기본 정보
- CAS
29767-20-2- 표준 SMILES
COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5COC(c6cccs6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O- InChIKey
NRUKOCRGYNPUPR-PSZSYXFXSA-N- 분자식
- C32H32O13S
- 평균 분자량
- 656.7 g/mol
- 단동위원소 질량
- 656.15636224
개요
Teniposide is a furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding. It has a role as an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a beta-D-glucoside, a member of thiophenes, a member of phenols, an aromatic ether, a gamma-lactone, a furonaphthodioxole, a cyclic acetal and a monosaccharide derivative. It is functionally related to a podophyllotoxin.
이름 및 식별자
- 우선 이름
- Teniposidum
- IUPAC
- (5S,5aR,8aR,9R)-5-[[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
- 영어명
- Teniposide
- 분자식
- C32H32O13S
- 분자량
- 656.65
이름 및 동의어
TeniposidumRefChem:1048736(5S,5aR,8aR,9R)-5-(((4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-(2)benzofuro(6,5-f)(1,3)benzodioxol-8-oneTeniposidum [INN-Latin]Teniposido [INN-Spanish]SCHEMBL94844(5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranosideFuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-.beta.-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-etpvehemvm-26
이름 더 보기
VumonEniposidensc122819Teniposid
물성
구조 계산 물성
- XLogP
- 1.2
- 극성 표면적
- 189 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 14
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 46
- 형식 전하
- 0
- 복잡도
- 1,090
실험 및 물리화학적 성질
LogP1.5
Solubility5.98e-02 g/L
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 244 · 244-247°C
- 끓는 점
- 650.86 °C · 650.86°C (rough estimate)
- 밀도
- 1.2568 · 1.2568 (rough estimate)
- 굴절률
- 1.553 · 1.5530 (estimate)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 10 mg/mL, · DMSO: 용해성10mg/mL, 투명
- 산도 계수 (pKa)
- 10.13 · 10.13(at 25℃)
- 물리적 상태
- 가루
- 색상
- 흰색에서 베이지색
- Merck
- 14 · 14,9145
- 안정성
- 흡습성
- InChIKey
- NRUKOCRGYNPUPR-QBPJDGROSA-N
- SMILES
- [s]1c(ccc1)[C@H]2O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@H]4[C@@H]5[C@@H]([C@@H](c7c4cc8c(c7)OCO8)c6cc(c(c(c6)OC)O)OC)C(=O)OC5)CO2
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
독성 정보
Toxicity Summary
The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.
Carcinogen Classification2A, probably carcinogenic to humans. (L135)
안전 데이터
- wgk
- 3
- rtecs
- KC0180000
- ridadr
- UN 2811 6.1 / PGIII
- 독성
- LD50 intraperitoneal in mouse: 29570ug/kg
- HS 번호
- 29349990
- risk_code
- 36/37/38-45
- hazard_code
- Xi,T
- safety_code
- 26-36-45-53
- Hazard Classifications
- Carc. 1B
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 유해 물질 데이터
- 29767-20-2(Hazardous Substances Data)
화학 및 산업
약리 정보
Metabolism/MetabolitesRoute of Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose.
Half Life: 5 hours
Cellular LocationsCytoplasm
Metabolite PathwaysTeniposide Action Pathway
용도 및 제조
UsesTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
응용 분야
용도Teniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.
일반 설명Teniposide is available in 50-mg ampules with Cremophor ELfor IV administration in the treatment of acute lymphoblasticleukemia (ALL). The agent is more potent as an inhibitor oftopoisomerase II. The pharmacokinetics of teniposide issimilar to that of etoposide; however, the more lipophilic teniposideis more highly protein bound (99%) and less isexcreted unchanged in the urine (10%–20%). There is alsogreater overall metabolism of teniposide; however, CYP3A4-mediated conversion to the active catechol is slower comparedwith etoposide. Elimination occurs primarily in the urine witha terminal elimination half-life of 5 hours.
상·하류 제품 정보
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