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106685-40-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:95 http://www.chembase.cn/molecule-95.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
IUPAC Traditional name
differin
Brand Name
Differin
Adaferin
Differin, Teva, Pimpal, Gallet, Adelene, Adeferin
Synonyms
Adapaleno [INN-Spanish]
Adapalenum [INN-Latin]
6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid
Differin
Adapalene
6-(3-(1-adamantyl)-4-methoxy-phenyl)Naphthalene-2-carboxylic acid
CAS Number
106685-40-9
MDL Number
MFCD03106112
PubChem SID
160963558
46505019
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 49.86113 Å3
Polar Surface Area 46.53 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 6.06  LOG S -8.01 
Solubility (Water) 4.01e-06 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Practically Insoluble expand Show data source
Hydrophobicity(logP)
8.6 expand Show data source
Storage Condition
-20°C expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
TSCA Listed
false expand Show data source
Admin Routes
Topical expand Show data source
Bioavailability
Very low expand Show data source
Excretion
Biliary expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
C expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Selleck Chemicals Selleck Chemicals
DrugBank - DB00210 external link
Item Information
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Adapalene
  • • Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. Pubmed
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PATENTS

PATENTS

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INTERNET

INTERNET

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