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    Chemistry

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    Also known as: 106685-40-9, Differin, Adapaleno, 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid, Adapalenum, Adapalenum [inn-latin]
    Molecular Formula
    C28H28O3
    Molecular Weight
    412.5  g/mol
    InChI Key
    LZCDAPDGXCYOEH-UHFFFAOYSA-N
    FDA UNII
    1L4806J2QF
    Adapalene
    A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.
    Adapalene is a Retinoid.
    1 2D Structure

    Adapalene

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
    2.1.2 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)
    2.1.3 InChI Key
    LZCDAPDGXCYOEH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
    2.2 Other Identifiers
    2.2.1 UNII
    1L4806J2QF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 271, Cd

    2. 6-(3-(1-adamantyl)-4-methoxyphenyl)-2-naphthoic Acid

    3. Adaferin

    4. Cd 271

    5. Cd-271

    6. Cd271

    7. Differin

    8. Differine

    2.3.2 Depositor-Supplied Synonyms

    1. 106685-40-9

    2. Differin

    3. Adapaleno

    4. 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic Acid

    5. Adapalenum

    6. Adapalenum [inn-latin]

    7. Adapaleno [inn-spanish]

    8. Cd 271

    9. Cd-271

    10. 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic Acid

    11. 6-(3-(1-adamantyl)-4-methoxyphenyl)-2-naphthoic Acid

    12. 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic Acid

    13. Mfcd03106112

    14. 6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic Acid

    15. Chembl1265

    16. 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid

    17. Adaferin

    18. Chebi:31174

    19. 1l4806j2qf

    20. 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic Acid

    21. Ncgc00164617-01

    22. Adapalen

    23. Differine

    24. 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic Acid

    25. 2-naphthalenecarboxylic Acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)-

    26. Dsstox_cid_26481

    27. Dsstox_rid_81652

    28. Dsstox_gsid_46481

    29. Differin Gel

    30. Cd271

    31. Differin (tn)

    32. Cas-106685-40-9

    33. Differin Gel 0.1%

    34. Adapalene [usan:inn:ban]

    35. Unii-1l4806j2qf

    36. Adapalene- Bio-x

    37. Ks-1196

    38. Adapalene [inn]

    39. Adapalene [jan]

    40. Adapalene [mi]

    41. Adapalene [usan]

    42. Adapalene [vandf]

    43. Adapalene [mart.]

    44. Adapalene [usp-rs]

    45. Adapalene [who-dd]

    46. Schembl2747

    47. Adapalene (jan/usp/inn)

    48. Mls000759463

    49. Mls006010036

    50. Bidd:gt0264

    51. Idp-126 Component Adapalene

    52. Gtpl5429

    53. Adapalene [orange Book]

    54. Adapalene [ep Monograph]

    55. Adapalene, >=98% (hplc)

    56. Chembl4303650

    57. Dtxsid5046481

    58. Epiduo Component Adapalene

    59. Adapalene [usp Monograph]

    60. Hms3264f15

    61. Hms3654f11

    62. Hms3715h16

    63. Bcp02081

    64. Hy-b0091

    65. Zinc3784182

    66. Adapalene Component Of Epiduo

    67. Tox21_112236

    68. Bdbm50048280

    69. S1276

    70. Stl453114

    71. Akos005145841

    72. Akos015895391

    73. Tox21_112236_1

    74. Ab13763

    75. Ac-1974

    76. Bcp9000231

    77. Ccg-213060

    78. Ccg-221237

    79. Cs-1789

    80. Db00210

    81. Ncgc00164617-02

    82. Ncgc00164617-04

    83. Ncgc00164617-05

    84. Ba164138

    85. Smr000466349

    86. Smr002529673

    87. Sy009767

    88. A2549

    89. Ft-0631040

    90. Sw219282-1

    91. D01112

    92. Ab01274764-01

    93. Ab01274764-02

    94. Ab01274764_03

    95. Ab01274764_04

    96. 685a409

    97. A801483

    98. Q352348

    99. Sr-01000942194

    100. Sr-01000942194-2

    101. 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoicacid

    102. Brd-k33127281-001-01-5

    103. F2173-0588

    104. 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoicacid

    105. Adapalene 100 Microg/ml In Acetonitrile:dimethylsulfoxide

    106. Adapalene, European Pharmacopoeia (ep) Reference Standard

    107. Adapalene, United States Pharmacopeia (usp) Reference Standard

    108. 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthalene-carboxylic Acid

    109. 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthalenecarboxylic Acid

    110. 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic Acid

    111. Adapalene, Pharmaceutical Secondary Standard; Certified Reference Material

    112. 6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic Acid;adapalene

    113. 6-[4-methoxy-3-(tricyclo[3.3.1.1~3,7~]dec-1-yl)phenyl]naphthalene-2-carboxylic Acid

    114. 6-[4-methoxy-3-(tricyclo[3.3.1.13,7]dec-1-yl)phenyl]naphthalene-2-carboxylic Acid

    115. Adapalene For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    116. 2-naphthalenecarboxylic Acid, 6-(4-methoxy-3-tricyclo(3.3.1.(sup 13,7))dec-1-ylphenyl)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 412.5 g/mol
    Molecular Formula C28H28O3
    XLogP37.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass412.20384475 g/mol
    Monoisotopic Mass412.20384475 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity645
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAdapalene
    PubMed HealthAdapalene (On the skin)
    Drug ClassesAntiacne
    Drug LabelAdapalene Gel, containing adapalene, is used for the topical treatment of acne vulgaris. Each gram of Adapalene Gel contains adapalene 0.1% (1 mg) in a vehicle consisting of carbomer homopolymer type C, disodium edetate, methylparaben, poloxamer 182,...
    Active IngredientAdapalene
    Dosage FormGel; Cream
    Routetopical; Topical
    Strength0.3%; 0.1%
    Market StatusTentative Approval; Prescription
    CompanyGlenmark Generics; Fougera Pharms; Actavis Mid Atlantic; Pliva Hrvatska Doo; Tolmar

    2 of 4  
    Drug NameDifferin
    PubMed HealthAdapalene (On the skin)
    Drug ClassesAntiacne
    Drug LabelDIFFERIN Gel, containing adapalene, is used for the topical treatment of acne vulgaris. Each gram of DIFFERIN Gel contains adapalene 0.1% (1 mg) in a vehicle consisting of carbomer 940, edetate disodium, methylparaben, poloxamer 182, propylene glyc...
    Active IngredientAdapalene
    Dosage FormLotion; Gel; Cream
    RouteTopical
    Strength0.3%; 0.1%
    Market StatusPrescription
    CompanyGalderma Labs

    3 of 4  
    Drug NameAdapalene
    PubMed HealthAdapalene (On the skin)
    Drug ClassesAntiacne
    Drug LabelAdapalene Gel, containing adapalene, is used for the topical treatment of acne vulgaris. Each gram of Adapalene Gel contains adapalene 0.1% (1 mg) in a vehicle consisting of carbomer homopolymer type C, disodium edetate, methylparaben, poloxamer 182,...
    Active IngredientAdapalene
    Dosage FormGel; Cream
    Routetopical; Topical
    Strength0.3%; 0.1%
    Market StatusTentative Approval; Prescription
    CompanyGlenmark Generics; Fougera Pharms; Actavis Mid Atlantic; Pliva Hrvatska Doo; Tolmar

    4 of 4  
    Drug NameDifferin
    PubMed HealthAdapalene (On the skin)
    Drug ClassesAntiacne
    Drug LabelDIFFERIN Gel, containing adapalene, is used for the topical treatment of acne vulgaris. Each gram of DIFFERIN Gel contains adapalene 0.1% (1 mg) in a vehicle consisting of carbomer 940, edetate disodium, methylparaben, poloxamer 182, propylene glyc...
    Active IngredientAdapalene
    Dosage FormLotion; Gel; Cream
    RouteTopical
    Strength0.3%; 0.1%
    Market StatusPrescription
    CompanyGalderma Labs

    4.2 Drug Indication

    Adapalene is indicated for the topical treatment of acne vulgaris in patients aged 12 and over.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Adapalene is anticomedogenic, preventing the formation of new comedones and inflammatory lesions, and also acts to reduce inflammation by modulating the innate immune response. Like other retinoid compounds, adapalene is chemically stable but photosensitive; use with sunscreen is recommended. Minor skin irritations, including erythema, scaling, dryness, and stinging/burning, have been reported.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ADAPALENE
    5.3.2 FDA UNII
    1L4806J2QF
    5.3.3 Pharmacological Classes
    Retinoids [CS]; Retinoid [EPC]
    5.4 ATC Code

    D10AD03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    D - Dermatologicals

    D10 - Anti-acne preparations

    D10A - Anti-acne preparations for topical use

    D10AD - Retinoids for topical use in acne

    D10AD03 - Adapalene

    5.5 Absorption, Distribution and Excretion

    Absorption

    Adapalene is applied topically and absorbed through the skin. In one clinical study treating patients once per day with 2g of 0.3% gel applied to 2 mg/cm2 of skin, 15 patients had detectable blood plasma adapalene levels (0.1 ng/ml) resulting in a mean Cmax of 0.553 0.466 ng/ml and a mean AUC of 8.37 8.46 ng\*h/ml on day 10.

    Route of Elimination

    Adapalene is primarily excreted by the biliary route at about 30 ng/g of the topically applied amount. Approximately 75% of the drug remains unchanged.

    Clearance

    Adapalene is rapidly cleared from blood plasma, typically undetectable after 72 hours following topical application.

    5.6 Metabolism/Metabolites

    Extensive information regarding adapalene metabolism in humans is unavailable, although it is known to accumulate in the liver and GI-tract. In human, mouse, rat, rabbit, and dog cultured hepatocytes, metabolism appears to affect the methoxybenzene moiety but remains incompletely characterized. The major products of metabolism are glucuronides. Approximately 25% of the drug is metabolized; the rest is excreted as parent drug.

    5.7 Biological Half-Life

    In one clinical study, after ten days of treatment with 2g of 0.3% cream or gel, the terminal half-life was between 7 and 51 hours, with a mean of 17.2 10.2.

    5.8 Mechanism of Action

    Adapalene is used for the treatment/maintenance of mild-to-severe acne (acne vulgaris). Acne is a multifactorial condition, and evidence exists to support multiple mechanisms of action for adapalene. Adapalene binds to retinoic acid receptor (RAR)-beta and RAR-gamma; this complex subsequently binds to one of three retinoid X receptors (RXRs), which as a complex is capable of binding DNA to modulate transcriptional activity. Although the full extent of transcriptional modulation is not described, retinoid activation is generally known to affect cellular proliferation and differentiation, and adapalene has been shown to inhibit HeLa cell proliferation and human keratinocyte differentiation. These effects primarily account for adapalene's comedolytic and anticomedogenic properties. In addition, adapalene modulates the immune response by down-regulating toll-like receptor 2 (TLR-2) expression and inhibiting the transcription factor activator protein 1 (AP-1). TLR-2 recognizes _Cutibacterium acnes_ (formerly _Propionibacterium acnes_), the bacterium primarily associated with acne. TLR-2 activation causes nuclear translocation of AP-1 and downstream pro-inflammatory gene regulation. Therefore, adapalene has a general anti-inflammatory effect, which reduces inflammation-mediated acne symptoms. When used with benzoyl peroxide, which possesses free radical-mediated bactericidal effects, the combination acts synergistically to reduced comedones and inflammatory lesions.

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    04-Jan-2021
    31-Aug-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DOSAGE - GEL;TOPICAL - 0.1%

    USFDA APPLICATION NUMBER - 20380

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    DOSAGE - GEL;TOPICAL - 0.3%

    USFDA APPLICATION NUMBER - 21753

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    DOSAGE - LOTION;TOPICAL - 0.1%

    USFDA APPLICATION NUMBER - 22502

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