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{{drugbox
{{DrugProjectFormSinglePage
| IUPAC_name = N,6,6-trimethyl-N-(naphthalen-1-ylmethyl) hept-2-en-4-yn-1-amine
|authorTag={{Ammu}}
|genericName=Terbinafine
|aOrAn=an
|drugClass=[[antifungal]]
|indicationType=treatment
|indication=[[itching]], [[burning]], cracking and scaling in [[athlete's foot]] and [[jock itch]]
|adverseReactions=[[diarrhea]], [[dyspepsia]], [[rash]], [[pruritis]], and [[urticaria]]
|blackBoxWarningTitle=<b><span style="color:#FF0000;">TITLE</span></b>
|blackBoxWarningBody=<i><span style="color:#FF0000;">Condition Name:</span></i> (Content)
|fdaLIADAdult=* Cures most [[athlete's foot]] ([[tinea pedis]])
* Cures most jock itch (tinea cruris) and ringworm (tinea corporis)
* Relieves itching, burning, cracking and scaling which accompany these conditions
|offLabelAdultGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of Terbinafine in adult patients.
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of Terbinafine in adult patients.
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of Terbinafine in pediatric patients.
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of Terbinafine in pediatric patients.
|warnings=* For external use only
* Do not use on nails or scalp in or near the mouth or the [[eyes]] for vaginal [[yeast]] infections
* When using this product do not get into the eyes. If eye contact occurs, rinse thoroughly with water.
* Stop use and ask a doctor if too much irritation occurs or gets worse.
* Side effects occur.
* Keep out of reach of children. If swallowed, get medical help or contact a poison control center right away.
 
|administration======Adults and Children 12 years and Older=====
* Use the tip of the cap to break the seal and open the tube
* wash the affected skin with soap and water and dry completely before applying for athlete's foot wear well-fitting, ventilated shoes.
* Change shoes and socks at least once daily.
:* between the toes only: apply twice a day (morning and night) for 1 week or as directed by a doctor.
:* on the bottom or sides of the foot: apply twice a day (morning and night) for 2 weeks or as directed by a doctor.
* For jock itch and ringworm: apply once a day (morning or night) for 1 week or as directed by a doctor.
* Wash hands after each use
|drugBox={{Drugbox2
| Verifiedfields = changed
| verifiedrevid = 457127366
| IUPAC_name = [(2''E'')-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
| image = Terbinafine.png
| image = Terbinafine.png
<!--Clinical data-->
| tradename = Lamisil
| Drugs.com = {{drugs.com|monograph|terbinafine-hydrochloride}}
| MedlinePlus = a699061
| pregnancy_category = B
| legal_status =  Low-strength preparations available without prescription
| routes_of_administration = Oral, [[topical]]
<!--Pharmacokinetic data-->
| bioavailability = Readily absorbed: 70–90%
| protein_bound = >99%
| metabolism = [[Hepatic]]
| elimination_half-life = Highly variable
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 91161-71-6
| CAS_number = 91161-71-6
| CAS_supplemental = 78628-80-5
| ATC_prefix = D01
| ATC_prefix = D01
| ATC_suffix = AE15
| ATC_suffix = AE15
| ATC_supplemental = {{ATC|D01|BA02}}
| ATC_supplemental =   {{ATC|D01|BA02}}
| PubChem = 5402
| PubChem = 1549008
| DrugBank = APRD00508
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00857
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1266005
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G7RIW8S0XP
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02375
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 822
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 9448
 
<!--Chemical data-->
| C=21 | H=25 | N=1
| C=21 | H=25 | N=1
| molecular_weight = 291.43 g/mol
| molecular_weight = 291.43 g/mol
| bioavailability = Readily absorbed
| smiles = C(#C\C=C\CN(C)Cc2cccc1ccccc12)C(C)(C)C
| protein_bound = >99%
| InChI = 1/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+
| metabolism = [[Hepatic]]
| InChIKey = DOMXUEMWDBAQBQ-WEVVVXLNBZ
| elimination_half-life = 36 hours
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_category = B
| StdInChI = 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+
| legal_status =  
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| routes_of_administration = Oral [[topical]]
| StdInChIKey = DOMXUEMWDBAQBQ-WEVVVXLNSA-N
}}
}}
{{SI}}
|storage=* Store at controlled room temperature 20°-25°C (68°-77°F)
|packLabel=[[File:Terbinafine01.jpg|thumb|none|400px|This image is provided by the National Library of Medicine.]]
|alcohol=Alcohol-Terbinafine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
|brandNames=*ANTIFUNGAL ®<ref>{{Cite web | title =ANTIFUNGAL- terbinafine hydrochloride cream  | url =http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9daf3136-74b6-4410-8256-cbc9dd700f61 }}</ref>


<!--Look-Alike Drug Names-->
}}


'''Terbinafine hydrochloride''' ('''Lamisil''' in UK, US, France, Canada, Romania and Hungary, also sold under the name '''Terbisil''') is a synthetic [[allylamine]] [[antifungal]]. It is highly [[lipophilic]] in nature and tends to accumulate in skin, [[Nail (anatomy)|nails]], and fatty tissues.  As a generic it is sold under the name '''Zabel''' in Australia. It is now also available as a generic in the U.S.
==Pharmacology==
Terbinafine [[hydrochloride]] is a white fine crystalline powder that is freely soluble in [[methanol]] and [[methylene chloride]], soluble in [[ethanol]], and slightly soluble in water. 
Like other allylamines, terbinafine inhibits [[ergosterol]] synthesis by inhibiting [[squalene epoxidase]], an enzyme that is part of the fungal [[cell wall]] synthesis pathway.
==Indications==
Terbinafine is mainly effective on the [[dermatophytes]] group of fungi.
As a 1% cream or powder it is used for superficial skin infections such as [[jock itch]] (''Tinea cruris''), [[athlete's foot]] (''Tinea pedis'') and other types of [[ringworm]]. 
Oral 250mg tablets are often prescribed for the treatment of [[onychomycosis]] of the [[toenail]] or fingernail due to the dermatophyte [[Tinea unguium]]. Fungal nail infections are located deep under the nail in the [[cuticle]] to which topically applied treatments are unable to penetrate in sufficient amounts. The tablets may, rarely, cause [[hepatotoxicity]], so patients are warned of this and may be monitored with [[liver function tests]]. Alcohol consumption should also be avoided while taking terbinafine.
===Specific US issues===
Many health insurance companies consider these infections to be a cosmetic problem, and either do not cover the cost of the months-long course of Lamisil, which can run into the thousands of dollars, or recommend use of less expensive alternatives like [[fluconazole]].
'''FDA approval'''
The FDA has approved the first generic versions of prescription Lamisil (terbinafine hydrochloride) tablets.  The remaining patent or exclusivity for Lamisil expired on [[June 30]], [[2007]].
On [[September 28]], [[2007]], the [[U.S.]] [[Food and Drug Administration]] stated that Lamisil (terbinafine hydrochloride, by [[Novartis AG]]) is a new [[treatment]] approved for use by [[children]] aged 4 up. The [[antifungal]] [[granules]] that can be sprinkled on a child's food to treat [[ringworm]] of the scalp, [[Tinea capitis]]. <ref>[http://www.reuters.com/article/governmentFilingsNews/idUSN2820532120070928  Reuters, US FDA approves oral granules for scalp ringworm]</ref>
==References==
<div class="references-small">
{{reflist|2}}
</div>
{{Antifungals}}


[[Category:Antifungals]]
[[Category:Antifungals]]
[[Category:Novartis]]
[[Category:Drugs]]
 
[[es:Terbinafina]]
[[ja:塩酸テルビナフィン]]
[[nl:Terbinafine]]
[[pt:Terbinafina]]
[[he:טרבינאפין]]
 
{{WH}}
{{WikiDoc Sources}}
{{jb1}}

Latest revision as of 11:04, 25 May 2015

Terbinafine (topical)
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Ammu Susheela, M.D. [2]

Disclaimer

WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.

Overview

Terbinafine (topical) is an antifungal that is FDA approved for the treatment of itching, burning, cracking and scaling in athlete's foot and jock itch. Common adverse reactions include diarrhea, dyspepsia, rash, pruritis, and urticaria.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

  • Cures most athlete's foot (tinea pedis)
  • Cures most jock itch (tinea cruris) and ringworm (tinea corporis)
  • Relieves itching, burning, cracking and scaling which accompany these conditions

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Terbinafine in adult patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Terbinafine in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

There is limited information regarding Terbinafine (topical) FDA-Labeled Indications and Dosage (Pediatric) in the drug label.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Terbinafine in pediatric patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Terbinafine in pediatric patients.

Contraindications

There is limited information regarding Terbinafine (topical) Contraindications in the drug label.

Warnings

  • For external use only
  • Do not use on nails or scalp in or near the mouth or the eyes for vaginal yeast infections
  • When using this product do not get into the eyes. If eye contact occurs, rinse thoroughly with water.
  • Stop use and ask a doctor if too much irritation occurs or gets worse.
  • Side effects occur.
  • Keep out of reach of children. If swallowed, get medical help or contact a poison control center right away.

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Terbinafine (topical) Clinical Trials Experience in the drug label.

Postmarketing Experience

There is limited information regarding Terbinafine (topical) Postmarketing Experience in the drug label.

Drug Interactions

There is limited information regarding Terbinafine (topical) Drug Interactions in the drug label.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA): There is no FDA guidance on usage of Terbinafine (topical) in women who are pregnant.
Pregnancy Category (AUS): There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Terbinafine (topical) in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Terbinafine (topical) during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Terbinafine (topical) in women who are nursing.

Pediatric Use

There is no FDA guidance on the use of Terbinafine (topical) in pediatric settings.

Geriatic Use

There is no FDA guidance on the use of Terbinafine (topical) in geriatric settings.

Gender

There is no FDA guidance on the use of Terbinafine (topical) with respect to specific gender populations.

Race

There is no FDA guidance on the use of Terbinafine (topical) with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Terbinafine (topical) in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Terbinafine (topical) in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Terbinafine (topical) in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Terbinafine (topical) in patients who are immunocompromised.

Administration and Monitoring

Administration

Adults and Children 12 years and Older
  • Use the tip of the cap to break the seal and open the tube
  • wash the affected skin with soap and water and dry completely before applying for athlete's foot wear well-fitting, ventilated shoes.
  • Change shoes and socks at least once daily.
  • between the toes only: apply twice a day (morning and night) for 1 week or as directed by a doctor.
  • on the bottom or sides of the foot: apply twice a day (morning and night) for 2 weeks or as directed by a doctor.
  • For jock itch and ringworm: apply once a day (morning or night) for 1 week or as directed by a doctor.
  • Wash hands after each use

Monitoring

There is limited information regarding Terbinafine (topical) Monitoring in the drug label.

IV Compatibility

There is limited information regarding the compatibility of Terbinafine (topical) and IV administrations.

Overdosage

There is limited information regarding Terbinafine (topical) overdosage. If you suspect drug poisoning or overdose, please contact the National Poison Help hotline (1-800-222-1222) immediately.

Pharmacology

Template:Px
Terbinafine (topical)
Systematic (IUPAC) name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Identifiers
CAS number 91161-71-6
78628-80-5
ATC code D01AE15 D01BA02 (WHO)
PubChem 1549008
DrugBank DB00857
Chemical data
Formula Template:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox 
Mol. mass 291.43 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability Readily absorbed: 70–90%
Protein binding >99%
Metabolism Hepatic
Half life Highly variable
Excretion ?
Therapeutic considerations
Pregnancy cat.

B

Legal status

Low-strength preparations available without prescription

Routes Oral, topical

Mechanism of Action

There is limited information regarding Terbinafine (topical) Mechanism of Action in the drug label.

Structure

There is limited information regarding Terbinafine (topical) Structure in the drug label.

Pharmacodynamics

There is limited information regarding Terbinafine (topical) Pharmacodynamics in the drug label.

Pharmacokinetics

There is limited information regarding Terbinafine (topical) Pharmacokinetics in the drug label.

Nonclinical Toxicology

There is limited information regarding Terbinafine (topical) Nonclinical Toxicology in the drug label.

Clinical Studies

There is limited information regarding Terbinafine (topical) Clinical Studies in the drug label.

How Supplied

There is limited information regarding Terbinafine (topical) How Supplied in the drug label.

Storage

  • Store at controlled room temperature 20°-25°C (68°-77°F)

Images

Drug Images

{{#ask: Page Name::Terbinafine (topical) |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

This image is provided by the National Library of Medicine.

{{#ask: Label Page::Terbinafine (topical) |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Terbinafine (topical) Patient Counseling Information in the drug label.

Precautions with Alcohol

Alcohol-Terbinafine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

  • ANTIFUNGAL ®[1]

Look-Alike Drug Names

There is limited information regarding Terbinafine (topical) Look-Alike Drug Names in the drug label.

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ "ANTIFUNGAL- terbinafine hydrochloride cream".
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