РУБИТЕКАН

Description

A nitro derivative of camptothecin, an alkaloid obtained from the bark and leaves of Camptotheca acuminata. Pentacyclic framework of 1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione with ethyl and hydroxyl groups at C-4 and a nitro group in the aromatic ring. Refers to topoisomerase I inhibitors. Systematic name on the card: 4-ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione.

Basic Attributes

• CAS No.: 104195-61-1 (corresponds to 10-nitrocamptothecin in registries)
• Chemical formula: C₂₀H₁₅N₃O₆
• Molecular weight: 393.35000
• Exact mass: 393.09608521 g/mol
• NSC Number: 369394
• PSA Specifications: 127.24000
• XLogP3: 2.51100

Physico-chemical characteristics

• Density: 1.63 g/cm³
• Boiling point: 816.3 °C
• Flash point: 447.5 °C

About position nomenclature

The card combines similar substances; when ordering, the name requires clarification. The name “rubitecan” is assigned to 9-nitrocamptothecin, its registration number is 91421-42-0, the development code is RFS 2000, and the trade name is Orathecin. The number 104195-61-1 indicated in the card corresponds to 10-nitrocamptothecin in the databases. Both isomers have the same gross formula C₂₀H₁₅N₃O₆ and molecular weight 393.35, which is consistent with the values ​​​​given in the card. The list of synonyms for the position also includes 9-aminocamptothecin - this is a different compound with a different formula.

Mechanism of action

The target is topoisomerase I. The substance stabilizes the enzyme complex with DNA and prevents the rejoining of single-strand breaks that occur during replication. The accumulation of unrepaired breaks stops the synthesis of DNA and RNA in dividing cells. Like other camptothecins, the compound contains an α-hydroxylactone ring, the state of which determines the activity: in an alkaline environment, the lactone opens to the carboxylate form.

Scope of application

• research inhibitor of topoisomerase I in oncology work
• reference substance for the analysis of camptothecin and its derivatives
• object of research on antitumor activity and dosage forms, including liposomal
• substance for preclinical and clinical programs on solid tumors

Storage and handling conditions

There are no transport codes or GHS classification on the card. As a cytotoxic substance, it requires handling according to the rules for antitumor substances: work in a fume hood or box, gloves, gown, respiratory and eye protection, avoiding dust formation. Keep the container tightly closed, store in a cool, dry place without access to light: nitro-substituted camptothecins are photosensitive, and the lactone cycle is hydrolyzed in a humid and alkaline environment. Collect waste separately as cytotoxic.