Adapalene

Adapalene

Systematic (IUPAC) name
6-[3-(1-adamantyl)-4-methoxy-phenyl] naphthalene-2-carboxylic acid
Clinical data
Trade names	Differin, Teva, Pimpal, Gallet, Adelene
AHFS/Drugs.com	monograph
MedlinePlus	a604001
Pregnancy cat.	C
Legal status	POM (UK) ℞-only (US)
Routes	Topical
Pharmacokinetic data
Bioavailability	Very low
Excretion	Biliary
Identifiers
CAS number	106685-40-9 Y
ATC code	D10AD03
PubChem	CID 60164
DrugBank	APRD00780
ChemSpider	54244 Y
UNII	1L4806J2QF Y
KEGG	D01112 Y
ChEBI	CHEBI:31174 Y
ChEMBL	CHEMBL1265 Y
Chemical data
Formula	C28H28O3
Mol. mass	412.52 g/mol
SMILES	eMolecules & PubChem
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) Y Key:LZCDAPDGXCYOEH-UHFFFAOYSA-N Y
N(what is this?)  (verify)

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.^[1]

History

Adapalene was approved in 1996 by the U.S. Food and Drug Administration (FDA) for use in the treatment of acne.^{[citation needed]}

Available forms

In the United States, adapalene is available under the brand name Differin in three different preparations: 0.1% cream, 0.1% gel, and 0.3% gel.^[2] As of June 2010, a 0.1% gel is also available under the generic name Teva.^[3][4] In Europe, only the 0.1% cream and 0.1% gel are available. In Pakistan, adapalene is available under the brand names Pimpal by Brookes Pharmaceuticals,and Gallet by Pharma Health Pakistan, Pimpal is in the form of 0.1% gel where as gallet is in cream. In India it is available under the trade name Adelene with 0.1 % Adapalene and 1 % Clindamycin phosphate.^{[citation needed]}

Pharmacology

Drug interactions

Adapalene has been shown to enhance the efficacy of topical clindamycin, although adverse effects are also increased.^[5] Application of adapalene gel to the skin 3–5 minutes before application of clindamycin enhances penetration of clindamycin into the skin, which may enhance the overall efficacy of the treatment as compared to clindamycin alone.^[6]

Unlike tretinoin (Retin-A), adapalene has also been shown to retain its efficacy when applied at the same time as benzoyl peroxide due to its more stable chemical structure.^[7]

Pharmacodynamics

Adapalene in small concentrations is a moderator of cellular differentiation, keratinization, and inflammatory processes. It has both exfoliating and anti-inflammatory effects. "Although the exact mode of action of adapalene is unknown, it is suggested that topical adapalene normalizes the differentiation of follicular epithelial cells resulting in decreased microcomedone formation."^[8]

Pharmacokinetics

"Absorption of adapalene from DIFFERIN® Cream through human skin is low. In a pharmacokinetic study with six acne patients treated once daily for 5 days with 2 grams of DIFFERIN®Cream applied to 1000 cm2 of acne involved skin, there were no quantifiable amounts (limit of quantification = 0.35 ng/mL) of adapalene in the plasma samples from any patient."^[8]

References

1. ^ Rolewski S (2003). "Clinical review: topical retinoids". Dermatol Nurs 15 (5): 447–50, 459–65. PMID 14619325. http://www.medscape.com/viewarticle/464026. 
2. ^ About Differin
3. ^ "Teva Introduces Adapalene Gel, 0.1%". PharmQD. 4 June 2010. http://www.pharmqd.com/pharmacy-news/teva-introduces-adapalene-gel-01. Retrieved 30 Aug. 2011. 
4. ^ Webber, Keith (2 June 2010). "FDA Approval Letter". Department of Health and Human Services. http://www.tevausa.com/assets/base/products/fda/Adap_090962.pdf. Retrieved 30 August 2011. 
5. ^ Wolf JE, Kaplan D, Kraus SJ, et al. (2003). "Efficacy and tolerability of combined topical treatment of acne vulgaris with adapalene and clindamycin: a multicenter, randomized, investigator-blinded study". J Am Acad Dermatol 49 (3 Suppl): S211–7. doi:10.1067/S0190-9622(03)01152-6. PMID 12963897. 
6. ^ Jain GK, Ahmed FJ (2007). "Adapalene pretreatment increases follicular penetration of clindamycin: in vitro and in vivo studies". Indian J Dermatol Venereol Leprol 73 (5): 326–9. doi:10.4103/0378-6323.34010. PMID 17921613. 
7. ^ Martin B, Meunier C, Montels D, Watts O (October 1998). "Chemical stability of adapalene and tretinoin when combined with benzoyl peroxide in presence and in absence of visible light and ultraviolet radiation". Br J Dermatol 139 Suppl 52: 8–11. doi:10.1046/j.1365-2133.1998.1390s2008.x. PMID 9990414. 
8. ^ ^{a b} "DIFFERIN® (adapalene) Cream, 0.1% Label". FDA. May 25, 2000. http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20748lbl.pdf. Retrieved 4 Oct. 2011. 

External links

• Differin product insert
• Adapalene General Information, Patient Information, Contraindications and Interactions
• Epiduo Prescribing Information