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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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K E Dooley et al.
Clinical pharmacology and therapeutics, 91(5), 881-888 (2012-04-05)
Rifapentine (RP T) is an antituberculosis drug that may shorten treatment duration when substituted for rifampin (RI F).The maximal tolerated daily dose of RP T and its potential for cytochrome 3A4 induction and autoinduction at clinically relevant doses are unknown.
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
John Gar Yan Chan et al.
Expert opinion on drug delivery, 11(3), 421-431 (2014-01-09)
Tuberculosis (TB) remains rampant throughout the world, in large part due to the lengthy treatment times of current therapeutic options. Rifapentine, a rifamycin antibiotic, is currently approved for intermittent dosing in the treatment of TB. Recent animal studies have shown
Neil A Martinson et al.
The New England journal of medicine, 365(1), 11-20 (2011-07-08)
Treatment of latent tuberculosis in patients infected with the human immunodeficiency virus (HIV) is efficacious, but few patients around the world receive such treatment. We evaluated three new regimens for latent tuberculosis that may be more potent and durable than
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