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QuickView for Terbinafine (compound)
PubChem
| Name: | terbinafine |
|---|---|
| PubChem Compound ID: | 1549007 |
| Molecular formula: | C21H26N+ |
| Molecular weight: | 292.438 g/mol |
| Synonyms: |
ZINC01530981
|
DrugBank
Identification
| Name: | terbinafine |
|---|---|
| Name (isomeric): | DB00857 |
| Drug Type: | small molecule |
| Synonyms: |
Ternbinafine HCl; Terbinafine HCl; Terbinafine hydrochloride
|
| Brand: | Lamisil AT, Lamasil, Bramazil, Terbina, Lamisil, Terbifoam, Lamisil Oral |
| Category: | Trypanocidal Agents, Antifungal Agents, Antifungals, Enzyme Inhibitors, Allylamines |
| CAS number: | 91161-71-6 |
Pharmacology
| Indication: | For the treatment of dermatophyte infections of the toenail or fingernail caused by susceptible fungi. Also for the treatment of tinea capitis (scalp ringworm) and tinea corporis (body ringworm) or tinea cruris (jock itch). |
|---|---|
| Pharmacology: |
Terbinafine is an allylamine antifungal agent and acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. In vitro, mammalian squalene monooxygenase (squalene 2,3-epoxidase) is only inhibited at higher (4000 fold) concentrations than is needed for inhibition of the...
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Terbinafine is an allylamine antifungal agent and acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. In vitro, mammalian squalene monooxygenase (squalene 2,3-epoxidase) is only inhibited at higher (4000 fold) concentrations than is needed for inhibition of the dermatophyte enzyme. Depending on the concentration of the drug and the fungal species test in vitro, Terbinafine may be fungicidal. However, the clinical significance of in vitro data is unknown.
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| Mechanism of Action: |
Terbinafine is hypothesized to act by inhibiting squalene monooxygenase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. This inhibition also results in an accumulation of squalene, which is a substrate catalyzed to 2,3-oxydo squalene by squalene monooxygenase. The resultant high concentration of squal...
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Terbinafine is hypothesized to act by inhibiting squalene monooxygenase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. This inhibition also results in an accumulation of squalene, which is a substrate catalyzed to 2,3-oxydo squalene by squalene monooxygenase. The resultant high concentration of squalene and decreased amount of ergosterol are both thought to contribute to terbinafine's antifungal activity.
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| Absorption: | Readily absorbed from gastrointestinal tract. |
| Protein binding: | >99% |
| Biotransformation: | Hepatic |
| Route of elimination: | Prior to excretion, terbinafine is extensively metabolized. |
| Half Life: | 36 hours |
| Affected organisms: | Fungi |
Interactions
| Drug interaction: |
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Targets
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway
| UniProt ID: | Q14534 | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Gene: | SQLE | ||||||||
| Actions: | inhibitor | ||||||||
| References: |
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Enzymes
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
| UniProt ID: | P11712 | ||
|---|---|---|---|
| Gene: | CYP2C9 | ||
| Actions: | substrate | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen
| UniProt ID: | P05177 | ||
|---|---|---|---|
| Gene: | CYP1A2 | ||
| Actions: | substrate | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | ||
|---|---|---|---|
| Gene: | CYP3A4 | ||
| Actions: | substrate, inducer | ||
| References: |
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Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)
| UniProt ID: | P10632 | ||
|---|---|---|---|
| Gene: | CYP2C8 | ||
| Actions: | substrate | ||
| References: |
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Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine
| UniProt ID: | P33261 | ||
|---|---|---|---|
| Gene: | CYP2C19 | ||
| Actions: | substrate | ||
| References: |
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Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
| UniProt ID: | P10635 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | CYP2D6 | ||||||
| Actions: | inhibitor | ||||||
| References: |
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May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells
| UniProt ID: | P23219 | |
|---|---|---|
| Gene: | PTGS1 | |
| Actions: | substrate | |
| References: |
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Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone
| UniProt ID: | P05108 | |
|---|---|---|
| Gene: | CYP11A1 | |
| Actions: | inhibitor | |
| References: |
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Catalyzes the formation of aromatic C18 estrogens from C19 androgens
| UniProt ID: | P11511 | |
|---|---|---|
| Gene: | CYP19A1 | |
| Actions: | inhibitor | |
| References: |
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