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	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 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
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:

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 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)

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
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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