Rifapentine | CAS#61379-65-5 | rifamycin antibiotic

MedKoo Cat#: 461089 | Name: Rifapentine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rifapentine is a rifamycin antibiotic and has been used to shorten the time required to treat tuberculosis.

Chemical Structure

Rifapentine

CAS#61379-65-5

Theoretical Analysis

MedKoo Cat#: 461089

Name: Rifapentine

CAS#: 61379-65-5

Chemical Formula: C47H64N4O12

Exact Mass: 876.4521

Molecular Weight: 877.04

Elemental Analysis: C, 64.37; H, 7.36; N, 6.39; O, 21.89

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks

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Synonym

Rifapentine; DL 473; DL-473; DL473; R 773; R-773; R773;

IUPAC/Chemical Name

3-(N-(4-Cyclopentyl-1-piperazinyl)formimidoyl)rifamycin

InChi Key

WDZCUPBHRAEYDL-GZAUEHORSA-N

InChi Code

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

SMILES Code

CO[C@H]1/C=C/O[C@]2(Oc(c(C)c3O)c(C2=O)c4c3c(O)c(NC(/C(C)=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(C)=O)C)O)C)O)C)=O)c(/C=N/N5CCN(C6CCCC6)CC5)c4O)C

Appearance

Solid powder

Purity

>90% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, and ethanol

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A21K04S20

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Rifapentine (DL 473) is an antibiotic compound used in the treatment of tuberculosis that inhibits DNA-dependent RNA polymerase activity in susceptible cells.

In vitro activity:

This study demonstrated that Rifapentine-loaded poly(lactic-co-glycolic acid) microspheres (RPMs)-loaded bone-like hydroxyapatite/poly amino acid (BHA/PAA) has an effective activity against Mycobacterium tuberculosis. This study demonstrates the potential value of RPM-loaded BHA/PAA in treating bone and joint tuberculosis. Reference: Cell Biol Int. 2017 Apr;41(4):369-373. https://pubmed.ncbi.nlm.nih.gov/28102559/

In vivo activity:

The incidence of leprosy among household contacts of patients with leprosy over 4 years was lower with single-dose rifapentine than with no intervention. In an intention-to-treat analysis, the cumulative incidence in the rifapentine treatment group was 84% lower than that in the control group Reference: N Engl J Med. 2023 May 18;388(20):1843-1852. https://pubmed.ncbi.nlm.nih.gov/37195940/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	34.20
	DMF	30.0	34.20
	Ethanol	2.0	2.30

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 877.04 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Liu Y, Jiang D. Effect of bone-like hydroxyapatite/poly amino acid loaded with rifapentine microspheres on bone and joint tuberculosis in vitro. Cell Biol Int. 2017 Apr;41(4):369-373. doi: 10.1002/cbin.10730. Epub 2017 Feb 27. PMID: 28102559. 2. Chan JG, Duke CC, Ong HX, Chan JC, Tyne AS, Chan HK, Britton WJ, Young PM, Traini D. A novel inhalable form of rifapentine. J Pharm Sci. 2014 May;103(5):1411-21. doi: 10.1002/jps.23911. Epub 2014 Mar 1. PMID: 24585270. 3. Wang L, Wang H, Yan L, Yu M, Yang J, Li J, Li J, Ning Y, Jiang H, Shi Y, Zhang W, Xiong L, Liu J, Kuang Y, Wang H, He J, Wang D, Li B, Liu Y, Shui T, Wang Y, Chen H, Sha X, Long H, Yu X, Shen C, Shen J, Yang X, Gu H, Zhang G, Wang B. Single-Dose Rifapentine in Household Contacts of Patients with Leprosy. N Engl J Med. 2023 May 18;388(20):1843-1852. doi: 10.1056/NEJMoa2205487. PMID: 37195940. 4. Sharan R, Ganatra SR, Singh DK, Cole J, Foreman TW, Thippeshappa R, Peloquin CA, Shivanna V, Gonzalez O, Day CL, Gandhi NR, Dick EJ Jr, Hall-Ursone S, Mehra S, Schlesinger LS, Rengarajan J, Kaushal D. Isoniazid and rifapentine treatment effectively reduces persistent M. tuberculosis infection in macaque lungs. J Clin Invest. 2022 Sep 15;132(18):e161564. doi: 10.1172/JCI161564. PMID: 35862216; PMCID: PMC9479578.

In vitro protocol:

In vivo protocol:

1. Wang L, Wang H, Yan L, Yu M, Yang J, Li J, Li J, Ning Y, Jiang H, Shi Y, Zhang W, Xiong L, Liu J, Kuang Y, Wang H, He J, Wang D, Li B, Liu Y, Shui T, Wang Y, Chen H, Sha X, Long H, Yu X, Shen C, Shen J, Yang X, Gu H, Zhang G, Wang B. Single-Dose Rifapentine in Household Contacts of Patients with Leprosy. N Engl J Med. 2023 May 18;388(20):1843-1852. doi: 10.1056/NEJMoa2205487. PMID: 37195940. 2. Sharan R, Ganatra SR, Singh DK, Cole J, Foreman TW, Thippeshappa R, Peloquin CA, Shivanna V, Gonzalez O, Day CL, Gandhi NR, Dick EJ Jr, Hall-Ursone S, Mehra S, Schlesinger LS, Rengarajan J, Kaushal D. Isoniazid and rifapentine treatment effectively reduces persistent M. tuberculosis infection in macaque lungs. J Clin Invest. 2022 Sep 15;132(18):e161564. doi: 10.1172/JCI161564. PMID: 35862216; PMCID: PMC9479578.

1: Dorman SE, Savic RM, Goldberg S, Stout JE, Schluger N, Muzanyi G, Johnson JL, Nahid P, Hecker EJ, Heilig CM, Bozeman L, Feng PJ, Moro RN, MacKenzie W, Dooley KE, Nuermberger EL, Vernon A, Weiner M; Tuberculosis Trials Consortium. Daily rifapentine for treatment of pulmonary tuberculosis. A randomized, dose-ranging trial. Am J Respir Crit Care Med. 2015 Feb 1;191(3):333-43. doi: 10.1164/rccm.201410-1843OC. Erratum in: Am J Respir Crit Care Med. 2015 May 15;191(10):1210. PubMed PMID: 25489785; PubMed Central PMCID: PMC5447287. 2: 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. PubMed PMID: 25512422; PubMed Central PMCID: PMC4335826. 3: Weiner M, Egelund EF, Engle M, Kiser M, Prihoda TJ, Gelfond JA, Mac Kenzie W, Peloquin CA. Pharmacokinetic interaction of rifapentine and raltegravir in healthy volunteers. J Antimicrob Chemother. 2014 Apr;69(4):1079-85. doi: 10.1093/jac/dkt483. Epub 2013 Dec 15. PubMed PMID: 24343893; PubMed Central PMCID: PMC4014856. 4: Chan JG, Bai X, Traini D. An update on the use of rifapentine for tuberculosis therapy. Expert Opin Drug Deliv. 2014 Mar;11(3):421-31. doi: 10.1517/17425247.2014.877886. Epub 2014 Jan 8. Review. PubMed PMID: 24397259. 5: 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. PubMed PMID: 25535219; PubMed Central PMCID: PMC4356204. 6: Podany AT, Bao Y, Swindells S, Chaisson RE, Andersen JW, Mwelase T, Supparatpinyo K, Mohapi L, Gupta A, Benson CA, Kim P, Fletcher CV; AIDS Clinical Trials Group A5279 Study Team. Efavirenz Pharmacokinetics and Pharmacodynamics in HIV-Infected Persons Receiving Rifapentine and Isoniazid for Tuberculosis Prevention. Clin Infect Dis. 2015 Oct 15;61(8):1322-7. doi: 10.1093/cid/civ464. Epub 2015 Jun 16. PubMed PMID: 26082504; PubMed Central PMCID: PMC4583578. 7: Vidal JS, Silva MT, Sanchez MN. Rifapentine for latent tuberculosis infection treatment in the general population and human immunodeficiency virus-positive patients: summary of evidence. Rev Soc Bras Med Trop. 2015 Sep-Oct;48(5):507-13. doi: 10.1590/0037-8682-0156-2014. Review. PubMed PMID: 26516958. 8: Chan JG, Tyne AS, Pang A, McLachlan AJ, Perera V, Chan JC, Britton WJ, Chan HK, Duke CC, Young PM, Traini D. Murine pharmacokinetics of rifapentine delivered as an inhalable dry powder. Int J Antimicrob Agents. 2015 Mar;45(3):319-23. doi: 10.1016/j.ijantimicag.2014.11.009. Epub 2014 Dec 16. PubMed PMID: 25554469. 9: Savic RM, Lu Y, Bliven-Sizemore E, Weiner M, Nuermberger E, Burman W, Dorman SE, Dooley KE. Population pharmacokinetics of rifapentine and desacetyl rifapentine in healthy volunteers: nonlinearities in clearance and bioavailability. Antimicrob Agents Chemother. 2014 Jun;58(6):3035-42. doi: 10.1128/AAC.01918-13. Epub 2014 Mar 10. PubMed PMID: 24614383; PubMed Central PMCID: PMC4068478. 10: Chan JG, Duke CC, Ong HX, Chan JC, Tyne AS, Chan HK, Britton WJ, Young PM, Traini D. A novel inhalable form of rifapentine. J Pharm Sci. 2014 May;103(5):1411-21. doi: 10.1002/jps.23911. Epub 2014 Mar 1. PubMed PMID: 24585270. 11: Jindani A, Harrison TS, Nunn AJ, Phillips PP, Churchyard GJ, Charalambous S, Hatherill M, Geldenhuys H, McIlleron HM, Zvada SP, Mungofa S, Shah NA, Zizhou S, Magweta L, Shepherd J, Nyirenda S, van Dijk JH, Clouting HE, Coleman D, Bateson AL, McHugh TD, Butcher PD, Mitchison DA; RIFAQUIN Trial Team. High-dose rifapentine with moxifloxacin for pulmonary tuberculosis. N Engl J Med. 2014 Oct 23;371(17):1599-608. doi: 10.1056/NEJMoa1314210. PubMed PMID: 25337749; PubMed Central PMCID: PMC4233406. 12: Villarino ME, Scott NA, Weis SE, Weiner M, Conde MB, Jones B, Nachman S, Oliveira R, Moro RN, Shang N, Goldberg SV, Sterling TR; International Maternal Pediatric and Adolescents AIDS Clinical Trials Group; Tuberculosis Trials Consortium. Treatment for preventing tuberculosis in children and adolescents: a randomized clinical trial of a 3-month, 12-dose regimen of a combination of rifapentine and isoniazid. JAMA Pediatr. 2015 Mar;169(3):247-55. doi: 10.1001/jamapediatrics.2014.3158. Erratum in: JAMA Pediatr. 2015 Sep;169(9):878. PubMed PMID: 25580725. 13: Zhou QT, Sun SP, Chan JG, Wang P, Barraud N, Rice SA, Wang J, Li J, Chan HK. Novel Inhaled Combination Powder Containing Amorphous Colistin and Crystalline Rifapentine with Enhanced Antimicrobial Activities against Planktonic Cells and Biofilm of Pseudomonas aeruginosa for Respiratory Infections. Mol Pharm. 2015 Aug 3;12(8):2594-603. doi: 10.1021/mp500586p. Epub 2014 Dec 24. PubMed PMID: 25423590. 14: Dooley KE, Savic RM, Park JG, Cramer Y, Hafner R, Hogg E, Janik J, Marzinke MA, Patterson K, Benson CA, Hovind L, Dorman SE, Haas DW; ACTG A5311 Study Team. Novel dosing strategies increase exposures of the potent antituberculosis drug rifapentine but are poorly tolerated in healthy volunteers. Antimicrob Agents Chemother. 2015;59(6):3399-405. doi: 10.1128/AAC.05128-14. Epub 2015 Mar 30. PubMed PMID: 25824215; PubMed Central PMCID: PMC4432148. 15: Egelund EF, Weiner M, Singh RP, Prihoda TJ, Gelfond JA, Derendorf H, Mac Kenzie WR, Peloquin CA. Protein binding of rifapentine and its 25-desacetyl metabolite in patients with pulmonary tuberculosis. Antimicrob Agents Chemother. 2014 Aug;58(8):4904-10. doi: 10.1128/AAC.01730-13. Epub 2014 May 19. PubMed PMID: 24841270; PubMed Central PMCID: PMC4136068. 16: Bliven-Sizemore EE, Sterling TR, Shang N, Benator D, Schwartzman K, Reves R, Drobeniuc J, Bock N, Villarino ME; TB Trials Consortium. Three months of weekly rifapentine plus isoniazid is less hepatotoxic than nine months of daily isoniazid for LTBI. Int J Tuberc Lung Dis. 2015 Sep;19(9):1039-44, i-v. doi: 10.5588/ijtld.14.0829. PubMed PMID: 26260821; PubMed Central PMCID: PMC5080618. 17: Zhang Z, Wu L, Li H, Long Z, Song X. Drug Release Characteristics and Tissue Distribution of Rifapentine Polylactic Acid Sustained-Release Microspheres in Rabbits after Paravertebral Implantation. Iran Red Crescent Med J. 2016 Aug 13;18(11):e38661. doi: 10.5812/ircmj.38661. eCollection 2016 Nov. PubMed PMID: 28210500; PubMed Central PMCID: PMC5301995. 18: Egelund EF, Peloquin CA. Rifapentine for the treatment of latent tuberculosis. Expert Rev Clin Pharmacol. 2016 Aug 22:1-9. [Epub ahead of print] PubMed PMID: 27545595. 19: Baciewicz AM, Chrisman CR, Finch CK, Self TH. Update on rifampin, rifabutin, and rifapentine drug interactions. Curr Med Res Opin. 2013 Jan;29(1):1-12. doi: 10.1185/03007995.2012.747952. Epub 2012 Nov 30. Review. PubMed PMID: 23136913. 20: Chan JG, Tyne AS, Pang A, Chan HK, Young PM, Britton WJ, Duke CC, Traini D. A rifapentine-containing inhaled triple antibiotic formulation for rapid treatment of tubercular infection. Pharm Res. 2014 May;31(5):1239-53. doi: 10.1007/s11095-013-1245-7. Epub 2013 Nov 16. PubMed PMID: 24242939.

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Cenupatide free base

MedKoo CAT#: 330166

CAS#: 1006388-38-0 (free base)