04797793	Taro Pharmaceuticals USA	Acne Vulgaris	May 18, 2020	Early Phase 1
NCT03585140	Centro Dermatológico Dr. Ladislao de la Pascua	Acne Vulgaris\|Diet Modification	January 1, 2016	Not Applicable
NCT00598832	Galderma R&D	Acne Vulgaris	November 2007	Phase 3
NCT00926367	Stiefel, a GSK Company\|GlaxoSmithKline	Acne Vulgaris	May 2009	Phase 4

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 10 mg/mL ( 24.24 mM ; ultrasonic and warming and heat to 60°C)

H ₂ O : < 0.1 mg/mL (insoluble)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.4241 mL	12.1206 mL	24.2412 mL
5 mM	0.4848 mL	2.4241 mL	4.8482 mL
10 mM	0.2424 mL	1.2121 mL	2.4241 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: 1 mg/mL (2.42 mM); Suspended solution; Need ultrasonic
2.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 1 mg/mL (2.42 mM); Clear solution

* All of the co-solvents are available by MCE.

References

Synonyms

2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-

6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid

CD 271

Adapalene

Differin

6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthalenecarboxylic acid

Differin Gel

6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid

CD 271 (pharmaceutical)

Aclene Gel

Aclene

6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid