ciclopirox 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antimycotics, pyridone derivatives 636 29342-05-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ciclopirox
  • penlac
  • ciclopirox olamine
  • ciclopirox ethanolamine
The mechanism of action of ciclopirox has been investigated using various in vitro and in vivo infection models. One in vitro study suggested that ciclopirox acts by chelation of polyvalent cations (Fe+3 or Al+3) resulting in the inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell. The clinical significance of this observation is not known.
  • Molecular weight: 207.27
  • Formula: C12H17NO2
  • CLOGP: 2.03
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 40.54
  • ALOGS: -2.17
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Dec. 30, 1982 FDA MEDIMETRIKS PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
PRIDE syndrome 31.72 25.15 4 1339 16 50603765

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Device dislocation 71.20 28.08 18 825 4509 29569175
Device malfunction 64.32 28.08 19 824 8488 29565196
Angioplasty 32.01 28.08 7 836 934 29572750
Drug ineffective 30.71 28.08 44 799 363126 29210558
Nail injury 29.20 28.08 4 839 31 29573653
Administration site dermatitis 28.40 28.08 3 840 0 29573684

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Device malfunction 75.96 22.99 25 1628 17608 64479471
Device dislocation 71.47 22.99 25 1628 21153 64475926
PRIDE syndrome 31.86 22.99 4 1649 16 64497063
Administration site dermatitis 28.72 22.99 3 1650 0 64497079
Drug ineffective 24.53 22.99 61 1592 840186 63656893

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D01AE14 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Other antifungals for topical use
ATC G01AX12 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Other antiinfectives and antiseptics
FDA MoA N0000000150 Protein Synthesis Inhibitors
FDA PE N0000008577 Decreased DNA Replication
FDA PE N0000008841 Decreased Protein Synthesis
FDA PE N0000008853 Decreased RNA Replication
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
CHEBI has role CHEBI:33282 bactericides
CHEBI has role CHEBI:59010 antiseborrheics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Tinea pedis indication 6020002 DOID:12403
Candidiasis of skin indication 49883006
Seborrheic dermatitis indication 50563003 DOID:8741
Pityriasis versicolor indication 56454009 DOID:9060
Tinea corporis indication 84849002
Pityriasis simplex indication 200767005
Tinea cruris indication 399029005
Onychomycosis due to dermatophyte indication 402134005
Skin irritation contraindication 367466007




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.74 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Poly [ADP-ribose] polymerase 1 Enzyme INHIBITOR IC50 6.80 IUPHAR
Deoxyhypusine hydroxylase Enzyme IC50 5.30 CHEMBL

External reference:

IDSource
4019678 VUID
N0000147770 NUI
D01364 KEGG_DRUG
41621-49-2 SECONDARY_CAS_RN
21090 RXNORM
4018464 VANDF
4019678 VANDF
C0055711 UMLSCUI
CHEBI:453011 CHEBI
B4O PDB_CHEM_ID
CHEMBL1413 ChEMBL_ID
DB01188 DRUGBANK_ID
CHEMBL242580 ChEMBL_ID
D000077768 MESH_DESCRIPTOR_UI
2749 PUBCHEM_CID
3101 INN_ID
11349 IUPHAR_LIGAND_ID
19W019ZDRJ UNII
16731 MMSL
207997 MMSL
44089 MMSL
4445 MMSL
8601 MMSL
002925 NDDF
004961 NDDF
372854000 SNOMEDCT_US
70169009 SNOMEDCT_US
79736009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0168-0314 LOTION 7.70 mg TOPICAL ANDA 16 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0168-0407 GEL 7.70 mg TOPICAL ANDA 19 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0168-0449 SHAMPOO 10 mg TOPICAL ANDA 25 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0168-0522 SHAMPOO 10 mg TOPICAL NDA authorized generic 27 sections
CICLOPIROX HUMAN PRESCRIPTION DRUG LABEL 1 0574-2061 GEL 7.70 mg TOPICAL ANDA 20 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0591-2159 SHAMPOO 10 mg TOPICAL ANDA 16 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0713-0317 SOLUTION 80 mg TOPICAL ANDA 12 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0713-0317 SOLUTION 80 mg TOPICAL ANDA 12 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 0713-0638 CREAM 7.70 mg TOPICAL ANDA 15 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 21695-475 SOLUTION 71.30 mg TOPICAL ANDA 24 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 42192-715 SOLUTION 80 mg TOPICAL ANDA 10 sections
Ciclodan HUMAN PRESCRIPTION DRUG LABEL 1 43538-500 SOLUTION 2.28 g TOPICAL ANDA 24 sections
Loprox HUMAN PRESCRIPTION DRUG LABEL 1 43538-540 CREAM 7.70 mg TOPICAL NDA 20 sections
Loprox HUMAN PRESCRIPTION DRUG LABEL 1 43538-550 SUSPENSION 7.70 mg TOPICAL NDA 20 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 45802-138 CREAM 7.70 mg TOPICAL ANDA 16 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 45802-141 SOLUTION 80 mg TOPICAL ANDA 23 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 45802-400 SUSPENSION 7.70 mg TOPICAL ANDA 17 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 45802-401 SHAMPOO 1 g TOPICAL ANDA 24 sections
CICLOPIROX OLAMINE HUMAN PRESCRIPTION DRUG LABEL 1 49999-646 CREAM 7.70 mg TOPICAL ANDA 11 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 50383-419 SOLUTION 71.30 mg TOPICAL ANDA 24 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 50383-419 SOLUTION 71.30 mg TOPICAL ANDA 24 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 51672-1318 CREAM 7.70 mg TOPICAL ANDA 20 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 51672-1323 SUSPENSION 7.70 mg TOPICAL ANDA 18 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 51672-1351 SHAMPOO 10 mg TOPICAL ANDA 27 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 51672-5302 SOLUTION 80 mg TOPICAL ANDA 24 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 52565-032 SHAMPOO 10 mg TOPICAL ANDA 27 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 53002-9450 CREAM 7.70 mg TOPICAL ANDA 19 sections
Ciclopirox Olamine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5270 CREAM 7.70 mg TOPICAL ANDA 17 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 54868-6064 SOLUTION 80 mg TOPICAL ANDA 13 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 61360-1351 SHAMPOO 10 mg TOPICAL ANDA 24 sections