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Podophyllotoxin

Podophyllotoxin 구조식 이미지
카스 번호:
518-28-5
상품명:
Podophyllotoxin
동의어(영문):
nsc24818;condylox;podofilox;Condyline;PODOPHYLLIN(RG);PODOPHYLLOTOXIN;Podophyllotoxin,95%;(-)-PODOPHYLLOTOXIN;Podophyllotoxin ,98%;Podophyllotoxin(PPT)
CBNumber:
CB1147810
분자식:
C22H22O8
포뮬러 무게:
414.41
MOL 파일:
518-28-5.mol

Podophyllotoxin 속성

녹는점
183-184 °C (lit.)
알파
-110.7 º (c=1, CHCl3)
끓는 점
453.31°C (rough estimate)
밀도
1.2649 (rough estimate)
굴절률
1.4480 (estimate)
저장 조건
2-8°C
물리적 상태
Powder
산도 계수 (pKa)
13.26±0.40(Predicted)
색상
White to off-white
optical activity
[α]/D 131±2°, c = 1 in chloroform
Merck
13,7628
BRN
99163
안정성
Very Hygroscopic
InChIKey
YJGVMLPVUAXIQN-XVVDYKMHSA-N
CAS 데이터베이스
518-28-5(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T
위험 카페고리 넘버 21-25-36/37/38-23/25-23/24/25
안전지침서 36/37/39-45-26
유엔번호(UN No.) UN 3462 6.1/PG 2
WGK 독일 3
RTECS 번호 LV2500000
F 고인화성물질 1-8-10
위험 등급 6.1(a)
포장분류 II
HS 번호 29189090
유해 물질 데이터 518-28-5(Hazardous Substances Data)
독성 LD50 in rats (mg/kg): 8.7 i.v.; 15 i.p. (Phillips)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H310 피부와 접촉하면 치명적임 급성 독성 물질 - 경피 구분 1,2 위험 P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P310 즉시 의료기관(의사)의 진찰을 받으시오. 삼켰다면 즉시 의료기관(의사)의 도움을 받으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P302+P350 피부에 묻은 경우,비눗물로 부드럽게 씻기
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

Podophyllotoxin MSDS


(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

Podophyllotoxin C화학적 특성, 용도, 생산

개요

Podophyllotoxin (2,3-butyl-4-aromatic naphthene) is isolated from guijiu 鬼臼属 (Podophyllum) . There are two species as the main source of podophyllotoxin, Podophyllum hexandrum Royle and Podophyllum peltatum .
Although podophyllotoxin has significant antitumor and antiviral activities, it showed several toxicity and side effects. Podophyllotoxin derivatives, etoposide (VP-16-213), Etopophos, amino sugar etoposide (NK6l1), and teniposide (VM26), have been developed as anticancer drugs. They are used to treat small cell lung cancer, testicular cancer, acute leukemia, malignant lymphoma, etc. But podophyllotoxin derivatives are not free of toxicity. Besides the narrowing of the anticancer spectrum and low water solubility, these drugs could induce severe myelosuppression, gastrointestinal side effects, etc.
Although the synthetic and biosynthetic pathways of podophyllotoxin have been elucidated, it is still the most effective, economic, and fast way to extract podophyllotoxin from the plant.

화학적 성질

off-white fine crystalline powder

물리적 성질

Appearance: white needle crystal powder. Solubility: freely soluble in chloroform, acetone, ethyl acetate, and benzene; soluble in ethanol and ethyl ether; and insoluble in water. Melting point: after drying the melting point is 183–184?°C. Specific optical rotation: 132.7?°C (chloroform).

역사

Podophyllotoxin was first found in the Podophyllum peltatum L.?The first time to isolate podophyllotoxin from podophyllin was in 1880. In 1942, it was found that venereal warts could be effectively treated by application of podophyllin.Subsequently, podophyllotoxin was reported to inhibit the growth of the tumor through the inhibition of the microtubule formation. The chemical structure of podophyllotoxin was elucidated in 1951.
In the 1960s, two main podophyllotoxin derivatives were synthesized, etoposide and teniposide (VM-26) . In 1983, etoposide was approved by FDA.?Etoposide and teniposide are used in frontline cancer therapy against various cancer types, such as small cell lung cancer, testicular cancer, etc. In 1996, etoposide phosphate analog (Etopophos) was launched in America. Etopophos is the prodrug of etoposide and can be rapidly absorbed and completely converted to the parent compound in?vivo. In 1990, WHO recommended 0.5% podophyllotoxin as the first-line drug for the treatment of condyloma acuminatum. Podophyllotoxin creams and gels are nowadays widely used in clinical practice.

용도

Skin treatment for genital warts caused by some types of HPVs.

용도

antineoplastic, inhibits microtubule assembly, and human DNA topoisomerase II; antimitotic agent

용도

Podophyllotoxin is a non-alkaloid toxin lignan extracted from the roots and rhizomes of Podophyllum species. It binds to topoisomerase II during the late S and early G2 stage, blocking tubulin polymerization and, thus, inhibiting mitosis. In addition to being used as a cathartic, purgative, antiviral agent, vesicant, and antihelminthic, podophyllotoxin is the starting material for the semi-synthesis of the anti-cancer drugs etoposide , teniposide , and etopophos.

정의

ChEBI: An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts.

Indications

Podophyllotoxin (Podofilox) is available alone and as the main cytotoxic ingredient in podophyllin (25% podophyllum resin), a mixture of toxic chemicals derived from May apple plants. The active ingredients inhibit cell mitosis. The drugs are used to treat condylomata acuminata. The most common toxic effects are skin irritation and less commonly, ulceration. Systemic absorption of podophyllin can occur (especially if applied to large, inflamed areas or mucosal surfaces), with gastrointestinal, hematological, renal, and hepatotoxic effects. In addition, seizures and peripheral neuropathy have been reported.

상표명

Condylox (Oclassen).

Pharmacology

Antineoplastic and antiviral activities are the most pronounced pharmacological. effects of podophyllotoxin . Podophyllotoxin shows a significant inhibitory effect on the division and proliferation of epithelial cells infected by human papillomavirus (HPV), disrupts the cell cytoskeleton, and induces the necrosis and shedding of warts. It was shown that the antitumor effect of podophyllotoxin is associated with the inhibition of microtubule assembly and the induction of apoptosis. However, the antitumor effect of podophyllotoxin analogs, such as etoposide, teniposide, and Etopophos, is related to disparate mechanisms including the inhibition of DNA topoisomerase II activity and the formation of stable nucleic acid-drugenzyme complex, which induce DNA double-strand or single-strand break and eventually lead to cell death . It was also found that podophyllotoxin derivatives have immunosuppressive and anti-inflammatory effects.

Clinical Use

Podophyllotoxin is a useful agent for the treatment of condyloma acuminatum . Podophyllotoxin and its derivatives are also widely used in the treatment of cancer, such as lymphomas and lung carcinoma. Because of the several toxicity of podophyllotoxin, for example, the irritation of skin and mucous membranes, combination therapies are used to treat condyloma acuminatum or cancer.

Anticancer Research

Podophyllotoxin (PTOX) is an aryl-tetralin lignan and has been originallyisolated from Podophyllum peltatum L. (American podophyllum or Mayapple;family Podophyllaceae). Later, it is also isolated from several species like P.hexandrum Royle (Indian podophyllum) and P. pleianthum (Taiwanese podophyllum).PTOX has also been reported in other plants such as Linum spp., Callitrisspp., Juniperus spp., Thuja spp., Hyptis spp., Thymus spp., Teucrium spp., Nepetaspp., Dysosma spp., Diphylleia spp., and Jeffersoniana spp. (Ionkova 2007;Yousefzadi et al. 2010). PTOX shows strong cytotoxic activity against various cancercell lines. However, PTOX is too toxic for the treatment of neoplastic diseasesin humans; it is used as a precursor for chemical synthesis of semisynthetic antineoplasticdrugs, etoposide, Etopophos, and teniposide , which are successfullyused as antitumor agents (Holthuis 1988; Cragg and Newman 2005).Podophyllotoxin derivatives are used in the treatment of lymphomas, acute leukemia,and testicular, lung, ovarian, bladder, and brain cancer (Srivastava et al. 2005).Podophyllum spp. are the major source of PTOX, and their availability is limited innature, and some species are categorized as endangered. Moreover, the chemicalsynthesis of podophyllotoxin is an expensive process; therefore, biotechnologicalproduction of podophyllotoxin using plant cell and tissue cultures has been preferredby various research groups (Farkya et al. 2004).

Anticancer Research

Podophyllotoxin istoxic for humancells and is aprecursor ofsemisyntheticantineoplastic drugs(e.g., etoposide,etopophos, andteniposide).

Purification Methods

The toxin recrystallises form *C6H6 (with 0.5C6H6), EtOH/*C6H6, aqueous EtOH (with 1-1.5H2O, m 114-115o) and CH2Cl2/pentane. When dried at 100o/10mm it has m 183-184o. [UV: Stoll et al. Helv Chim Acta 37 1747 1954, IR: Schecler et al. J Org Chem 21 288 1956.] It is an inhibitor of microtubule assembly [Prasad et al. Biochemistry 25 739 1986]. [Beilstein 19/10 V 666.]

Podophyllotoxin 준비 용품 및 원자재

원자재

준비 용품


Podophyllotoxin 공급 업체

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career henan chemical co
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