Pr 104
기본 정보
- CAS
851627-62-8- 표준 SMILES
CS(=O)(=O)OCCN(CCBr)c1c(C(=O)NCCOP(=O)(O)O)cc([N+](=O)[O-])cc1[N+](=O)[O-]- InChIKey
GZSOKPMDWVRVMG-UHFFFAOYSA-N- 분자식
- C14H20BrN4O12PS
- 평균 분자량
- 579.3 g/mol
- 단동위원소 질량
- 577.97194
개요
Nitrogen Mustard Prodrug PR-104 is a non-toxic, small-molecule, hypoxia-activated, 3,5-dinitrobenzamide nitrogen mustard pre-prodrug with potential antitumor activity. Upon intravenous administration, PR-104 is converted by systemic phosphatases to the alcohol intermediate PR-104A, which is reduced to form the active DNA-crosslinking mustard species hydroxylamine PR-104H intracellularly under hypoxic conditions. PR-104H specifically crosslinks hypoxic tumor cell DNA, resulting in the inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis in susceptible hypoxic tumor cell populations while sparing normoxic tissues.
이름 및 식별자
- 우선 이름
- Pr 104
- IUPAC
- 2-[N-(2-bromoethyl)-2,4-dinitro-6-(2-phosphonooxyethylcarbamoyl)anilino]ethyl methanesulfonate
- 영어명
- PR104
- 분자식
- C14H20BrN4O12PS
- 분자량
- 579.27
이름 및 동의어
PR-104851627-62-8PR 104V16D2ZT7DT((2-BROMOETHYL)-2,4-DINITRO-6-(((2-(PHOSPHONOOXY)ETHYL)AMINO)-CARBONYL)ANILINO)ETHYL METHANESULPHONATERefChem:868364(2-((2-((2-bromoethyl)(2-(methanesulfonyloxy)ethyl)amino)-3,5-dinitrophenyl)formamido)ethoxy)phosphonic acidPR104UNII-V16D2ZT7DT2-((2-Bromoethyl)(2,4-dinitro-6-((2-(phosphonooxy)ethyl)carbamoyl)phenyl)amino)ethyl methanesulfonatePR-104/104A2-[(2-bromoethyl)(2,4-dinitro-6-{[2-(phosphonooxy)ethyl]carbamoyl}phenyl)amino]ethyl methanesulfonate
이름 더 보기
GZSOKPMDWVRVMG-UHFFFAOYSA-NBenzamide, 2-[(2-bromoethyl)[2-[(methylsulfonyl)oxy]ethyl]amino]-3,5-dinitro-N-[2-(phosphonooxy)ethyl]-
2-[N-(2-bromoethyl)-2,4-dinitro-6-(2-phosphonooxyethylcarbamoyl)anilino]ethyl methanesulfonateBenzamide, 2-((2-bromoethyl)(2-((methylsulfonyl)oxy)ethyl)amino)-3,5- dinitro-N-(2-(phosphonooxy)ethyl)-C14H20BrN4O12PSSCHEMBL367963orb1693859CHEMBL4297321PR 104 [WHO-DD]SCHEMBL31060232
물성
구조 계산 물성
- XLogP
- -0.6
- 극성 표면적
- 242 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 13
- 회전 가능 결합 수
- 12
- 무거운 원자 수
- 33
- 형식 전하
- 0
- 복잡도
- 839
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
물리화학적 성질
- 저장 조건
- 4 °C, · 4°C, away from moisture and light
- 물리적 상태
- Solid
- 색상
- White to yellow
화학 및 산업
약리 정보
Mechanism of Action
PR-104 is a novel hypoxia-activated DNA cross-linking agent with marked activity against human tumor xenografts, both as monotherapy and combined with radiotherapy and chemotherapy. Upon intravenous administration, PR-104 is converted by systemic phosphatases to the alcohol intermediate PR-104A, which is reduced to form the active DNA-crosslinking mustard species hydroxylamine PR-104H intracellularly under hypoxic conditions. PR-104H specifically crosslinks hypoxic tumor cell DNA, resulting in the inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis in susceptible hypoxic tumor cell populations while sparing normoxic tissues.
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