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

• ChemBase ID: 95
• Molecular Formular: C28H28O3
• Molecular Mass: 412.52012
• Monoisotopic Mass: 412.20384476
• SMILES: O(c1c(C23CC4CC(C2)CC(C3)C4)cc(cc1)c1cc2c(cc1)cc(cc2)C(=O)O)C
• Canonical SMILES: COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
• IUPAC Traditional name: differin
• Brand Name: Differin, Teva, Pimpal, Gallet, Adelene, Adeferin; Differin; Adaferin
• Synonyms: 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid; Adapaleno [INN-Spanish]; Adapalenum [INN-Latin]; Adapalene; Differin; 6-(3-(1-adamantyl)-4-methoxy-phenyl)Naphthalene-2-carboxylic acid

Database IDs

• CAS Number: 106685-40-9
• MDL Number: MFCD03106112
• PubChem SID: 46505019; 160963558
• PubChem CID: 60164
• CHEBI ID: 31174
• ATC CODE: D10AD03
• CHEMBL: 1265
• Chemspider ID: 54244
• DrugBank ID: DB00210
• KEGG ID: D01112
• Unique Ingredient Identifier: 1L4806J2QF
• Wikipedia Title: Adapalene
• Medline Plus: a604001

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.9892612
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.938707
• LogD (pH = 7.4): 3.2933044
• Log P: 6.4585013
• Molar Refractivity: 122.0719 cm^3
• Polarizability: 49.86113 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.06
• LOG S: -8.01
• Solubility (Water): 4.01e-06 g/l

PROPERTIES

Physical Property

• Solubility: Practically Insoluble
• Hydrophobicity(logP): 8.6

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Topical
• Bioavailability: Very low
• Excretion: Biliary
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C

Product Information

• Purity: 95+%; 97%
• Salt Data: Free Base

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]

REFERENCES

• Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. Pubmed
• http://en.wikipedia.org/wiki/Adapalene