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1. Rifamycins
2. Rifomycin
3. Rifomycins
1. Rifamycin Sv
2. Rifocin
3. Rifamicine Sv
4. Rifomycin Sv
5. Rifamicina
6. Rifamycine
7. Rifamycinum
8. Rifocyn
9. 6998-60-3
10. Cb-01-11
11. Aemcolo
12. Du69t8zzpa
13. M-14
14. Chebi:29673
15. 6998-60-3 (free Acid)
16. 15105-92-7
17. Rifamycin Sv, An Antibiotic Produced By Certain Strains Of Streptomyces Mediterranei, Or The Same Substance Produced By Any Other Means
18. Rifamycine [inn-french]
19. Rifamycinum [inn-latin]
20. Rifamicina [inn-spanish]
21. (7s,9e,11s,12r,13s,14r,15r,16r,17s,18s,19e,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl Acetate
22. [(7s,9e,11s,12r,13s,14r,15r,16r,17s,18s,19e,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] Acetate
23. Rifomycin
24. Einecs 230-273-3
25. Unii-du69t8zzpa
26. Tuborin
27. Rifamycin-sv
28. Nsc133100
29. Rifamycin [usan:inn:ban:dcf]
30. Rifamycin [inn]
31. Rifamycin (usan/inn)
32. Rifamycin [usan]
33. Rifamycin Sv [mi]
34. Rifamycin [who-dd]
35. Schembl151824
36. Chembl437765
37. Gtpl4570
38. Dtxsid1032014
39. Rifamycin Sv [ep Impurity]
40. Bdbm50391000
41. Lmpk05000005
42. Akos024281286
43. Zinc169633673
44. Db11753
45. 2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2h)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
46. Rifaximin Impurity C [ep Impurity]
47. D02549
48. Sr-01000872597
49. Sr-01000872597-1
50. (pentahydroxy-methoxy-heptamethyl-dioxo-[?]yl) Acetate
51. Q26270990
52. (2s,12z,14e,16s,17s,18r,19r,20r,21s,22r,23s,24e)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl Acetate
53. (7s,11s,12r,13s,14r,15r,16r,17s,18s,19z,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl Acetate
54. (7s,11s,13s,17s,18s,12r,14r,15r,16r)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7 ,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1<4, 7>.0<5,28>]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl Acetate
55. 2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2h)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2s,16s,17s,18r,19r,20r,21s,22r,23s)-
56. 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2h)-dione 21-acetate
| Molecular Weight | 697.8 g/mol |
|---|---|
| Molecular Formula | C37H47NO12 |
| XLogP3 | 4.9 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 3 |
| Exact Mass | 697.30982593 g/mol |
| Monoisotopic Mass | 697.30982593 g/mol |
| Topological Polar Surface Area | 201 Ų |
| Heavy Atom Count | 50 |
| Formal Charge | 0 |
| Complexity | 1330 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Rifamycin is indicated for the treatment of adult patients with travelers' diarrhea caused by noninvasive strains of _E. coli_. The status of the disease should not be complicated by fever or blood in the stool. To prevent drug-resistant bacteria, it is important to mention that the use of rifamycin for this indication should be only done in cases where the infection is proven or strongly suspected to be caused by bacteria. Travallers' diarrhea is very common problem affecting 20-60% of the travellers and it is defined as an increase in frequency of bowel movements to three or more loose stools per day during a trip abroad. This condition is rarely life threatening but in severe cases it can produce dehydration and sepsis. The most common cause of travellers' diarrhea is a pathogen and from the pathogens identified, bacteria is the most common cause followed by norovirus, rotavirus and similar viruses.
FDA Label
Treatment of acute infectious diarrhoea
Treatment of acute infectious diarrhoea
Rifamycin is known to be effective against Gram-positive and Gram-negative pathogens and mycobacteria. It is very effective against _E. coli_ reporting a MIC90 of 64-128 mcg/ml without showing cross-resistance with other antimicrobial agents. The specific indication of rifamycin is extremely important as ther were previous reports that indicated a high risk factor in the generation of resistant _E. coli_ strains in patients with inflammatory bowel disease. In clinical trials, rifamycin was tested in a randomized clinical trial of travellers' coming from Mexico and Guatemala. In this trial, rifamycin was proven to significantly reduce the symptoms of travellers' diarrhea.
Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
J04AB03
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
A - Alimentary tract and metabolism
A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents
A07A - Intestinal antiinfectives
A07AA - Antibiotics
A07AA13 - Rifamycin
D - Dermatologicals
D06 - Antibiotics and chemotherapeutics for dermatological use
D06A - Antibiotics for topical use
D06AX - Other antibiotics for topical use
D06AX15 - Rifamycin
J - Antiinfectives for systemic use
J04 - Antimycobacterials
J04A - Drugs for treatment of tuberculosis
J04AB - Antibiotics
J04AB03 - Rifamycin
S - Sensory organs
S01 - Ophthalmologicals
S01A - Antiinfectives
S01AA - Antibiotics
S01AA16 - Rifamycin
S - Sensory organs
S02 - Otologicals
S02A - Antiinfectives
S02AA - Antiinfectives
S02AA12 - Rifamycin
Absorption
Rifamycin has a very poor absorption and thus, the generation of an oral modified-release formulation using the technology of the multi-matrix structure was required for the generation of the FDA approved product. This preparation allows the delivery of the active ingredient in the distal small bowel and colon without interfering with the flora in the upper gastrointestinal tract. The multi-matrix is made by a lipophiic matrix surrounded in a hydrophilic matrix which allows for the protection of the active ingredient from dissolution in the intestinal aqueous fluids before it arrives in the cecum. All this matrix is surrounded by a gastro-resistant polymer that only desintegrate in a pH lower than 7. All this administration-customed formulation allows for a bioavailability of <0.1% and the plasma concentrations are reported to be of <2 ng/ml in patients receiving a dose of 400 mg. This confirms that the site of action of rifamycin stays in the small intestine and colon which prevents the need for dose adjustments in special populations as well as systemic drug interactions. The reported Cmax, tmax, AUC and mean residence time after a dosage of 250 mg of rifamycin is 36 mg/L, 5 min, 11.84 mg.h/L and 0.49 h respectively.
Route of Elimination
From the administered dose, 18%, 50% and 21% is recovered in feces during the first 24, 48 and 72h after administration. This will represent about 90% of the administered dose eliminated by the feces while the urinary secretion is negligible.
Volume of Distribution
The reported volume of distribution after measured after a dosage of 250 mg of rifamycin is 101.8 L.
Clearance
The reported clearance when a dose of 250 mg of rifamycin was administered is 23.3 L/h.
When absorbed, rifamycin is mainly metabolzied in hepatocytes and intestinal microsomes to a 25-deacetyl metabolite.
The reported half-life when a dose of 250 mg of rifamycin was administered is 3 h.
Rifamycins, as well as all the other members of this group, present an antibacterial mechanism of action related to the inhibition of RNA synthesis. This mechanism of action is done by the strong binding to the DNA-dependent RNA polymerase of prokaryotes. The inhibition of the RNA synthesis is thought to be related with the initiation phase of the process and to involve stacking interactions between the naphthalene ring and the aromatic moiety in the polymerase. As well, it has been suggested that the presence of zinc atoms in the polymerase allows for the binding of phenolic -OH groups of the naphthalene ring. In eukaryotic cells, the binding is significantly reduced making them at least 100 to 10,000 times less sensitive to the action of rifamycins. The members of the rifamycin family present the same mechanism of action and the structural modifications are usually related to pharmacokinetic properties as well as to the interaction with eukaryotic cells.
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