Rifaximin

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Contents

Rifaximin (Xifaxan, Spiraxin, Zaxine, Rifacol)

Effective Against

Traveler's diarrhea and Hepatic encephalopathy

Rifaximin is an antibiotic that fights bacterial infection only in the intestines. Rifaximin works differently from other antibiotics because it passes through your stomach and into your intestines without being absorbed into your blood stream.

Cost

From Sigma-Aldrich: 88.20 USD (1g) or 352.50 USD (5g)







Reported Route of Synthesis

Image:090171-01-a.jpg

The reaction of rifamycin S (I) with pyridine perbromide (II) in 2-propanol/chloroform (70/30) mixture at 0 C gives 3-bromorifamicin S (III), which is then condensed with 2-amino-4-methyl -pyridine (IV) at 10 C. The o-quinoniminic compound (V) is then obtained. This compound is finally reduced with ascorbic acid.

de Angelis, L. L-105. Drugs of the Future 1982, 7(4) 260. US 262123

Cost of Intermediates:
Rifamycin SV sodium salt from Sigma-Aldrich: 255.50 USD (5g)
Rifamycin SV sodium salt from MP Biomedicals: 216.25 USD (5g)
Pyridine tribromide from Sigma-Aldrich: 86.1 USD (100g)
2-Amino-4-picoline (2-amino-4-methyl-pyridine) from Sigma-Aldrich: 26.4 USD (100g)
L-Ascorbic Acid from Sigma-Aldrich: 73.1 USD (100g)

Submitted Syntheses