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Merck

R0533

Rifapentine

Sinónimos:

3-(((4-cyclopentyl-1-piperazinyl)imino)methyl)rifamycin, Cyclopentylrifampicin, DL 473

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Fórmula empírica (notación de Hill):
C47H64N4O12
Número CAS:
61379-65-5
Peso molecular:
877.03
UNSPSC Code:
51283603
PubChem Substance ID:
329823987
EC Number:
262-743-9
NACRES:
NA.85

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SMILES string

N5(CCN(CC5)C6CCCC6)N=Cc1c2c(c3c(c4c(c(c3O)C)O[C@](O\C=C\C([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](\C=C\C=C(/C(=O)N2)\C)C)O)C)O)C)OC(=O)C)C)OC)(C4=O)C)c1O)O

InChI key

WDZCUPBHRAEYDL-OABFQHKQSA-N

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/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23?/t24-,26+,27+,28+,33?,38-,39+,43+,47-/m0/s1

assay

≥93.5%

form

powder or crystals

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

mode of action

enzyme | inhibits

Quality Level

200

storage temp.

2-8°C

Categorías relacionadas

General description

Chemical structure: macrolide

Application

Rifapentine is an antibiotic clinically used to treat tuberculosis. It is used in tuberculosis research.

Biochem/physiol Actions

Rifapentine is a semisynthetic derivative of rifampicin with antibacterial activity against Gram-positive and Gram-negative bacteria and against Mycobacterium tuberculosis. Rifapentine inhibits DNA-dependant RNA polymerase and prevents RNA transcription. It interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.
Semisynthetic derivative of rifampicin with antibacterial activity against Gram-positive and Gram-negative bacterial and against Mycobacterium tuberculosis. Rifapentine inhibits DNA-dependant RNA polymerase and prevents RNA transcription.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000474742
0000474742
0000398815
0000398816
0000377954

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Simbarashe P Zvada et al.
Antimicrobial agents and chemotherapy, 56(8), 4471-4473 (2012-05-16)
We described the population pharmacokinetics of moxifloxacin and the effect of high-dose intermittent rifapentine in patients with pulmonary tuberculosis who were randomized to a continuation-phase regimen of 400 mg moxifloxacin and 900 mg rifapentine twice weekly or 400 mg moxifloxacin
Susan E Dorman et al.
The Journal of infectious diseases, 206(7), 1030-1040 (2012-08-02)
Rifapentine administered 5 days per week has potent activity in mouse models of antituberculosis chemotherapy, but efficacy and safety data are limited in humans. We compared the antimicrobial activity and safety of rifapentine vs rifampin during the first 8 weeks
Ian M Rosenthal et al.
Antimicrobial agents and chemotherapy, 56(8), 4331-4340 (2012-06-06)
In previous experiments, replacing the 10-mg/kg of body weight daily dose of rifampin with 7.5 to 10 mg/kg of rifapentine in combinations containing isoniazid and pyrazinamide reduced the duration of treatment needed to cure tuberculosis in BALB/c mice by approximately
Timothy R Sterling et al.
The New England journal of medicine, 365(23), 2155-2166 (2011-12-14)
Treatment of latent Mycobacterium tuberculosis infection is an essential component of tuberculosis control and elimination. The current standard regimen of isoniazid for 9 months is efficacious but is limited by toxicity and low rates of treatment completion. We conducted an
Kelly E Dooley et al.
The lancet. HIV, 7(6), e401-e409 (2020-04-03)
Short-course preventive therapy with 12 doses of once-weekly rifapentine (900 mg) plus isoniazid (900 mg) could greatly improve tuberculosis control, especially in areas with high co-endemicity with HIV. However, a small previous trial of such therapy with dolutegravir in healthy
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