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

Stem definitionDrug idCAS RN
squalene monooxygenase inhibitors, antifungals 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 5.659 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.455 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.933 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 24.831 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.080 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.100 % High 1
herg hERG pIC50 5.356 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 79.250 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 193.197 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.080 % High 1
kinase-safety-class ACVR2A,ACVR2B,AKT1,AKT2,AKT3,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,JAK3,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MARK4,MET,MTOR,NTRK2,PAK4,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 56
kinase-selectivity-class AXL,BRAF,GRK2 3
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.068 High 1
mh-clint Mouse hepatocyte intrinsic clearance 261.216 High 1
mppb Mouse plasma protein binding (% unbound) 0.150 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.289 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.560 % High 1
rh-clint Rat hepatocyte intrinsic clearance 222.331 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 0.440 % High 1
rppb Rat plasma protein binding (% unbound) 0.100 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 0.383 uM High 1

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
Acute generalised exanthematous pustulosis 267.64 15.93 88 10368 13615 90604376
Subacute cutaneous lupus erythematosus 209.67 15.93 54 10402 3528 90614463
Ageusia 186.23 15.93 70 10386 16006 90601985
Pathogen resistance 96.37 15.93 36 10420 8079 90609912
Lip swelling 90.34 15.93 56 10400 38554 90579437
Rash pustular 85.81 15.93 33 10423 8016 90609975
Somatic delusion 81.77 15.93 18 10438 596 90617395
Drug resistance 78.51 15.93 47 10409 30402 90587589
Dysgeusia 74.67 15.93 56 10400 52504 90565487
Pruritus 70.43 15.93 177 10279 541348 90076643
Skin exfoliation 70.11 15.93 60 10396 67853 90550138
Gliosis 68.63 15.93 15 10441 480 90617511
Polyserositis 64.04 15.93 15 10441 658 90617333
Pouchitis 63.96 15.93 15 10441 662 90617329
Chromaturia 63.89 15.93 35 10421 19152 90598839
Erythema multiforme 60.08 15.93 29 10427 12217 90605774
Toxic skin eruption 58.75 15.93 31 10425 15743 90602248
Rash maculo-papular 56.77 15.93 43 10413 40890 90577101
Rash 55.35 15.93 209 10247 795891 89822100
Premature menopause 53.91 15.93 15 10441 1314 90616677
Drug interaction 52.26 15.93 105 10351 276348 90341643
Ovarian failure 50.77 15.93 15 10441 1628 90616363
Antiphospholipid syndrome 50.04 15.93 16 10440 2258 90615733
Cutaneous lupus erythematosus 48.92 15.93 17 10439 3101 90614890
Erythema 48.09 15.93 91 10365 229155 90388836
Photosensitivity reaction 47.23 15.93 28 10428 17779 90600212
Skin lesion 44.77 15.93 36 10420 37329 90580662
Gastrointestinal motility disorder 44.37 15.93 19 10437 6072 90611919
Proctectomy 44.33 15.93 9 10447 200 90617791
Jaundice 40.38 15.93 32 10424 32485 90585506
Oral discomfort 40.17 15.93 21 10435 10462 90607529
Somatic symptom disorder 39.89 15.93 15 10441 3426 90614565
Abnormal faeces 39.50 15.93 18 10438 6664 90611327
Urine odour abnormal 38.11 15.93 18 10438 7226 90610765
Drug-induced liver injury 37.35 15.93 49 10407 90269 90527722
Periostitis 37.03 15.93 9 10447 463 90617528
Venous thrombosis limb 36.20 15.93 14 10442 3448 90614543
Rash erythematous 36.15 15.93 41 10415 65063 90552928
Cardiac tamponade 35.92 15.93 16 10440 5616 90612375
Skin plaque 35.44 15.93 19 10437 9956 90608035
Fluorosis 34.76 15.93 7 10449 149 90617842
Swollen tongue 34.52 15.93 34 10422 45922 90572069
Dermatitis exfoliative generalised 32.85 15.93 15 10441 5578 90612413
Rash pruritic 31.53 15.93 43 10413 82171 90535820
Musculoskeletal discomfort 31.22 15.93 23 10433 20968 90597023
Rash papulosquamous 30.81 15.93 6 10450 107 90617884
Xerosis 30.67 15.93 10 10446 1501 90616490
Tinea pedis 30.13 15.93 10 10446 1587 90616404
Ileostomy closure 30.11 15.93 7 10449 297 90617694
Urticarial vasculitis 29.94 15.93 9 10447 1036 90616955
Oesophageal irritation 29.31 15.93 7 10449 334 90617657
Respiratory gas exchange disorder 28.05 15.93 7 10449 402 90617589
Tinea infection 27.76 15.93 9 10447 1327 90616664
Cholestasis 27.53 15.93 27 10429 36272 90581719
Drug intolerance 25.31 15.93 10 10446 447581 90170410
Papule 25.00 15.93 14 10442 7988 90610003
Liver function test abnormal 24.85 15.93 30 10426 50815 90567176
Ileostomy 24.41 15.93 9 10447 1945 90616046
Pustule 24.37 15.93 10 10446 2873 90615118
Pulpless tooth 24.20 15.93 3 10453 0 90617991
Product use in unapproved indication 23.82 15.93 89 10367 336147 90281844
Scedosporium infection 23.17 15.93 7 10449 819 90617172
Chloasma 22.97 15.93 5 10451 157 90617834
Tinea capitis 22.78 15.93 4 10452 39 90617952
Lupus-like syndrome 22.55 15.93 28 10428 48818 90569173
Pustular psoriasis 22.48 15.93 18 10438 18538 90599453
Infusion related reaction 22.45 15.93 10 10446 416770 90201221
Intestinal anastomosis 22.42 15.93 7 10449 915 90617076
Pythium insidiosum infection 22.12 15.93 3 10453 3 90617988
Cheilitis 22.00 15.93 11 10445 4996 90612995
Rash macular 21.99 15.93 22 10434 30258 90587733
Contraindicated product administered 21.99 15.93 5 10451 320134 90297857
Mycotic endophthalmitis 21.97 15.93 5 10451 193 90617798
Hepatitis cholestatic 21.50 15.93 13 10443 8548 90609443
Pericarditis 21.18 15.93 3 10453 270148 90347843
Aplastic anaemia 20.77 15.93 15 10441 13254 90604737
Drug reaction with eosinophilia and systemic symptoms 20.53 15.93 25 10431 42733 90575258
Joint swelling 20.27 15.93 17 10439 503283 90114708
Intervertebral disc protrusion 20.20 15.93 20 10436 27176 90590815
Depression 19.99 15.93 78 10378 300523 90317468
Pneumonia respiratory syncytial viral 19.79 15.93 7 10449 1344 90616647
Dermatitis 19.66 15.93 18 10438 22202 90595789
Erythema annulare 19.63 15.93 5 10451 312 90617679
Linear IgA disease 19.61 15.93 8 10448 2266 90615725
Skin burning sensation 19.56 15.93 17 10439 19594 90598397
Tinea faciei 19.38 15.93 3 10453 12 90617979
Systemic lupus erythematosus rash 19.22 15.93 8 10448 2381 90615610
Urticaria 19.08 15.93 79 10377 312655 90305336
Pemphigus 18.97 15.93 7 10449 326857 90291134
Fundoscopy abnormal 18.67 15.93 3 10453 16 90617975
Cholestatic liver injury 18.65 15.93 9 10447 3788 90614203
Macule 18.37 15.93 8 10448 2661 90615330
Onychomycosis 18.18 15.93 22 10434 37354 90580637
Potassium hydroxide preparation positive 17.97 15.93 3 10453 21 90617970
Erythema nodosum 17.84 15.93 10 10446 5714 90612277
Therapeutic product effect decreased 17.77 15.93 5 10451 277566 90340425
Chronic spontaneous urticaria 17.76 15.93 7 10449 1813 90616178
Gastrointestinal disorder 17.64 15.93 4 10452 256683 90361308
Peritonitis 17.50 15.93 16 10440 19689 90598302
Fungal infection 17.40 15.93 23 10433 42638 90575353
Red blood cell count decreased 17.40 15.93 24 10432 46327 90571664
Aphasia 17.34 15.93 23 10433 42789 90575202
Dermoid cyst 17.29 15.93 5 10451 503 90617488
Faeces pale 17.25 15.93 7 10449 1956 90616035
Skin oedema 16.98 15.93 6 10450 1148 90616843
Rhabdomyolysis 16.97 15.93 25 10431 51231 90566760
Dermatitis bullous 16.93 15.93 12 10444 10304 90607687
Body tinea 16.64 15.93 7 10449 2141 90615850
Thrombophlebitis 16.60 15.93 9 10447 4819 90613172
Weight decreased 16.57 15.93 87 10369 379823 90238168
Prothrombin time shortened 16.24 15.93 7 10449 2271 90615720
Skin hyperpigmentation 16.17 15.93 10 10446 6841 90611150

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 255.84 15.71 98 10090 11352 42599795
Drug resistance 189.71 15.71 112 10076 34136 42577011
Acute generalised exanthematous pustulosis 89.91 15.71 43 10145 8552 42602595
Treatment failure 86.69 15.71 90 10098 62534 42548613
Ageusia 72.27 15.71 41 10147 11564 42599583
Drug ineffective 66.37 15.71 311 9877 629886 41981261
Onychomycosis 59.16 15.71 23 10165 2763 42608384
Diaphragmatic spasm 54.85 15.71 11 10177 105 42611042
Rash 54.23 15.71 167 10021 276787 42334360
Pruritus 49.87 15.71 127 10061 188644 42422503
Scedosporium infection 48.34 15.71 17 10171 1541 42609606
Faecal volume decreased 47.73 15.71 11 10177 211 42610936
Symmetrical drug-related intertriginous and flexural exanthema 45.18 15.71 14 10174 854 42610293
Rash pustular 44.28 15.71 24 10164 6191 42604956
Chromaturia 44.18 15.71 34 10154 15955 42595192
Skin exfoliation 37.62 15.71 48 10140 41505 42569642
Hepatic lesion 36.67 15.71 19 10169 4475 42606672
Pustular psoriasis 36.27 15.71 15 10173 2114 42609033
Rosacea 35.21 15.71 13 10175 1355 42609792
Drug-induced liver injury 34.31 15.71 44 10144 38229 42572918
Death 33.62 15.71 38 10150 471147 42140000
Faeces pale 33.12 15.71 13 10175 1601 42609546
Jaundice 32.97 15.71 41 10147 34548 42576599
Skin plaque 31.95 15.71 19 10169 5844 42605303
Impetigo 31.58 15.71 12 10176 1354 42609793
Erythema nodosum 31.42 15.71 13 10175 1835 42609312
Urticaria 31.04 15.71 60 10128 73976 42537171
Discomfort 30.88 15.71 34 10154 25185 42585962
Swelling of eyelid 29.65 15.71 13 10175 2115 42609032
Abscess sweat gland 29.36 15.71 4 10184 0 42611147
Choluria 28.77 15.71 7 10181 171 42610976
Eczema 28.71 15.71 38 10150 34048 42577099
Fungaemia 27.74 15.71 14 10174 3122 42608025
Subacute cutaneous lupus erythematosus 27.11 15.71 11 10177 1477 42609670
Hypotension 26.96 15.71 14 10174 257617 42353530
Tongue discomfort 26.85 15.71 9 10179 706 42610441
Rash erythematous 25.84 15.71 35 10153 32056 42579091
Tinea versicolour 25.55 15.71 8 10180 505 42610642
Liver function test abnormal 24.08 15.71 34 10154 32357 42578790
Erythrodermic psoriasis 23.18 15.71 9 10179 1077 42610070
Trichophytosis 23.08 15.71 7 10181 397 42610750
Deficiency of bile secretion 22.92 15.71 4 10184 16 42611131
Product substitution issue 22.77 15.71 20 10168 11270 42599877
Genital disorder 22.73 15.71 4 10184 17 42611130
CARD9 deficiency 22.20 15.71 4 10184 20 42611127
Systemic mycosis 22.13 15.71 11 10177 2376 42608771
Hepatocellular carcinoma 21.71 15.71 17 10171 8177 42602970
Erythema 21.55 15.71 66 10122 108727 42502420
Transient acantholytic dermatosis 21.37 15.71 6 10182 259 42610888
Skin lesion 20.91 15.71 29 10159 27145 42584002
Chronic spontaneous urticaria 20.80 15.71 6 10182 286 42610861
Photosensitivity reaction 20.75 15.71 20 10168 12682 42598465
Seborrhoeic dermatitis 20.74 15.71 10 10178 2022 42609125
Neutrophilia 20.46 15.71 14 10174 5478 42605669
Skin warm 20.38 15.71 11 10177 2812 42608335
Hairy cell leukaemia 19.69 15.71 5 10183 146 42611001
Chemical burn 19.67 15.71 6 10182 347 42610800
Benign breast neoplasm 19.48 15.71 3 10185 4 42611143
Biliary obstruction 19.00 15.71 11 10177 3218 42607929
Eustachian tube disorder 18.72 15.71 3 10185 6 42611141
Nail pitting 18.40 15.71 6 10182 432 42610715
Sinus bradycardia 18.14 15.71 20 10168 14833 42596314
Dermatitis contact 18.02 15.71 12 10176 4491 42606656
Toxicity to various agents 17.95 15.71 17 10171 229119 42382028
Macule 17.75 15.71 9 10179 2026 42609121
Intertrigo 17.68 15.71 6 10182 489 42610658
Periorbital oedema 17.65 15.71 12 10176 4645 42606502
Mycotic endophthalmitis 17.48 15.71 5 10183 231 42610916
Papule 17.44 15.71 13 10175 5813 42605334
Vitamin E deficiency 17.19 15.71 3 10185 12 42611135
Onycholysis 16.85 15.71 7 10181 998 42610149
Prostatic haemorrhage 16.74 15.71 5 10183 269 42610878
Needle issue 16.69 15.71 15 10173 8712 42602435
Pustule 15.77 15.71 7 10181 1172 42609975
Pityriasis rosea 15.75 15.71 4 10184 117 42611030

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
Pathogen resistance 356.13 13.98 128 18604 17544 110553023
Acute generalised exanthematous pustulosis 337.87 13.98 130 18602 21534 110549033
Drug resistance 262.22 13.98 146 18586 56228 110514339
Subacute cutaneous lupus erythematosus 205.20 13.98 62 18670 4932 110565635
Ageusia 177.87 13.98 80 18652 19565 110551002
Rash pustular 128.21 13.98 56 18676 12773 110557794
Chromaturia 109.72 13.98 66 18666 29294 110541273
Pruritus 95.50 13.98 264 18468 581296 109989271
Rash 89.18 13.98 323 18409 820641 109749926
Skin exfoliation 85.38 13.98 89 18643 87562 110483005
Somatic delusion 82.10 13.98 20 18712 701 110569866
Scedosporium infection 73.73 13.98 24 18708 2434 110568133
Jaundice 70.34 13.98 67 18665 59169 110511398
Toxic skin eruption 68.65 13.98 48 18684 27467 110543100
Lip swelling 67.29 13.98 61 18671 50606 110519961
Photosensitivity reaction 64.68 13.98 45 18687 25544 110545023
Erythema 60.84 13.98 145 18587 291302 110279265
Liver function test abnormal 60.06 13.98 66 18666 68884 110501683
Diaphragmatic spasm 57.90 13.98 11 18721 113 110570454
Gliosis 57.06 13.98 15 18717 717 110569850
Rash erythematous 55.69 13.98 69 18663 81763 110488804
Drug-induced liver injury 54.17 13.98 83 18649 119984 110450583
Skin plaque 54.01 13.98 31 18701 12614 110557953
Ovarian failure 52.79 13.98 15 18717 961 110569606
Polyserositis 51.93 13.98 15 18717 1019 110569548
Pustular psoriasis 51.90 13.98 31 18701 13574 110556993
Premature menopause 51.82 13.98 15 18717 1027 110569540
Drug interaction 50.11 13.98 192 18540 499991 110070576
Erythema multiforme 48.46 13.98 35 18697 21062 110549505
Faeces pale 48.25 13.98 19 18713 3338 110567229
Rash maculo-papular 47.98 13.98 61 18671 74161 110496406
Skin lesion 47.72 13.98 51 18681 51580 110518987
Cutaneous lupus erythematosus 47.54 13.98 19 18713 3469 110567098
Pouchitis 47.48 13.98 15 18717 1382 110569185
Drug ineffective 47.21 13.98 427 18305 1520113 109050454
Cholestasis 46.49 13.98 56 18676 64462 110506105
Faecal volume decreased 44.40 13.98 11 18721 414 110570153
Symmetrical drug-related intertriginous and flexural exanthema 42.98 13.98 15 18717 1882 110568685
Antiphospholipid syndrome 42.40 13.98 16 18716 2507 110568060
Urine odour abnormal 42.26 13.98 22 18710 7393 110563174
Pustule 40.63 13.98 17 18715 3487 110567080
Mycotic endophthalmitis 38.93 13.98 10 18722 436 110570131
Dysgeusia 38.27 13.98 53 18679 69932 110500635
Proctectomy 36.32 13.98 9 18723 339 110570228
Oral discomfort 36.09 13.98 23 18709 11288 110559279
Somatic symptom disorder 35.54 13.98 15 18717 3144 110567423
Rash macular 35.37 13.98 38 18694 38648 110531919
Chronic spontaneous urticaria 34.80 13.98 13 18719 1980 110568587
Gastrointestinal motility disorder 34.21 13.98 19 18713 7257 110563310
Hepatic lesion 34.09 13.98 20 18712 8473 110562094
Urticaria 34.04 13.98 125 18607 318732 110251835
Neutrophilia 32.95 13.98 21 18711 10308 110560259
Periostitis 32.87 13.98 10 18722 813 110569754
Abnormal faeces 32.54 13.98 20 18712 9216 110561351
Treatment failure 32.43 13.98 112 18620 277122 110293445
Hypotension 32.17 13.98 25 18707 523824 110046743
Fungaemia 31.69 13.98 17 18715 6069 110564498
Venous thrombosis limb 31.09 13.98 16 18716 5249 110565318
Tinea infection 30.79 13.98 11 18721 1477 110569090
Macule 30.07 13.98 14 18718 3699 110566868
Systemic mycosis 29.66 13.98 14 18718 3815 110566752
Fluorosis 29.53 13.98 7 18725 218 110570349
Toxicity to various agents 29.42 13.98 23 18709 480532 110090035
Trichophytosis 28.73 13.98 8 18724 476 110570091
Impetigo 28.25 13.98 12 18720 2556 110568011
Erythema nodosum 27.58 13.98 16 18716 6637 110563930
Swelling of eyelid 27.58 13.98 16 18716 6637 110563930
Urticarial vasculitis 27.05 13.98 9 18723 977 110569590
Onychomycosis 27.03 13.98 33 18699 38498 110532069
Tinea pedis 26.94 13.98 12 18720 2863 110567704
Thrombotic thrombocytopenic purpura 26.60 13.98 16 18716 7095 110563472
Cardiac tamponade 26.52 13.98 19 18713 11288 110559279
Dermatitis exfoliative 26.46 13.98 19 18713 11328 110559239
Stevens-Johnson syndrome 26.36 13.98 36 18696 46865 110523702
Rash pruritic 26.31 13.98 54 18678 98015 110472552
Papule 26.03 13.98 18 18714 10115 110560452
Ileostomy closure 26.02 13.98 7 18725 366 110570201
Eczema 25.84 13.98 45 18687 72248 110498319
Rash papulosquamous 25.72 13.98 6 18726 174 110570393
Infusion related reaction 24.94 13.98 17 18715 381145 110189422
Glossodynia 24.67 13.98 4 18728 222000 110348567
Seborrhoeic dermatitis 24.42 13.98 11 18721 2696 110567871
Abscess sweat gland 24.30 13.98 4 18728 16 110570551
Choluria 24.27 13.98 7 18725 473 110570094
Pericarditis 24.23 13.98 4 18728 219110 110351457
Pityriasis rosea 24.03 13.98 6 18726 233 110570334
CARD9 deficiency 23.57 13.98 4 18728 20 110570547
Cholestatic liver injury 23.54 13.98 15 18717 7361 110563206
Dermatitis 23.12 13.98 26 18706 27811 110542756
Hepatitis cholestatic 23.02 13.98 21 18711 17545 110553022
Tinea versicolour 22.85 13.98 7 18725 583 110569984
Rosacea 22.80 13.98 13 18719 5223 110565344
Oesophageal irritation 22.58 13.98 6 18726 299 110570268
Genital disorder 22.55 13.98 4 18728 27 110570540
Contraindicated product administered 22.53 13.98 7 18725 248260 110322307
Transient acantholytic dermatosis 22.13 13.98 6 18726 323 110570244
Hypersensitivity vasculitis 21.87 13.98 14 18718 6923 110563644
Drug reaction with eosinophilia and systemic symptoms 21.78 13.98 45 18687 82050 110488517
Hypertension 21.71 13.98 33 18699 510051 110060516
Completed suicide 21.70 13.98 7 18725 242374 110328193
Periorbital oedema 21.36 13.98 16 18716 10176 110560391
Hepatitis toxic 21.31 13.98 13 18719 5908 110564659
Musculoskeletal discomfort 21.30 13.98 23 18709 23515 110547052
Neuropsychiatric symptoms 21.04 13.98 8 18724 1280 110569287
Kerion 20.97 13.98 3 18729 3 110570564
Erythrodermic psoriasis 20.82 13.98 9 18723 2001 110568566
Systemic lupus erythematosus rash 20.71 13.98 9 18723 2026 110568541
Drug intolerance 20.69 13.98 23 18709 406489 110164078
Hairy cell leukaemia 20.67 13.98 5 18727 170 110570397
Lung disorder 20.56 13.98 3 18729 180044 110390523
Myalgia 20.30 13.98 83 18649 222298 110348269
Drug eruption 19.96 13.98 34 18698 53625 110516942
Respiratory gas exchange disorder 19.96 13.98 7 18725 891 110569676
Prostatic haemorrhage 19.91 13.98 5 18727 199 110570368
Death 19.82 13.98 57 18675 698812 109871755
Pythium insidiosum infection 19.76 13.98 3 18729 6 110570561
Antiphospholipid antibodies positive 19.70 13.98 7 18725 926 110569641
Intestinal anastomosis 19.64 13.98 7 18725 934 110569633
Hepatocellular carcinoma 19.58 13.98 15 18717 9865 110560702
Pulpless tooth 19.44 13.98 3 18729 7 110570560
Ileostomy 19.31 13.98 9 18723 2383 110568184
Stomatitis 19.12 13.98 11 18721 270231 110300336
Dermatitis contact 18.91 13.98 17 18715 13936 110556631
Fungal skin infection 18.91 13.98 13 18719 7236 110563331
Lower respiratory tract infection 18.52 13.98 9 18723 243097 110327470
Nail discolouration 18.49 13.98 10 18722 3625 110566942
Swollen tongue 18.31 13.98 35 18697 60327 110510240
Tinea faciei 18.23 13.98 3 18729 12 110570555
Subcorneal pustular dermatosis 18.21 13.98 4 18728 88 110570479
Dermatitis exfoliative generalised 18.19 13.98 15 18717 10957 110559610
Anal haemorrhage 18.15 13.98 11 18721 4941 110565626
Type 2 diabetes mellitus 17.98 13.98 4 18728 177228 110393339
Pemphigus 17.84 13.98 7 18725 214563 110356004
Tongue discomfort 17.70 13.98 9 18723 2879 110567688
Skin oedema 17.64 13.98 8 18724 1991 110568576
Eustachian tube disorder 17.61 13.98 4 18728 103 110570464
Cerebral palsy 17.45 13.98 5 18727 330 110570237
Dermatitis bullous 17.41 13.98 18 18714 17511 110553056
Chemical burn 17.27 13.98 6 18726 742 110569825
Therapeutic product effect decreased 17.21 13.98 10 18722 244306 110326261
Biliary obstruction 16.99 13.98 11 18721 5547 110565020
Colectomy 16.76 13.98 10 18722 4368 110566199
Product substitution issue 16.58 13.98 20 18712 23041 110547526
Erectile dysfunction 16.56 13.98 18 18714 18538 110552029
Mobility decreased 16.32 13.98 10 18722 237412 110333155
Septal panniculitis 16.29 13.98 4 18728 145 110570422
Skin warm 16.18 13.98 13 18719 9157 110561410
Rhabdomyolysis 16.17 13.98 51 18681 120350 110450217
Drug abuse 16.10 13.98 5 18727 177406 110393161
Arthropathy 16.07 13.98 15 18717 287507 110283060
Abscess fungal 15.93 13.98 5 18727 451 110570116
Sinus bradycardia 15.62 13.98 22 18710 29461 110541106
Nail pitting 15.60 13.98 5 18727 483 110570084
Vitamin E deficiency 15.52 13.98 3 18729 34 110570533
Impaired healing 15.42 13.98 7 18725 196710 110373857
Lupus-like syndrome 15.37 13.98 26 18706 40766 110529801
Intervertebral disc protrusion 15.17 13.98 21 18711 27677 110542890
Fusarium infection 15.16 13.98 8 18724 2763 110567804
Product use in unapproved indication 14.95 13.98 128 18604 447249 110123318
Abnormal loss of weight 14.90 13.98 13 18719 10244 110560323
Fungal infection 14.85 13.98 29 18703 50777 110519790
Skin hyperpigmentation 14.65 13.98 12 18720 8684 110561883
Nail dystrophy 14.38 13.98 6 18726 1222 110569345
Intertrigo 14.33 13.98 6 18726 1232 110569335
Weight decreased 14.14 13.98 131 18601 467926 110102641

FDA Adverse Event Reporting System (Pediatric)

None

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
FDA EPC N0000175874 Allylamine Antifungal
CHEBI has role CHEBI:50183 P450 inhibitor
CHEBI has role CHEBI:59285 EC 1.14.13.132 (squalene monooxygenase) inhibitor
CHEBI has role CHEBI:64951 anti-HBV agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:83317 sterol biosynthesis inhibitor

Related Drugs by ATC class:

D01AE Other antifungals for topical use 23 drugs
2-(4-chlorphenoxy)-ethanolamorolfinebromochlorosalicylanilidebutenafinechlorphenesin carbamateciclopiroxdimazoleethyl hydroxybenzoateflucytosinehaloproginliranaftatemethylrosaniline show all 23 →
D01BA Antifungals for systemic use 1 drug
griseofulvin

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

SpeciesUseRelation
Dogs Otitis externa caused by yeast, Malassezia pachydermatis Indication

🐶 Veterinary products

ProductApplicantIngredients
Osurnia Dechra, Ltd. 3
CLARO Elanco US Inc. 3

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
Squalene monooxygenase Enzyme Ki 7.52 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 5.67 DRUG MATRIX
Squalene epoxidase Enzyme INHIBITOR CHEMBL CHEMBL
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 7.66 DRUG MATRIX
Squalene monooxygenase Enzyme IC50 4.03 CHEMBL

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
DB00857 DRUGBANK_ID
D000077291 MESH_DESCRIPTOR_UI
1549008 PUBCHEM_CID
5657 INN_ID
G7RIW8S0XP UNII
235838 RXNORM
116863 MMSL
24434 MMSL
5547 MMSL
d04012 MMSL
004051 NDDF
004052 NDDF
108925005 SNOMEDCT_US
108927002 SNOMEDCT_US
373450007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
WalgreensAthletes 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
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 0363-4502 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 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 14 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 43063-906 TABLET 250 mg ORAL ANDA 33 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-906 TABLET 250 mg ORAL ANDA 33 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
Silka Antifungal HUMAN OTC DRUG LABEL 1 50066-080 CREAM 1 g TOPICAL ANDA 14 sections
Silka Jock Itch HUMAN OTC DRUG LABEL 1 50066-208 CREAM 1 g TOPICAL ANDA 14 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1048 TABLET 250 mg ORAL ANDA 32 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 50090-1278 CREAM 1 g TOPICAL ANDA 15 sections
Terbinafine Human Prescription Drug Label 1 50090-3575 TABLET 250 mg ORAL ANDA 27 sections
Terbinafine Human Prescription Drug Label 1 50090-3654 TABLET 250 mg ORAL ANDA 27 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 50090-5810 CREAM 1 g TOPICAL ANDA 15 sections