Details of the Drug

General Information of Drug (ID: DMI6HUW)

Drug Name

Terbinafine

Synonyms

Bramazil; Lamasil; TerbiFoam; Terbina; Lamisil AT; Lamisil Tablet; Ternbinafine HCl; Lamasil (TN); Lamisil (TN); SF 86-327; Terbisil (TN); Zabel (TN); SF-86-327; Terbinafine (USAN/INN); Terbinafine [USAN:BAN:INN]; Lamisil, Terbinex, Corbinal, Zabel, Terbinafine; Terbinafine, SF-86-327, Lamisil, TBNF; (2E)-N,6,6-trimethyl-N-(1-naphthylmethyl)-2-hepten-4-yn-1-amine; (2E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine; (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine; (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine; (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine; (E)-N-(6,6-dimethyl-2-heptenynyl)-N-methyl-1-naphthalenementhamin hydrochloride

Indication

Disease Entry	ICD 11	Status	REF
Fungal infection	1F29-1F2F	Approved	[1]
Tinea corporis	1F28.Y	Approved	[2]
Tinea cruris	1F28.3	Approved	[2]
Tinea versicolor	1F2D.0	Approved	[2]
Onychomycosis	EE12.1	Phase 2	[3]
Tinea pedis	1F28.2	Investigative	[2]
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Therapeutic Class

Antifungal Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

291.4

Logarithm of the Partition Coefficient (xlogp)

5.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 4.56 mgh/L [4]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1 mg/L [4]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2 h [4]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [5]
Clearance: The clearance of drug is 76 L/h [6]
Elimination: Terbinafine is approximately 80% eliminated in urine, while the remainder is eliminated in feces [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 36 hours [4]
Metabolism: The drug is metabolized via the CYP2C9, 2B6, 2C8, 1A2, 3A4, and 2C19 [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 92.64339 micromolar/kg/day [8]
Vd: The volume of distribution (Vd) of drug is 947.5 L or 16.6 L/kg [6]

Chemical Identifiers

Formula: C21H25N
IUPAC Name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
Canonical SMILES: CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21
InChI: InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+
InChIKey: DOMXUEMWDBAQBQ-WEVVVXLNSA-N

Cross-matching ID

PubChem CID: 1549008
ChEBI ID: CHEBI:9448
CAS Number: 91161-71-6
DrugBank ID: DB00857
TTD ID: D01AYJ
INTEDE ID: DR1557
ACDINA ID: D00663

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Candida Squalene epoxidase (Candi ERG1)	TTM9XSU	ERG1_CANAL	Modulator	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[10]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[11]
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[11]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[10]
Prostaglandin G/H synthase 1 (COX-1)	DE073H6	PGH1_HUMAN	Substrate	[10]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[12]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[13]
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[13]
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Gene/Protein Processing	[14]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[15]
Focal adhesion kinase 1 (PTK2)	OT3Q1JDY	FAK1_HUMAN	Post-Translational Modifications	[12]
HLA class I histocompatibility antigen, A alpha chain (HLA-A)	OTAH14LU	HLAA_HUMAN	Drug Response	[16]
Interleukin-4 (IL4)	OTOXBWAU	IL4_HUMAN	Gene/Protein Processing	[17]
Interleukin-5 (IL5)	OTAFPSCO	IL5_HUMAN	Gene/Protein Processing	[17]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[18]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Terbinafine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Ketoconazole	DMPZI3Q	Moderate	Decreased metabolism of Terbinafine caused by Ketoconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[19]
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Coadministration of a Drug Treating the Disease Different from Terbinafine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[20]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Terbinafine caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[21]
Oliceridine	DM6MDCF	Major	Decreased metabolism of Terbinafine caused by Oliceridine mediated inhibition of CYP450 enzyme.	Acute pain [MG31]	[22]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[23]
Desipramine	DMT2FDC	Moderate	Decreased metabolism of Terbinafine caused by Desipramine mediated inhibition of CYP450 enzyme.	Attention deficit hyperactivity disorder [6A05]	[24]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Terbinafine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[25]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Terbinafine caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[26]
Dihydrocodeine	DMB0FWL	Moderate	Decreased metabolism of Terbinafine caused by Dihydrocodeine mediated inhibition of CYP450 enzyme.	Chronic pain [MG30]	[24]
Sertraline	DM0FB1J	Moderate	Decreased metabolism of Terbinafine caused by Sertraline mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[24]
Vortioxetine	DM6F1PU	Major	Decreased metabolism of Terbinafine caused by Vortioxetine mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[27]
Clomipramine	DMINRKW	Moderate	Decreased metabolism of Terbinafine caused by Clomipramine mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[24]
Doxepin	DMPI98T	Moderate	Decreased metabolism of Terbinafine caused by Doxepin mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[24]
Ingrezza	DMVPLNC	Major	Decreased metabolism of Terbinafine caused by Ingrezza mediated inhibition of CYP450 enzyme.	Dystonic disorder [8A02]	[28]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Cannabidiol.	Epileptic encephalopathy [8A62]	[21]
Tolterodine	DMSHPW8	Minor	Decreased metabolism of Terbinafine caused by Tolterodine mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[29]
Carvedilol	DMHTEAO	Moderate	Decreased metabolism of Terbinafine caused by Carvedilol mediated inhibition of CYP450 enzyme.	Heart failure [BD10-BD1Z]	[24]
Rifampin	DMA8J1G	Minor	Increased metabolism of Terbinafine caused by Rifampin mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[30]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[31]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Terbinafine and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[32]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Terbinafine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[19]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Terbinafine and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[33]
Nebivolol	DM7F1PA	Moderate	Decreased metabolism of Terbinafine caused by Nebivolol mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[24]
Pindolol	DMD2NV7	Moderate	Decreased metabolism of Terbinafine caused by Pindolol mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[24]
Pirfenidone	DM6VZFQ	Moderate	Decreased metabolism of Terbinafine caused by Pirfenidone mediated inhibition of CYP450 enzyme.	Idiopathic interstitial pneumonitis [CB03]	[21]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Terbinafine caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[20]
Primaquine	DMWQ16I	Moderate	Decreased metabolism of Terbinafine caused by Primaquine mediated inhibition of CYP450 enzyme.	Malaria [1F40-1F45]	[24]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[34]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Idelalisib.	Mature B-cell leukaemia [2A82]	[35]
Promethazine	DM6I5GR	Moderate	Decreased metabolism of Terbinafine caused by Promethazine mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[24]
Ondansetron	DMOTQ1I	Moderate	Decreased metabolism of Terbinafine caused by Ondansetron mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[24]
Dexfenfluramine	DMJ7YDS	Moderate	Decreased metabolism of Terbinafine caused by Dexfenfluramine mediated inhibition of CYP450 enzyme.	Obesity [5B80-5B81]	[24]
Methamphetamine	DMPM4SK	Moderate	Decreased metabolism of Terbinafine caused by Methamphetamine mediated inhibition of CYP450 enzyme.	Pain [MG30-MG3Z]	[24]
Hydrocodone	DMQ2JO5	Moderate	Decreased metabolism of Terbinafine caused by Hydrocodone mediated inhibition of CYP450 enzyme.	Pain [MG30-MG3Z]	[24]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Terbinafine caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[36]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Terbinafine caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[37]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Terbinafine caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[38]
Levomepromazine	DMIKFEL	Moderate	Decreased metabolism of Terbinafine caused by Levomepromazine mediated inhibition of CYP450 enzyme.	Psychotic disorder [6A20-6A25]	[24]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Terbinafine and Leflunomide.	Rheumatoid arthritis [FA20]	[19]
Oxamniquine	DM2QDX1	Moderate	Decreased metabolism of Terbinafine caused by Oxamniquine mediated inhibition of CYP450 enzyme.	Schistosomiasis [1F86]	[24]
Mesoridazine	DM2ZGAN	Moderate	Decreased metabolism of Terbinafine caused by Mesoridazine mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[24]
Aripiprazole	DM3NUMH	Moderate	Decreased metabolism of Terbinafine caused by Aripiprazole mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[39]
Pimozide	DMW83TP	Major	Decreased metabolism of Terbinafine caused by Pimozide mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[19]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Terbinafine caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[20]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Terbinafine and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[21]
LEE011	DMMX75K	Moderate	Decreased metabolism of Terbinafine caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[40]
Pitolisant	DM8RFNJ	Major	Decreased metabolism of Terbinafine caused by Pitolisant mediated inhibition of CYP450 enzyme.	Somnolence [MG42]	[21]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Terbinafine caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[41]
Methdilazine	DMAUHQX	Moderate	Decreased metabolism of Terbinafine caused by Methdilazine mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[24]
Trimeprazine	DMEMV9D	Moderate	Decreased metabolism of Terbinafine caused by Trimeprazine mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[24]
Propafenone	DMPIBJK	Moderate	Decreased metabolism of Terbinafine caused by Propafenone mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[24]
Flecainide	DMSQDLE	Moderate	Decreased metabolism of Terbinafine caused by Flecainide mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[24]
Amiodarone	DMUTEX3	Moderate	Decreased metabolism of Terbinafine caused by Amiodarone mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[19]
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⏷ Show the Full List of 52 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
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⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Terbinafine Hydrochloride eq 250mg base tablet	eq 250mg base	Tablet	Oral
Terbinafine 250 mg tablet	250 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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4	FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets
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