clotrimazole Indications/Contra | FAERs | Orange Book | 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

Drug dosage:

DoseUnitRoute
0.10 g V

Approvals:

DateAgencyCompanyOrphan
Feb. 3, 1975 FDA

FDA Adverse Event Reporting System

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
Purpura senile 93.82 54.42 10 215 22 3385612
Tarsal tunnel syndrome 78.93 54.42 9 216 44 3385590
Exposure during pregnancy 71.47 54.42 21 204 27542 3358092
Drug hypersensitivity 66.12 54.42 21 204 35659 3349975
Resorption bone increased 64.08 54.42 9 216 267 3385367
Vestibular disorder 62.56 54.42 9 216 318 3385316
Hypersensitivity 62.47 54.42 19 206 27881 3357753

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 EPC N0000175487 Azole Antifungal
FDA Chemical/Ingredient N0000008217 Azoles
MeSH PA D058888 14-alpha Demethylase Inhibitors
CHEBI has role CHEBI:35441 antiinfective agent
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 D006730 Hormones, Hormone Substitutes, and Hormone Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D065088 Steroid Synthesis Inhibitors

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 DOID:12179
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 DOID:1272
Abdominal pain - cause unknown contraindication 314212008
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Atrophoderma contraindication 399979006 DOID:2733
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
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
D(4) dopamine receptor GPCR Ki 5.16 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
Nuclear receptor subfamily 1 group I member 3 Nuclear hormone receptor ANTAGONIST IC50 6.16 IUPHAR
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
DB00257 DRUGBANK_ID
2330 IUPHAR_LIGAND_ID
4018265 VUID
N0000146595 NUI
C0009074 UMLSCUI
D00282 KEGG_DRUG
CHEMBL104 ChEMBL_ID
4018265 VANDF
N0000006579 NDFRT
N0000146595 NDFRT
002916 NDDF
2623 RXNORM
387325003 SNOMEDCT_US
5797005 SNOMEDCT_US
4482 MMSL
d01236 MMSL
2812 PUBCHEM_CID
D003022 MESH_DESCRIPTOR_UI
G07GZ97H65 UNII
2912 INN_ID
CHEBI:3764 CHEBI
CL6 PDB_CHEM_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0054-4146 LOZENGE 10 mg ORAL ANDA 13 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0054-8146 LOZENGE 10 mg ORAL ANDA 13 sections
Lotrisone HUMAN PRESCRIPTION DRUG LABEL 2 0085-0924 CREAM 10 mg TOPICAL NDA 16 sections
Good Sense Athletes Foot HUMAN OTC DRUG LABEL 1 0113-0857 CREAM 1 g TOPICAL OTC monograph final 9 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0168-0133 CREAM 10 mg TOPICAL ANDA 12 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0168-0258 CREAM 10 mg TOPICAL ANDA 15 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0168-0370 LOTION 10 mg TOPICAL ANDA 13 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0179-8014 CREAM 10 mg TOPICAL OTC MONOGRAPH FINAL 10 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0363-0220 CREAM 10 mg VAGINAL ANDA 10 sections
Clotrimazole Antifungal HUMAN OTC DRUG LABEL 1 0363-0857 CREAM 1 g TOPICAL OTC monograph final 9 sections
WALGREENS CLOTRIMAZOLE HUMAN OTC DRUG LABEL 1 0363-1299 CREAM 1 g TOPICAL OTC monograph final 10 sections
athletes foot HUMAN OTC DRUG LABEL 1 0363-1857 CREAM 1 g TOPICAL OTC monograph final 9 sections
Walgreens HUMAN OTC DRUG LABEL 1 0363-2062 CREAM 2 g VAGINAL NDA 9 sections
Walgreens HUMAN OTC DRUG LABEL 1 0363-2109 CREAM 10 mg TOPICAL OTC MONOGRAPH FINAL 10 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0363-3492 LIQUID 1 mg TOPICAL OTC monograph final 7 sections
Jock Itch HUMAN OTC DRUG LABEL 1 0363-3510 CREAM 1 g TOPICAL OTC MONOGRAPH FINAL 10 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 VAGINAL ANDA 10 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 0472-0350 CREAM 10 mg TOPICAL OTC MONOGRAPH FINAL 13 sections
Clotrimazole and Betamethasone Dipropionate HUMAN PRESCRIPTION DRUG LABEL 2 0472-0379 CREAM 10 mg TOPICAL ANDA 15 sections
Clotrimazole HUMAN PRESCRIPTION DRUG LABEL 1 0574-0107 LOZENGE 10 mg ORAL ANDA 13 sections
Major Clotrimazole HUMAN OTC DRUG LABEL 1 0904-7822 CREAM 10 mg TOPICAL OTC monograph final 9 sections
Lotrimin HUMAN OTC DRUG LABEL 1 11523-0963 CREAM 10 mg TOPICAL OTC monograph final 10 sections
Lotrimin HUMAN OTC DRUG LABEL 1 11523-1125 CREAM 10 mg TOPICAL OTC monograph final 10 sections
Lotrimin HUMAN OTC DRUG LABEL 1 11523-6549 CREAM 10 mg TOPICAL OTC monograph final 10 sections
Dr Sheffield Athletes Foot HUMAN OTC DRUG LABEL 1 11527-071 CREAM 10 mg TOPICAL OTC monograph final 9 sections
Up and Up Jock Itch Relief HUMAN OTC DRUG LABEL 1 11673-504 CREAM 1 g TOPICAL OTC monograph final 9 sections
up and up athletes foot HUMAN OTC DRUG LABEL 1 11673-857 CREAM 1 g TOPICAL OTC monograph final 9 sections
UpandUp HUMAN OTC DRUG LABEL 1 11673-910 CREAM 10 mg TOPICAL OTC MONOGRAPH FINAL 10 sections
Clotrimazole HUMAN OTC DRUG LABEL 1 11822-0220 CREAM 10 mg VAGINAL ANDA 10 sections