켈리도닌

켈리도닌
켈리도닌 구조식 이미지
카스 번호:
476-32-4
한글명:
켈리도닌
동의어(한글):
켈리도닌
상품명:
CHELIDONINE
동의어(영문):
CHELIDONIN;khelidonin;helidonine;Aids002651;STYLOPHORIN;CHELIDONINE;chelidoniny;STYLOPHORON;Aids-002651;STYLOPHORINE
CBNumber:
CB8347796
분자식:
C20H19NO5
포뮬러 무게:
353.37
MOL 파일:
476-32-4.mol

켈리도닌 속성

녹는점
135-140°C
알파
D22 +115 ±3° (ethanol); D20 +117° (c = 3 in CHCl3)
끓는 점
bp0.002 220° (air-bath temp)
밀도
1.2976 (rough estimate)
굴절률
1.5800 (estimate)
저장 조건
Sealed in dry,2-8°C
용해도
Soluble in chloroform; slightly soluble in methan
물리적 상태
가루
산도 계수 (pKa)
14.11±0.20(Predicted)
색상
무색의
Merck
13,2061
InChIKey
GHKISGDRQRSCII-ZOCIIQOWSA-N
LogP
2.899 (est)
CAS 데이터베이스
476-32-4(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
위험품 표기 Xn
위험 카페고리 넘버 25-20/21/22
안전지침서 20-45-36/37
유엔번호(UN No.) 2811
WGK 독일 3
RTECS 번호 FL9450000
독성 LD50 in mice (mg/kg): 34.6 ±2.44 i.v. (Anderson, Chen)
그림문자(GHS): GHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
예방조치문구:
NFPA 704
0
3 0

켈리도닌 C화학적 특성, 용도, 생산

개요

Chelidonine, also named ranunculine, is a kind of alkaloid isolated from the whole plant of Chelidonium majus. L . As a kind of traditional Chinese medicine, Chelidonium majus. L was firstly recorded in Chiu Huang Pen Ts’ao of Ming dynasty. In the seventeenth century, it has been used for the treatment of jaundice, biliary colic, and cholelithiasis. In 1941, a researcher from Soviet Union reported that it showed good effect for the treatment of cutaneous tuberculosis. This plant has multiple effects on different diseases, including anti-inflammatory, analgesia, relieving cough, inducing diuresis, anticancer, antifungal, relieving asthma, and detoxification. It was recorded in the Pharmacopoeia of the People’s Republic of China (1977) .
The material basis for Chelidonium majus. L is alkaloid. Among which, chelidonine, a benzophenanthridine alkaloid, is the main effective ingredient . Although great progresses have been made in the chemical synthesis of chelidonine recently, the biosynthetic pathways of chelidonine remain unclear, which still need in-depth study and exploration in the future

화학적 성질

White, crystalline powder alkaloid.

물리적 성질

Appearance: white crystal or crystalline powder, monoclinic prism crystal. Solubility: insoluble in water; soluble in ethanol, chloroform, and amyl alcohol. Melting point: 135–136 °C. Boiling point: 220 °C. Specific optical rotation: +115°.

역사

Chelidonine was isolated from Chelidonium majus. L in 1824 for the first time. Pharmacological studies found that it exerted antitumor effect via different mechanisms. However, its poor bioavailability limited its application. Some researchers developed a chelidonine/polylactic acid copolymer nanoparticle using nanotechnology. The nano-chelidonine showed good tissue distribution without causing any toxicity in mice and could enter into the brain tissues, showing great application potential. In addition, nano-chelidonine showed protective effect on liver injury induced by cadmium in mice .
In 1981, an Austrian researcher isolated a novel compound ukrain (phosphorothioate derivative of chelidonine) from Chelidonium majus. L. Ukrain could inhibit tumor cell proliferation through a variety of mechanisms. Currently, ukrain is used as an antitumor drug for the clinical treatment of lung cancer, breast cancer, prostate cancer, and pancreatic cancer . In 2004, quarter amine chelidonine phosphorothioate derivatives have been applied for an invention patent as anticancer drugs in China.
Chelidonine has morphine-like analgesic effects suggesting that its analgesic effect is mainly peripheral and cannot be antagonized by the morphine receptor antagonist naloxone . The 6-alkoxy and 6-acyloxy derivatives of chelidonine can inhibit the central nervous system, especially for nerve terminal, and show sedative and hypnotic effects .

용도

Poison; central nervous system depres- sant causing sleepiness, depression, slowing of the pulse, coma and circulatory failure.

Clinical Use

Chelidonine has been used as a painkiller in clinical application due to its significant analgesic effect. Chelidonine phosphate can be used for treatment of gastrointestinal and ulcer pain, as a substitute of morphine preparations. Wei Tong Shu capsule is used to treat pain caused by gastric convulsion, chronic gastritis, gastric ulcer, and duodenal ulcer. Its main effective compositions are chelidonine and protopine. Fu Fang Zhong Yao Tong An injection has collateral dredging and analgesic effects and can be used for the treatment of moderate pain caused by chemoradiotherapy or non-chemoradiotherapy of gastric cancer, lung cancer, and liver cancer. Its two main components are chelidonine and sinomenine. Ukrain (NSC-631570), a phosphorothioate derivative of chelidonine, has been used in clinical treatment as an effective antitumor drug for the treatment of lung cancer, breast cancer, prostate cancer, and pancreatic cancer.

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