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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

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

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
Antibacterial activity of DL 473, a new semisynthetic rifamycin derivative.
1981 Aug
Comparison of the sensitivity of mycobacteria to the cyclopentyl rifamycin DL473 and rifampicin.
1982 Aug
Comparative in vitro activities of MDL 473, rifampin, and ansamycin against Mycobacterium intracellulare.
1985 Sep
[In-vitro antimycobacterial activity of rifapentine (comparison with rifampicin)].
1986 Dec
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987
In vitro properties of rifapentine (MDL473) relevant to its use in intermittent chemotherapy of tuberculosis.
1987 Jun
In vitro activity of new rifamycins against rifampicin-resistant M. tuberculosis and MAIS-complex mycobacteria.
1987 Sep
New antibacterial drugs for the treatment of mycobacterial disease in man.
1988 Jul
In vitro activities against mycobacteria of two long-acting rifamycins, FCE22807 and CGP40/469A (SPA-S-565).
1990 Jun
Bactericidal activity in vitro of various rifamycins against Mycobacterium avium and Mycobacterium tuberculosis.
1990 Mar
Activities of sparfloxacin, azithromycin, temafloxacin, and rifapentine compared with that of clarithromycin against multiplication of Mycobacterium avium complex within human macrophages.
1991 Jul
In vivo activities of newer rifamycin analogs against Mycobacterium avium infection.
1991 Oct
Activity in vitro of rifabutin, FCE 22807, rifapentine, and rifampin against Mycobacterium microti and M. tuberculosis and their penetration into mouse peritoneal macrophages.
1992 Jan
Activity of rifapentine against Mycobacterium avium infection in beige mice.
1992 May
Effectiveness of rifampin, rifabutin, and rifapentine for preventive therapy of tuberculosis in mice.
1993 Dec
Azithromycin, rifabutin, and rifapentine for treatment and prophylaxis of Mycobacterium avium complex in rats treated with cyclosporine.
1993 Mar
Intermittent azithromycin for treatment of Mycobacterium avium infection in beige mice.
1994 Aug
Comparative in vivo activities of rifabutin and rifapentine against Mycobacterium avium complex.
1994 Feb
Effectiveness of various antimicrobial agents against Mycobacterium avium complex in the beige mouse model.
1994 Nov
Effectiveness of rifabutin alone or in combination with isoniazid in preventive therapy of mouse tuberculosis.
1994 Oct
Mutation position and type of substitution in the beta-subunit of the RNA polymerase influence in-vitro activity of rifamycins in rifampicin-resistant Mycobacterium tuberculosis.
1995 Feb
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
Analysis of rifapentine for preventive therapy in the Cornell mouse model of latent tuberculosis.
1999 Sep
In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials.
2000 Jan
Antituberculosis activity of once-weekly rifapentine-containing regimens in mice. Long-term effectiveness with 6- and 8-month treatment regimens.
2000 May
Comparison of the in vitro activities of rifapentine and rifampicin against Mycobacterium tuberculosis complex.
2000 Oct
Activity of rifapentine and its metabolite 25-O-desacetylrifapentine compared with rifampicin and rifabutin against Mycobacterium tuberculosis, Mycobacterium africanum, Mycobacterium bovis and M. bovis BCG.
2000 Oct
Effectiveness of once-weekly rifapentine and moxifloxacin regimens against Mycobacterium tuberculosis in mice.
2001 Dec
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.
2003 Jan
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.
2006 Oct
Potent in vitro antifungal activities of naturally occurring acetylenic acids.
2008 Jul
Structure and anti-TB activity of trachylobanes from the liverwort Jungermannia exsertifolia ssp. cordifolia.
2010 Apr 23
Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: rifampicin, rifabutin, and rifapentine.
2011 Dec 1
Short-course chemotherapy with TMC207 and rifapentine in a murine model of latent tuberculosis infection.
2011 Sep 15
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:47:16 UTC 2019
Edited
by admin
on Mon Oct 21 19:47:16 UTC 2019
Record UNII
XJM390A33U
Record Status Validated (UNII)
Record Version
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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
NCI_THESAURUS C280
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
FDA ORPHAN DRUG 89495
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
WHO-VATC QJ04AB05
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
NDF-RT N0000175501
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
FDA ORPHAN DRUG 89695
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
LIVERTOX 846
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
EU-Orphan Drug EU/3/10/750
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
FDA ORPHAN DRUG 89595
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
WHO-ATC J04AB05
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
Code System Code Type Description
EVMPD
SUB10311MIG
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
MERCK INDEX
M9614
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C66516
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
WIKIPEDIA
Rifapentine
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
DRUG BANK
DB01201
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
INN
4765
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
LactMed
61379-65-5
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
EPA CompTox
61379-65-5
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
RXCUI
35617
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY RxNorm
CAS
61379-65-5
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
ECHA (EC/EINECS)
262-743-9
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
ChEMBL
CHEMBL1660
Created by admin on Mon Oct 21 19:47:16 UTC 2019 , Edited by admin on Mon Oct 21 19:47:16 UTC 2019
PRIMARY
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