91421-42-0

Basic information

• Product Name: Rubitecan
• Synonyms: 9-NITRO-CPT;9-NITRO-20(S)-CAMPTOTHECIN;(4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione;CAMPTOTHECIN, 9-NITRO-20(S)-;RUBETICAN;RUBITECAN;orathecin;Rubitecane
• CAS NO: 91421-42-0
• Molecular Formula: C₂₀H₁₅N₃O₆
• Molecular Weight: 393.35
• Product Categories: API;Intermediates & Fine Chemicals;Pharmaceuticals;Anti-cancer & immunity
• Mol File: 91421-42-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 182-186°C
• Boiling Point: 816.3 °C at 760 mmHg
• Flash Point: 106℃
• Appearance: Yellow amorphous powder
• Density: 1.63
• Vapor Pressure: 3.53E-28mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: Room temp
• Solubility: DMSO, Chloroform, Methanol
• PKA: 11.16±0.20(Predicted)
• Merck: 14,8288
• CAS DataBase Reference: Rubitecan(CAS DataBase Reference)
• NIST Chemistry Reference: Rubitecan(91421-42-0)
• EPA Substance Registry System: Rubitecan(91421-42-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: UQ0493300
• Hazardous Substances Data: 91421-42-0(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 91421-42-0 differently. You can refer to the following data:
1. Rubitecan, marketed by Supergen as Orathecin, is a promising oral treatment for solid melanoma, prostate, breast, ovarian, and other cancers, as well as leukemia. It is a derivative of camptothecin, a topoisomerase inhibitor known from Chinese Traditional Medicine. It selectively targets the critical S-stage of cellular reproduction – particularly in acidic environments, as in many cancer cells – relaxing DNA supercoiling and generating lethal breaks in the DNA. Due to insolubility, its biological delivery mechanism is not yet effective, and it has not been approved for clinical use.
2. Rubitecan 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.

Reference

https://www.sciencedirect.com/topics/medicine-and-dentistry/rubitecan https://en.wikipedia.org/wiki/Rubitecan https://en.wikipedia.org/wiki/Topoisomerase_inhibitor https://en.wikipedia.org/wiki/Camptothecin#cite_note-Y.Pommier_2003-14 https://www.ncbi.nlm.nih.gov/pubmed/1995300

Uses

Different sources of media describe the Uses of 91421-42-0 differently. You can refer to the following data:
1. Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic
2. Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic.

Definition

ChEBI: 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.

InChI:InChI=1/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

Upstream product

• 7689-03-4 camptothecin 
• 164159-93-7 Methanesulfonic acid (S)-4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 172917-94-1 Benzenesulfonic acid (S)-4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 164159-99-3 9-nitro-10-(p-toluenesulfonyl)camptothecin 
• 172917-95-2 Naphthalene-1-sulfonic acid (S)-4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 151585-77-2 2,6-dinitrobenzaldehyde ethylene acetal 
• 151585-78-3 2-amino-6-nitrobenzaldehyde ethylene acetal 
• 606-31-5 2,6-dinitrobenzaldehyde 
• 870527-52-9 1,2,6,7-tetrahydro-(20S)-camphthotecine 
• 104267-73-4 9-nitro-10-hydroxy-20(S)-camptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 172917-96-3 4-nitro-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 164159-91-5 4-fluoro-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 909094-10-6 4-bromo-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 

Downstream Products

• 7689-03-4 camptothecin 
• 39026-92-1 9-methoxycamptothecin 
• 67656-30-8 10-hydroxycamptothecin 
• 91421-43-1 9-amino-20(S)-camptothecin 

Relevant articles and documents

A practical regiospecific synthesis of 9-nitrocamptothecin

9-Nitrocamptothecin has shown potent antitumor activity against many types of human cancers. A practical scale-up procedure for this compound is reported by selective reduction of corresponding sulfonate. Georg Thieme Verlag Stuttgart.

Urea-mediated regioselective nitration of (20s)-camptothecin

A facile and efficient procedure for the regioselective nitration of (20S) camptothecin, using urea mediated reagent system under relatively mild experimental conditions, yielding promising anticancer drug 9-nitro-(20S)- camptothecin in 40% yield with purity of 94.5% (on HPLC) is being reported.

Aromatic esters of camptothecins and methods to treat cancers

Aromatic camptothecin ester compounds having the formula: are described as well as formulations containing the compounds. Methods of treating cancer and/or tumors are also disclosed.