Adapalene

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Drug Info:

Adapalene

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Brand names: Differin®

Chemical formula:



Adapalene Topical cream

What is this medicine?

ADAPALENE is applied to the skin to treat mild to moderate acne.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•eczema
•seborrheic dermatitis
•skin abrasions
•sunburn
•an unusual or allergic reaction to adapalene, vitamin A, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

This medicine is for external use only, do not take by mouth. Follow the directions on the prescription label. Make sure the skin is clean and dry. Apply just enough to cover the affected area. Rub in gently. Do not get in the eyes, inside the nose, on wounds, or any other sensitive areas of skin.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

•topical antibiotics like clindamycin or erythromycin

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Your acne may get worse at first, and then should start to get better. It may take 2 to 12 weeks before you see the full effect.

Do not wash your face more than 3 times a day unless your doctor or health care professional tells you to. Do not use products that may dry the skin like medicated cosmetics, products that contain alcohol, or abrasive soaps or cleaners. Do not use other acne or skin treatment on the same area that you use this medicine unless your doctor or health care professional tells you to. If you use these together they can cause severe skin irritation.

This medicine can make you more sensitive to the sun. Keep out of the sun. If you cannot avoid being in the sun, wear protective clothing and use sunscreen. Do not use sun lamps or tanning beds/booths.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•severe burning, reddening, crusting, or swelling of the treated areas

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•inflamed, stinging, and irritated skin
•skin that peels after a few days of use

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Do not freeze. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.


A drug that resembles the retinoids and is used for the treatment of mild to moderate acne in which blackheads and pustules predominate. It is available as a cream or gel on prescription only.

Side effects:
adapalene may irritate the skin. If irritation is severe, treatment should be stopped.

Precautions:
adapalene should not be used on broken or sunburnt skin, by people with eczema or a personal or family history of skin cancer, or by pregnant women (effective contraception should be used during treatment). It should not be applied near the eyes, lips, nostrils, or mouth, and excessive exposure of treated skin to sunlight should be avoided. Adapalene should not be used with retinoids or keratolytics.

Proprietary preparation:
Differin.

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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 YesY
ATC code D10AD03
PubChem CID 60164
DrugBank DB00210
ChemSpider 54244 YesY
UNII 1L4806J2QF YesY
KEGG D01112 YesY
ChEBI CHEBI:31174 YesY
ChEMBL CHEMBL1265 YesY
Chemical data
Formula C28H28O3 
Mol. mass 412.52 g/mol
SMILES eMolecules & PubChem
 YesY (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]

Contents

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 whereas gallet is in cream. In India it is available under the trade name Adelene or "Adaferin Gel" 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

The exact mechanism of action is unknown. Adapalene in small concentrations is supposedly a moderator of differentiation of follicular epithelial cells, keratinization, and inflammatory processes. It has both exfoliating and anti-inflammatory effects.[8]

Pharmacokinetics

Absorption of adapalene through the skin is low. A study with six acne patients treated once daily for five days with two grams of adapalene cream applied to 1000 cm² of skin found no quantifiable amounts, or less than 0.35 ng/mL of the drug, in the patients' blood plasma.[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. 

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