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R0533

Rifapentine

Name: Rifapentine
Brand: SIGMA

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

UNSPSC Code:

51283603

PubChem Substance ID:

329823987

EC Number:

262-743-9

NACRES:

NA.85

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Properties

assay

≥93.5%

Quality Level

200

form

powder or crystals

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

mode of action

enzyme | inhibits

storage temp.

2-8°C

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

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品

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Cost-effectiveness of one month of daily isoniazid and rifapentine versus three months of weekly isoniazid and rifapentine for prevention of tuberculosis among people receiving antiretroviral therapy in Uganda.

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

Antibiofilm and intraosteoblastic activities of rifamycins against Staphylococcus aureus: promising in vitro profile of rifabutin.

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

Once-weekly rifapentine and isoniazid for tuberculosis prevention in patients with HIV taking dolutegravir-based antiretroviral therapy: a phase 1/2 trial.

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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Global Trade Item Number

SKU	GTIN
R0533-25MG	04061833255568
R0533-100MG	04061833255551