86639-62-5

Basic information

• Product Name: 9-Nitrocamptothecin
• Synonyms: RUBETICAN;CAMPTOTHECIN, 9-NITRO-20(S)-;9-NITRO-CPT;9-Nitrocamptothecin (Rubitecan);9-Nitrocamptothecin;4α-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;9-Nitro-20(S)-camptothecine;(S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 86639-62-5
• Molecular Formula: C₂₀H₁₅N₃O₆
• Molecular Weight: 393.35
• Product Categories: Natural Anti-cancer Medical Materials and It's Derivatives
• Mol File: 86639-62-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 827.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.63±0.1 g/cm3(Predicted)
• PKA: 11.17±0.20(Predicted)
• CAS DataBase Reference: 9-Nitrocamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Nitrocamptothecin(86639-62-5)
• EPA Substance Registry System: 9-Nitrocamptothecin(86639-62-5)

Safety Data

• Hazardous Substances Data: 86639-62-5(Hazardous Substances Data)

Usage

General Description

9-Nitrocamptothecin is a semi-synthetic derivative of camptothecin, a natural product found in the Chinese tree Camptotheca acuminate. It is a potent inhibitor of topoisomerase I, an enzyme involved in DNA replication and transcription. This inhibition leads to the accumulation of DNA strand breaks and ultimately induces cell death in cancer cells. 9-Nitrocamptothecin has demonstrated anti-tumor activity in preclinical studies and has been investigated as a potential treatment for various types of cancer, including lung, breast, and ovarian cancers. Its unique chemical structure and mechanism of action make it a promising candidate for further development as a cancer therapy.

Upstream product

• 56008-61-8 2-amino-5-nitrobenzaldehyde 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 86639-72-7 (4R,5bS,11aS)-4-Ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione 
• 86639-48-7 Camptothecin 1-oxide 
• 53544-22-2 1,2,6,7-tetrahydrocamptothecin 
• 7689-03-4 camptothecin 

Downstream Products

• 86639-63-6 10-amino-20(S)-camptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 19685-10-0 10-methoxycamptothecin 

Relevant articles and documents

Plant Antitumor Agents. 30. Synthesis and Structure Activity of Novel Camptothecin Analogs

A large number of camptothecin (CPT) analogs have been prepared in the 20S, 20RS, and 20R configurations with a number of ring A substituents.Topoisomerase I (T-I) inhibition data (IC50) have been obtained by standard procedures.In general, substitution at the 9 or 10 positions with amino, halogeno, or hydroxyl groups in compounds with 20S configuration results in compounds with enhanced T-1 inhibition.Compounds in the 20RS configuration were less active in vitro and in vivo and those in the 20R configuration were inactive.Compounds with 10,11-methylenedioxy substitution on ring A displayed a marked increase in potency in the T-I inhibition assay.The activities of some of the analogs as determined in a variety of in vivo assays including the L-1210 mouse leukemia assay were, in general, in accord with T-I inhibition.A number of water-soluble analogs such as 20-glycinate esters, 9-glycinamides, or hydrolyzed lactone salts were prepared and tested in in vitro and in vivo assays.In general, these compounds were less active than CPT both in terms of T-I inhibition and life prolongation in the L-1210 assay.However, certain 20-glycinate esters showed good in vivo activity after iv administration.