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78628-80-5

78628-80-5 structure
78628-80-5 structure
  • Name: terbinafine hydrochloride
  • Chemical Name: terbinafine hydrochloride
  • CAS Number: 78628-80-5
  • Molecular Formula: C21H26ClN
  • Molecular Weight: 327.891
  • Catalog: API Synthetic anti-infective drugs Antifungal drugs
  • Create Date: 2018-07-12 19:04:15
  • Modify Date: 2024-01-01 22:48:47
  • Terbinafine hydrochloride (TDT 067 hydrochloride) is an antifungal medication used to treat fungal infections. It is a potent non-competitive inhibitor of squalene epoxidase from Candida with a Ki of 30 nM.
Name terbinafine hydrochloride
Synonyms (2E)-N,6,6-Trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-in-1-aminhydrochlorid
(2E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride (1:1)
1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-, hydrochloride (1:1)
MFCD00145430
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)-2-hepten-4-yn-1-amine hydrochloride (1:1)
(2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine hydrochloride (1:1)
Lamisil
trans-N-Methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl-1-amine hydrochloride
(2E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride
Terbinafine HCl
Terbinafine hydrochloride
EINECS 245-385-8
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine monohydrochloride
Description Terbinafine hydrochloride (TDT 067 hydrochloride) is an antifungal medication used to treat fungal infections. It is a potent non-competitive inhibitor of squalene epoxidase from Candida with a Ki of 30 nM.
Related Catalog
Target

Ki: 30 nM (squalene epoxidase)[1]

In Vitro Terbinafine has a primary fungicidal action in vitro against most fungal pathogens, including dermatophytes, and dimorphic and filamentous fungi. Terbinafine specifically inhibits fungal ergosterol biosynthesis at the point of squalene epoxidation. The treated fungal cells rapidly accumulate tlic intermediate squalene and become deficient in the end-product of the pathway, ergosterol[1].
In Vivo Terbinafine is not only active after topical application but is very effective in experimental dermatophytoses following oral administration. In fungi infected guinea-pigs, the skin temperature dropps dramatically after the fourth treatment of terbinafine[2].
Animal Admin Guinea-pigs: The backs (lumbar regions) of guinea-pigs, which have been mechanically depilated, are infected with 0.1 mL Sabouraud's dextrose 2% broth containing 106 c.f.u. of Truhophyton mentagrophytes. The treatments commence 48 h post-inoculation. The test compounds (Terbinafine) are suspended in 2% tylose and Tween 80 and administered via a stomach tube once daily on 9 consecutive days, or dissolved in a mixture of polyethylene glycol 400 and etbanol and spread on the infected part ot the body in a volume of 0.4 mL with a Hrigalski spatula once daily for 1-7 consecutive days[2].
References

[1]. Ryder NS, et al. Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-8.

[2]. Mieth H, et al. Preclinical evaluation of terbinafine in vivo. Clin Exp Dermatol. 1989 Mar;14(2):104-8.
Density 1.007g/cm3
Boiling Point 417.9ºC at 760 mmHg
Melting Point 204-208°C
Molecular Formula C21H26ClN
Molecular Weight 327.891
Flash Point 183.7ºC
Exact Mass 327.175385
PSA 3.24000
LogP 5.67930
Index of Refraction 1.586
Storage condition -20°C Freezer

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QJ8600100
CHEMICAL NAME :
1-Naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-, (E)-, monohydrochloride
CAS REGISTRY NUMBER :
78628-80-5
LAST UPDATED :
199510
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C21-H25-N.Cl-H
MOLECULAR WEIGHT :
327.93

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
210 mg/kg/6W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Taste) - change in function
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 339,1483,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia Blood - changes in spleen
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7922,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia Blood - changes in spleen
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7922,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia Blood - changes in spleen
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7888,1990 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3960 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 24,7925,1990
Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning
Hazard Statements H315-H319-H335-H410
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi: Irritant;N: Dangerous for the environment;
Risk Phrases R36/37/38
Safety Phrases S26-S36/37/39-S61-S60
RIDADR UN 3077 9/PG 3
RTECS QJ8600100
HS Code 2921499090
14489-75-9 structure

14489-75-9

78629-20-6 structure

78629-20-6

~80%

78628-80-5 structure

78628-80-5

Literature: HYDEX CHEMICALS PVT LTD. Patent: WO2005/110968 A1, 2005 ; Location in patent: Page/Page column 9-10 ;
91161-71-6 structure

91161-71-6

~77%

78628-80-5 structure

78628-80-5

Literature: F.I.S. FABBRICA ITALIANA SINTETICI S.P.A.; DELLA NEGRA, Frederico Patent: WO2005/121155 A1, 2005 ; Location in patent: Page/Page column 37-38 ;
126764-17-8 structure

126764-17-8

14489-75-9 structure

14489-75-9

~%

78628-80-5 structure

78628-80-5

Literature: WO2007/52089 A1, ; Page/Page column 7 ;
65473-13-4 structure

65473-13-4

287471-30-1 structure

287471-30-1

~%

78628-80-5 structure

78628-80-5

Literature: US2006/84826 A1, ; Page/Page column 3 ;
123944-73-0 structure

123944-73-0

86-52-2 structure

86-52-2

~%

78628-80-5 structure

78628-80-5

Literature: US5231183 A1, ; US 5231183 A
126764-17-8 structure

126764-17-8

65473-13-4 structure

65473-13-4

~%

78628-80-5 structure

78628-80-5

Literature: WO2007/44273 A1, ; Page/Page column 16; 17 ;
HS Code 2921499090
Summary 2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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