918633-87-1

Basic information

• Product Name: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
• Synonyms: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester;TH 302;EvofosfaMide;TH-302, >=98%;TH-302 (Evofosfamide);(1-methyl-2-nitro-1H-imidazol-5-yl)methylN,N'-bis(2-bromoethyl)diamidophosphate;EOS-61724;Evofosfamide(TH 302)
• CAS NO: 918633-87-1
• Molecular Formula: C9H16Br2N5O4P
• Molecular Weight: 449.036201
• Product Categories: TH-302
• Mol File: 918633-87-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 565.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.97
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 0.34±0.70(Predicted)
• CAS DataBase Reference: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester(918633-87-1)
• EPA Substance Registry System: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester(918633-87-1)

Safety Data

• Hazardous Substances Data: 918633-87-1(Hazardous Substances Data)

Usage

Description

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester, also known as TH-302, is a hypoxia-activated prodrug and DNA alkylating agent with anticancer activity. It is selectively cytotoxic to certain human cancer cells grown under hypoxic conditions.

Uses

Used in Oncology:
TH-302 is used as a hypoxia-activated prodrug for the treatment of various types of cancer, including non-small cell lung cancer (NSCLC), small cell lung cancer, melanoma, prostate cancer, and pancreatic cancer. It exhibits hypoxia-selective cytotoxicity and DNA damage in human cancer cells, leading to reduced survival and tumor growth inhibition.
Used in Cancer Research:
TH-302 is used as a research tool to study the effects of hypoxia on cancer cell growth and the mechanisms of hypoxia-activated prodrugs in cancer therapy. It helps researchers understand the role of hypoxia in cancer progression and develop new strategies for cancer treatment.

Upstream product

• 141025-16-3 N,N'-bis(2-bromoethyl)phosphorodiamidic acid 
• 39070-14-9 1-methyl-2-nitro-5-hydroxymethylimidazole 
• 40361-77-1 2-amino-1-methyl-1H-imidazole-5-carboxylic acid methyl ester 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 39070-13-8 ethyl 1-N-methyl-2-nitro-1H-imidazole-5-carboxylate 

Relevant articles and documents

Preparation method of evofosfamide

The invention relates to a synthetic method for preparing evofosfamide, namely N,N'-bis(2-bromoethyl)diaminophosphonic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester (I), and belongs to the field of organic synthesis. The synthetic method has the advantages of safe and stable route, convenient operation, easy purification, high yield and the like.

TH-302 SOLID FORMS AND METHODS RELATED THERETO

The present invention provides a new method for making TH-302 and solid forms thereof. The compound in its solid form is an effective anti-cancer agent and may be used in various pharmaceutical compositions, and are particularly effective for the treatment of cancer. The invention also provides a method for preparing such compounds and forms and for treating cancer in a mammal comprising the step of administering a therapeutically effective amount of a solid form of TH-302 thereof.

PHOSPHORAMIDATE ALKYLATOR PRODRUGS

Phosphoramidate alkylator prodrugs can be used to treat cancer when administered alone or in combination with one or more anti-neoplastic agents.