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106685-40-9

106685-40-9 | 6-[3-(1-Adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid

CAS No: 106685-40-9 Catalog No: AG0038BR MDL No:MFCD03106112

Product Description

Catalog Number:
AG0038BR
Chemical Name:
6-[3-(1-Adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid
CAS Number:
106685-40-9
Molecular Formula:
C28H28O3
Molecular Weight:
412.5201
MDL Number:
MFCD03106112
IUPAC Name:
6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
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)
InChI Key:
LZCDAPDGXCYOEH-UHFFFAOYSA-N
SMILES:
COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
UNII:
1L4806J2QF

Properties

Complexity:
645  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
412.204g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
412.529g/mol
Monoisotopic Mass:
412.204g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
46.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.7  

Literature

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Spotlight on adapalene in acne vulgaris. American journal of clinical dermatology 20040101
Comparison of topical retinoids in the treatment of acne. Clinics in dermatology 20040101
Facial tolerability of topical retinoid therapy. Journal of drugs in dermatology : JDD 20040101
Cumulative irritancy potential of adapalene cream 0.1% compared with adapalene gel 0.1% and several tretinoin formulations. Cutis 20031201
The synthetic retinoid adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. International journal of cancer 20031110
Clinical review: topical retinoids. Dermatology nursing 20031001
A review of the use of combination therapies for the treatment of acne vulgaris. Journal of the American Academy of Dermatology 20030901
Efficacy and tolerability of combined topical treatment of acne vulgaris with adapalene and clindamycin: a multicenter, randomized, investigator-blinded study. Journal of the American Academy of Dermatology 20030901
Is combined oral and topical therapy better than oral therapy alone in patients with moderate to moderately severe acne vulgaris? A comparison of the efficacy and safety of lymecycline plus adapalene gel 0.1%, versus lymecycline plus gel vehicle. Journal of the American Academy of Dermatology 20030901
Cumulative irritancy comparison of adapalene gel 0.1% versus other retinoid products when applied in combination with topical antimicrobial agents. Journal of the American Academy of Dermatology 20030901
Single-blind and comparative clinical study of the efficacy and safety of benzoyl peroxide 4% gel (BID) and adapalene 0.1% Gel (QD) in the treatment of acne vulgaris for 11 weeks. The Journal of dermatological treatment 20030901
Assessment of adapalene gel for the treatment of actinic keratoses and lentigines: a randomized trial. Journal of the American Academy of Dermatology 20030701
Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations. Cutis 20030701
Retinoids: fascinating up-and-coming scenario. The Journal of dermatology 20030501
13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochemical and biophysical research communications 20030328
Management of acne. The Journal of family practice 20030101
The rationale for using a topical retinoid for inflammatory acne. American journal of clinical dermatology 20030101
Topical treatment in acne: current status and future aspects. Dermatology (Basel, Switzerland) 20030101
Optimizing treatment with topical tazarotene. American journal of clinical dermatology 20030101
Current concepts of the pathogenesis of acne: implications for drug treatment. Drugs 20030101
Axillary granular parakeratosis. Journal of cutaneous medicine and surgery 20030101
Safety and efficacy of adapalene gel 0.1% in acne vulgaris: results of a post-marketing surveillance study. Indian journal of dermatology, venereology and leprology 20030101
Prospective study of depressive symptoms and quality of life in acne vulgaris patients treated with isotretinoin compared to antibiotic and topical therapy. The Australasian journal of dermatology 20021101
Efficacy and cutaneous safety of adapalene in black patients versus white patients with acne vulgaris. Cutis 20021001
Topical adapalene gel 0.1% vs. isotretinoin gel 0.05% in the treatment of acne vulgaris: a randomized open-label clinical trial. The British journal of dermatology 20020901
Adapalene in the treatment of melasma: a preliminary report. The Journal of dermatology 20020801
Perioral dermatitis successfully treated with topical adapalene. Journal of the European Academy of Dermatology and Venereology : JEADV 20020301
A multicenter, double-blind, randomized comparison study of the efficacy and tolerability of once-daily tazarotene 0.1% gel and adapalene 0.1% gel for the treatment of facial acne vulgaris. Cutis 20020201
Comparison of the effects of tretinoin, adapalene and collagenase in an experimental model of wound healing. European journal of dermatology : EJD 20020101
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment. Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20020101
Randomised, controlled trial of the efficacy and safety of adapalene gel 0.1% and tretinoin cream 0.05% in patients with acne vulgaris. European journal of dermatology : EJD 20020101
Potential anti-inflammatory effects of topical retinoids and retinoid analogues. Advances in therapy 20020101
Randomized controlled trial of the tolerability, safety, and efficacy of adapalene gel 0.1% and tretinoin microsphere gel 0.1% for the treatment of acne vulgaris. Cutis 20011001
Randomized, controlled, bilateral (split-face) comparison trial of the tolerability and patient preference of adapalene gel 0.1% and tretinoin microsphere gel 0.1% for the treatment of acne vulgaris. Cutis 20011001
Polarized light photography and videomicroscopy greatly enhance the capability of estimating the therapeuic response to a topical retinoid (adapalene) in acne vulgaris. Cutis 20011001
Efficacy and tolerance of adapalene cream 0.1% compared with its cream vehicle for the treatment of acne vulgaris. Cutis 20011001
Adapalene gel 0.1% is effective and well tolerated in acne patients in a dermatology practice setting. Cutis 20011001
Adapalene gel 0.1% for topical treatment of acne vulgaris in African patients. Cutis 20011001
Adapalene gel 0.1%: effective and well tolerated in the topical treatment of acne vulgaris in Chinese patients. Cutis 20011001
Adapalene in clinical practice. Cutis 20011001
Developments in topical retinoid therapy for acne. Seminars in cutaneous medicine and surgery 20010901
A comparative trial of two retinoids commonly used in the treatment of acne vulgaris. The Journal of dermatological treatment 20010901
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. The British journal of dermatology 20010701
Synthesis, high-performance liquid chromatography-nuclear magnetic resonance characterization and pharmacokinetics in mice of CD271 glucuronide. Journal of chromatography. B, Biomedical sciences and applications 20010605
Comparison of treatment of acne vulgaris with alternate-day applications of tazarotene 0.1% gel and once-daily applications of adapalene 0.1% gel: a randomized trial. Cutis 20010601
Randomized facial tolerability studies comparing gel formulations of retinoids used to treat acne vulgaris. Cutis 20010601
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction. Cutis 20010201
Comparison of the cumulative irritation potential of adapalene gel and cream with that of erythromycin/tretinoin solution and gel and erythromycin/isotretinoin gel. Clinical therapeutics 20010201
Acral Darier's disease successfully treated with adapalene. Acta dermato-venereologica 20010101
The modern age of acne therapy: a review of current treatment options. The Mount Sinai journal of medicine, New York 20010101
Retinoids--which dermatological indications will benefit in the near future? Skin pharmacology and applied skin physiology 20010101
Current perspectives on the treatment of acne vulgaris and implications for future directions. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
New photographic techniques for clinical evaluation of acne. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
Pivotal clinical trials of adapalene in the treatment of acne. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
An update of recent clinical trials examining adapalene and acne. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
A comparison of adapalene gel 0.1% vs. tretinoin gel 0.025% in the treatment of acne vulgaris in China. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
Adapalene in the treatment of African patients. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
The integral role of topical and oral retinoids in the early treatment of acne. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne. Journal of the European Academy of Dermatology and Venereology : JEADV 20010101
Treatment of cervical intraepithelial neoplasia levels 2 and 3 with adapalene, a retinoid-related molecule. Journal of lower genital tract disease 20010101
The role of specific retinoid receptors in sebocyte growth and differentiation in culture. The Journal of investigative dermatology 20000201
Pharmacology of adapalene. The British journal of dermatology 19981001
Adapalene 0.1% gel and adapalene 0.1% cream stimulate retinoic acid receptor mediated gene transcription without significant irritative effects in the skin of healthy human volunteers. The British journal of dermatology 19981001
A new concept of drug delivery for acne. Dermatology (Basel, Switzerland) 19980101
Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes. Journal of medicinal chemistry 19951222
Comparison of CD271 (adapalene) and all-trans retinoic acid in human skin: dissociation of epidermal effects and CRABP-II mRNA expression. The Journal of investigative dermatology 19930901

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