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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(C2=O)C4=C(O)C(\C=N\N5CCN(CC5)C6CCCC6)=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(O)=C4C(O)=C3C

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PRIFTIN

Cmax

ValueDoseCo-administeredAnalytePopulation
25.8 μg/mL
900 mg single, oral
RIFAPENTINE plasma
Homo sapiens
15.05 μg/mL
600 mg 1 times / 3 days steady-state, oral
RIFAPENTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
817 μg × h/mL
900 mg single, oral
RIFAPENTINE plasma
Homo sapiens
319.54 μg × h/mL
600 mg 1 times / 3 days steady-state, oral
RIFAPENTINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.6 h
900 mg single, oral
RIFAPENTINE plasma
Homo sapiens
13.19 h
600 mg 1 times / 3 days steady-state, oral
RIFAPENTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2.3%
600 mg 1 times / 3 days steady-state, oral
RIFAPENTINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

PubMed

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
Record UNII
XJM390A33U
Record Status Validated (UNII)
Record Version