Synthetic pathway- Mechlorethamine, 6-Mercaptopurine

Description

1. synthetic pathway- Mechlorethamine, 6-Mercaptopurine
2. 6-Mercaptopurine (6-MP)
3. IUPAC nomenclature
4. 3,7-dihydropurine-6-thione

5. Methods of Synthesis

   In the presence of tetraline as a solvent, hypoxanthine is heated along with 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)

   1. Nitrogen Mustards  Mechlorethamine (Mustine HCl)  Cyclophosphamide,  Ifosfamide,  Chlorambucil,  Melphalan 2.Ethylenimine  Thio-TEPA 3.Alkyl sulfonate  Busulfan 4.Nitrosoureas  Carmustine (BCNU),  Lomustine (CCNU) 5.Triazine  Dacarbazine (OTIC)
   2. 6.  Also knows as Mustine HCl.  1st nitrogen mustard ; highly reactive ; local vesicant .  Administration only by IV route .  Nausea , vomiting , haemodynamic 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 interval).