Rifapentine
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| Category | Antibiotics |
| Catalog number | BBF-03916 |
| CAS | 61379-65-5 |
| Molecular Weight | 877.03 |
| Molecular Formula | C47H64N4O12 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03916 | 1 g | $259 | In stock |
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Add to cartDescription
Rifapentine (Priftin) is a semi-synthetic antibiotic compound used in the treatment of tuberculosis.
Specification
| Synonyms | MDL473; MDL 473; MDL-473; DL 473; DL-473; DL473; R 773; R-773; R773 |
| Storage | Store at -20°C |
| IUPAC Name | [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-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 |
| Canonical SMILES | CC1C=CC=C(C(=O)NC2=C(C3=C(C(=C4C(=C3C(=O)C2=CNN5CCN(CC5)C6CCCC6)C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C |
| InChI | InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,48,53-55,57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14+,32-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1 |
| InChI Key | RISDZDVHYCURHD-BFYHYZIMSA-N |
Properties
| Appearance | Red Solid |
| Boiling Point | 969.3±65.0°C at 760 mmHg |
| Melting Point | >168°C (dec.) |
| Density | 1.35 g/cm3 |
| Solubility | Soluble in DMSO |
| LogP | 4 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. |
Reference Reading
1.In Vitro Evaluation of Inhalable Verapamil-Rifapentine Particles for Tuberculosis Therapy.
Parumasivam T1, Chan JG1,2, Pang A3, Quan DH4, Triccas JA4, Britton WJ4,3, Chan HK1. Mol Pharm. 2016 Mar 7;13(3):979-89. doi: 10.1021/acs.molpharmaceut.5b00833. Epub 2016 Feb 12.
Recent studies have demonstrated that efflux pumps of Mycobacterium tuberculosis (M. tb) provide a crucial mechanism in the development of drug resistant to antimycobacterial drugs. Drugs that inhibit these efflux pumps, such as verapamil, have shown the potential in enhancing the treatment success. We therefore hypothesized that the combined inhaled administration of verapamil and a first-line rifamycin antibiotic will further improve the treatment efficacy. An inhalable dry powder consisting of amorphous verapamil and crystalline rifapentine with l-leucine as an excipient was produced by spray drying. The in vitro aerosol characteristic of the powder, its microbiological activity and stability were assessed. When the powder was dispersed by an Osmohaler, the total fine particle fraction (FPFtotal, wt % of particles in aerosol <5 μm) of verapamil and rifapentine was 77.4 ± 1.1% and 71.5 ± 2.0%, respectively. The combination drug formulation showed a minimum inhibitory concentration (MIC90) similar to that of rifapentine alone when tested against both M.
2.Interspecies scaling of excretory amounts using allometry - retrospective analysis with rifapentine, aztreonam, carumonam, pefloxacin, miloxacin, trovafloxacin, doripenem, imipenem, cefozopran, ceftazidime, linezolid for urinary excretion and rifapentine, cabotegravir, and dolutegravir for fecal excretion.
Srinivas NR1. Xenobiotica. 2015 Dec 29:1-9. [Epub ahead of print]
1. Interspecies allometry scaling for prediction of human excretory amounts in urine or feces was performed for numerous antibacterials. Antibacterials used for urinary scaling were: rifapentine, pefloxacin, trovafloxacin (Gr1/low; <10%); miloxacin, linezolid, PNU-142300 (Gr2/medium; 10-40%); aztreonam, carumonam, cefozopran, doripenem, imipenem, and ceftazidime (Gr3/high; >50%). Rifapentine, cabotegravir, and dolutegravir was used for fecal scaling (high; >50%). 2. The employment of allometry equation: Y = aWb enabled scaling of urine/fecal amounts from animal species. Corresponding predicted amounts were converted into % recovery by considering the respective human dose. Comparison of predicted/observed values enabled fold difference and error calculations (mean absolute error [MAE] and root mean square error [RMSE]). Comparisons were made for urinary/fecal data; and qualitative assessment was made amongst Gr1/Gr2/Gr3 for urine.
3.School-Based Study to Identify and Treat Adolescent Students at Risk for Tuberculosis Infection.
Hatzenbuehler LA1, Starke JR, Graviss EA, Smith EO, Cruz AT. Pediatr Infect Dis J. 2016 Apr 13. [Epub ahead of print]
BACKGROUND: Screening for and treating tuberculosis (TB) infection in children and adolescents is an effective way of decreasing future TB cases. However, current approaches leave many children at risk for TB unidentified.
4.Characterization of 22 anti-tuberculosis drugs for the inhibitory interaction potential on organic anionic transporter polypeptides (OATPs) mediated uptake.
Parvez MM1, Jung JA2, Shin HJ1, Kim DH1, Shin JG3. Antimicrob Agents Chemother. 2016 Mar 14. pii: AAC.02765-15. [Epub ahead of print]
We investigated inhibitory interaction potential of 22 currently marketed anti-tuberculosis (TB) drugs on organic anion-transporting polypeptide (OATP)1B1-, OATP2B1-, and OATP1B3-mediated uptake using in vitro Xenopus oocytes and HEK-cells. Rifabutin, ethambutol, amoxicillin, linezolid, p-amino salicylic acid, and rifapentine exhibited mild-to-moderate inhibitory effects on OATP-mediated uptake of estrone-3 sulfate, estradiol 17β-D-glucuronide, and rosuvastatin. The IC50 values of rifabutin, amoxicillin, ethambutol, p-amino salicylic acid, and linezolid were 35.4, 36.2, 57.6, 72.6, and 65.9 μM respectively for organic anionic transporter polypeptide 1B1 (OATP1B1) and 28.8, 28.9, 53.9, 31.5, and 61.0 μM, respectively for organic anionic transporter polypeptide 1B3 (OATP1B3)-mediated uptake. Streptomycin and linezolid showed greater inhibition of organic anionic transporter polypeptide 2B1 (OATP2B1)-mediated uptake, with IC50 values of 33.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C47H64N4O12
Molecular Weight (Monoisotopic Mass): 876.4521 Da
Molecular Weight (Avergae Mass): 877.0307 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C47H64N4O12
Molecular Weight (Monoisotopic Mass): 876.4521 Da
Molecular Weight (Avergae Mass): 877.0307 Da
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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 ╳
