Adapalene

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Cat Number

API0232216

CAS Number

106685-40-9

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CAS Number

106685-40-9

EINECS

620-513-9

Storage

Store at room temperature

Synonyms

Differin; Adapaleno; Adapalenum; Adaferin; CD-271; 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid

Molecular Formula

C28H28O3

Molecular Weight

412.5

Smiles

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

Appearance

White crystalline solid

Melting Point

319-322°C

Boiling Point

606.3±55.0°C (Predicted)

Relative Density

1.233±0.06 (Predicted)

General Description

Adapalene is a synthetic naphthoic acid derivative with a unique adamantyl group, structurally distinct from other retinoids such as tretinoin and isotretinoin. Its chemical structure is 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid.

Mechanism of Action

Adapalene acts as a selective agonist for retinoic acid receptor beta (RAR-β) and gamma (RAR-γ), modulating gene expression and promoting the differentiation of keratinocytes. It also exerts anti-inflammatory effects by inhibiting the activation of the NF-κB pathway and reducing the release of pro-inflammatory cytokines. Unlike tretinoin, adapalene has a lower affinity for the retinoic acid receptor alpha (RAR-α) and is less irritating to the skin.

Application

Adapalene is indicated for the topical treatment of acne vulgaris, including comedonal, papular, and pustular lesions. It is effective in reducing the formation of microcomedones and preventing new lesions. The drug is also used for the management of keratosis pilaris and photoaging, and it has been shown to be as effective as tretinoin but with better tolerability.

Adapalene (ADA), identified by idock screening of FDA-approved drugs, inhibited CDK2 in colon cancer cells. ADA increased G1-phase population, decreased CDK2, cyclin E, Rb, and their phosphorylation. In DLD1 xenografts, ADA (20 mg/kg oral) showed anti-tumor activity comparable to oxaliplatin. The combination produced the highest effect. ADA is a potential CDK2 inhibitor for colorectal cancer treatment.

Fig. 1 Comparison of the effects of nine candidate cyclin-dependent kinase 2 inhibitors on the viability of LoVo and DLD1 colorectal cancer cells. (Shi XN, et al., 2015)

References

Shi XN, et al. Adapalene inhibits the activity of cyclin-dependent kinase 2 in colorectal carcinoma. Mol Med Rep. 2015;12(5):6501-6508.

In two phase 3 trials (pooled n=363), fixed‑dose triple‑combination clindamycin 1.2%/adapalene 0.15%/benzoyl peroxide 3.1% gel (CAB) achieved 50% treatment success at week 12 vs 22.6% for vehicle (P<0.001), with >70% reductions in inflammatory and non‑inflammatory lesions. Local skin reactions resolved by week 12. CAB is highly efficacious and well tolerated for moderate‑to‑severe acne.

Fig. 2 Pathogenesis of acne and treatment with triple-combination CAB gel. (Kircik LH, et al., 2024)

References

Kircik LH, et al. Triple Combination Clindamycin Phosphate 1.2%/Adapalene 0.15%/Benzoyl Peroxide 3.1% for Acne: Efficacy and Safety from a Pooled Phase 3 Analysis. Dermatol Ther (Heidelb). 2024;14(5):1211-1227.

Does Adapalene require protection from light during storage?

Yes, it is highly photosensitive. Light exposure causes photodegradation and isomerization of the naphthoic acid ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Adapalene?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate degradation.

Is Adapalene stable in topical gel and cream formulations?

Yes, when formulated with preservatives and protected from light.

How is the impurity adapalene cis-isomer (photodegradation product) monitored?

This geometric isomer is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.