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QuickView for Rifapentine (compound)

Summary
General Info

PubChem

PubChem Compound 6323497

PubChem Compound 6323497

Name:	rifapentine
PubChem Compound ID:	6323497
Molecular formula:	C₄₇H₆₄N₄O₁₂
Molecular weight:	877.031 g/mol
Synonyms:	Cyclopentylrifampicin; MDL 473; KTC 1; DL-473; 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin; RPE; Priftin; Cyclopentyl rifampin; M000473; 3-[N-(4-Cyclopentyl-1-piperazinyl)formimidoyl]rifamycin. show more » Cyclopentylrifampicin; MDL 473; KTC 1; DL-473; 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin; RPE; Priftin; Cyclopentyl rifampin; M000473; 3-[N-(4-Cyclopentyl-1-piperazinyl)formimidoyl]rifamycin; AIDS007686; D00879; (2R,16S,17R,18R,19R,20S,21S,22S,23S)-8-{[(4-CYCLOPENTYLPIPERAZIN-1-YL)IMINO]METHYL}-5,6,9,17,19-PENTAHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-1,11-DIOXO-1,2-DIHYDRO-2,7-(EPOXYPENTADECA[1,11,13]TRIENOIMINO)NAPHTHO[2,1-B]FURAN-21-YL ACETATE; MDL-473; RPT; Rifamycin AF/ACPP; 61379-65-5; MDL473; R 77-3; AIDS-007686; DL473; Priftin (TN); CHEBI:8861; Rifapentine (USAN); (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-{(E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl}-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1(4,7).0(5,28)]triaconta-1(28),1(29),2,4; C08059; Rifapentine; DL 473 show less «

DrugBank

Identification

Name:	rifapentine
Name (isomeric):	DB01201
Drug Type:	small molecule
Synonyms:	Cyclopentyl rifampin
Brand:	Priftin
Category:	Antimycobacterials, Antibiotics, Antitubercular, Leprostatic Agents
CAS number:	61379-65-5

Pharmacology

Indication:	For the treatment of pulmonary tuberculosis.
Pharmacology:	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. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aerugino... show more » 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. 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. show less «
Mechanism of Action:	Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of... show more » Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. show less «
Absorption:	Rapidly and well absorbed from the gastrointestinal tract.
Protein binding:	97.7% (bound to plasma proteins)
Biotransformation:	Hepatic
Route of elimination:	Following a single 600 mg oral dose of radiolabeled rifapentine to healthy volunteers (n=4), 87% of the total 14C rifapentine was recovered in the urine (17%) and feces (70%).
Clearance:	Apparent Oral cl=2.51 +/- 0.14 L/h [Male tuberculosis patients who received 600 mg rifapentine in combination with isoniazid, pyrazinamide and ethambutol] Apparent Oral cl=1.69 +/- 0.41 L/h [Female tuberculosis patients who received 600 mg rifapentine in combination with isoniazid, pyrazinamide and ethambutol]
Affected organisms:	Mycobacterium

Interactions

Drug interaction:

Erlotinib	Decreased levels/effect of erlotinib
Ethinyl Estradiol	This product may cause a slight decrease of contraceptive effect
Trazodone	The CYP3A4 inducer, Rifapentine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Rifapentine is initiated, discontinued or dose changed.
Norethindrone	This product may cause a slight decrease of contraceptive effect
Telithromycin	Rifapentine may decrease the plasma concentration of Telithromycin. Consider alternate therapy.

Erlotinib	Decreased levels/effect of erlotinib
Ethinyl Estradiol	This product may cause a slight decrease of contraceptive effect
Trazodone	The CYP3A4 inducer, Rifapentine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Rifapentine is initiated, discontinued or dose changed.
Norethindrone	This product may cause a slight decrease of contraceptive effect
Telithromycin	Rifapentine may decrease the plasma concentration of Telithromycin. Consider alternate therapy.
Terbinafine	Rifapentine may increase the metabolism and clearance of Terbinafine. To avoid Terbinafine treatment failure, co-administration should be avoided.
Zidovudine	Rifapentin may decrease the serum concentration of zidovudine by increasing its metabolism. Monitor for changes in the serum concentration and therapeutic and adverse effects of zidovudine if rifapentin is initiated, discontinued or dose changed.
Voriconazole	Rifapentine may decrease the serum concentration of voriconazole likely by increasing its metabolism via CYP3A enzymes. Voriconazole may increase the serum concentration of rifapentin likely by inhibiting its metabolism via CYP3A. Concomitant therapy is contraindicated.
Bromazepam	Rifapentine may decrease the serum concentration of bromazepam by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of bromazepam if rifapentine is initiated, discontinued or dose changed.
Verapamil	Rifapentine, a CYP3A4 inducer, may decrease the serum concentration of Verapamil by increasing its metabolism (particularly in the intestinal mucosa) and decreasing its absorption. Monitor for changes in the therapeutic/adverse effects of Verapamil if Rifapentine is initiated, discontinued or dose changed.
Tramadol	Rifapentine may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
Methadone	The rifamycin decreases the effect of methadone
Tipranavir	Concomitant therapy may cause decreased Tipranavir and increased Rifapentine plasma concentrations.
Temsirolimus	Rifapentine may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Tretinoin	The strong CYP2C8 inducer, Rifapentine, may increase the metabolism and clearance of oral Tretinoin. Consider alternate therapy to avoid failure of Tretinoin therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Rifapentine is initiated, discontinued or dose changed.

Targets

DNA-directed RNA polymerase beta' chain

Enzymes

Cytochrome P450 2C9

Cytochrome P450 3A4

Cytochrome P450 2C8

Cytochrome P450 2D6

Cytochrome P450 3A43

Cytochrome P450 3A5

Cytochrome P450 3A7