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

Rubitecan, marketed by Supergen as Orathecin, is a semisynthetic camptothecin derivative and a DNA topoisomerase I inhibitor. It is a promising oral treatment for various solid cancers, including melanoma, prostate, breast, ovarian, and leukemia, as well as other cancers. Rubitecan selectively targets the critical S-stage of cellular reproduction, particularly in acidic environments like those found in many cancer cells, relaxing DNA supercoiling and generating lethal breaks in the DNA. However, due to its insolubility, its biological delivery mechanism is not yet effective, and it has not been approved for clinical use.

Uses

Used in Oncology:
Rubitecan is used as an antineoplastic agent for inhibiting the growth of various cancer cells, such as A121 ovarian, H460 lung, and doxorubicin-susceptible and -resistant MCF-7 breast cancer cells. It demonstrates potent inhibitory effects on tumor growth, with IC50s of 4 nM, 2 nM, 2 nM, and 3 nM, respectively.
Used in Preclinical Cancer Research:
Rubitecan is used as a prodrug of 9-aminocamptothecin in preclinical cancer research, where it has shown to reduce tumor growth in a U937 leukemia mouse xenograft model when administered at a dosage of 4 mg/kg twice per week. This highlights its potential as a promising candidate for further development and investigation in cancer treatment.

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

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

• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 130133-53-8 2-amino-6-nitrobenzaldehyde 
• 7689-03-4 camptothecin 
• 172917-97-4 4-methoxy-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 
• 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 
• 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 
• 164159-93-7 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 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 104267-73-4 9-nitro-10-hydroxy-20(S)-camptothecin 
• 870527-52-9 1,2,6,7-tetrahydro-(20S)-camphthotecine 

Downstream Products

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