| Identification | Back Directory | [Name]
RIFAMYCIN SV | [CAS]
6998-60-3 | [Synonyms]
rifocin
rifocyn
RIFAMYCIN SV
rifamicinesv
RIFAMYCIN INN
Rifamycin S-Na
Rifamycin (9CI)
RIFAMYCIN SV USP/EP/BP
Rifaximin EP Impurity C
Rifaximin impurity C (EP)
Rifampicin Impurit Ⅱ:rifamycin SV
Rifampicin Impurit Ⅱ:rifamycin SV
19,21,25(29),26-octaen-13-yl acetate
Rifaximin EP Impurity C (Rifamycin SV)
Rifaximin Impurity 3 (Rifaximin EP Impurity C)
17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-21-acetate
RifamycinQ: What is
Rifamycin Q: What is the CAS Number of
Rifamycin Q: What is the storage condition of
Rifamycin Q: What are the applications of
Rifamycin
(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,
(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-(Acetyloxy)-5,6,9,17,19-pentahydroxy-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 | [EINECS(EC#)]
230-273-3 | [Molecular Formula]
C37H47NO12 | [MDL Number]
MFCD01741300 | [MOL File]
6998-60-3.mol | [Molecular Weight]
697.77 |
| Chemical Properties | Back Directory | [Melting point ]
300° (dec 140°) | [alpha ]
D20 -4° (methanol) | [Boiling point ]
701.9°C (rough estimate) | [density ]
1.2275 (rough estimate) | [refractive index ]
1.5350 (estimate) | [pka]
5.17±0.70(Predicted) |
| Hazard Information | Back Directory | [Uses]
Rifogal (Rifaximin EP Impurity C NA) is a antibacterial drug which functions by inhibiting bacterial RNA polymerase (RNAP), is an important part of the antibacteral armamentarium. Also, it is one of the few drugs in a multidrug regimens for treating lung disease (LD) due to Mycobacterium avium complex (MAC). | [Definition]
ChEBI: A member of the class of rifamycins that exhibits antibiotic and antitubercular properties. | [Pharmaceutical Applications]
The simplest rifamycin in clinical use, obtained by elimination of a glycolic moiety from rifamycin B. Formulated as sodium salt for parenteral administration. Also available for topical use. Its activity, general properties and pharmacokinetics are very similar to those of rifamide. It is orally absorbed and excreted mainly in the bile. Intramuscular doses of 250 mg produce mean plasma levels of about 2 mg/L. The plasma half-life is around 2 h.
In addition to uses similar to those of rifamide, it is administered topically in surgery and has been proposed for the treatment of synovitis by intra-articular injections. A topical preparation is used for application to wounds and bedsores. Cases of anaphylactic reactions have been reported after local administration of the drug. | [in vivo]
Rifamycin (5 mg/day; s.c.; 3 days a week) is effective in mice infected with M. tuberculosis, significantly reducing the number of viable bacteria in the body[4].
Rifamycin (12.5-25 mg/kg; peritoneal lavage) can improve the survival rate of rats with experimental intraperitoneal infection and significantly reduce the number of intraperitoneal bacteria and adhesion formation[6].
Rifamycin (5-40 mg/kg; esophageal gavage; once a day, 5 days a week; 4 weeks) shortens oral treatment duration in a mouse model of Mycobacterium ulcerans disease[8].
Rifamycin (0.1 mL; intraaural administration; twice daily; 10 days) does not cause hearing loss in adult or weanling rats[9].
Rifamycin (1 mg i.v. bolus followed by 4 mg i.v. infusion; 70 min) interferes with three major steps of Bile acid metabolism in rats with intravenous Sodium cholate (HY-N0324A) infusion, resulting in a significant decrease in bile acid uptake and excretion[10].
Rifamycin (10-160 mg/kg; s.c.; single dose) is approximately 11 times less effective than Metronidazole (HY-B0318) in a mouse Bacteroides fragilis thigh infection model[11].
| Animal Model: | Male Wistar rats (weight 200-250 g), cecal ligation puncture (CLP)-induced intra-abdominal infection model[6] | | Dosage: | 25 mg/kg, 12.5 mg/kg | | Administration: | Peritoneal lavage | | Result: | Improved survival from 50% in the control group to 91.7% in the 25 mg/kg group and 100% in the 12.5 mg/kg group.
Significantly reduced adhesion formation.
Showed a greater reduction in bacterial counts in peritoneal fluid (25 mg/kg).
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| [Purification Methods]
Rifamycin SV gives yellow-orange crystals from Et2O/pet ether or aqueous EtOH, is very soluble in MeOH, EtOH, Me2CO and EtOAc, and is less soluble in Et2O and HCO3-, but slightly soluble in H2O and pet ether. Its UV has max at 223, 314 and 445nm ( 1cm 586, 322 and 204) in phosphatebuffer pH 7. [NMR: Bergamini & Fowst Arzneim.-Forsch 15 951 1965.] |
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