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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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API Reference Price

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01-Jan-2021
30-Oct-2024
KGS
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