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| CAS No.: | 91161-71-6 |
|---|---|
| Name: | Terbinafine hydrochloride |
| Article Data: | 20 |
| Molecular Structure: | |
|
|
|
| Formula: | C21H25N |
| Molecular Weight: | 291.436 |
| Synonyms: | 1-Naphthalenemethanamine,N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-, (E)-;1-Naphthalenemethanamine,N-[(2E)-6,6-dimethyl-2-hepten-4-ynyl]-N-methyl- (9CI);Eksifine;Fungoterbin;Lamasil;Mycoterbin;SF 86-327;Terbisil;YY 1084; |
| EINECS: | 618-706-8 |
| Density: | 1.007g/cm3 |
| Melting Point: | 203-205 °C |
| Boiling Point: | 417.9 °C at 760 mmHg |
| Flash Point: | 183.7 °C |
| Appearance: | white to off-white crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 3.24000 |
| LogP: | 4.87730 |
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Chemistry
Structure of Terbinafine (CAS NO.91161-71-6):
IUPAC Name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
Empirical Formula: C21H25N
Molecular Weight: 291.4299
Index of Refraction: 1.586
Molar Refractivity: 97.09 cm3
Molar Volume: 289.1 cm3
Polarizability: 38.48×10-24cm3
Surface Tension: 41 dyne/cm
Density: 1.007 g/cm3
Flash Point: 183.7 °C
Enthalpy of Vaporization: 67.13 kJ/mol
Boiling Point: 417.9 °C at 760 mmHg
Vapour Pressure: 3.42E-07 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;Terbinafine
Synonyms of Terbinafine (CAS NO.91161-71-6): (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-
naphthalenemethylamine ; Lamasil ; Lamisil ; Lamisil AT ; Lamisil Tablet
Canonical SMILES: CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21
Isomeric 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
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| man | TDLo | oral | 3918ug/kg (3.918mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Kiso to Rinsho. Clinical Report. Vol. 27, Pg. 6087, 1993. |
| man | TDLo | oral | 89mg/kg/25D-I (89mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Gastroenterology. Vol. 93, Pg. 459, 1998. |
| mouse | LD50 | intravenous | 393mg/kg (393mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H. and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983Vol. 6, Pg. 116/52, 1983. |
| mouse | LD50 | oral | 4gm/kg (4000mg/kg) | Drugs of the Future. Vol. 9, Pg. 427, 1984. | |
| rat | LD50 | intravenous | 213mg/kg (213mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H. and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983Vol. 6, Pg. 116/52, 1983. |
| rat | LD50 | oral | 4gm/kg (4000mg/kg) | Drugs of the Future. Vol. 9, Pg. 427, 1984. | |
| women | TDLo | oral | 200mg/kg/40D- (200mg/kg) | BEHAVIORAL: ANOREXIA (HUMAN LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Journal of Hepathology. Vol. 24, Pg. 753, 1996. |
| women | TDLo | oral | 210mg/kg/6W-I (210mg/kg) | SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE | Lancet. Vol. 340, Pg. 728, 1992. |
Safety Profile
Hazard Codes: 
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
Specification
Terbinafine (CAS NO.91161-71-6) 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 (Tinea corporis).
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. Alternatives to oral administration have been studied. In 2009, results from a clinical study of a new formulation (terbinafine in Transfersomes, referred to as TDT-067) for topical treatment of onychomycosis were reported by Celtic Pharma.
It has been found that terbinafine hydrochloride may induce or exacerbate subacute cutaneous lupus erythematosus. Persons with lupus erythematosus should first discuss possible risks with their doctor before initiation of therapy.