Rifapentine
Rifapentine
CAS: 61379-65-5
Molecular Formula: C47H64N4O12
Rifapentine - Names and Identifiers
Rifapentine - Physico-chemical Properties
| Molecular Formula | C47H64N4O12 |
| Molar Mass | 877.03 |
| Density | 1.35±0.1 g/cm3(Predicted) |
| Melting Point | 179-1800C |
| Boling Point | 969.3±65.0 °C(Predicted) |
| Solubility | methanol: soluble2mg/mL, clear, red to red-brown |
| Appearance | powder |
| Color | Red |
| pKa | 4.81±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.63 |
| Physical and Chemical Properties | Crystallized from ethyl acetate, melting point 179-180 °c. UV absorption maximum: 475,334nm (φ15200, 26700). Acute toxicity LD50 mice (mg/kg):>2000 oral, 750 intraperitoneal injection. There are also reports of acute toxicity LD50 mice (mg/kg):3300 oral, 710 intraperitoneal injection. |
| Use | For semi-synthetic long-acting rifamycin derivatives, its antibacterial mechanism, role, use and rifampicin the same |
Rifapentine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | JQ0902000 |
| Toxicity | LD50 in mice (mg/kg): >2000 orally; 750 i.p. (Cricchio); LD50 in mice (mg/kg): 3300 orally; 710 i.p. (Aroli) |
Rifapentine - Upstream Downstream Industry
| Raw Materials | Acetic acid Manganese(IV) oxide Methyl alcohol Formic acid Sulfuric acid Sodium Chloride Citric acid Ethyl Alcohol Isobutyraldehyde 1-Butanol |
Rifapentine - Reference Information
| Introduction | The antibacterial spectrum of rifapentine is the same as that of rifampicin. Compared with rifampicin, this drug has a lower rate of deacetylation, and the blood concentration of rifampicin is similar to that of rifampicin once a day when taken twice a week, thus reducing the burden on the liver. The results showed that the total effective rate of the study group was higher than that of the control group, and the positive rate of sputum bacterial smear test results and the incidence of severe liver function damage were lower than those of the control group. The effect of rifapentine in the treatment of pulmonary tuberculosis is exact, which can effectively kill Mycobacterium tuberculosis in patients and reduce the incidence of severe liver function damage. |
| preparation | A preparation method of rifapentine, comprising the following steps: A. Reaction with rifamycin S in a first organic solvent with dimethylol terbutylamine to convert to the intermediate rifaoxazine; B. In a second organic solvent, a catalyst and a reducing agent are added to hydrolyze and open the ring of the intermediate rifaoxazine; C. Synthesis of rifapentine solution from hydrolysis product of rifaximin and 1-amino-4-cyclopentylpiperazine; D. The rifapentine solution is filtered, segmented crystallization at multiple crystallization temperatures, first separation, washing, second separation, drying, soaking, third separation, rinsing, spin-drying, sieving, drying, the final product of rifapentine was obtained from the refining process of mixed powder. |
| indication | 1. Combined with other anti-tuberculosis drugs for the treatment of various types, the system of initial treatment and re-treatment of tuberculosis; Bone and Joint Tuberculosis curative effect is better. 2. For the treatment of non-tuberculous mycobacterial infection. 3. Combined with other anti-leprosy drugs in the treatment of leprosy. 4. For other anti-Staphylococcus aureus antibiotic resistance of severe Staphylococcus aureus infection. |
| pharmacological action and mechanism of action | rifapentine is a semi-synthetic rifamycin. It has antibacterial effect on Mycobacterium tuberculosis, leprae, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus, Neisseria meningitidis and influenza. Among them, the MIC of Mycobacterium tuberculosis is 0.02~0.2 μg/ml; The Neisseria gonorrhoeae, Escherichia coli, Aerobacter, Shigella, Serratia also have strong antibacterial activity, the MIC of Neisseria gonorrhoeae was 0.02~2.5 μg/ml; The activity of Virus, chlamydia, Mycoplasma and other microorganisms was active; The effect of anti Mycobacterium tuberculosis was 3~6 times. |
| Use | a novel semi-synthetic long-acting Rifamycin antibiotic. For tuberculosis, leprosy, acute lung infection, suppurative skin disease treatment. It is a semi-synthetic long-acting rifamycin derivative with the same antibacterial mechanism, action and use as rifampicin drug substance (long-acting anti-tuberculosis antibiotic) |
| production method | 0.01ml of 3-aldrifamycin SV is dissolved in Tetrahydrofuran, 0.011mol of 1-amino-4-cyclopentylpiperazine was added at room temperature. The reaction was followed with thin layer, until the point of raw material disappeared, which was in approximate condition. The solvent was distilled off and the residue was recrystallized from ethyl acetate to obtain rifapentine in 55% yield with a melting point of 179-180 °c. |
Last Update：2024-04-09 02:00:10
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Raw Materials for Rifapentine