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 662.30 42.11 122 1628 1876 2354459
Pruritus 410.63 42.11 156 1594 43184 2313151
Rash 389.44 42.11 164 1586 59394 2296941
Dysgeusia 378.68 42.11 100 1650 8359 2347976
Aspartate aminotransferase increased 343.56 42.11 101 1649 12511 2343824
Alanine aminotransferase increased 328.61 42.11 100 1650 13932 2342403
Gamma-glutamyltransferase increased 273.68 42.11 71 1679 5491 2350844
Blood alkaline phosphatase increased 271.66 42.11 73 1677 6472 2349863
Acute generalised exanthematous pustulosis 258.21 42.11 54 1696 1604 2354731
Erythema 223.91 42.11 87 1663 25072 2331263
Weight decreased 217.23 42.11 88 1662 28283 2328052
Rash pustular 215.08 42.11 46 1704 1521 2354814
Urticaria 195.04 42.11 78 1672 24183 2332152
Cutaneous lupus erythematosus 192.89 42.11 36 1714 581 2355754
Malaise 177.63 42.11 94 1656 55491 2300844
Decreased appetite 175.26 42.11 76 1674 28815 2327520
Chromaturia 168.98 42.11 42 1708 2711 2353624
Erythema multiforme 168.34 42.11 40 1710 2135 2354200
Toxic skin eruption 166.81 42.11 40 1710 2220 2354115
Pyrexia 163.54 42.11 88 1662 53620 2302715
Jaundice 157.65 42.11 46 1704 5462 2350873
Skin exfoliation 151.02 42.11 45 1705 5745 2350590
Blood lactate dehydrogenase increased 149.62 42.11 40 1710 3444 2352891
Rash erythematous 145.30 42.11 44 1706 5932 2350403
Hepatitis 142.75 42.11 44 1706 6293 2350042
Liver disorder 142.23 42.11 44 1706 6370 2349965
Blood bilirubin increased 141.37 42.11 42 1708 5303 2351032
Hepatic function abnormal 135.95 42.11 42 1708 6050 2350285
Blister 123.37 42.11 40 1710 6731 2349604
Subacute cutaneous lupus erythematosus 122.19 42.11 23 1727 388 2355947
Drug interaction 114.96 42.11 57 1693 29106 2327229
White blood cell count decreased 113.71 42.11 49 1701 18159 2338176
Myalgia 111.31 42.11 52 1698 23281 2333054
Nausea 108.61 42.11 90 1660 112099 2244236
Liver function test abnormal 107.59 42.11 37 1713 7453 2348882
Somatic delusion 102.41 42.11 16 1734 80 2356255
Anosmia 99.39 42.11 22 1728 850 2355485
C-reactive protein increased 98.05 42.11 33 1717 6222 2350113
Red blood cell count decreased 93.36 42.11 29 1721 4237 2352098
Lip swelling 89.87 42.11 29 1721 4792 2351543
Rash maculo-papular 89.26 42.11 28 1722 4224 2352111
Photosensitivity reaction 86.11 42.11 24 1726 2403 2353932
Oral discomfort 85.51 42.11 21 1729 1282 2355053
Headache 85.05 42.11 68 1682 80111 2276224
Cholestasis 84.39 42.11 26 1724 3695 2352640
Alopecia 77.76 42.11 40 1710 21961 2334374
Depression 76.61 42.11 43 1707 28089 2328246
Swollen tongue 75.14 42.11 26 1724 5317 2351018
Gastrointestinal motility disorder 74.62 42.11 16 1734 531 2355804
Abnormal faeces 73.01 42.11 16 1734 589 2355746
Eosinophilia 72.64 42.11 22 1728 2948 2353387
Blood creatine phosphokinase increased 72.25 42.11 25 1725 5111 2351224
Musculoskeletal discomfort 70.64 42.11 20 1730 2118 2354217
Bilirubin conjugated increased 70.33 42.11 15 1735 485 2355850
Urine odour abnormal 70.11 42.11 16 1734 710 2355625
Rash pruritic 69.98 42.11 27 1723 7508 2348827
Exposure during pregnancy 64.45 42.11 37 1713 25182 2331153
Antinuclear antibody positive 63.76 42.11 16 1734 1066 2355269
Hepatitis cholestatic 62.69 42.11 16 1734 1141 2355194
Dizziness 60.42 42.11 49 1701 58616 2297719
Fatigue 59.61 42.11 57 1693 84816 2271519
Dyspnoea 59.34 42.11 55 1695 78678 2277657
Drug eruption 58.24 42.11 19 1731 3240 2353095
Skin lesion 58.18 42.11 20 1730 4005 2352330
Dry mouth 57.33 42.11 24 1726 8229 2348106
Systemic lupus erythematosus 57.25 42.11 20 1730 4201 2352134
Dermatitis exfoliative 56.77 42.11 15 1735 1226 2355109
Pustular psoriasis 56.73 42.11 14 1736 870 2355465
Hypersensitivity 55.98 42.11 33 1717 23560 2332775
Abdominal pain upper 55.31 42.11 32 1718 22068 2334267
Arthralgia 55.14 42.11 45 1705 54240 2302095
Neutropenia 53.39 42.11 31 1719 21517 2334818
Hypoacusis 53.34 42.11 18 1732 3407 2352928
Insomnia 53.27 42.11 33 1717 25754 2330581
Stevens-Johnson syndrome 53.26 42.11 19 1731 4240 2352095
Ear infection 53.26 42.11 18 1732 3423 2352912
Rash macular 52.80 42.11 18 1732 3513 2352822
Pain 52.02 42.11 46 1704 61811 2294524
Hepatic enzyme increased 50.19 42.11 23 1727 9779 2346556
Drug hypersensitivity 50.17 42.11 40 1710 46603 2309732
Rash papular 49.62 42.11 16 1734 2628 2353707
Abortion induced 49.37 42.11 17 1733 3419 2352916
Thrombocytopenia 48.65 42.11 28 1722 19103 2337232
Rhabdomyolysis 48.25 42.11 20 1730 6684 2349651
Oedema peripheral 48.03 42.11 30 1720 23733 2332602
Asthenia 47.83 42.11 39 1711 46887 2309448
Haemoglobin decreased 47.31 42.11 27 1723 18124 2338211
Pain in extremity 46.84 42.11 37 1713 42503 2313832
Inflammation 46.28 42.11 19 1731 6194 2350141
Dermatitis bullous 44.87 42.11 13 1737 1491 2354844
Exfoliative rash 43.95 42.11 10 1740 437 2355898
Aphasia 43.39 42.11 17 1733 4911 2351424
Face oedema 43.34 42.11 16 1734 3932 2352403
Erythema nodosum 43.02 42.11 11 1739 789 2355546
Cheilitis 42.25 42.11 11 1739 848 2355487

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
Aspartate aminotransferase increased 409.82 37.31 125 1627 10631 1734398
Alanine aminotransferase increased 385.20 37.31 123 1629 12155 1732874
Gamma-glutamyltransferase increased 289.56 37.31 81 1671 5017 1740012
Blood creatine phosphokinase increased 249.48 37.31 82 1670 8774 1736255
Rash 227.39 37.31 116 1636 38577 1706452
Ageusia 223.25 37.31 52 1700 1522 1743507
Jaundice 215.23 37.31 67 1685 5995 1739034
Blood alkaline phosphatase increased 212.39 37.31 64 1688 5131 1739898
Chromaturia 196.33 37.31 52 1700 2598 1742431
Pruritus 194.64 37.31 89 1663 23133 1721896
Blood bilirubin increased 176.56 37.31 58 1694 6152 1738877
Pyrexia 167.29 37.31 101 1651 46299 1698730
Liver function test abnormal 160.80 37.31 53 1699 5673 1739356
Liver disorder 149.57 37.31 50 1702 5586 1739443
Blood lactate dehydrogenase increased 140.26 37.31 43 1709 3632 1741397
Malaise 139.94 37.31 77 1675 29488 1715541
Rhabdomyolysis 130.02 37.31 54 1698 11036 1733993
Decreased appetite 129.15 37.31 68 1684 23803 1721226
Acute generalised exanthematous pustulosis 127.39 37.31 31 1721 1091 1743938
Rash erythematous 124.60 37.31 40 1712 3925 1741104
Skin exfoliation 123.31 37.31 41 1711 4494 1740535
Myalgia 118.27 37.31 56 1696 15602 1729427
Hepatic function abnormal 116.27 37.31 44 1708 7030 1737999
Cholestasis 111.15 37.31 36 1716 3629 1741400
Rash pustular 110.71 37.31 28 1724 1156 1743873
Asthenia 105.54 37.31 68 1684 34602 1710427
Drug interaction 103.15 37.31 62 1690 27896 1717133
Dysgeusia 99.85 37.31 36 1716 5013 1740016
Nausea 98.96 37.31 76 1676 51120 1693909
Erythema 98.73 37.31 48 1704 14140 1730889
C-reactive protein increased 83.78 37.31 33 1719 5852 1739177
Hepatitis 81.99 37.31 31 1721 4924 1740105
Blister 80.21 37.31 29 1723 4063 1740966
Hepatic enzyme increased 76.63 37.31 32 1720 6589 1738440
Arthralgia 76.16 37.31 48 1704 23396 1721633
Oedema peripheral 74.61 37.31 41 1711 15509 1729520
Erythema multiforme 73.24 37.31 22 1730 1724 1743305
Urticaria 69.16 37.31 36 1716 12205 1732824
Fatigue 67.89 37.31 61 1691 50720 1694309
Abdominal pain 64.78 37.31 42 1710 21448 1723581
Onychomycosis 63.87 37.31 14 1738 306 1744723
Drug reaction with eosinophilia and systemic symptoms 63.71 37.31 26 1726 5044 1739985
Dermatitis exfoliative 62.58 37.31 19 1733 1542 1743487
Scedosporium infection 62.53 37.31 12 1740 131 1744898
Headache 61.73 37.31 49 1703 34327 1710702
Drug ineffective 59.66 37.31 63 1689 63738 1681291
Cutaneous lupus erythematosus 59.64 37.31 12 1740 170 1744859
Epstein-Barr virus antibody positive 58.75 37.31 11 1741 104 1744925
Hepatitis cholestatic 56.92 37.31 17 1735 1304 1743725
Antinuclear antibody positive 55.62 37.31 13 1739 382 1744647
Weight decreased 48.59 37.31 36 1716 22717 1722312
Drug eruption 47.25 37.31 18 1734 2908 1742121
Red blood cell count decreased 46.62 37.31 19 1733 3667 1741362
Platelet count decreased 46.58 37.31 31 1721 16492 1728537
Urinary retention 45.86 37.31 21 1731 5374 1739655
Pain in extremity 45.77 37.31 32 1720 18440 1726589
Vasculitis 45.77 37.31 15 1737 1560 1743469
Haemoglobin decreased 45.59 37.31 31 1721 17083 1727946
White blood cell count increased 45.57 37.31 23 1729 7289 1737740
Lymphadenopathy 44.60 37.31 19 1733 4095 1740934
Condition aggravated 44.11 37.31 33 1719 21117 1723912
Symmetrical drug-related intertriginous and flexural exanthema 42.54 37.31 7 1745 28 1745001
Abdominal pain upper 41.93 37.31 25 1727 10976 1734053
Depression 41.57 37.31 29 1723 16640 1728389
Product dispensing error 41.00 37.31 14 1738 1652 1743377
Haematocrit decreased 40.66 37.31 18 1734 4255 1740774
Erythrodermic psoriasis 40.44 37.31 9 1743 211 1744818
Joint swelling 39.63 37.31 20 1732 6333 1738696
Toxic skin eruption 39.32 37.31 14 1738 1869 1743160
Hypoacusis 38.92 37.31 15 1737 2498 1742531
Stevens-Johnson syndrome 38.03 37.31 16 1736 3341 1741688
Thrombocytopenia 37.41 37.31 30 1722 21219 1723810

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 Chemical/Ingredient N0000007522 Allylamine
FDA EPC N0000175874 Allylamine Antifungal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D004791 Enzyme Inhibitors

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
D000077291 MESH_DESCRIPTOR_UI
4023600 VUID
N0000021605 NUI
C0076110 UMLSCUI
D02219 KEGG_DRUG
012C11ZU6G UNII
78628-80-5 SECONDARY_CAS_RN
108925005 SNOMEDCT_US
4023600 VANDF
d04012 MMSL
37801 RXNORM
373450007 SNOMEDCT_US
004051 NDDF
CHEBI:9448 CHEBI
CHEMBL822 ChEMBL_ID
DB00857 DRUGBANK_ID
CHEMBL1200832 ChEMBL_ID
5657 INN_ID
1549008 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
LAMISIL HUMAN OTC DRUG LABEL 1 0067-6296 AEROSOL, SPRAY 0.84 g TOPICAL NDA 9 sections
LAMISIL HUMAN OTC DRUG LABEL 1 0067-6297 AEROSOL, SPRAY 0.84 g TOPICAL NDA 9 sections
Lamisil AT HUMAN OTC DRUG LABEL 1 0067-8100 CREAM 1 g TOPICAL ANDA 10 sections
Lamisil AT HUMAN OTC DRUG LABEL 1 0067-8114 CREAM 1 g TOPICAL ANDA 10 sections
KAISER PERMANENTE HUMAN OTC DRUG LABEL 1 0179-8715 CREAM 1 g TOPICAL ANDA 10 sections
Walgreens HUMAN OTC DRUG LABEL 1 0363-2080 CREAM 1 g TOPICAL ANDA 10 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 0363-2083 CREAM 1 g TOPICAL ANDA 10 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 0536-1117 CREAM 1 g TOPICAL ANDA 10 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 11673-080 CREAM 1 g TOPICAL ANDA 10 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 10 sections
terbinafine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-501 TABLET 250 mg ORAL ANDA 17 sections
Terbinafine HUMAN PRESCRIPTION DRUG LABEL 1 16714-795 TABLET 250 mg ORAL ANDA 17 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 21130-080 CREAM 1 g TOPICAL ANDA 9 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-630 TABLET 250 mg ORAL ANDA 12 sections
Good Neighbor Pharmacy HUMAN OTC DRUG LABEL 1 24385-524 CREAM 1 g TOPICAL ANDA 10 sections
Kroger HUMAN OTC DRUG LABEL 1 30142-080 CREAM 1 g TOPICAL ANDA 10 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 31722-209 TABLET 250 1 ORAL ANDA 16 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 36800-080 CREAM 1 g TOPICAL ANDA 10 sections
Shopko HUMAN OTC DRUG LABEL 1 37012-080 CREAM 1 g TOPICAL ANDA 10 sections
Terbinafine Hydrochloride HUMAN OTC DRUG LABEL 1 37205-941 CREAM 1 g TOPICAL ANDA 10 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 37808-080 CREAM 1 g TOPICAL ANDA 10 sections
athletes foot HUMAN OTC DRUG LABEL 1 41163-080 CREAM 1 g TOPICAL ANDA 10 sections
ShopRite HUMAN OTC DRUG LABEL 1 41190-083 CREAM 1 g TOPICAL ANDA 10 sections
Antifungal HUMAN OTC DRUG LABEL 1 41250-080 CREAM 1 g TOPICAL ANDA 10 sections
Antifungal Foot HUMAN OTC DRUG LABEL 1 41520-080 CREAM 1 g TOPICAL ANDA 10 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-906 TABLET 250 mg ORAL ANDA 18 sections
Terbinafine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-893 TABLET 250 mg ORAL ANDA 19 sections
equate HUMAN OTC DRUG LABEL 1 49035-080 CREAM 1 g TOPICAL ANDA 10 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 49348-790 CREAM 1 g TOPICAL ANDA 9 sections