CAS 106685-40-9|Adapalene|Adaferin|Adapalenum [INN-Latin]|Differin|Adapaleno [INN-Spanish]|differin|6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid|6-(3-(Adamantan-1-yl)-4-methox...

General Information

Structure

Molecular Formula

C₂₈H₂₈O₃

Molecular Mass

412.52012

Exact Mass

412.20384476

Charge

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)

InChIKey

LZCDAPDGXCYOEH-UHFFFAOYSA-N

Canonic Smiles

COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O

Isomeric Smiles

O(c1c(C23CC4CC(C2)CC(C3)C4)cc(cc1)c1cc2c(cc1)cc(cc2)C(=O)O)C

Calculated Properties

JChem

Acid pKa

3.9892612

H Acceptors

H Donor

LogD (pH = 5.5)

4.938707

LogD (pH = 7.4)

3.2933044

Log P

6.4585013

Molar Refractivity

122.0719

Polarizability

49.86113

Polar Surface Area

46.53

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

6.06

LOG S

-8.01

Solubility (Water)

4.01e-06 g/l

Data Source

Names and Identifiers

Synonyms

AdapaleneAdapalenum [INN-Latin]Adapaleno [INN-Spanish]6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acidDifferin6-(3-(1-adamantyl)-4-methoxy-phenyl)Naphthalene-2-carboxylic acid

Brand Name

AdaferinDifferinDifferin, Teva, Pimpal, Gallet, Adelene, Adeferin

IUPAC Traditional name

differin

IUPAC name

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

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem CID

Medline Plus

DrugBank ID

CHEBI ID

CHEMBL

Unique Ingredient Identifier

Wikipedia Title

ATC CODE

PubChem SID

KEGG ID

Chemspider ID

Registration numbers

Properties

Physical Property

Solubility

Practically Insoluble

Hydrophobicity(logP)

8.6

Safety Information

MSDS Link

Download link

Storage Warning

IRRITANT

TSCA Listed

false

-20°C

Product Information

95+%

97%

Free Base

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00210

Drug Groups

approved

Description

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. [Wikipedia]

Indication

For the topical treatment of comedo, papular and pustular acne (acne vulgaris) of the face, chest or back.

Pharmacology

Adapalene is a chemically stable retinoid-like compound. Biochemical and pharmacological profile studies have demonstrated that adapalene is a modulator of cellular differentiation, keratinization, and inflammatory processes all of which represent important features in the pathology of acne vulgaris.

Toxicity

The acute oral toxicity of adapalene in mice and rats is greater than 10 mL/kg. Chronic ingestion of the drug may lead to the same side effects as those associated with excessive oral intake of Vitamin A.

Affected Organisms

Humans and other mammals

Biotransformation

Metabolized mainly by O-demethylation, hydroxylation and conjugation, and excretion is primarily by the biliary route.

Absorption

Absorption of adapalene through human skin is low. Only trace amounts (<0.25 ng/mL) of parent substance have been found in the plasma of acne patients following chronic topical application of adapalene in controlled clinical trials

Elimination

Excretion appears to be primarily by the biliary route.

References

• Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1276

Research Area: Endocrinology
Biological Activity:
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. Adapalene is possibly more effective than tretinoin 0.025% gel in the treatment of acne vulgaris. [1]

Wikipedia

Adapalene

Molecule Details

References

PubChem Literature

From Data Sources

• Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. Pubmed

• http://en.wikipedia.org/wiki/Adapalene

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

AdapaleneAdapalenum [INN-Latin]Adapaleno [INN-Spanish]6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acidDifferin6-(3-(1-adamantyl)-4-methoxy-phenyl)Naphthalene-2-carboxylic acid

Brand Name

AdaferinDifferinDifferin, Teva, Pimpal, Gallet, Adelene, Adeferin

IUPAC Traditional name

differin

IUPAC name

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

Registration numbers

CAS Number

106685-40-9

MDL Number

MFCD03106112

PubChem CID