Rubitecan
기본 정보
- CAS
104195-61-1- 표준 SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1- InChIKey
VHXNKPBCCMUMSW-FQEVSTJZSA-N- 분자식
- C20H15N3O6
- 평균 분자량
- 393.3 g/mol
- 단동위원소 질량
- 393.09608521
개요
Rubitecan is a pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. It has a role as an antineoplastic agent, a prodrug and an EC 5.99.1.2 (DNA topoisomerase) inhibitor. It is a delta-lactone, a tertiary alcohol, a C-nitro compound, a pyranoindolizinoquinoline and a semisynthetic derivative.
이름 및 식별자
- 우선 이름
- Rubitecan
- IUPAC
- (19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
- 영어명
- Rubitecan
- 분자식
- C20H15N3O6
- 분자량
- 393.35
이름 및 동의어
Rubitecan9-Nitrocamptothecin91421-42-09-nitro-20(S)-camptothecinOrathecinCamptogenRFS 2000RFS-2000NitrocamptothecinrubitecanumH19C446XXB9-nitro-20-(S)-camptothecin
이름 더 보기
9-Nitrocellulose camptothecine9-NCOratheciRUBETICANRubitecane9-NITRO-CPT
DTXSID7046752CHEBI:90225RFS20009-nitro-(20S)-camptothecinDTXCID50267521H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-10-nitro-, (4S)-(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo(11.8.0.0^(2,11).0^(4,9).0^(15,20))henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
데이터베이스 식별자
- CAS
104195-61-1、91421-42-0- PubChem CID
- 472335
- DTXSID
DTXSID7046752- ChEMBL
CHEMBL77305
물성
구조 계산 물성
- XLogP
- 0.8
- 극성 표면적
- 126 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 861
실험 및 물리화학적 성질
LogP2.16
물리화학적 성질
- 녹는점
- 182 · 182-186°C
- 끓는 점
- 816.3 · 816.3±65.0 °C(Predicted)
- 밀도
- 1.63 · 1.63
- 인화점
- 106 ℃ · 106℃
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- DMSO, 클로로포름, 메탄올에 용해됨
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 11.16 · 11.16±0.20(Predicted)
- 색상
- 노란색
- 생물학적 소스
- synthetic (organic)
- Merck
- 14 · 14,8288
- InChI
- InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
- InChIKey
- VHXNKPBCCMUMSW-FQEVSTJZSA-N
- SMILES
- N1C2C(=C([N+]([O-])=O)C=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O
화학적 성질
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- wgk
- 3
- rtecs
- UQ0493300
- HS 번호
- 29399990
- safety_code
- 24/25
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Mechanism of ActionRubitecan prevents DNA from unwinding during replication via DNA topoisomerase 1, therefore interfering with tumor growth.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds that inhibit the activity of DNA TOPOISOMERASE I.
응용 분야
개요Rubitecan is a DNA topoisomerase I inhibitor. It inhibits DNA topoisomerase I and increases the fraction of supercoiled DNA in a cell-free assay in a concentration-dependent manner. Rubitecan inhibits the growth of A121 ovarian and H460 lung cancer cells (IC50s = 4 and 2 nM, respectively). It also inhibits the growth of doxorubicin-susceptible and -resistant MCF-7 breast cancer cells (IC50s = 2 and 3 nM, respectively). Rubitecan (4 mg/kg twice per week) reduces tumor growth in a U937 leukemia mouse xenograft model.
추가 설명
정의ChEBI: A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.
관련 반응
7건
화합물 노트
불러오는 중…