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R0533

Sigma-Aldrich

Rifapentine

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C47H64N4O12
CAS Number:
61379-65-5
Molecular Weight:
877.03
EC Number:
262-743-9
UNSPSC Code:
51283603
PubChem Substance ID:
329823987
NACRES:
NA.85

Assay

≥93.5%

form

powder or crystals

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

Mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

2-8°C

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

InChI key

WDZCUPBHRAEYDL-OABFQHKQSA-N

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Olivia Ferguson et al.
Journal of the International AIDS Society, 23(10), e25623-e25623 (2020-10-20)
Preventive therapy is essential for reducing tuberculosis (TB) burden among people living with HIV (PLWH) in high-burden settings. Short-course preventive therapy regimens, such as three-month weekly rifapentine and isoniazid (3HP) and one-month daily rifapentine and isoniazid (1HP), may help facilitate uptake
Lélia Abad et al.
The Journal of antimicrobial chemotherapy, 75(6), 1466-1473 (2020-03-04)
Targeting biofilm-embedded and intraosteoblastic Staphylococcus aureus, rifampicin gained a pivotal role in bone and joint infection (BJI) treatment. Two other rifamycins, rifabutin and rifapentine, may represent better-tolerated alternatives, but their activity against bacterial reservoirs associated with BJI chronicity has never
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
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
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
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