Synthesis and Uses of Amsacrine and Prochlorperazine

1. Synthesis and Uses of Amsacrine and Prochlorperazine
Presented by
• Kamal Lochan Misra
• Roll No. 22MPH020
• M. Pharm 1st Semester
• Department of Pharmaceutical Chemistry
• Institute of Pharmacy and Technology, Salipur, Cuttack

2. CONTENT
 Introduction of Amsacrine
 Synthesis of Amsacrine
 Uses of Amsacrine
 Introduction of Prochlorperazine
 Synthesis of Prochlorperazine
 Uses of Prochlorperazine

3. AMSACRINE
• Anticancer drug first synthesized in 1970 by Professor Cain and colleagues.
• Also called as amsidine.
• Effective in treating acute leukemias and malignant lymphomas, but has poor activity in
treating solid tumors.
• Major limitation of amsacrine analog is that it is highly lipophilic, making it
nonconductive to intravenous administration.
• Produces consistent but acceptable myelosuppression and cardio toxic effects.

4. Molecular Formula: C21H19N3O3S
Molecular Weight: 393.5
IUPAC NAME : n-[4-(9- acridinyl amino)-3-methoxyphenyl]methane sulphonamide

5. Vardanyan RS., Hruby VJ., 30-Antineoplastics, Synthesis of essential drugs, 2006, 389-418
Synthesis:1

6. Current Patent Assignee: HENAN UNIVERSITY - CN104402818, 2016, BLocation in patent: Paragraph 0035; 0048; 0049
Synthesis:2

7. Uses:
It is a potential antineoplastic agent used to treat liquid cancers or blood cancers, solid
cancer including refractory acute leukemias, non-lymphocytic leukemias, Hodgkin’s
disease, non-Hodgkin’s lymphomas, and head and neck cancers.
Side Effects:
It carries high risk of cardiotoxicity in patients, and nausea, vomiting, and diarrhea, Ulcer
are common side effects

8. PROCHLORPHERAZINE
Introduction
• It was approved for medical use in the United States in 1956.
• Available as a generic medication In 2020, it was the 355th most commonly prescribed
medication in the United States
• Prochlorperazine, formerly sold under the brand name Compazine.
• A synthetic compound derived from Phenothiazine.
• It is thought to exert its antipsychotic effects by dopamine receptors.
• Available as tablets, suppositories, and in an injectable form.
• As of September 2017 it was marketed under the trade names Ametil, Antinaus, Buccastem,
Bukatel, and Chlormeprazine.

9. • Molecular Formula - C20H24ClN3S
• IUPAC Name - 2-chloro-10-[3-(4-methyl-1 piperazinyl)propyl]-10H-phenothiazine
• Molecular Mass - 373.94 g·mol−1
• Structure -

10. NaNH2
+
R. J. Horclois, GB 780193; DE 1037561; FR 1167627; US 2902484
Synthesis:1

11. +
R. J. Horclois, GB 780193; DE 1037561; FR 1167627; US 2902484
NaOH, Toluene, 15h
Reflux
Synthesis:2

12. Midha.K, Journal of Pharmaceutical Sciences, 72, 1983, 702-703
Synthesis:3

13. Uses:
• It is used to prevent vomiting caused by chemotherapy and radiation therapy.
• However, it is generally intravenously used to treat migraine.
• In the UK prochlorperazine maleate has been used for labyrinthitis.
Side Effects:
• Prochlorperazine can also cause a life-threatening condition called Neuroleptic malignant syndrome
(NMS).
• Rather than this, some include high fever, stiff muscles, neck muscle spasms, irregular pulse or blood
pressure, fast heart rate (tachycardia), sweating, abnormal heart rhythms (arrhythmias)

14. Thank you