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Naftifine

Product Name
Naftifine
CAS No.
65472-88-0
Chemical Name
Naftifine
Synonyms
Naftin;naftifin;Exoderil;NAFTIFINE;AW-105-843;SN-105-843;Naftifungin;Naftifine D3;Naftifinebase;Naftifine 13CD3
CBNumber
CB5211922
Molecular Formula
C21H21N
Formula Weight
287.4
MOL File
65472-88-0.mol
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Naftifine Property

Melting point:
177 °C
Boiling point:
bp0.015 torr 162-167°
Density 
1.082±0.06 g/cm3(Predicted)
solubility 
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
form 
Thick Oil
pka
7.99±0.50(Predicted)
color 
Colourless to Dark Yellow
Merck 
6355
CAS DataBase Reference
65472-88-0(CAS DataBase Reference)
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Safety

HS Code 
29214990
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
N213310
Product name
(E)-Naftifine
Packaging
25mg
Price
$110
Updated
2021/12/16
TRC
Product number
N213310
Product name
(E)-Naftifine
Packaging
1g
Price
$475
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0009134
Product name
NAFTIFINE
Purity
95.00%
Packaging
5MG
Price
$502.66
Updated
2021/12/16
AvaChem
Product number
1706B
Product name
Naftifine
Packaging
10mg
Price
$29
Updated
2021/12/16
AvaChem
Product number
1706B
Product name
Naftifine
Packaging
100mg
Price
$39
Updated
2021/12/16
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Naftifine Chemical Properties,Usage,Production

Originator

Naftifine,Sandoz (Novartis)

Uses

Naftifine is only permitted to be used externally and only superficially as a drug with a broad spectrum of action against dermatophytes and candida infections. According to the initial data, it exceeds the activity of econazole. Moreover, it does not have a locally irritating effect. It is believed that the fungicide activity of this drug is based on its ability to inhibit the fungal enzyme squalene epoxidase, thus lowering the concentration of ergosterol. The corresponding enzyme in mammals is inhibited significantly less. Synonyms of this drug are exoderil, naftin, and others.

Uses

(E)-Naftifine is an intermediate in synthesizing Naftifine N-Oxide (N213110), which is an impurity or metabolite of Naftifine Hydrochloride (N213100), an allylamine antifungal agent.

Uses

Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans.

Definition

ChEBI: A tertiary amine in which the nitrogen is substituted by methyl, alpha-naphthylmethyl, and (1E)-cinnamyl groups. It is used (usually as its hydrochloride salt) for the treatment of fungal skin infections.

Indications

Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans.

Manufacturing Process

To a mixture of 1.42 g of methyl-(1-naphthylmethyl)amine hydrochloride, 2.89 g of sodium carbonate and 10 ml of dimethylformamide is added, at room temperature, 1.25 g of cinnamyl chloride, dropwise. After 18 hours stirring, at room temperature, the mixture is filtered and the filtrate is evaporated in vacuo. The residue is dissolved in toluene and, after drying over sodium sulphate, evaporated to obtain the trans-N-(cinnamylmethyl)-Nmethyl-(1-naphthylmethyl)amine compound, boiling point 162-167°C/0.015 Torr.
The free base may be converted, with isopropanolic hydrogen chloride solution, into the hydrochloride form, melting point 177°C (from propanol).

brand name

Naftin (Merz).

Therapeutic Function

Antifungal

Synthesis Reference(s)

Journal of Medicinal Chemistry, 29, p. 112, 1986 DOI: 10.1021/jm00151a019
Tetrahedron Letters, 25, p. 2535, 1984 DOI: 10.1016/S0040-4039(01)81224-7

Antimicrobial activity

Naftifine is fungicidal against dermatophytes such as Epidermophyton floccosum, Trichophyton and Microsporum species. Against pathogenic yeasts such as Candida species and moulds, it shows only an intermediate fungistatic activity in vitro.

Pharmaceutical Applications

A topical antifungal used as a 1% cream for the treatment of dermatophytoses, including tinea pedis, tinea corporis and tinea cruris.

Pharmacokinetics

Naftifine penetrates well into the stratum corneum of the skin; 2 – 4 % of the topically administered dose were absorbed after administration of a 1 % gel preperation. After occlusion, an absorption of 6% of the administered dose was observed.

Clinical Use

Naftifine was the first allyl amine to be discovered and marketed. It is subject to extensive first-pass metabolism to be orally active and, consequently, is only available in topical preparations. The widest use of naftifine is against various tinea infections of the skin.

Side effects

Naftifine is well tolerated although rare cases of local skin irritations and contact dermatitis have been found, which might also be due the galenic formulation.

Synthesis

Naftifine, (E)-N-methyl-N-(3-phenyl-2-propenyl)-1-naphthalinmethanamine (35.3.1), is synthesized by alkylating N-methyl-(1-naphthylmethyl)-amine with cinnamyl chloride in the presence of sodium carbonate.

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Naftifine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10194
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9816
Advantage
59
9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22519
Advantage
55
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3750
Advantage
55
Chizhou Kailong Import and Export Trade Co., Ltd.
Tel
Fax
-
Email
xg01_gj@163.com
Country
China
ProdList
9503
Advantage
50
AN PharmaTech Co Ltd
Tel
86(21)68097365
Fax
86(21)33321566
Email
sales@anpharma.net
Country
China
ProdList
4901
Advantage
55
Shandong Xiya Chemical Co., Ltd.
Tel
4009903999 13395398332
Fax
0539-6365991
Email
sales@xiyashiji.com
Country
China
ProdList
20811
Advantage
60
Raw material medicin reagent co.,Ltd
Tel
025-57798860
Email
sales@njromanme.com
Country
China
ProdList
4534
Advantage
58
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View Lastest Price from Naftifine manufacturers

Dideu Industries Group Limited
Product
Naftifine 65472-88-0
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-19
Shaanxi Dideu Medichem Co. Ltd
Product
Naftifine 65472-88-0
Price
US $0.01-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50 tons
Release date
2020-05-12
Career Henan Chemical Co
Product
Naftifine 65472-88-0
Price
US $16.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg, 10kg, 50kg
Release date
2020-03-09

65472-88-0, NaftifineRelated Search:


  • naftifin
  • n-trans-cinnamyl-n-methyl-(1-naphthylmethyl)amine
  • NAFTIFINE
  • (e)-n-methyl-n-(1-naphthyl methyl)-3-phenyl-2-propen-1-amine
  • AW-105-843
  • Exoderil
  • Naftifungin
  • Naftin
  • SN-105-843
  • N-[(E)-3-Phenyl-2-propenyl]-N-methylnaphthalene-1-methanamine
  • N-Methyl-N-[(E)-3-phenyl-2-propenyl]-1-naphthalenemethanamine
  • (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenyl-prop-2-en-1-amine
  • (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine
  • METHYL-NAPHTHALEN-1-YLMETHYL-((E)-3-PHENYL-ALLYL)-AMINE
  • Naftifinebase
  • N-TRANS-CINNAMYL-N-METHYL-(1-NAPPHTHYLMETHYL)AMINE HYDROCHLORIDE
  • (E)-N-Methyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine
  • methyl-(1-naphthylmethyl)-[(E)-3-phenylallyl]amine
  • 1-NaphthaleneMethanaMine,N-Methyl-N-[(2E)-3-phenyl-2-propen-1-yl]-
  • N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine Hydrochloride, ≥ 98.0%
  • Naftifine USP/EP/BP
  • Naftifine 13CD3
  • Naftifine D3
  • 65472-88-0