clotrimazole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
719 23593-75-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clotrimazole
  • lotrimin
  • rimazole
  • locasten
An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal CELL MEMBRANES. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane.
  • Molecular weight: 344.84
  • Formula: C22H17ClN2
  • CLOGP: 5
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 17.82
  • ALOGS: -5.37
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g V

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.07 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Feb. 3, 1975 FDA

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
Schizoaffective disorder 71.62 12.60 23 12277 1429 46672333
Vanishing bile duct syndrome 38.74 12.60 12 12288 662 46673100
Eye infection toxoplasmal 38.55 12.60 10 12290 288 46673474
Sinus rhythm 35.74 12.60 11 12289 594 46673168
Vulvovaginal candidiasis 34.99 12.60 16 12284 2605 46671157
Macular degeneration 33.82 12.60 22 12278 7183 46666579
Purpura senile 31.08 12.60 10 12290 625 46673137
Vulvovaginal inflammation 27.96 12.60 9 12291 563 46673199
Drug level increased 27.69 12.60 29 12271 18412 46655350
Tarsal tunnel syndrome 26.76 12.60 9 12291 646 46673116
Tongue blistering 26.29 12.60 11 12289 1447 46672315
Candida infection 24.88 12.60 30 12270 22210 46651552
Post viral fatigue syndrome 24.22 12.60 6 12294 143 46673619
Rheumatoid arthritis 24.03 12.60 17 12283 240198 46433564
Resorption bone increased 22.00 12.60 9 12291 1118 46672644
Toxicity to various agents 21.16 12.60 15 12285 211751 46462011
Angiodermatitis 21.11 12.60 5 12295 98 46673664
Eczema 20.38 12.60 26 12274 20374 46653388
Vestibular disorder 20.34 12.60 9 12291 1357 46672405
Oral candidiasis 20.18 12.60 24 12276 17508 46656254
Vaginal infection 20.13 12.60 15 12285 6078 46667684
Blister 18.36 12.60 38 12262 44593 46629169
Exfoliative rash 17.52 12.60 10 12290 2585 46671177
Bulimia nervosa 16.54 12.60 6 12294 539 46673223
Mouth ulceration 16.27 12.60 27 12273 26805 46646957
Stevens-Johnson syndrome 16.26 12.60 25 12275 23272 46650490
Swollen tongue 15.86 12.60 28 12272 29204 46644558
Thrombophlebitis superficial 15.83 12.60 12 12288 4991 46668771
Rash 15.72 12.60 153 12147 356359 46317403
Swelling face 15.02 12.60 39 12261 53020 46620742
Vertigo positional 14.77 12.60 9 12291 2621 46671141
Pruritus 13.77 12.60 110 12190 242242 46431520
Congenital absence of bile ducts 13.36 12.60 3 12297 46 46673716
Stoma site haemorrhage 13.12 12.60 6 12294 976 46672786
Post transplant distal limb syndrome 13.07 12.60 4 12296 212 46673550
Oropharyngeal pain 12.95 12.60 46 12254 74122 46599640
Therapeutic product effect decreased 12.83 12.60 3 12297 82598 46591164
Vulvovaginal pruritus 12.79 12.60 8 12292 2439 46671323

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
Cerebrovascular accident 27.26 14.53 57 6330 83420 29862671
Stomatitis 23.41 14.53 34 6353 37245 29908846
Enterocolitis bacterial 22.42 14.53 6 6381 243 29945848
Rash pruritic 17.81 14.53 23 6364 22549 29923542
Microtia 17.57 14.53 5 6382 255 29945836
Cryptococcosis 16.68 14.53 8 6379 1794 29944297
Polydipsia 16.41 14.53 10 6377 3603 29942488
Congenital umbilical hernia 15.50 14.53 5 6382 390 29945701
Hypersensitivity 15.46 14.53 35 6352 53993 29892098
Cellulitis 15.31 14.53 32 6355 46752 29899339
Psoriasis area severity index increased 14.67 14.53 3 6384 36 29946055
Lymphopenia 14.67 14.53 16 6371 13147 29932944
Leukopenia 14.56 14.53 35 6352 56124 29889967
Toxicity to various agents 14.55 14.53 10 6377 177173 29768918

Pharmacologic Action:

SourceCodeDescription
ATC A01AB18 ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Antiinfectives and antiseptics for local oral treatment
ATC D01AC01 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
ATC G01AF02 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Imidazole derivatives
FDA CS M0002083 Azoles
MeSH PA D058888 14-alpha Demethylase Inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000891 Anti-Infective Agents, Local
MeSH PA D000935 Antifungal Agents
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006727 Hormone Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D065088 Steroid Synthesis Inhibitors
FDA EPC N0000175487 Azole Antifungal
CHEBI has role CHEBI:35441 anti-infective drugs
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:78298 environmental contaminants

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Tinea pedis indication 6020002 DOID:12403
Candidiasis of skin indication 49883006
Pityriasis versicolor indication 56454009 DOID:9060
Candidal vulvovaginitis indication 72605008 DOID:2272
Candidiasis of mouth indication 79740000 DOID:14262
Tinea corporis indication 84849002
Diaper rash indication 91487003
Tinea cruris indication 399029005
Prevention of Oropharyngeal Candidiasis indication
Oropharyngeal Candidiasis indication
Paronychia off-label use 71906005 DOID:13117
Telangiectasia disorder contraindication 247479008
Abdominal pain - cause unknown contraindication 314212008
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Atrophoderma contraindication 399979006
Peripheral vascular disease contraindication 400047006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.4 Basic

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
Nuclear receptor subfamily 1 group I member 3 Nuclear hormone receptor ANTAGONIST IC50 6.16 IUPHAR
Beta-1 adrenergic receptor GPCR Ki 5.19 DRUG MATRIX
Prostaglandin G/H synthase 2 Enzyme IC50 4.38 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 6.14 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.35 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.39 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 5.15 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.35 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.51 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.10 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 5.00 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.50 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.13 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.12 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.23 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.43 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.05 DRUG MATRIX
Histamine H1 receptor GPCR Ki 5.47 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.29 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 5.78 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.29 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 5.68 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 5.79 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 5.83 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 5.27 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.35 DRUG MATRIX
Adenosine receptor A1 GPCR Ki 5.11 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.57 DRUG MATRIX
Carbonic anhydrase 2 Enzyme IC50 4.52 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.13 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.60 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.76 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 4.71 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 7.80 DRUG MATRIX
Platelet-activating factor receptor GPCR Ki 4.65 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.16 DRUG MATRIX
Substance-P receptor GPCR Ki 5.06 DRUG MATRIX
Cytochrome P450 2C19 Enzyme IC50 7.80 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 4.50 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.18 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 7.85 DRUG MATRIX
Substance-K receptor GPCR Ki 5.47 DRUG MATRIX
Steroid 17-alpha-hydroxylase/17,20 lyase Enzyme IC50 7.09 WOMBAT-PK
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 7.70 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 5.17 WOMBAT-PK
Intermediate conductance calcium-activated potassium channel protein 4 Ion channel IC50 7.15 CHEMBL
Bile acid receptor Nuclear hormone receptor IC50 5.49 CHEMBL
Aromatase Enzyme IC50 8.74 CHEMBL
Lanosterol 14-alpha demethylase Enzyme IC50 6.89 CHEMBL
Vasopressin V2 receptor GPCR IC50 5.60 CHEMBL
Malate dehydrogenase cytoplasmic Enzyme IC50 4.46 CHEMBL
C-C chemokine receptor type 4 GPCR IC50 5.80 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.52 CHEMBL
C-X-C chemokine receptor type 1 GPCR IC50 5.70 CHEMBL
Potassium voltage-gated channel subfamily A member 3 Ion channel IC50 5.22 CHEMBL
Cysteinyl leukotriene receptor 1 GPCR Ki 4.78 CHEMBL
D(4) dopamine receptor GPCR Ki 5.16 DRUG MATRIX
Lanosterol 14-alpha demethylase Enzyme INHIBITOR CHEMBL CHEMBL
Androgen receptor Transcription factor Ki 5.11 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 4.91 DRUG MATRIX
Cysteinyl leukotriene receptor 1 GPCR Ki 4.78 DRUG MATRIX
Progesterone receptor Transcription factor Ki 5.94 DRUG MATRIX
Beta-lactamase Enzyme IC50 4.70 CHEMBL
Alpha-chymotrypsin Unclassified IC50 4.07 CHEMBL
Lanosterol 14-alpha demethylase Enzyme Kd 6.70 CHEMBL
14-alpha sterol demethylase Enzyme Kd 6.99 CHEMBL
14-alpha sterol demethylase Cyp51A Enzyme Kd 5.32 CHEMBL
Putative cytochrome P450 130 Unclassified Kd 4.88 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.29 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.23 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 4.75 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 4.58 CHEMBL

External reference:

IDSource
4018265 VUID
N0000146595 NUI
D00282 KEGG_DRUG
4018265 VANDF
C0009074 UMLSCUI
CHEBI:3764 CHEBI
CL6 PDB_CHEM_ID
CHEMBL104 ChEMBL_ID
DB00257 DRUGBANK_ID
D003022 MESH_DESCRIPTOR_UI
2812 PUBCHEM_CID
2330 IUPHAR_LIGAND_ID
2912 INN_ID
G07GZ97H65 UNII
202859 RXNORM
1284 MMSL
4482 MMSL
d01236 MMSL
002916 NDDF
387325003 SNOMEDCT_US
5797005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0054-4146 LOZENGE 10 mg ORAL ANDA 14 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0054-8146 LOZENGE 10 mg ORAL ANDA 14 sections
Lotrisone HUMAN PRESCRIPTION DRUG LABEL 2 0085-0924 CREAM 10 mg TOPICAL NDA 26 sections
Good Sense Athletes Footantifungal HUMAN OTC DRUG LABEL 1 0113-0857 CREAM 1 g TOPICAL OTC monograph final 13 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0168-0133 CREAM 10 mg TOPICAL ANDA 20 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0168-0258 CREAM 10 mg TOPICAL ANDA 27 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0168-0370 LOTION 10 mg TOPICAL ANDA 20 sections
Fungicure Liquid Gel HUMAN OTC DRUG LABEL 1 0295-1363 LIQUID 10 mg TOPICAL OTC monograph final 9 sections
Fungicure Manicure Pedicure Anti Fungal HUMAN OTC DRUG LABEL 1 0295-6307 LIQUID 1 mg TOPICAL OTC monograph final 10 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0363-0220 CREAM 10 mg VAGINULLL ANDA 16 sections
WALGREENS CLOTRIMAZOLE HUMAN OTC DRUG LABEL 1 0363-1299 CREAM 1 g TOPICAL OTC monograph final 11 sections
athletes foot HUMAN OTC DRUG LABEL 1 0363-1857 CREAM 1 g TOPICAL OTC monograph final 13 sections
Walgreens Clotrimazole 3 HUMAN OTC DRUG LABEL 1 0363-2062 CREAM 2 g VAGINULLL NDA 16 sections
Ringworm HUMAN OTC DRUG LABEL 1 0363-2107 CREAM 10 mg TOPICAL OTC MONOGRAPH FINULLL 14 sections
Walgreens Jock Itch HUMAN OTC DRUG LABEL 1 0363-2109 CREAM 10 mg TOPICAL OTC MONOGRAPH FINULLL 14 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0363-3492 LIQUID 1 mg TOPICAL OTC monograph final 8 sections
Walgreens Clotrimazole Antifungal HUMAN OTC DRUG LABEL 1 0363-7412 CREAM 1 g TOPICAL OTC monograph final 11 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0472-0220 CREAM 10 mg VAGINULLL ANDA 16 sections
ClotrimazoleAntifungal HUMAN OTC DRUG LABEL 1 0472-0350 CREAM 10 mg TOPICAL OTC MONOGRAPH FINULLL 13 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0472-0379 CREAM 10 mg TOPICAL ANDA 24 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0536-1181 SOLUTION 1 g TOPICAL OTC monograph final 13 sections
Rugby Clotrimazole Antifungal Cream HUMAN OTC DRUG LABEL 1 0536-1265 CREAM 1 g TOPICAL OTC monograph final 12 sections
RUGBY ANTIFUNGAL CLOTRIMAZOLE HUMAN OTC DRUG LABEL 1 0536-1272 CREAM 0.01 g TOPICAL OTC monograph final 14 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0574-0107 LOZENGE 10 mg ORAL ANDA 19 sections
Major Clotrimazole HUMAN OTC DRUG LABEL 1 0904-7822 CREAM 10 mg TOPICAL OTC monograph final 11 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 10135-671 SOLUTION 1 g TOPICAL OTC MONOGRAPH FINULLL 13 sections
Lotrimin HUMAN OTC DRUG LABEL 1 11523-0963 CREAM 10 mg TOPICAL OTC monograph final 14 sections
LotriminAntifungal HUMAN OTC DRUG LABEL 1 11523-1125 CREAM 10 mg TOPICAL OTC monograph final 14 sections
Lotrimin HUMAN OTC DRUG LABEL 1 11523-6549 CREAM 10 mg TOPICAL OTC monograph final 14 sections
Dr Sheffield Athletes Foot HUMAN OTC DRUG LABEL 1 11527-071 CREAM 10 mg TOPICAL OTC monograph final 11 sections