ニクロサミド

ニクロサミド · マンソニル · セストシド · トレデミン · リンテックス · ベルミチド · 5-クロロ-N-(2-クロロ-4-ニトロフェニル)-2-ヒドロキシベンズアミド · ヨメサン

識別子と物理属性

CAS No.	50-65-7
分子式	C13H8Cl2N2O4
平均分子量	327.12 g/mol
単同位体質量	325.9861121 g/mol
SMILES	O=C(Nc1ccc([N+](=O)[O-])cc1Cl)c1cc(Cl)ccc1O
InChIKey	RJMUSRYZPJIFPJ-UHFFFAOYSA-N
PubChem CID	4477
ChEMBL	CHEMBL1448
ChEBI	CHEBI:7553
EC No.	200-056-8
DTXSID	DTXSID7040362
現地名	ニクロサミド

化学・物理的性質

XLogP	4
極性表面積	95.2
水素結合供与体数	2
水素結合受容体数	4
回転可能結合数	2
重原子数	21
形式電荷	0
複雑度	404
医薬品	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics
LogP（分配係数）	log Kow = 10 @ pH 9.6
味	Tasteless
Color/Form	PALE, YELLOW CRYSTALSALMOST COLORLESS CRYSTALSA cream-colored or yellowish-white powderBright yellow crystalline solid
溶解度	SPARINGLY SOL IN CHLOROFORM, ETHER, ETHANOLSOL IN ACETONESol at 20 °C in 150 parts of alcoholIn water = 5-8 mg/L at 20 °CFor more Solubility (Complete) data for NICLOSAMIDE (8 total), please visit the HSDB record page.アセトン:メタノール:可溶50mg/mL (メタノール:アセトン(1:1))13.32mg/L(25℃)
Human Drugs	Breast FeedingLactationAnti-infective AgentsAntiparasitic AgentsAnthelminticsAnticestodal AgentsAntinematodal AgentsMolluscacidesFDA approved drugs -> Active ingredientIntestinal anthelminthics
融点	225-230 °C225-230°
蒸気圧	<9.87X10-9 mm Hg at 20 °C
Physical Description	Solid
Stability/Shelf Life	TABLETS ARE SENSITIVE TO MOISTURE.Decomp more rapidly in the presence of ... UV irradiation.It is stable to heat and is hydrolysed by concentrated acid or alkali.
Collision Cross Section	164.6 Å² [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID7040362]168.3 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental Properties	Hydrolysed in aqueous solution with a decomposition half-life at 20 °C of 7 days (pH 6.9), 18.8 days (pH 13.3). Stable to heat. Decomposes under UV irradiation. Hydrolysed by concentrated acid or alkali.Decomposes at 208 °CIts biological effectiveness in water is stable at pH 5-9 and is also largely independent of the concentration of calcium and magnesium ions.
沸点	424.5±45.0 °C(Predicted)
密度	1.6646 (rough estimate)
屈折率	1.6200 (estimate)
貯蔵条件	Sealed in dry,Room Temperature
外観・状態	淡黄色固体
pKa（酸解離定数）	7.45±0.43(Predicted)
色	黄色
BRN	2820605
ヘンリー定数	1.5×104 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	4
安定性	DMSO溶液またはエタノール溶液で-20°Cで最大3か月保存できます。
主な用途	医薬品（低分子化合物）
InChI	1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)
InChIKey	RJMUSRYZPJIFPJ-UHFFFAOYSA-N
SMILES	Oc1ccc(Cl)cc1C(=O)Nc2ccc(cc2Cl)[N+]([O-])=O
CAS データベース	50-65-7(CAS DataBase Reference)
EPAの化学物質情報	Niclosamide (50-65-7)

化学的特性

Yellowish-white or yellowish, fine crystals.Yellow-white crystalline powder, odorless, tasteless. Melting point 225-230 ℃. Insoluble in water, soluble in hot ethanol, chloroform, cyclohexanone, diethyl ether and sodium hydroxide solution.

安全性と法規制

GHS 分類	WarningH400 (96%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P273, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 75 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Chemical: Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-Niclosamide: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-: Environment tier I assessment
FDA 要件	Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).Niclosamide tablets. Oral dosage form new animal drugs. Specifications and conditions of use provided for dogs.Niclosamide. New animal drugs for use in animal feeds. Conditions of use provided for laboratory mice.
Hazard Classes and Categories	Aquatic Acute 1 (96%)
保管条件	... stored at a temp less than 30 °Cfreezing of the tablets should be avoided.
処分方法	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Niclosamide is reported to be highly stable to heat but it is hydrolized by strong alkali or acids. Recommendable methods: Incineration & landfill. Peer review: Incinerate niclosamide in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
相互作用	IT WAS CONCLUDED THAT CARBARYL POTENTIATED TOXICITY OF BAYER 73 TO RAINBOW TROUT BY INCREASING ITS UPTAKE FROM WATER, POSSIBLY BY EFFECTS ON GILL BLOOD FLOW OR PERMEABILITY.

用途

ニクロサミド(Niclosamide)は商標名のクロサイド(Niclocide)で売られているサナダムシの駆虫に使用される医薬品である。裂頭条虫症、ヒメノレア症、テニヤ条虫症に対して効果がある。その他のぎょう虫感染症または線形動物に対しては効果がない。

使用

Niclosamide has been used extensively in the treatment of tapeworm infections caused by Taenia saginata, Taenia solium, Diphyllobothrium latum, Fasciolopsis buski, and Hymenolepis nana. It is an effective alternative to praziquantel for treating infections caused by T. saginata (beef tapeworm), T. solium (pork tapeworm), and D. latum (fish tapeworm) and is active against most other tapeworm infections. It is absorbed by intestinal cestodes but not nematodes.A single dose is usually adequate to produce a cure rate of 95%.With H. nana (dwarf tapeworm), a longer treatment course (up to 7 days) is necessary. Niclosamide is administered orally after the patient has fasted overnight and may be followed in 2 hours by purging (magnesium sulfate 15–30 g) to encourage complete expulsion of the cestode, especially T. solium, although this is not always considered necessary. Cure is assessed by follow-up stool examination in 3 to 5 months.With the availability of other agents, niclosamide is no longer widely used.The most widely employed agents are praziquantel and the benzimidazoles.

一般的な説明

A cell-permeable salicylanilide that, in addition to its well-known antihelmintic efficacy, acts as a mammalian mTORC1, but not mTORC2, signaling inhibitor mechanistically distinct from rapamycin. Likely a direct consequence of autophagy activation, Niclosamide is demonstrated to induce Wnt-independent Frizzled1 and Dishevelled-2 downregulation. Unrelated to its autophagy induction activity, Niclosamide is also shown to inhibit Stat3 signaling (IC50 = 0.25 M in HeLa reporter assays). Efficiently inhibits breast cancer stem-like cells in vitro and in vivo.