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

Stem definitionDrug idCAS RN
2597 91161-71-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • terbinafine
  • terbinol
  • terbinafine hydrochloride
  • terbinafine HCl
A naphthalene derivative that inhibits fungal SQUALENE EPOXIDASE and is used to treat DERMATOMYCOSES of the skin and nails.
  • Molecular weight: 291.44
  • Formula: C21H25N
  • CLOGP: 5.96
  • LIPINSKI: 1
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -5.60
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.25 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 92.64 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 30, 1992 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
Ageusia 396.61 15.29 135 10854 11337 46663736
Subacute cutaneous lupus erythematosus 186.01 15.29 50 10939 1865 46673208
Acute generalised exanthematous pustulosis 174.19 15.29 70 10919 9335 46665738
Dysgeusia 173.98 15.29 112 10877 40379 46634694
Rash pustular 112.69 15.29 47 10942 6882 46668191
Pruritus 105.10 15.29 197 10792 242155 46432918
Gamma-glutamyltransferase increased 103.36 15.29 74 10915 31666 46643407
Cutaneous lupus erythematosus 96.14 15.29 32 10957 2497 46672576
Erythema multiforme 94.49 15.29 46 10943 9658 46665415
Aspartate aminotransferase increased 94.29 15.29 104 10885 78596 46596477
Blood alkaline phosphatase increased 86.74 15.29 73 10916 39536 46635537
Alanine aminotransferase increased 81.21 15.29 102 10887 88349 46586724
Toxic skin eruption 81.14 15.29 45 10944 12342 46662731
Rash 78.77 15.29 222 10767 356290 46318783
Skin exfoliation 72.71 15.29 61 10928 32877 46642196
Chromaturia 68.04 15.29 43 10946 14976 46660097
Pathogen resistance 62.85 15.29 30 10959 6030 46669043
Jaundice 60.75 15.29 52 10937 28793 46646280
Somatic delusion 59.49 15.29 16 10973 597 46674476
Erythema 51.92 15.29 108 10881 142712 46532361
Anosmia 51.78 15.29 23 10966 3921 46671152
Urticaria 49.87 15.29 95 10894 117797 46557276
Rash erythematous 49.26 15.29 50 10939 34300 46640773
Hepatic function abnormal 47.36 15.29 49 10940 34372 46640701
Hepatitis 44.58 15.29 46 10943 32169 46642904
Blister 43.36 15.29 53 10936 44578 46630495
Scedosporium infection 43.02 15.29 12 10977 514 46674559
Blood lactate dehydrogenase increased 41.22 15.29 36 10953 20464 46654609
Blood bilirubin increased 40.57 15.29 45 10944 34139 46640934
Photosensitivity reaction 37.48 15.29 28 10961 12764 46662309
Lip swelling 36.47 15.29 37 10952 25358 46649715
Pustular psoriasis 35.99 15.29 18 10971 3999 46671074
Skin lesion 34.91 15.29 37 10952 26676 46648397
Liver disorder 32.62 15.29 42 10947 37204 46637869
Drug eruption 32.33 15.29 32 10957 21297 46653776
Oral discomfort 31.74 15.29 21 10968 7897 46667176
Weight decreased 31.47 15.29 115 10874 210734 46464339
Abnormal faeces 30.09 15.29 16 10973 4033 46671040
Drug resistance 29.99 15.29 28 10961 17340 46657733
Dermatophytosis 28.87 15.29 7 10982 171 46674902
Gastrointestinal motility disorder 28.58 15.29 16 10973 4462 46670611
Rash maculo-papular 28.53 15.29 34 10955 27840 46647233
Hepatitis cholestatic 27.47 15.29 18 10971 6659 46668414
Urine odour abnormal 27.06 15.29 16 10973 4946 46670127
Onychomycosis 26.98 15.29 15 10974 4128 46670945
Rash papular 26.63 15.29 23 10966 12875 46662198
Death 26.53 15.29 24 10965 335524 46339549
Skin oedema 25.74 15.29 9 10980 814 46674259
Rash pruritic 25.66 15.29 41 10948 44174 46630899
Systemic lupus erythematosus rash 25.39 15.29 10 10979 1262 46673811
Dermatitis exfoliative 24.97 15.29 16 10973 5700 46669373
Cholestasis 24.61 15.29 31 10958 26862 46648211
Tinea pedis 24.37 15.29 10 10979 1403 46673670
Red blood cell count decreased 24.30 15.29 34 10955 32589 46642484
Bilirubin conjugated increased 23.91 15.29 12 10977 2686 46672387
Tinea infection 23.76 15.29 9 10980 1023 46674050
Antinuclear antibody positive 23.60 15.29 16 10973 6264 46668809
Hypotension 23.14 15.29 13 10976 232576 46442497
Drug-induced liver injury 22.83 15.29 29 10960 25339 46649734
Erythema nodosum 22.74 15.29 13 10976 3773 46671300
Blood creatine phosphokinase increased 22.31 15.29 30 10959 27694 46647379
Toxicity to various agents 22.29 15.29 11 10978 211755 46463318
Rheumatoid arthritis 21.72 15.29 15 10974 240200 46434873
Musculoskeletal discomfort 21.13 15.29 21 10968 14035 46661038
Drug interaction 21.00 15.29 99 10890 202995 46472078
Fungal skin infection 20.65 15.29 12 10977 3590 46671483
Rash macular 20.55 15.29 24 10965 19236 46655837
Pythium insidiosum infection 19.99 15.29 3 10986 3 46675070
Decreased appetite 19.68 15.29 94 10895 193742 46481331
Off label use 19.02 15.29 38 10951 379803 46295270
Abortion induced 18.60 15.29 17 10972 10243 46664830
Drug intolerance 18.14 15.29 6 10983 147043 46528030
Liver function test abnormal 17.84 15.29 36 10953 46451 46628622
Drug ineffective 17.67 15.29 91 10898 677747 45997326
Face oedema 17.40 15.29 22 10967 19131 46655942
Pityriasis rosea 17.36 15.29 4 10985 78 46674995
Eosinophilia 17.34 15.29 22 10967 19195 46655878
Hepatitis toxic 17.22 15.29 10 10979 2990 46672083
Fundoscopy abnormal 17.05 15.29 3 10986 13 46675060
Cheilitis 17.02 15.29 11 10978 3977 46671096
Swollen tongue 16.81 15.29 27 10962 29205 46645868
Rash papulosquamous 16.61 15.29 4 10985 95 46674978
Dermatitis bullous 16.53 15.29 14 10975 7629 46667444
C-reactive protein increased 16.42 15.29 40 10949 58550 46616523
Lymphocyte stimulation test positive 16.35 15.29 6 10983 624 46674449
Eosinophil count increased 16.18 15.29 14 10975 7852 46667221

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
Pathogen resistance 163.81 14.37 75 11512 8335 29932556
Aspartate aminotransferase increased 121.98 14.37 136 11451 63286 29877605
Gamma-glutamyltransferase increased 105.87 14.37 89 11498 29261 29911630
Alanine aminotransferase increased 100 14.37 133 11454 74143 29866748
Ageusia 97.90 14.37 54 11533 8899 29931992
Chromaturia 85.57 14.37 58 11529 13807 29927084
Drug resistance 82.98 14.37 66 11521 20067 29920824
Acute generalised exanthematous pustulosis 81.36 14.37 42 11545 6056 29934835
Jaundice 78.99 14.37 79 11508 32407 29908484
Blood creatine phosphokinase increased 74.06 14.37 88 11499 43760 29897131
Blood alkaline phosphatase increased 71.86 14.37 74 11513 31413 29909478
Onychomycosis 64.21 14.37 26 11561 2137 29938754
Symmetrical drug-related intertriginous and flexural exanthema 60.33 14.37 14 11573 166 29940725
Death 55.61 14.37 35 11552 357248 29583643
Rash pustular 51.58 14.37 29 11558 4954 29935937
Skin exfoliation 50.23 14.37 53 11534 23119 29917772
Scedosporium infection 49.21 14.37 16 11571 699 29940192
Liver function test abnormal 47.17 14.37 59 11528 30891 29910000
Diaphragmatic spasm 46.42 14.37 10 11577 82 29940809
Rash 46.34 14.37 171 11416 191718 29749173
Faecal volume decreased 46.00 14.37 10 11577 86 29940805
Liver disorder 45.84 14.37 57 11530 29665 29911226
Pruritus 45.70 14.37 124 11463 118080 29822811
Blood bilirubin increased 43.77 14.37 62 11525 36574 29904317
Hypotension 43.38 14.37 12 11575 200553 29740338
Blood lactate dehydrogenase increased 40.93 14.37 45 11542 20556 29920335
Rash erythematous 39.43 14.37 46 11541 22406 29918485
Epstein-Barr virus antibody positive 38.02 14.37 11 11576 323 29940568
Swelling of eyelid 37.80 14.37 11 11576 330 29940561
Cutaneous lupus erythematosus 35.58 14.37 12 11575 588 29940303
Treatment failure 34.69 14.37 54 11533 34625 29906266
Hepatic function abnormal 33.47 14.37 59 11528 41886 29899005
Erythema multiforme 32.50 14.37 26 11561 7959 29932932
Antinuclear antibody positive 31.78 14.37 14 11573 1418 29939473
Cholestasis 30.94 14.37 43 11544 24907 29915984
Toxicity to various agents 30.88 14.37 15 11572 177168 29763723
Trichophytosis 30.10 14.37 9 11578 297 29940594
Erythema nodosum 26.76 14.37 11 11576 939 29939952
Erythema 26.69 14.37 78 11509 77373 29863518
Dermatitis exfoliative 25.60 14.37 22 11565 7434 29933457
Rhabdomyolysis 24.82 14.37 67 11520 63513 29877378
Tinea pedis 24.77 14.37 11 11576 1135 29939756
Myalgia 24.33 14.37 75 11512 76592 29864299
Hepatic lesion 23.94 14.37 15 11572 3121 29937770
Dysgeusia 22.57 14.37 37 11550 24764 29916127
Erythrodermic psoriasis 22.07 14.37 9 11578 753 29940138
Rosacea 21.94 14.37 10 11577 1097 29939794
Blister 21.79 14.37 33 11554 20650 29920241
Completed suicide 21.38 14.37 6 11581 99486 29841405
Lymphocyte stimulation test positive 20.79 14.37 9 11578 874 29940017
Hodgkin's disease 20.32 14.37 9 11578 923 29939968
Hairy cell leukaemia 19.98 14.37 5 11582 83 29940808
Skin warm 19.80 14.37 11 11576 1835 29939056
Urticaria 19.77 14.37 56 11531 54550 29886341
Tenosynovitis stenosans 19.66 14.37 4 11583 24 29940867
Deficiency of bile secretion 19.66 14.37 4 11583 24 29940867
Pneumonia 19.10 14.37 66 11521 334240 29606651
Hepatitis cholestatic 18.84 14.37 19 11568 7853 29933038
Pythium insidiosum infection 18.50 14.37 3 11584 3 29940888
Drug-induced liver injury 18.37 14.37 31 11556 21243 29919648
Benign breast neoplasm 18.03 14.37 3 11584 4 29940887
Liver injury 17.86 14.37 23 11564 12377 29928514
Chromoblastomycosis 17.04 14.37 4 11583 50 29940841
Biliary obstruction 16.91 14.37 11 11576 2442 29938449
Faeces pale 16.39 14.37 9 11578 1468 29939423
Tongue discomfort 16.24 14.37 6 11581 385 29940506
Neutrophil percentage decreased 16.02 14.37 6 11581 400 29940491
Eyelid pain 15.90 14.37 4 11583 68 29940823
Hepatic enzyme increased 15.87 14.37 38 11549 33456 29907435
Off label use 15.76 14.37 47 11540 249243 29691648
Product dispensing error 15.56 14.37 15 11572 5874 29935017
Malaise 15.47 14.37 114 11473 166848 29774043
Peyronie's disease 15.43 14.37 4 11583 77 29940814
Nail discolouration 15.39 14.37 7 11580 764 29940127
Tooth abscess 15.35 14.37 14 11573 5112 29935779
Smooth muscle antibody positive 15.21 14.37 3 11584 15 29940876
Vitamin E deficiency 15.21 14.37 3 11584 15 29940876
Dermatitis 14.82 14.37 17 11570 8125 29932766
Neuropsychiatric symptoms 14.81 14.37 6 11581 493 29940398

Pharmacologic Action:

SourceCodeDescription
ATC D01AE15 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Other antifungals for topical use
ATC D01BA02 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR SYSTEMIC USE
Antifungals for systemic use
FDA CS M0000751 Allylamine
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D004791 Enzyme Inhibitors
CHEBI has role CHEBI:50183 cytochrome p450 inhibitor
CHEBI has role CHEBI:59285 squalene-2,3-epoxidase inhibitors
CHEBI has role CHEBI:83317 sterol biosynthesis inhibitors
FDA EPC N0000175874 Allylamine Antifungal

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Tinea capitis indication 5441008
Tinea pedis indication 6020002 DOID:12403
Pityriasis versicolor indication 56454009 DOID:9060
Tinea corporis indication 84849002
Tinea cruris indication 399029005
Onychomycosis due to dermatophyte indication 402134005
Onychomycosis of fingernails indication 403058003
Onychomycosis of toenails indication 403059006
Candidiasis of skin off-label use 49883006
Chromoblastomycosis off-label use 187079000
Alcoholism contraindication 7200002
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.02 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
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.63 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.39 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.70 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.67 DRUG MATRIX
Squalene monooxygenase Enzyme Ki 7.52 CHEMBL
Squalene epoxidase Enzyme INHIBITOR CHEMBL CHEMBL
Squalene monooxygenase Unclassified IC50 4.03 CHEMBL
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 7.66 DRUG MATRIX

External reference:

IDSource
4023600 VUID
N0000021605 NUI
D02219 KEGG_DRUG
78628-80-5 SECONDARY_CAS_RN
4020792 VANDF
4023600 VANDF
C0076110 UMLSCUI
CHEBI:9448 CHEBI
CHEMBL822 ChEMBL_ID
CHEMBL1200832 ChEMBL_ID
D000077291 MESH_DESCRIPTOR_UI
5657 INN_ID
DB00857 DRUGBANK_ID
G7RIW8S0XP UNII
1549008 PUBCHEM_CID
235838 RXNORM
116863 MMSL
5547 MMSL
d04012 MMSL
004051 NDDF
004052 NDDF
108925005 SNOMEDCT_US
108927002 SNOMEDCT_US
373450007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
LamisilAT Jock Itch HUMAN OTC DRUG LABEL 1 0067-3999 CREAM 10 mg TOPICAL NDA 13 sections
LAMISILAT HUMAN OTC DRUG LABEL 1 0067-6296 AEROSOL, SPRAY 0.84 g TOPICAL NDA 13 sections
LAMISILAT HUMAN OTC DRUG LABEL 1 0067-6297 AEROSOL, SPRAY 0.84 g TOPICAL NDA 13 sections
Lamisil AT HUMAN OTC DRUG LABEL 1 0067-8100 CREAM 1 g TOPICAL ANDA 14 sections
Lamisil ATfor Jock Itch HUMAN OTC DRUG LABEL 1 0067-8114 CREAM 1 g TOPICAL ANDA 14 sections
Walgreens Athletes Foot HUMAN OTC DRUG LABEL 1 0363-2080 CREAM 1 g TOPICAL ANDA 14 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 0363-2083 CREAM 1 g TOPICAL ANDA 14 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 11673-080 CREAM 1 g TOPICAL ANDA 14 sections
athletes foot HUMAN OTC DRUG LABEL 1 11673-401 CREAM 10 mg TOPICAL NDA 7 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 11822-0080 CREAM 1 g TOPICAL ANDA 14 sections
terbinafine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-501 TABLET 250 mg ORAL ANDA 20 sections
Terbinafine Human Prescription Drug Label 1 16714-795 TABLET 250 mg ORAL ANDA 27 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 21130-080 CREAM 1 g TOPICAL ANDA 13 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-630 TABLET 250 mg ORAL ANDA 19 sections
Good Neighbor Pharmacy HUMAN OTC DRUG LABEL 1 24385-524 CREAM 1 g TOPICAL ANDA 14 sections
Kroger Antifungal HUMAN OTC DRUG LABEL 1 30142-080 CREAM 1 g TOPICAL ANDA 14 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 31722-209 TABLET 250 1 ORAL ANDA 26 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 36800-080 CREAM 1 g TOPICAL ANDA 14 sections
Shopko Athletes Foot HUMAN OTC DRUG LABEL 1 37012-080 CREAM 1 g TOPICAL ANDA 14 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 37808-080 CREAM 1 g TOPICAL ANDA 14 sections
athletes foot HUMAN OTC DRUG LABEL 1 41163-080 CREAM 1 g TOPICAL ANDA 14 sections
ShopRite HUMAN OTC DRUG LABEL 1 41190-083 CREAM 1 g TOPICAL ANDA 14 sections
Antifungal HUMAN OTC DRUG LABEL 1 41250-080 CREAM 1 g TOPICAL ANDA 14 sections
Antifungal Foot HUMAN OTC DRUG LABEL 1 41520-080 CREAM 1 g TOPICAL ANDA 14 sections
terbinafine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42043-410 TABLET 250 mg ORAL ANDA 20 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-598 TABLET 250 mg ORAL ANDA 30 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-906 TABLET 250 mg ORAL ANDA 31 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-893 TABLET 250 mg ORAL ANDA 31 sections
equate Athletes Foot HUMAN OTC DRUG LABEL 1 49035-080 CREAM 1 g TOPICAL ANDA 14 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 49348-790 CREAM 1 g TOPICAL ANDA 13 sections