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

Stem definition	Drug id	CAS RN
	2597	91161-71-6

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.25	g	O

ADMET properties:

Property	Value	Reference
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

Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1992	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (acidic/basic)
pKa1	7.02	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		Ki	6.63	DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	5.39	DRUG MATRIX
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	6.70	DRUG MATRIX
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.67	DRUG MATRIX
Squalene monooxygenase	Enzyme	Q14534	ERG1_HUMAN		Ki	7.52	CHEMBL
Squalene epoxidase	Enzyme		Q4JEY0_TRIRU	INHIBITOR			CHEMBL	CHEMBL
Squalene monooxygenase	Unclassified		ERG1_RAT		IC50	4.03	CHEMBL
Membrane-associated progesterone receptor component 1	Membrane receptor		PGRC1_RAT		Ki	7.66	DRUG MATRIX

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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