106685-40-9 (Adapalene)

Identification

Name	Adapalene
Formula	C28H28O3
MW	412.52
CAS No.	106685-40-9
EINECS

Smiles	O=C(C1=CC2=CC=C(C3=CC=C(OC)C(C45C[[email protected]@H](C[[email protected]](C6)C5)C[[email protected]@H]6C4)=C3)C=C2C=C1)O
Synonyms	CD 271;CD271;CD-271;Differin; 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid
InChI	InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)/t17-,18+,19-,28?

Introduction

Adapalene(CD-271; Differin), a synthetic retinoid, is a retinoic acid receptor agonist (RAR). Target: Retinoic acid receptor agonist (RAR) Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions.

Background Information

Blocker of the synthesis of prostaglandins, inhibiting cyclooxygenase ......by AOBIOUS INC

Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. ......by AdooQ BioScience, LLC

Adapalene is more active than indomethacin, betamethasone valerate, tretinoin, isotretinoin or etretinate in inhibiting lipoxygease activity, but it has little activity against cyclo-oxygenase. ......by BOC Sciences

Adapalene is a retinoic acid analog that is a RARβ and RARγ agonist. It inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro and displays comedolytic activity. ......by MedKoo Biosciences, Inc.

Adapalene is a dual RAR and RXR agonist, used in the treatment of acne. ......by Selleck Chemicals LLC

Adapalene is a topical retinoid primarily used in the treatment of acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. It is currently marketed by Galderma under the trade names Differin in some countries, and Adaferin in India. ......by Target Molecule Corp.

Retinoic acid analog that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro. Displays comedolytic activity. ......by Tocris Bioscience Inc.

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

Physical and Chemical Properties

Appearance:White to off-white Solid

EBNumber:EB000013210

Storage condition

Store at +4°C

by Tocris Bioscience Inc.

Solubility

DMSO 8 mg/mL; Water <1 mg/mL	by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 8 mg/mL (19.39 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM)	by Selleck Chemicals LLC
Soluble to 25 mM in DMSO	by Tocris Bioscience Inc.

Mechanism and Indication

Signaling Pathways	Metabolic Enzyme/Protease

Target	RAR/RXR

Research Area	Inflammation/Immunology

Indications

Clinical Information

Product Name	Sponsor & Collaborators	Indications	Start Date	End Date	Phase
Adapalene	-				Launched

Safety Data of Adapalene

MSDS Available

Spectral Information

HNMR Available HPLC Available

Suppliers List

Company	Price and Availability	Country/Region
AOBIOUS INC	1mg/USD11()	USA
AdooQ BioScience, LLC		USA
Ark Pharm, Inc.		USA
Asia Talent Chemical Limited		China
BOC Sciences
Beijing Dezhong Wanquan Medicines Technological Development Co., Ltd.		China
Beijing FaMuRuiSi Pharmaceuticals Co., Ltd.		China
Beijing Mediking Biopharm Co., Ltd.		China
Beijing Mesochem Technology Co., Ltd.		China
Biochempartner Co., Ltd		China
Broad Pharmaceutical Co., Ltd.		China
CHEMSCENE, LLC	50mg/USD60();100mg/USD96()	USA
Cayman Chemical Company		USA
Dyna International (Huaian) Co., Ltd		CHINA
Hangzhou Best Chemical Co., Ltd.		China
Hangzhou Hysen Pharma Co., Ltd.		China
Hubei Widely Chemical Technology Co., Ltd.		China
Huzhou Hengyuan Biochem. Tech. Co., Ltd.		China
Jiangsu Zhongdan Group Co., Ltd.		China
Jinan Chuancheng Pharmaceutical Co., Ltd.		China
MedChemexpress Co., Ltd.	50mg/USD60();100mg/USD96()	USA
MedKoo Biosciences, Inc.		USA
Selleck Chemicals LLC	25mg/USD97(In stock);10mM/1mLIn DMSO/USD130(In stock);50mg/USD170(In stock)	USA
Shanghai Haoyuan Chemexpress Co., Ltd.	50mg/USD60();100mg/USD96()	China
Shanghai RenYoung Pharmaceutical Co., Ltd.		China
Target Molecule Corp.	2mg/USD20();10mg/USD56();25mg/USD108();50mg/USD198()	USA
Tocris Bioscience Inc.		USA
Wonder Synthesis (Beijing) Science and Development Co., Ltd.		China

Related Products

Other Forms of 106685-40-9

Name	CAS No	Formula	MW
Adapalene (sodium salt)	911110-93-5	C28H27NaO3	434.5
Hydroxy Adapalene	1346599-76-5	C28H28O4	428.52

Recommended Compounds in RAR/RXR

Name	CAS No	Formula	MW
AGN 205728	859498-05-8	C29H27NO3	437.53
AGN 196996	958295-17-5	C24H20BrNO5	482.32
AGN 194310	229961-45-9	C28H24O2S	424.55
Acitretin (sodium)	925701-88-8	C21H25NaO3	348.41
Acitretin	55079-83-9	C21H26O3	326.43
Adapalene (sodium salt)	911110-93-5	C28H27NaO3	434.5
TTNPB	71441-28-6	C24H28O2	348.48
Magnolol	528-43-8	C18H18O2	266.33
Tazarotene	118292-40-3	C21H21NO2S	351.46
Fenretinide	65646-68-6	C26H33NO2	391.55
LG 100268	153559-76-3	C24H29NO2	363.49
Isotretinoin	4759-48-2	C20H28O2	300.44
Palovarotene	410528-02-8	C27H30N2O2	414.54
Retinoic acid	302-79-4	C20H28O2	300.44
AM580	102121-60-8	C22H25NO3	351.44
(R)-Flurbiprofen	51543-40-9	C15H13FO2	244.2609
Tamibarotene	94497-51-5	C22H25NO3	351.44
Bexarotene	153559-49-0	C24H28O2	348.48
AGN 195183	367273-07-2	C22H22ClF2NO4	437.86
AR7	80306-38-3	C15H12ClNO	0.0

Recommended Compounds in Same Indication

Name	CAS No	Formula	MW

Route of Synthesis

References

[1]. Ellis CN, et al. Comparison of adapalene 0.1% solution and tretinoin 0.025% gel in the topical treatment of acne vulgaris. Br J Dermatol. 1998 Oct;139 Suppl 52:41-7.

[2]. Akdeniz N, et al. Anti-inflammatory effects of tretinoin (all-trans-retinoic acid) 0.1% and adapalene 0.1% in rats. Clin Exp Dermatol. 2005 Sep;30(5):570-2.

Protocol Reference

More Information

Adapalene