Rifapentine

Identification

Summary

Rifapentine is an antibiotic agent used in the treatment of pulmonary tuberculosis.

Brand Names
Priftin
Generic Name
Rifapentine
DrugBank Accession Number
DB01201
Background

Rifapentine is an antibiotic drug used in the treatment of tuberculosis. It inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 877.0307
Monoisotopic: 876.452073532
Chemical Formula
C47H64N4O12
Synonyms
  • 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
  • Cyclopentylrifampicin
  • Rifapentin
  • Rifapentine
External IDs
  • ANTIBIOTIC DL-473IT
  • DL-473
  • KTC-1
  • MDL-473
  • R-77-3
  • R-773

Pharmacology

Indication

For the treatment of pulmonary tuberculosis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatActive tuberculosis••••••••••••
Used in combination to treatLatent tuberculosis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

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 RNA synthesis and cell death.

TargetActionsOrganism
ADNA-directed RNA polymerase subunit beta'
inhibitor
Mycobacterium tuberculosis
Absorption

Rapidly and well absorbed from the gastrointestinal tract.

Volume of distribution
  • 70.2 ± 9.1 L
Protein binding

97.7% (bound to plasma proteins)

Metabolism

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%).

Half-life

Not Available

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]
Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be increased when combined with Rifapentine.
AbametapirThe serum concentration of Rifapentine can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Rifapentine.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Rifapentine.
AbrocitinibThe metabolism of Abrocitinib can be increased when combined with Rifapentine.
Food Interactions
  • Take with food. Taking rifapentine with food increases its bioavailability and reduces gastrointestinal upset. Rifapentine tablets can be crushed and mixed with semisolid food if necessary.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Rifapentine hydrochloride5915QBW8LA127923-87-9YAXMCEWRTZAGIM-ZYFLDTFVSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PriftinTablet, film coated150 mg/1Oralsanofi-aventis U.S. LLC2009-03-302020-11-30US flag
PriftinTablet, film coated150 mg/1OralRpk Pharmaceuticals, Inc.2017-02-08Not applicableUS flag
PriftinTablet, film coated150 mg/1Oralsanofi-aventis U.S. LLC2017-02-08Not applicableUS flag
PriftinTablet, film coated150 mg/1OralA-S Medication Solutions2017-02-08Not applicableUS flag

Categories

ATC Codes
J04AB05 — Rifapentine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolactams
Sub Class
Not Available
Direct Parent
Macrolactams
Alternative Parents
Naphthofurans / Naphthols and derivatives / Benzofurans / Coumarans / Aryl alkyl ketones / Hydroquinones / Ketals / N-alkylpiperazines / Amino acids and derivatives / Trialkylamines
show 13 more
Substituents
1,4-diazinane / 1-naphthol / Acetal / Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-alkylpiperazine, N-iminopiperazine, rifamycin (CHEBI:45304)
Affected organisms
  • Mycobacterium tuberculosis
  • Mycobacterium

Chemical Identifiers

UNII
XJM390A33U
CAS number
61379-65-5
InChI Key
WDZCUPBHRAEYDL-GZAUEHORSA-N
InChI
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
IUPAC Name
(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),2,4,9,19,21,25(29),26-octaen-13-yl acetate
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(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\N1CCN(CC1)C1CCCC1)=C2O

References

General References
Not Available
Human Metabolome Database
HMDB15332
KEGG Drug
D00879
KEGG Compound
C08059
PubChem Compound
6323497
PubChem Substance
46507322
ChemSpider
10482075
RxNav
35617
ChEBI
45304
ChEMBL
CHEMBL1660
ZINC
ZINC000169621228
Therapeutic Targets Database
DAP000426
PharmGKB
PA164783809
PDBe Ligand
RPT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rifapentine
PDB Entries
2a69 / 6beh
MSDS
Download (58.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionTuberculosis (TB)1
4CompletedPreventionTuberculosis (TB)1
4Not Yet RecruitingPreventionHIV Seropositivity / Household Contact / Tuberculosis (TB)1
4Not Yet RecruitingPreventionKidney Failure / Late phase Tuberculosis1
4RecruitingHealth Services ResearchTuberculosis (TB)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Gruppo Lepetit SPA
  • Sanofi-Aventis Inc.
Dosage Forms
FormRouteStrength
Tablet, coatedOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral150 MG
Prices
Unit descriptionCostUnit
Priftin 150 mg tablet3.96USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0213 mg/mLALOGPS
logP4.83ALOGPS
logP3.7Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.99Chemaxon
pKa (Strongest Basic)7.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area220.15 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity242 m3·mol-1Chemaxon
Polarizability93.56 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6848
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6609
P-glycoprotein substrateSubstrate0.8997
P-glycoprotein inhibitor IInhibitor0.7632
P-glycoprotein inhibitor IINon-inhibitor0.5252
Renal organic cation transporterNon-inhibitor0.8267
CYP450 2C9 substrateNon-substrate0.8555
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7246
CYP450 1A2 substrateNon-inhibitor0.8865
CYP450 2C9 inhibitorNon-inhibitor0.8436
CYP450 2D6 inhibitorNon-inhibitor0.9073
CYP450 2C19 inhibitorNon-inhibitor0.8449
CYP450 3A4 inhibitorNon-inhibitor0.7042
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8274
Ames testNon AMES toxic0.598
CarcinogenicityNon-carcinogens0.8187
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3722 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9221
hERG inhibition (predictor II)Inhibitor0.6821
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-0000000090-da6c759d6ed05b0bf6cd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fc0-1000000190-1bc351d29c9749625ffe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0171-0000000490-9a3e31a1783e733facc0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000010-195b839028a8d74f2a8a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0171-3300000090-70959d4278a02aa3e82c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bwd-3900000330-1c54d7bbd293e8debae7
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-298.7473641
predicted
DarkChem Lite v0.1.0
[M-H]-283.543
predicted
DeepCCS 1.0 (2019)
[M+H]+301.7804641
predicted
DarkChem Lite v0.1.0
[M+H]+285.1962
predicted
DeepCCS 1.0 (2019)
[M+Na]+291.35303
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Inhibitor
General Function
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
Specific Function
Dna binding
Gene Name
rpoC
Uniprot ID
P9WGY7
Uniprot Name
DNA-directed RNA polymerase subunit beta'
Molecular Weight
146768.085 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Williams DL, Spring L, Collins L, Miller LP, Heifets LB, Gangadharam PR, Gillis TP: Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 1998 Jul;42(7):1853-7. [Article]
  4. Tupin A, Gualtieri M, Roquet-Baneres F, Morichaud Z, Brodolin K, Leonetti JP: Resistance to rifampicin: at the crossroads between ecological, genomic and medical concerns. Int J Antimicrob Agents. 2010 Jun;35(6):519-23. doi: 10.1016/j.ijantimicag.2009.12.017. Epub 2010 Feb 24. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
  2. Rana R, Chen Y, Ferguson SS, Kissling GE, Surapureddi S, Goldstein JA: Hepatocyte nuclear factor 4{alpha} regulates rifampicin-mediated induction of CYP2C genes in primary cultures of human hepatocytes. Drug Metab Dispos. 2010 Apr;38(4):591-9. doi: 10.1124/dmd.109.030387. Epub 2010 Jan 19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. FDA Clinical Pharmacology Review: Rifapentine [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...

Components:
References
  1. Burman WJ, Gallicano K, Peloquin C: Comparative pharmacokinetics and pharmacodynamics of the rifamycin antibacterials. Clin Pharmacokinet. 2001;40(5):327-41. doi: 10.2165/00003088-200140050-00002. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Li AP, Reith MK, Rasmussen A, Gorski JC, Hall SD, Xu L, Kaminski DL, Cheng LK: Primary human hepatocytes as a tool for the evaluation of structure-activity relationship in cytochrome P450 induction potential of xenobiotics: evaluation of rifampin, rifapentine and rifabutin. Chem Biol Interact. 1997 Nov 6;107(1-2):17-30. [Article]
  2. Shimokawa Y, Yoda N, Kondo S, Yamamura Y, Takiguchi Y, Umehara K: Inhibitory Potential of Twenty Five Anti-tuberculosis Drugs on CYP Activities in Human Liver Microsomes. Biol Pharm Bull. 2015;38(9):1425-9. doi: 10.1248/bpb.b15-00313. Epub 2015 Jun 20. [Article]
  3. Winter H, Egizi E, Murray S, Erondu N, Ginsberg A, Rouse DJ, Severynse-Stevens D, Pauli E: Evaluation of the pharmacokinetic interaction between repeated doses of rifapentine or rifampin and a single dose of bedaquiline in healthy adult subjects. Antimicrob Agents Chemother. 2015 Feb;59(2):1219-24. doi: 10.1128/AAC.04171-14. Epub 2014 Dec 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
The rifamycin derivative antibacterials are known to induce CYP2C9. This enzyme action is based on the drug class of Rifapentine.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zheng C, Hu X, Zhao L, Hu M, Gao F: Clinical and pharmacological hallmarks of rifapentine's use in diabetes patients with active and latent tuberculosis: do we know enough? Drug Des Devel Ther. 2017 Oct 11;11:2957-2968. doi: 10.2147/DDDT.S146506. eCollection 2017. [Article]
  2. Asaumi R, Toshimoto K, Tobe Y, Hashizume K, Nunoya KI, Imawaka H, Lee W, Sugiyama Y: Comprehensive PBPK Model of Rifampicin for Quantitative Prediction of Complex Drug-Drug Interactions: CYP3A/2C9 Induction and OATP Inhibition Effects. CPT Pharmacometrics Syst Pharmacol. 2018 Mar;7(3):186-196. doi: 10.1002/psp4.12275. Epub 2018 Feb 5. [Article]
  3. Yamashita F, Sasa Y, Yoshida S, Hisaka A, Asai Y, Kitano H, Hashida M, Suzuki H: Modeling of rifampicin-induced CYP3A4 activation dynamics for the prediction of clinical drug-drug interactions from in vitro data. PLoS One. 2013 Sep 24;8(9):e70330. doi: 10.1371/journal.pone.0070330. eCollection 2013. [Article]
  4. Rifapentine FDA label [File]
  5. Induction of Drug Metabolism Enzymes and MDR1 Using a Novel Human Hepatocyte Cell Line [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Svensson EM, Murray S, Karlsson MO, Dooley KE: Rifampicin and rifapentine significantly reduce concentrations of bedaquiline, a new anti-TB drug. J Antimicrob Chemother. 2015 Apr;70(4):1106-14. doi: 10.1093/jac/dku504. Epub 2014 Dec 21. [Article]
  2. Li AP, Reith MK, Rasmussen A, Gorski JC, Hall SD, Xu L, Kaminski DL, Cheng LK: Primary human hepatocytes as a tool for the evaluation of structure-activity relationship in cytochrome P450 induction potential of xenobiotics: evaluation of rifampin, rifapentine and rifabutin. Chem Biol Interact. 1997 Nov 6;107(1-2):17-30. [Article]
  3. Shimokawa Y, Yoda N, Kondo S, Yamamura Y, Takiguchi Y, Umehara K: Inhibitory Potential of Twenty Five Anti-tuberculosis Drugs on CYP Activities in Human Liver Microsomes. Biol Pharm Bull. 2015;38(9):1425-9. doi: 10.1248/bpb.b15-00313. Epub 2015 Jun 20. [Article]
  4. Williamson B, Dooley KE, Zhang Y, Back DJ, Owen A: Induction of influx and efflux transporters and cytochrome P450 3A4 in primary human hepatocytes by rifampin, rifabutin, and rifapentine. Antimicrob Agents Chemother. 2013 Dec;57(12):6366-9. doi: 10.1128/AAC.01124-13. Epub 2013 Sep 23. [Article]
  5. Dooley KE, Bliven-Sizemore EE, Weiner M, Lu Y, Nuermberger EL, Hubbard WC, Fuchs EJ, Melia MT, Burman WJ, Dorman SE: Safety and pharmacokinetics of escalating daily doses of the antituberculosis drug rifapentine in healthy volunteers. Clin Pharmacol Ther. 2012 May;91(5):881-8. doi: 10.1038/clpt.2011.323. [Article]
  6. Burman WJ, Gallicano K, Peloquin C: Comparative pharmacokinetics and pharmacodynamics of the rifamycin antibacterials. Clin Pharmacokinet. 2001;40(5):327-41. doi: 10.2165/00003088-200140050-00002. [Article]
  7. Aristoff PA, Garcia GA, Kirchhoff PD, Showalter HD: Rifamycins--obstacles and opportunities. Tuberculosis (Edinb). 2010 Mar;90(2):94-118. doi: 10.1016/j.tube.2010.02.001. Epub 2010 Mar 16. [Article]
  8. Priftin (Rifapentine) FDA Label [Link]

Drug created at June 13, 2005 13:24 / Updated at August 07, 2021 00:11