| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
Rifamycin (CB-0111; NSC-133100; Rifocin; Rifocyn; Aemcolo) belongs to the group of naturally occurring antibiotics called Rifamycin, which are isolated from the bacterium Amycolatopsis rifamycinica. They inhibit prokaryotic DNA-dependent RNA synthesis and protein synthesis, thereby blocking RNA-polymerase transcription initiation. Anti-gram-positive bacterial and mycobacterium activities.
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
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. 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. The reported volume of distribution after measured after a dosage of 250 mg of rifamycin is 101.8 L. The reported clearance when a dose of 250 mg of rifamycin was administered is 23.3 L/h. Metabolism / Metabolites When absorbed, rifamycin is mainly metabolzied in hepatocytes and intestinal microsomes to a 25-deacetyl metabolite. Biological Half-Life The reported half-life when a dose of 250 mg of rifamycin was administered is 3 h. |
|---|---|
| Toxicity/Toxicokinetics |
Hepatotoxicity
In prelicensure controlled trials in patients with traveler’s diarrhea, rates of serum ALT elevations were similar in subjects treated with rifamycin compared to placebo or comparator agent (ciprofloxacin) and no participants developed clinically apparent liver injury. Since its approval, there have been no published reports of hepatotoxicity attributed to rifamycin. Because of its minimal absorption rifamycin is considered unlikely to cause liver injury. Likelihood score: E (unlikely cause of clinically apparent liver injury). Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Rifamycin is negligibly absorbed orally and used only for gastrointestinal infections. It is not likely to reach the breastmilk or bloodstream of the infant or cause any adverse effects in breastfed infants after maternal use. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. Protein Binding The protein binding of rifamycin is of about 80-95%. |
| Additional Infomation |
Pharmacodynamics
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. |
| Molecular Formula |
C37H47NO12
|
|---|---|
| Molecular Weight |
697.78
|
| Exact Mass |
697.31
|
| CAS # |
6998-60-3
|
| Related CAS # |
Rifamycin sodium;14897-39-3
|
| PubChem CID |
6324616
|
| Appearance |
Typically exists as solid at room temperature
|
| Melting Point |
300° (dec 140°)
|
| LogP |
4.892
|
| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
12
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
50
|
| Complexity |
1330
|
| Defined Atom Stereocenter Count |
9
|
| SMILES |
[C@H]1(C)[C@@H]([C@@H]([C@H](C=CO[C@]2(OC=3C(C2=O)=C4C(C(=C(NC(C(=CC=C[C@H](C)[C@@H]([C@@H](C)[C@H]1O)O)C)=O)C=C4O)O)=C(C3C)O)C)OC)C)OC(=O)C
|
| InChi Key |
HJYYPODYNSCCOU-ODRIEIDWSA-N
|
| InChi Code |
InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
|
| Chemical Name |
[(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
|
| Synonyms |
Rifamycin Rifocin CB0111Rifocin RifocynAemcolo CB-0111NSC-133100CB-01-11 CB01-11 CB 01-11 CB 0111 NSC 133100Rifamicine SV Rifamycin SV Rifomycin SV
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4331 mL | 7.1656 mL | 14.3312 mL | |
| 5 mM | 0.2866 mL | 1.4331 mL | 2.8662 mL | |
| 10 mM | 0.1433 mL | 0.7166 mL | 1.4331 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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