| 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 extremely low absorption rates; therefore, to obtain FDA approval, a multi-matrix structure technology was required to develop an oral sustained-release formulation. This formulation delivers the active ingredient to the distal small intestine and colon without interfering with the flora of the upper digestive tract. The multi-matrix structure consists of a lipophilic matrix encapsulated within a hydrophilic matrix, protecting the active ingredient from dissolution by intestinal aqueous fluids before reaching the cecum. All these matrices are encapsulated in a layer of acid-resistant polymer that disintegrates only at a pH below 7. This formulation, designed for a specific route of administration, achieves bioavailability of less than 0.1%, with reported plasma concentrations below 2 ng/mL in patients taking a 400 mg dose. This confirms that rifamycin's site of action is in the small and colonic intestines, thus eliminating the need for dose adjustments in specific populations and avoiding systemic drug interactions. According to reports, after administration of 250 mg rifamycin, the peak plasma concentration (Cmax), time to peak concentration (tmax), area under the curve (AUC), and mean residence time were 36 mg/L, 5 min, 11.84 mg·h/L, and 0.49 h, respectively. Within 24, 48, and 72 hours post-administration, 18%, 50%, and 21% of the drug were excreted in feces, respectively. This represents approximately 90% of the administered dose excreted in feces, while urinary excretion was negligible. The volume of distribution after administration of 250 mg rifamycin was reported to be 101.8 L. The clearance after administration of 250 mg rifamycin was reported to be 23.3 L/h. Metabolism/Metabolites After absorption, rifamycin is primarily metabolized in hepatocytes and intestinal microsomes to a 25-deacetylated metabolite. Biological half-life It has been reported that the half-life of 250 mg rifamycin is 3 hours. |
|---|---|
| Toxicity/Toxicokinetics |
Hepatotoxicity
In premarket controlled trials of rifamycin in patients with traveler's diarrhea, the rate of serum ALT elevation was similar in the rifamycin treatment group compared to the placebo or control drug (ciprofloxacin) group, and no clinically visible liver injury was observed in any subjects. No reports of hepatotoxicity have been published since rifamycin's approval. Due to its minimal absorption, rifamycin is considered unlikely to cause liver injury. Probability score: E (unlikely to cause clinically visible liver injury). Use during Pregnancy and Lactation ◉ Overview of Use During Lactation Rifamycin is minimally absorbed orally and is used only to treat gastrointestinal infections. After maternal use, the drug is unlikely to enter breast milk or the infant's bloodstream and is unlikely to have any adverse effects on breastfed infants. ◉ Effects on Breastfed Infants No relevant published information was found as of the revision date. ◉ Effects on Lactation and Breast Milk No relevant published information was found as of the revision date. Protein binding The protein binding rate of rifamycin is approximately 80-95%. |
| Additional Infomation |
Pharmacodynamics
Rifamycin is effective against Gram-positive, Gram-negative, and mycobacteria. It is particularly effective against Escherichia coli, with an MIC90 of 64-128 mcg/ml, and shows no cross-resistance with other antibacterial drugs. The selection of indications for rifamycin is crucial because previous studies have shown that patients with inflammatory bowel disease are a high-risk factor for the development of drug-resistant E. coli strains. In clinical trials, a randomized clinical trial involving travelers from Mexico and Guatemala tested rifamycin. This trial confirmed that rifamycin significantly reduced the symptoms of traveler's 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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