Adapalene | CAS#106685-40-9 | RARβ and RARγ agonist

MedKoo Cat#: 317159 | Name: Adapalene

Description:

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

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.

Chemical Structure

Adapalene

CAS#106685-40-9

Theoretical Analysis

MedKoo Cat#: 317159

Name: Adapalene

CAS#: 106685-40-9

Chemical Formula: C28H28O3

Exact Mass: 412.2038

Molecular Weight: 412.53

Elemental Analysis: C, 81.52; H, 6.84; O, 11.63

Price and Availability

Size	Price	Availability
10mg	USD 50.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 225.00	Ready to ship
500mg	USD 350.00	Ready to ship
1g	USD 450.00	Ready to ship
2g	USD 650.00	2 Weeks
5g	USD 1,250.00	2 Weeks

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Synonym

ADAPALENE; Differin; Adaferin; Adapaleno; Adapalenum; CD-271; CD271; CD 271.

IUPAC/Chemical Name

6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid

InChi Key

LZCDAPDGXCYOEH-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5

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 (5 mg/mL)

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T9C06I17

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Adapalene (CD-271; Differin), a synthetic retinoid, is a retinoic acid receptor agonist (RAR).

In vitro activity:

The present study investigated the effects of ADA (adapalene) on the expression of significant proteins involved in G1-to-S-phase transition, including CDK2, cyclin E, Rb, pho-CDK2 and pho-Rb by western blot analysis in LoVo and DLD1 cells. As shown in Fig. 3A and B, ADA reduced the expression of CDK2, Rb, pho-CDK2, pho-Rb and cyclin E (Fig. 3). By contrast, the expression of cyclin D1 and cyclin B1 was not affected. This observed activity pattern was typical for CDK2 inhibitors. Reference: Mol Med Rep. 2015 Nov; 12(5): 6501–6508. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4626183/

In vivo activity:

Progressive increases in astrogliosis and microglial activation over time have been demonstrated in the SOD1G93A mouse model. The effects of Adap-NP (adapalene within nanoparticles) on neuroinflammatory markers within the spinal cords was determined. Iba-1 labeled activated microglia in the spinal cord were significantly reduced by treatment with Adap-NPs (Figure 7A). Quantification revealed a significant reduction of average microglia per image in the ventral horn of the spinal cord in Adap-NP treated mice (92.3 ± 8.03) compared to Ctl-NP (drug-empty nanoparticles) treated mice (149.8 ± 8.7) (p = 0.008). In addition, Adap-NP treatment tended to reduce GFAP staining in the ventral horn of the spinal cord in SOD1G93A transgenic mice when compared to mice treated with Ctl-NP, although this change was not significant (Figure 7B). Reference: Front Bioeng Biotechnol. 2020; 8: 224. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7118553/

	Solvent	mg/mL	mM
Solubility
	DMSO	13.1	31.70
	DMF	5.0	12.12

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 412.53 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.

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. Shi XN, Li H, Yao H, Liu X, Li L, Leung KS, Kung HF, Lin MC. Adapalene inhibits the activity of cyclin-dependent kinase 2 in colorectal carcinoma. Mol Med Rep. 2015 Nov;12(5):6501-8. doi: 10.3892/mmr.2015.4310. Epub 2015 Sep 10. PMID: 26398439; PMCID: PMC4626183. 2. Kolarcik CL, Bowser R. Retinoid signaling alterations in amyotrophic lateral sclerosis. Am J Neurodegener Dis. 2012;1(2):130-45. Epub 2012 Jul 23. PMID: 23383387; PMCID: PMC3560459. 3. Medina DX, Chung EP, Teague CD, Bowser R, Sirianni RW. Intravenously Administered, Retinoid Activating Nanoparticles Increase Lifespan and Reduce Neurodegeneration in the SOD1G93A Mouse Model of ALS. Front Bioeng Biotechnol. 2020 Mar 27;8:224. doi: 10.3389/fbioe.2020.00224. PMID: 32292776; PMCID: PMC7118553. 4. Yadav P, Bhatt B, Balaji KN. Selective Activation of MST1/2 Kinases by Retinoid Agonist Adapalene Abrogates AURKA-Regulated Septic Arthritis. J Immunol. 2021 May 24:ji2001360. doi: 10.4049/jimmunol.2001360. Epub ahead of print. PMID: 34031150.

In vitro protocol:

In vivo protocol:

1. Yadav P, Bhatt B, Balaji KN. Selective Activation of MST1/2 Kinases by Retinoid Agonist Adapalene Abrogates AURKA-Regulated Septic Arthritis. J Immunol. 2021 May 24:ji2001360. doi: 10.4049/jimmunol.2001360. Epub ahead of print. PMID: 34031150. 2. Medina DX, Chung EP, Teague CD, Bowser R, Sirianni RW. Intravenously Administered, Retinoid Activating Nanoparticles Increase Lifespan and Reduce Neurodegeneration in the SOD1G93A Mouse Model of ALS. Front Bioeng Biotechnol. 2020 Mar 27;8:224. doi: 10.3389/fbioe.2020.00224. PMID: 32292776; PMCID: PMC7118553.

1: Bhalekar M, Upadhaya P, Madgulkar A. Formulation and evaluation of Adapalene-loaded nanoparticulates for epidermal localization. Drug Deliv Transl Res. 2015 Oct 19. [Epub ahead of print] PubMed PMID: 26483036. 2: Shi XN, Li H, Yao H, Liu X, Li L, Leung KS, Kung HF, Lin MC. Adapalene inhibits the activity of cyclin-dependent kinase 2 in colorectal carcinoma. Mol Med Rep. 2015 Sep 10. doi: 10.3892/mmr.2015.4310. [Epub ahead of print] PubMed PMID: 26398439. 3: Chularojanamontri L, Tuchinda P, Kulthanan K, Varothai S, Winayanuwattikun W. A double-blinded, randomized, vehicle-controlled study to access skin tolerability and efficacy of an anti-inflammatory moisturizer in treatment of acne with 0.1% adapalene gel. J Dermatolog Treat. 2015 Sep 2:1-6. [Epub ahead of print] PubMed PMID: 26293170. 4: Modi PB, Shah NJ. Novel Stability-Indicating RP-HPLC Method for the Simultaneous Estimation of Clindamycin Phosphate and Adapalene along with Preservatives in Topical Gel Formulations. Sci Pharm. 2014 Jun 20;82(4):799-813. doi: 10.3797/scipharm.1404-01. eCollection 2014 Dec. PubMed PMID: 26171325; PubMed Central PMCID: PMC4475806. 5: Kwon HH, Park SY, Yoon JY, Min S, Suh DH. Do tutorials on application method enhance adapalene-benzoyl peroxide combination gel tolerability in the treatment of acne? J Dermatol. 2015 Jun 20. doi: 10.1111/1346-8138.12979. [Epub ahead of print] PubMed PMID: 26096777. 6: Uehara A, Abe M, Shimizu A, Motegi SI, Amano H, Ishikawa O. Successful treatment of lichen spinulosus with topical adapalene. Eur J Dermatol. 2015 Jun 17. [Epub ahead of print] PubMed PMID: 26080857. 7: Gollnick HP, Friedrich M, Peschen M, Pettker R, Pier A, Streit V, Jöstingmeyer P, Porombka D, Rojo Pulido I, Jäckel A. Effect of adapalene 0.1%/benzoyl peroxide 2.5% topical gel on quality of life and treatment adherence during long-term application in patients with predominantly moderate acne with or without concomitant medication - additional results from the non-interventional cohort study ELANG. J Eur Acad Dermatol Venereol. 2015 Jun;29 Suppl 4:23-9. doi: 10.1111/jdv.13195. PubMed PMID: 26059731. 8: Gollnick HP, Friedrich M, Peschen M, Pettker R, Pier A, Streit V, Jöstingmeyer P, Porombka D, Rojo Pulido I, Jäckel A. Safety and efficacy of adapalene 0.1% / benzoyl peroxide 2.5% in the long-term treatment of predominantly moderate acne with or without concomitant medication - results from the non-interventional cohort study ELANG. J Eur Acad Dermatol Venereol. 2015 Jun;29 Suppl 4:15-22. doi: 10.1111/jdv.13194. PubMed PMID: 26059730. 9: Gollnick HP, Funke G, Kors C, Titzmann T, Jöstingmeyer P, Jäckel A. Efficacy of adapalene/benzoyl peroxide combination in moderate inflammatory acne and its impact on patient adherence. J Dtsch Dermatol Ges. 2015 Jun;13(6):557-65. doi: 10.1111/ddg.12613. English, German. PubMed PMID: 26018369. 10: Numata T, Jo R, Kobayashi Y, Tsuboi R, Okubo Y. Allergic contact dermatitis caused by adapalene. Contact Dermatitis. 2015 Sep;73(3):187-8. doi: 10.1111/cod.12410. Epub 2015 May 11. PubMed PMID: 25960068.