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Merck

R0533

Rifapentine

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C47H64N4O12
Numéro CAS:
61379-65-5
Poids moléculaire :
877.03
UNSPSC Code:
51283603
PubChem Substance ID:
329823987
EC Number:
262-743-9
NACRES:
NA.85

Principaux documents

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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

Catégories apparentées

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.

General description

Chemical structure: macrolide

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000474742
0000474742
0000398815
0000398816
0000377954

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Consulter la Bibliothèque de documents

Kathy Williams et al.
Antimicrobial agents and chemotherapy, 56(6), 3114-3120 (2012-04-04)
Novel oral regimens composed of new drugs with potent activity against Mycobacterium tuberculosis and no cross-resistance with existing agents are needed to shorten and simplify treatment for both drug-susceptible and drug-resistant tuberculosis. As part of a continuing effort to evaluate
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
Ruth N Moro et al.
Annals of the American Thoracic Society, 15(5), 570-580 (2018-02-03)
Data are limited regarding the safety of 12-dose once-weekly isoniazid (H, 900 mg) plus rifapentine (P, 900 mg) (3HP) for latent infection treatment during pregnancy. To assess safety and pregnancy outcomes among pregnant women who were inadvertently exposed to study
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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