U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C47H64N4O12
Molecular Weight 877.0307
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RIFAPENTINE

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C(\C=N\N5CCN(CC5)C6CCCC6)=C(O)C4=C3C2=O

InChI

InChIKey=WDZCUPBHRAEYDL-GZAUEHORSA-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

HIDE SMILES / InChI

Description

PRIFTIN® (rifapentine) is indicated in adults and children 12 years and older for the treatment of active pulmonary tuberculosis (TB) caused by Mycobacterium tuberculosis. PRIFTIN must always be used in combination with one or more antituberculosis (anti-TB) drugs to which the isolate is susceptible. Rifapentine is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. And it acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifampin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency. Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages.

Approval Year

Targets

Targets

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
New drugs for tuberculosis.
1995 Sep
Comparison of activities of rifapentine and rifampin against Mycobacterium tuberculosis residing in human macrophages.
1995 Sep
Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis.
1996 Dec
How effective is KRM-1648 in treatment of disseminated Mycobacterium avium complex infections in beige mice?
1996 Feb
Rifapentine is active in vitro and in vivo against Toxoplasma gondii.
1996 Jun
Comparative antimycobacterial activities of rifampin, rifapentine, and KRM-1648 against a collection of rifampin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations.
1996 Nov
[In vitro anti-MAC activities of new quinolones in focus (1)].
1996 Sep
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis.
1998 Jul
Development of rifapentine susceptibility tests for Mycobacterium tuberculosis.
1999 Jan
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.
2015 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
600 mg twice weekly for two months
Route of Administration: Oral
In Vitro Use Guide
In a comparison of in vitro properties of rifapentine (RIF), the minimal inhibitory concentration of RIF against Mycobacterium tuberculosis in Tween-albumin liquid medium was usually 0.02 micrograms/ml; the bactericidal activity against a log phase culture was slightly less than that of RMP and the recovery after pulsed exposures to 1 microgram/ml of RIF lasting 6, 24 and 96 h was identical for the two rifamycins.
Name Type Language
RIFAPENTINE
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
KTC-1
Code English
RIFAPENTINE [VANDF]
Common Name English
R-773
Code English
DL-473
Code English
R-77-3
Code English
RIFAPENTINE [INN]
Common Name English
RIFAPENTINE [MART.]
Common Name English
RIFAMYCIN AF/ACPP
Common Name English
MDL 473
Code English
RIFAPENTINE [MI]
Common Name English
3-((4-CYCLOPENTYL-1-PIPERAZINYL)IMINO)METHYL)RIFAMYCIN
Common Name English
RIFAMYCIN, 3-(((4-CYCLOPENTYL-1-PIPERAZINYL)IMINO)METHYL)-
Common Name English
3-(((4-CYCLOPENTYL-1-PIPERAZINYL)IMINO)METHYL)RIFAMYCIN
Common Name English
RIFAPENTIN
Common Name English
RIFAPENTINE [ORANGE BOOK]
Common Name English
RIFAPENTINE [WHO-DD]
Common Name English
PRIFITIN
Brand Name English
PRIFTIN
Brand Name English
ANTIBIOTIC DL-473IT
Code English
RIFAPENTINE [USAN]
Common Name English
MDL-473
Code English
3-(N-(4-CYCLOPENTYL-1-PIPERAZINYL)FORMIMIDOYL)RIFAMYCIN
Common Name English
Classification Tree Code System Code
NDF-RT N0000007911
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
NDF-RT N0000007911
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
NDF-RT N0000007911
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
WHO-VATC QJ04AB05
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
NDF-RT N0000175501
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
LIVERTOX 846
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
WHO-ATC J04AB05
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
NDF-RT N0000007911
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
Code System Code Type Description
EVMPD
SUB10311MIG
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
MERCK INDEX
M9614
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY Merck Index
NCI_THESAURUS
C66516
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
WIKIPEDIA
Rifapentine
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
DRUG BANK
DB01201
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
INN
4765
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
LactMed
61379-65-5
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
EPA CompTox
61379-65-5
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
RXCUI
35617
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY RxNorm
CAS
61379-65-5
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
ECHA (EC/EINECS)
262-743-9
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY
ChEMBL
CHEMBL1660
Created by admin on Tue Mar 06 11:22:07 UTC 2018 , Edited by admin on Tue Mar 06 11:22:07 UTC 2018
PRIMARY