ciclopirox 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,MAP3K21,MAP3K7,MAPK12,MAPK7,MAPK9,MAPKAPK2,MARK4,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2 51
kinase-selectivity-class AXL,EIF2AK3,GRK2 3
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 31.50 21.56 4 2531 16 90625896
Dry skin 30.93 21.56 23 2512 88050 90537862
Dermatitis atopic 23.55 21.56 12 2523 23460 90602452
Psoriasis 22.43 21.56 24 2511 147730 90478182
Fall 21.72 21.56 44 2491 481766 90144146
Chronic cutaneous lupus erythematosus 21.68 21.56 5 2530 861 90625051

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 154.87 23.97 39 1463 7792 42612041
Device malfunction 141.87 23.97 40 1462 12287 42607546
Drug ineffective 84.30 23.97 106 1396 630091 41989742
Angioplasty 29.79 23.97 7 1495 1037 42618796
Nail injury 28.23 23.97 4 1498 32 42619801
Administration site dermatitis 27.76 23.97 3 1499 0 42619833
Dermatitis atopic 24.95 23.97 11 1491 12393 42607440

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 153.38 20.21 48 3153 25510 110560588
Device dislocation 147.19 20.21 49 3152 31655 110554443
Drug ineffective 63.96 20.21 137 3064 1520403 109065695
Dermatitis atopic 33.97 20.21 16 3185 25525 110560573
PRIDE syndrome 29.74 20.21 4 3197 26 110586072
Administration site dermatitis 28.35 20.21 3 3198 0 110586098
Dry skin 22.23 20.21 21 3180 107632 110478466

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 antibacterial agent
CHEBI has role CHEBI:59010 antiseborrheic
CHEBI has role CHEBI:173084 ferroptosis inhibitor
CHEBI has role CHEBI:176497 geroprotector
CHEBI has role CHEBI:50177 dermatologic drug

Related Drugs by ATC class:

D01AE Other antifungals for topical use 23 drugs
2-(4-chlorphenoxy)-ethanolamorolfinebromochlorosalicylanilidebutenafinechlorphenesin carbamatedimazoleethyl hydroxybenzoateflucytosinehaloproginliranaftatemethylrosanilinenaftifine show all 23 →
G01AX Other antiinfectives and antiseptics 10 drugs
clodantoinfurazolidonehexetidineinosinemethylrosanilinenifurateloctenidinepolicresulenpovidone-iodineprotiofate

Drug Use | Suggest Off label Use Form| |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
Lysine-specific demethylase 4B Enzyme IC50 5.42 CHEMBL

External reference:

IDSource
4019678 VUID
N0000147770 NUI
D01364 KEGG_DRUG
41621-49-2 SECONDARY_CAS_RN
21090 RXNORM
C0055711 UMLSCUI
CHEBI:453011 CHEBI
CHEMBL1413 ChEMBL_ID
DB01188 DRUGBANK_ID
CHEMBL242580 ChEMBL_ID
D000077768 MESH_DESCRIPTOR_UI
2749 PUBCHEM_CID
11349 IUPHAR_LIGAND_ID
3101 INN_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
B4O PDB_CHEM_ID
4018464 VANDF
4019678 VANDF

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 0574-2061 GEL 7.70 mg TOPICAL ANDA 19 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 0591-2159 SHAMPOO 10 mg TOPICAL ANDA 16 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 21922-053 SOLUTION 80 mg TOPICAL ANDA 17 sections
CICLOPIROX HUMAN PRESCRIPTION DRUG LABEL 1 21922-053 SOLUTION 80 mg TOPICAL ANDA 17 sections
CICLOPIROX HUMAN PRESCRIPTION DRUG LABEL 1 21922-105 SHAMPOO 1 g TOPICAL ANDA 27 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
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 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 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 HUMAN PRESCRIPTION DRUG LABEL 1 45802-401 SHAMPOO 1 g TOPICAL ANDA 24 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 50090-6562 SOLUTION 80 mg TOPICAL ANDA 10 sections
Ciclopirox HUMAN PRESCRIPTION DRUG LABEL 1 50090-6562 SOLUTION 80 mg TOPICAL ANDA 10 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 51672-1351 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
CICLOPIROX HUMAN PRESCRIPTION DRUG LABEL 1 61748-200 SOLUTION 80 mg TOPICAL ANDA 26 sections