Rifaximin EP Impurity B
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| Category | Antibiotics |
| Catalog number | BBF-02631 |
| CAS | 13929-35-6 |
| Molecular Weight | 755.80 |
| Molecular Formula | C39H49NO14 |
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Description
Rifaximin EP Impurity B is an impurity of Rifaximin. Rifaximin is a semi-synthetic, nonsystemic antibiotic derived from rifamycin SV with antibacterial activity. It also acts as a pregnane X receptor (PXR) agonist. It is approved for the treatment of traveler's diarrhea, irritable bowel syndrome, and hepatic encephalopathy.
Specification
| Synonyms | Rifamycin B; Nancimycin; 4-O-(Carboxymethyl)rifamycin; 4-O-(Carboxymethyl)rifamycin; [(1,2-Dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]acetic Acid 21-Acetate |
| Storage | Store at -20°C |
| IUPAC Name | 2-[[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-13-acetyloxy-2,15,17,29-tetrahydroxy-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-27-yl]oxy]acetic acid |
| Canonical SMILES | CC1C=CC=C(C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)OCC(=O)O)C |
| InChI | InChI=1S/C39H49NO14/c1-17-11-10-12-18(2)38(49)40-24-15-26(51-16-27(42)43)28-29(34(24)47)33(46)22(6)36-30(28)37(48)39(8,54-36)52-14-13-25(50-9)19(3)35(53-23(7)41)21(5)32(45)20(4)31(17)44/h10-15,17,19-21,25,31-32,35,44-47H,16H2,1-9H3,(H,40,49)(H,42,43)/b11-10+,14-13+,18-12-/t17-,19+,20+,21+,25-,31-,32+,35+,39-/m0/s1 |
| InChI Key | SQTCRTQCPJICLD-KTQDUKAHSA-N |
Properties
| Appearance | Yellow Prismatic Needle Crystal |
| Application | A Rifamycin (R508200) derivative as antibacterial agent. |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 907.1°C at 760 mmHg |
| Density | 1.37 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated) |
Reference Reading
1. Update on the Management of Diarrhea-Predominant Irritable Bowel Syndrome: Focus on Rifaximin and Eluxadoline.
Rivkin A1, Rybalov S2. Pharmacotherapy. 2016 Mar;36(3):300-16. doi: 10.1002/phar.1712. Epub 2016 Mar 11.
Diarrhea-predominant irritable bowel syndrome (IBS-D) is one of the most common diagnoses made by gastroenterologists. Current pharmacologic treatments for IBS-D include fiber supplements, antidiarrheal over-the-counter medications, probiotics, antispasmodics, antidepressants, and a 5-hydroxytryptophan 3 receptor antagonist. All of these options have limited efficacy in managing IBS-D. Rifaximin, a nonabsorbable antibiotic, has been evaluated in patients with IBS-D. In two randomized, double-blind, placebo-controlled phase III trials evaluating rifaximin 550 mg by mouth 3 times/day for 14 days, the primary efficacy end point was achieved by 9% more patients randomized to the rifaximin group compared with placebo (40.7% vs 31.7%, p<0.001, number needed to treat ~11). The primary efficacy end point was defined as the proportion of patients having adequate relief of global IBS symptoms for at least 2 of the 4 weeks during the primary follow-up period (weeks 3-6).
2. Rifaximin preserves intestinal microbiota balance in patients undergoing allogeneic stem cell transplantation.
Weber D1, Oefner PJ2, Dettmer K2, Hiergeist A3, Koestler J3, Gessner A3, Weber M4, Stämmler F5, Hahn J1, Wolff D1, Herr W1, Holler E1. Bone Marrow Transplant. 2016 Mar 21. doi: 10.1038/bmt.2016.66. [Epub ahead of print]
Intestinal dysbiosis has been associated with acute gastrointestinal GvHD and poor outcome following allogeneic stem cell transplantation (ASCT). To assess the effect of a switch in 2012 from ciprofloxacin/metronidazole to rifaximin for gut decontamination on intestinal microbiota composition and ASCT outcome, we retrospectively analyzed 394 patients receiving ASCT from September 2008 through June 2015. In 131 and 90 patients, respectively, urinary 3-indoxyl sulfate levels and intestinal enterococcal load were measured before conditioning and weekly within the first 28 days after ASCT. The use of rifaximin correlated with lower enterococcal positivity (6.9 vs 21.9%, P=0.05) and higher urinary 3-indoxyl sulfate concentrations (10.5 vs 4.6 μmoL/mmoL crea, P<0.001) after ASCT. Patients on rifaximin showed lower 1-year transplant-related mortality (P=0.04) and higher overall survival (P=0.008). Treatment of infectious complications with systemic antibiotics did not abrogate the beneficial effects of rifaximin on intestinal microbiota composition in the early course of ASCT and outcome.
3. Development of an experimental rat model of hyperammonemic encephalopathy and evaluation of the effects of rifaximin.
Tamaoki S1, Suzuki H2, Okada M3, Fukui N4, Isobe M5, Saito T6. Eur J Pharmacol. 2016 May 15;779:168-76. doi: 10.1016/j.ejphar.2016.03.024. Epub 2016 Mar 12.
Hepatic encephalopathy (HE) is a neuropsychiatric syndrome associated with hepatic dysfunction. However, the precise mechanism of HE is unclear. To elucidate the mechanism, we developed a new rat model of HE with coma using a combination of subcutaneous splenic transposition, partial hepatectomy and portal vein stenosis. In this model, blood ammonia levels increase in the postcaval vein over time and markedly increase in the cerebrospinal fluid (CSF). The distribution of ammonia in the various blood vessels in the HE model suggests that the origin of peripheral blood and CSF ammonia is the mesenteric veins that drain blood from the gastrointestinal tract. Behavioral analysis revealed decreased pain response, increased passivity, and decreased pinna and corneal reflexes, followed by the development of coma. The development of coma in this model was frequent and reproducible. Increased S100 calcium-binding protein B (S100B: a biomarker for brain injury) in venous blood, as well as damaged brain tissue, increased intracranial pressure and cerebral edema were observed in rats with coma.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
