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

Stem definition	Drug id	CAS RN
squalene monooxygenase inhibitors, antifungals	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:

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Property	Value	Reference
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
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1992	FDA

FDA Adverse Event Reporting System (Female)

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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	355.45	14.60	124	12199	13604	63463095
Acute generalised exanthematous pustulosis	252.13	14.60	91	12232	11008	63465691
Subacute cutaneous lupus erythematosus	179.59	14.60	50	12273	2593	63474106
Dysgeusia	151.88	14.60	101	12222	46609	63430090
Rash pustular	105.34	14.60	43	12280	7239	63469460
Gamma-glutamyltransferase increased	99.65	14.60	69	12254	33962	63442737
Cutaneous lupus erythematosus	91.85	14.60	30	12293	2682	63474017
Aspartate aminotransferase increased	90.23	14.60	99	12224	90178	63386521
Pruritus	90.09	14.60	209	12114	361244	63115455
Toxic skin eruption	84.74	14.60	44	12279	12841	63463858

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FDA Adverse Event Reporting System (Male)

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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	200.65	13.74	87	12166	9395	34935283
Aspartate aminotransferase increased	116.88	13.74	131	12122	67652	34877026
Gamma-glutamyltransferase increased	107.44	13.74	86	12167	29145	34915533
Drug resistance	98.96	13.74	78	12175	25849	34918829
Ageusia	95.76	13.74	54	12199	10254	34934424
Alanine aminotransferase increased	92.27	13.74	127	12126	80688	34863990
Chromaturia	78.73	13.74	54	12199	14466	34930212
Jaundice	77.22	13.74	74	12179	31808	34912870
Blood alkaline phosphatase increased	74.83	13.74	72	12181	31103	34913575
Blood creatine phosphokinase increased	72.67	13.74	84	12169	44773	34899905

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FDA Adverse Event Reporting System (Geriatric)

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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	310.33	12.56	129	21175	16503	79706581
Pathogen resistance	276.91	12.56	114	21190	14228	79708856
Acute generalised exanthematous pustulosis	269.54	12.56	118	21186	17136	79705948
Aspartate aminotransferase increased	163.20	12.56	193	21111	138448	79584636
Subacute cutaneous lupus erythematosus	161.09	12.56	53	21251	3508	79719576
Chromaturia	156.25	12.56	93	21211	25653	79697431
Gamma-glutamyltransferase increased	156.09	12.56	124	21180	54556	79668528
Rash pustular	143.74	12.56	67	21237	11244	79711840
Alanine aminotransferase increased	135.83	12.56	191	21113	162379	79560705
Drug resistance	134.09	12.56	102	21202	42111	79680973

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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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
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:59285	squalene monooxygenase inhibitors
CHEBI has role	CHEBI:83317	sterol biosynthesis inhibitors
FDA CS	M0000751	Allylamine
FDA EPC	N0000175874	Allylamine Antifungal
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000935	Antifungal Agents
MeSH PA	D004791	Enzyme Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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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

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🐶 Veterinary Drug Use

Species	Use	Relation
Dogs	Otitis externa caused by yeast, Malassezia pachydermatis	Indication

🐶 Veterinary products

Product	Applicant	Ingredients
CLARO	Elanco US Inc.	3
Osurnia	Dechra, Ltd.	3

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:

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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
Squalene monooxygenase	Enzyme	Q14534	ERG1_HUMAN		Ki	7.52	CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.67	DRUG MATRIX
Squalene epoxidase	Enzyme		Q4JEY0_TRIRU	INHIBITOR			CHEMBL	CHEMBL
Membrane-associated progesterone receptor component 1	Membrane receptor		PGRC1_RAT		Ki	7.66	DRUG MATRIX
Squalene monooxygenase	Enzyme		ERG1_RAT		IC50	4.03	CHEMBL

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External reference:

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ID	Source
004051	NDDF
004052	NDDF
108925005	SNOMEDCT_US
108927002	SNOMEDCT_US
116863	MMSL
1549008	PUBCHEM_CID
235838	RXNORM
24434	MMSL
373450007	SNOMEDCT_US
4020792	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Antifungal	HUMAN OTC DRUG LABEL	1	41250-080	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
Athletes Foot	HUMAN OTC DRUG LABEL	1	11673-080	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	14 sections
Athletes Foot	HUMAN OTC DRUG LABEL	1	11822-0080	CREAM	1 g	TOPICAL	ANDA	14 sections
Athletes Foot	HUMAN OTC DRUG LABEL	1	21130-080	CREAM	1 g	TOPICAL	ANDA	14 sections
Athletes Foot	HUMAN OTC DRUG LABEL	1	21130-080	CREAM	1 g	TOPICAL	ANDA	14 sections
Athletes Foot	HUMAN OTC DRUG LABEL	1	36800-080	CREAM	1 g	TOPICAL	ANDA	14 sections

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