Synthetic Pathway: Mechlorethamine and 6-Mercaptopurine
Keywords: Download PDF, Notes, PPT, Synthetic Pathway, Mechlorethamine, 6-Mercaptopurine, Nitrogen Mustards, Purine Antagonist
This document provides detailed information on the synthetic pathways of Mechlorethamine and 6-Mercaptopurine, including their methods of synthesis, chemical properties, and therapeutic applications.
Synthetic Pathway: Mechlorethamine and 6-Mercaptopurine
6-Mercaptopurine (6-MP)
IUPAC Nomenclature: 3,7-dihydropurine-6-thione
Methods of Synthesis
In the presence of tetraline as a solvent, hypoxanthine is heated along with an excess of phosphorous pentasulfide. These are heated at 200 °C for a few hours.
Purine Antagonist: 6-Mercaptopurine
- These are highly effective antineoplastic drugs.
- 6-Mercaptopurine is the thiol analog of hypoxanthine.
- 6-MP and 6-thioguanine were the first purine analogs to prove beneficial for treating neoplastic disease (Azathioprine, an immunosuppressant, exerts its cytotoxic effects after conversion to 6-MP).
- Purine antagonist used for the treatment of malignant diseases (mercaptopurine, thioguanine), but also for immunosuppression (azathioprine) and antiviral chemotherapy (acyclovir, ganciclovir, vidarabine, and zidovudine).
Nitrogen Mustards
- Mechlorethamine (Mustine HCl)
- Cyclophosphamide
- Ifosfamide
- Chlorambucil
- Melphalan
Ethylenimine
- Thio-TEPA
Alkyl Sulfonate
- Busulfan
Nitrosoureas
- Carmustine (BCNU)
- Lomustine (CCNU)
Triazine
- Dacarbazine (OTIC)
Mechlorethamine (Mustine HCl)
- Also known as Mustine HCl.
- First nitrogen mustard; highly reactive; local vesicant.
- Administration only by IV route.
- Nausea, vomiting, hemodynamic changes (acute effects) are common side effects.
- Extravasation during IV injection may cause sloughing.
- Dose – 0.1 mg/Kg IV daily * 4 days (courses may be repeated at suitable intervals).
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