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Chemistry

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Also known as: 29342-05-0, Loprox, Penlac, Hoe 296b, Cyclopirox, Ciclopiroxum
Molecular Formula
C12H17NO2
Molecular Weight
207.27  g/mol
InChI Key
SCKYRAXSEDYPSA-UHFFFAOYSA-N
FDA UNII
19W019ZDRJ

Ciclopirox
A cyclohexane and pyridinone derivative that is used for the treatment of fungal infections of the skin and nails, and for treatment of VAGINAL YEAST INFECTIONS.
The mechanism of action of ciclopirox is as a Protein Synthesis Inhibitor. The physiologic effect of ciclopirox is by means of Decreased DNA Replication, and Decreased Protein Synthesis, and Decreased RNA Replication.
1 2D Structure

Ciclopirox

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
2.1.2 InChI
InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
2.1.3 InChI Key
SCKYRAXSEDYPSA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=O)N(C(=C1)C2CCCCC2)O
2.2 Other Identifiers
2.2.1 UNII
19W019ZDRJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridone Ethanolamine Salt

2. Batrafen

3. Ciclopirox Olamine

4. Ciclopiroxolamine

5. Cyclopirox

6. Cyclopyroxolamine

7. Dafnegin Csc

8. Dafnegin-csc

9. Hoe 296

10. Hoe-296

11. Hoe296

12. Loprox

13. Penlac

2.3.2 Depositor-Supplied Synonyms

1. 29342-05-0

2. Loprox

3. Penlac

4. Hoe 296b

5. Cyclopirox

6. Ciclopiroxum

7. Hoe-296b

8. Ciclopiroxum [inn-latin]

9. 2(1h)-pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-

10. 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1h)-one

11. 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one

12. 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridinone

13. Hoe296b

14. Ciclopirox (penlac)

15. Loprox (tn)

16. 19w019zdrj

17. Terit

18. Chebi:453011

19. 29342-05-0 (free)

20. Stieprox

21. Ciclopirox Gel

22. Loprox Cream

23. Loprox Gel

24. Ciclopirox Olamin

25. Ciclopirox-olamin

26. 6-cyclohexyl-4-methyl-1-oxidanyl-pyridin-2-one

27. 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridone

28. 6-cyclohexyl-1-hydroxy-4-methyl-1h-pyridin-2-one

29. Mls002153867

30. Penlac (tn)

31. Ciclopirox (usp/inn)

32. Cnl8

33. Smr001233223

34. Einecs 249-577-2

35. Unii-19w019zdrj

36. Ciclodan

37. Ciclopirox [usan:usp:inn:ban]

38. 2(1h)-pyridone, 6-cyclohexyl-1-hydroxy-4-methyl-

39. Ciclopirox [mi]

40. Ciclopirox [inn]

41. Prestwick0_000541

42. Prestwick1_000541

43. Prestwick2_000541

44. Prestwick3_000541

45. Spectrum2_000146

46. Spectrum3_000351

47. Spectrum4_000288

48. Spectrum5_000747

49. Ciclopirox [usan]

50. Ciclopirox [vandf]

51. 6-cyclohexyl-1-hydroxy-4-methyl-pyridin-2-one

52. Ciclopirox [mart.]

53. Chembl1413

54. Ciclopirox [usp-rs]

55. Ciclopirox [who-dd]

56. Schembl34424

57. Bspbio_000581

58. Bspbio_002041

59. Kbiogr_000816

60. 6-cyclohexyl-1-hydroxy-4-methyl-2-(1h)-pyridone

61. Cid_38911

62. Bidd:gt0080

63. (6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridone)

64. Spbio_000252

65. Spbio_002502

66. Bpbio1_000641

67. Zinc1145

68. Ciclopirox [orange Book]

69. Ciclopirox, >=98% (hplc)

70. Dtxsid9048564

71. Bdbm66087

72. Gtpl11349

73. Kbio3_001261

74. Ciclopirox [ep Monograph]

75. Ciclopirox [usp Monograph]

76. Hms3656i12

77. Bcp28530

78. Hy-b0450

79. Mfcd00599441

80. S2528

81. Akos015895717

82. Ab06517

83. Ccg-266632

84. Db01188

85. Ks-5085

86. Ncgc00017112-04

87. Ncgc00017112-05

88. Ncgc00017112-06

89. Ncgc00017112-08

90. Ncgc00017112-11

91. Ncgc00178850-01

92. Ncgc00178850-02

93. Ac-24195

94. Ciclopirox 100 Microg/ml In Acetonitrile

95. Sbi-0206690.p002

96. Db-047566

97. Hoe 296; Hoe-296;ciclopiroxum; Penlac

98. 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone

99. Ft-0602961

100. Sw196923-5

101. 6-cyclohexyl-1-hydroxy-4-methyl-2-pyridinone

102. D03488

103. Ab00053438_09

104. Ab00053438_10

105. Ab00053438_11

106. 342c050

107. A819878

108. Q419468

109. Sr-05000001589-5

110. W-106995

111. 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridinone #

112. Brd-k13044802-213-04-1

113. Brd-k13044802-213-09-0

114. 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methyl-2-pyridone

115. 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one

116. Ciclopirox, European Pharmacopoeia (ep) Reference Standard

117. 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methyl-2-pyridinone

118. 2-azanylethanol;6-cyclohexyl-4-methyl-1-oxidanyl-pyridin-2-one

119. Ciclopirox, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 207.27 g/mol
Molecular Formula C12H17NO2
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass207.125928785 g/mol
Monoisotopic Mass207.125928785 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count15
Formal Charge0
Complexity325
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 6  
Drug NameCiclopirox
PubMed HealthCiclopirox (On the skin)
Drug ClassesAntifungal
Drug LabelCiclopirox Topical Solution, 8% (Nail Lacquer) contains a synthetic antifungal agent, ciclopirox. It is intended for topical use on fingernails and toenails and immediately adjacent skin.Each gram of Ciclopirox Topical Solution, 8% (Nail Lacquer) con...
Active IngredientCiclopirox
Dosage FormGel; Shampoo; Cream; Solution; Suspension
RouteTopical
Strength8%; 1%; 0.77%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Glenmark Pharms; Hi Tech Pharma; Paddock; Versapharm; Actavis Mid Atlantic; Perrigo; Perrigo New York; Taro Pharm Inds; Taro; Tolmar; G And W Labs; Cipla

2 of 6  
Drug NameLoprox
PubMed HealthCiclopirox (On the skin)
Drug ClassesAntifungal
Drug LabelLOPROX (ciclopirox) Shampoo 1% contains the synthetic antifungal agent, ciclopirox for topical use.Each gram (equivalent to 0.96 mL) of LOPROX Shampoo contains 10 mg ciclopirox in a shampoo base consisting of disodium laureth sulfosuccinate, laureth-...
Active IngredientCiclopirox
Dosage FormShampoo; Cream; Suspension; Gel
RouteTopical
Strength1%; 0.77%
Market StatusPrescription
CompanyCnty Line Pharms; Medicis; Medimetriks Pharms

3 of 6  
Drug NamePenlac
Drug LabelPENLAC NAIL LACQUER (ciclopirox) Topical Solution, 8%, contains a synthetic antifungal agent, ciclopirox. It is intended for topical use on fingernails and toenails and immediately adjacent skin. Each gram of PENLAC NAIL LACQUER (ciclopirox) Topi...
Active IngredientCiclopirox
Dosage FormSolution
RouteTopical
Strength8%
Market StatusPrescription
CompanyValeant Bermuda

4 of 6  
Drug NameCiclopirox
PubMed HealthCiclopirox (On the skin)
Drug ClassesAntifungal
Drug LabelCiclopirox Topical Solution, 8% (Nail Lacquer) contains a synthetic antifungal agent, ciclopirox. It is intended for topical use on fingernails and toenails and immediately adjacent skin.Each gram of Ciclopirox Topical Solution, 8% (Nail Lacquer) con...
Active IngredientCiclopirox
Dosage FormGel; Shampoo; Cream; Solution; Suspension
RouteTopical
Strength8%; 1%; 0.77%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Glenmark Pharms; Hi Tech Pharma; Paddock; Versapharm; Actavis Mid Atlantic; Perrigo; Perrigo New York; Taro Pharm Inds; Taro; Tolmar; G And W Labs; Cipla

5 of 6  
Drug NameLoprox
PubMed HealthCiclopirox (On the skin)
Drug ClassesAntifungal
Drug LabelLOPROX (ciclopirox) Shampoo 1% contains the synthetic antifungal agent, ciclopirox for topical use.Each gram (equivalent to 0.96 mL) of LOPROX Shampoo contains 10 mg ciclopirox in a shampoo base consisting of disodium laureth sulfosuccinate, laureth-...
Active IngredientCiclopirox
Dosage FormShampoo; Cream; Suspension; Gel
RouteTopical
Strength1%; 0.77%
Market StatusPrescription
CompanyCnty Line Pharms; Medicis; Medimetriks Pharms

6 of 6  
Drug NamePenlac
Drug LabelPENLAC NAIL LACQUER (ciclopirox) Topical Solution, 8%, contains a synthetic antifungal agent, ciclopirox. It is intended for topical use on fingernails and toenails and immediately adjacent skin. Each gram of PENLAC NAIL LACQUER (ciclopirox) Topi...
Active IngredientCiclopirox
Dosage FormSolution
RouteTopical
Strength8%
Market StatusPrescription
CompanyValeant Bermuda

4.2 Drug Indication

Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.


5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CICLOPIROX
5.3.2 FDA UNII
19W019ZDRJ
5.3.3 Pharmacological Classes
Decreased Protein Synthesis [PE]; Decreased RNA Replication [PE]; Protein Synthesis Inhibitors [MoA]; Decreased DNA Replication [PE]
5.4 ATC Code

D01AE14

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

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AE - Other antifungals for topical use

D01AE14 - Ciclopirox


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AX - Other antiinfectives and antiseptics

G01AX12 - Ciclopirox


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed after oral administration. Mean absorption of ciclopirox after application to nails of all twenty digits and adjacent 5 millimeters of skin once daily for 6 months in patients with dermatophytic onychomycoses was less than 5% of the applied dose. Ciclopirox olamine also penetrates into hair and through the epidermis and hair follicles into sebaceous glands and dermis.


Route of Elimination

Most of the compound is excreted either unchanged or as glucuronide. After oral administration of 10 mg of radiolabeled drug (14C-ciclopirox) to healthy volunteers, approximately 96% of the radioactivity was excreted renally within 12 hours of administration. Ninety-four percent of the renally excreted radioactivity was in the form of glucuronides.


5.6 Metabolism/Metabolites

Glucuronidation is the main metabolic pathway of ciclopirox.


5.7 Biological Half-Life

1.7 hours for 1% topical solution.


5.8 Mechanism of Action

Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.


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15-Feb-2021
24-Jun-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

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

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CREAM;TOPICAL - 0.77%

USFDA APPLICATION NUMBER - 18748

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DOSAGE - SUSPENSION;TOPICAL - 0.77%

USFDA APPLICATION NUMBER - 19824

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DOSAGE - GEL;TOPICAL - 0.77% **Federal Regist...DOSAGE - GEL;TOPICAL - 0.77% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20519

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DOSAGE - SOLUTION;TOPICAL - 8% **Federal Regi...DOSAGE - SOLUTION;TOPICAL - 8% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21022

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DOSAGE - SHAMPOO;TOPICAL - 1%

USFDA APPLICATION NUMBER - 21159

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