Quinupristin | CAS#120138-50-3 | Antibiotic

MedKoo Cat#: 318604 | Name: Quinupristin

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Description:

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

Quinupristin is an antibiotic, often used in combination with dalfopristin. It is active against Gram-positive bacteria, atypical but not Gram negatives. They inhibit protein synthesis of the cells. Quinupristin & dalfopristin are not active against Enterococcus faecalis and they need to be given in combination with other antibacterials for mixed infections which also involve Gram negative organisms.

Chemical Structure

Quinupristin

CAS#120138-50-3 (free)

Theoretical Analysis

MedKoo Cat#: 318604

Name: Quinupristin

CAS#: 120138-50-3 (free)

Chemical Formula: C53H67N9O10S

Exact Mass: 1021.4732

Molecular Weight: 1022.22

Elemental Analysis: C, 62.27; H, 6.61; N, 12.33; O, 15.65; S, 3.14

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 650.00	2 weeks

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Related CAS #

120138-50-3 (free)

Synonym

Quinupristin; RP 68888; RP-68888; RP68888; RP-57669; RP 57669; RP57669; Antibiotic RP 57669; Quinupristin.

IUPAC/Chemical Name

N-((6R,9S,10R,13S,15aS,18R,22S,24aS)-22-(4-(dimethylamino)benzyl)-6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyl-18-((((S)-quinuclidin-3-yl)thio)methyl)docosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l][1]oxa[4,7,10,13,16]pentaazacyclononadecin-9-yl)-3-hydroxypicolinamide

InChi Key

WTHRRGMBUAHGNI-LCYNINFDSA-N

InChi Code

InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1

SMILES Code

O=C(N[C@@H]1C(N[C@H](CC)C(N2[C@](CCC2)([H])C(N(C)[C@@H](CC3=CC=C(N(C)C)C=C3)C(N4[C@](CC([C@H](CS[C@@H]5CN6CCC5CC6)C4)=O)([H])C(N[C@@H](C7=CC=CC=C7)C(O[C@@H]1C)=O)=O)=O)=O)=O)=O)C8=NC=CC=C8O

Appearance

Solid powder

Purity

>98% (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 and ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinupristin binds to a nearby site on the 50S ribosomal subunit and prevents elongation of the polypeptide, as well as causing incomplete chains to be released. Quinupristin and dalfopristin are protein synthesis inhibitor; while both are only bacteriostatic agents, their combination shows bactericidal activity.

In vitro activity:

The treatment of chronic or recurrent Staphylococcus aureus infections may require using antibiotics with activity against intracellular multiresistant organisms. In this study, quinupristin/dalfopristin was examined. Compared with treatments of ifampicin, fluoroquinolones, lipoglycopeptides and other antistaphylococcal drugs, quinupristin/dalfopristin appears to be one of the most active antibiotics against intracellular S. aureus studied. Reference: J Antimicrob Chemother. 2010 Jun;65(6):1228-36. https://pubmed.ncbi.nlm.nih.gov/20378672/

In vivo activity:

This study compared the effect of quinupristin-dalfopristin treatment to that of vancomycin in murine models of hematogenous pulmonary infections caused by methicillin-resistant Staphylococcus aureus (MRSA) and VCM-insensitive S. aureus (VISA). Their results suggest that quinupristin-dalfopristin treatment is potent and effective in the treatment of MRSA and VISA hematogenous pulmonary infections. Reference: Chemotherapy. 2004 Nov;50(5):260-4. https://pubmed.ncbi.nlm.nih.gov/15528893/

	Solvent	mg/mL	mM
Solubility
	Ethanol	100.0	97.83
	DMSO	50.0	48.91

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 1,022.22 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. Baudoux P, Lemaire S, Denis O, Tulkens PM, Van Bambeke F, Glupczynski Y. Activity of quinupristin/dalfopristin against extracellular and intracellular Staphylococcus aureus with various resistance phenotypes. J Antimicrob Chemother. 2010 Jun;65(6):1228-36. doi: 10.1093/jac/dkq110. Epub 2010 Apr 8. PMID: 20378672. 2. Harms JM, Schlünzen F, Fucini P, Bartels H, Yonath A. Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin. BMC Biol. 2004 Apr 1;2:4. doi: 10.1186/1741-7007-2-4. PMID: 15059283; PMCID: PMC400760. 3. Yanagihara K, Okada M, Fukuda Y, Imamura Y, Kaneko Y, Ohno H, Higashiyama Y, Miyazaki Y, Tsukamoto K, Hirakata Y, Tomono K, Kadota J, Tashiro T, Murata I, Kohno S. Efficacy of quinupristin-dalfopristin against methicillin-resistant Staphylococcus aureus and vancomycin-insensitive S. aureus in a model of hematogenous pulmonary infection. Chemotherapy. 2004 Nov;50(5):260-4. doi: 10.1159/000081948. Epub 2004 Nov 3. PMID: 15528893. 4. García LA, Torres C, López AR, Rodríguez CO, Valencia CS. Antimicrobial Resistance of Enterococcus Species Isolated from Wild Mammals in Aragón, Spain. J Vet Res. 2022 Apr 22;66(2):151-159. doi: 10.2478/jvetres-2022-0020. PMID: 35892100; PMCID: PMC9281524.

In vitro protocol:

In vivo protocol:

1. Yanagihara K, Okada M, Fukuda Y, Imamura Y, Kaneko Y, Ohno H, Higashiyama Y, Miyazaki Y, Tsukamoto K, Hirakata Y, Tomono K, Kadota J, Tashiro T, Murata I, Kohno S. Efficacy of quinupristin-dalfopristin against methicillin-resistant Staphylococcus aureus and vancomycin-insensitive S. aureus in a model of hematogenous pulmonary infection. Chemotherapy. 2004 Nov;50(5):260-4. doi: 10.1159/000081948. Epub 2004 Nov 3. PMID: 15528893. 2. García LA, Torres C, López AR, Rodríguez CO, Valencia CS. Antimicrobial Resistance of Enterococcus Species Isolated from Wild Mammals in Aragón, Spain. J Vet Res. 2022 Apr 22;66(2):151-159. doi: 10.2478/jvetres-2022-0020. PMID: 35892100; PMCID: PMC9281524.

1: Maraki S, Samonis G, Dimopoulou D, Mantadakis E. Susceptibility of Glycopeptide-Resistant Enterococci to Linezolid, Quinupristin/dalfopristin, Tigecycline and Daptomycin in a Tertiary Greek Hospital. Infect Chemother. 2014 Dec;46(4):253-6. doi: 10.3947/ic.2014.46.4.253. Epub 2014 Dec 29. PubMed PMID: 25566405; PubMed Central PMCID: PMC4285005. 2: Yu F, Lu C, Liu Y, Sun H, Shang Y, Ding Y, Li D, Qin Z, Parsons C, Huang X, Li Y, Hu L, Wang L. Emergence of quinupristin/dalfopristin resistance among livestock-associated Staphylococcus aureus ST9 clinical isolates. Int J Antimicrob Agents. 2014 Nov;44(5):416-9. doi: 10.1016/j.ijantimicag.2014.06.020. Epub 2014 Aug 17. PubMed PMID: 25218154. 3: You YH, Wang HB, Tao XX, Song YY, Meng FL, Yan XM, Luo FJ, Zhang JZ. Antimicrobial susceptibility of Streptococcus sp. to quinupristin-dalfopristin in China. Biomed Environ Sci. 2014 May;27(5):388-90. doi: 10.3967/bes2014.065. PubMed PMID: 24827721. 4: Isogai N, Urushibara N, Kawaguchiya M, Ghosh S, Suzaki K, Watanabe N, Quiñones D, Kobayashi N. Characterization of Enterococcus faecium with macrolide resistance and reduced susceptibility to quinupristin/dalfopristin in a Japanese hospital: detection of extensive diversity in erm(B)-regulator regions. Microb Drug Resist. 2013 Aug;19(4):298-307. doi: 10.1089/mdr.2012.0176. Epub 2013 Feb 26. PubMed PMID: 23442208. 5: Kali A, Stephen S, Umadevi S, Kumar S. Detection of quinupristin-dalfopristin resistance in methicillin-resistant Staphylococcus aureus in South India. Indian J Pathol Microbiol. 2013 Jan-Mar;56(1):73-4. doi: 10.4103/0377-4929.116164. PubMed PMID: 23924572. 6: Stroh EM. Quinupristin/dalfopristin in vancomycin-resistant Staphylococcus aureus endophthalmitis. Arch Ophthalmol. 2012 Oct;130(10):1323-4. doi: 10.1001/archophthalmol.2012.1504. PubMed PMID: 23044949. 7: Nailor MD, Sobel JD. Antibiotics for gram-positive bacterial infection: vancomycin, teicoplanin, quinupristin/dalfopristin, oxazolidinones, daptomycin, telavancin, and ceftaroline. Med Clin North Am. 2011 Jul;95(4):723-42, vii. doi: 10.1016/j.mcna.2011.03.011. PubMed PMID: 21679789. 8: Hernandez-Da Mota SE. Quinupristin/dalfopristin in Staphylococcus aureus endophthalmitis: a case report. J Med Case Rep. 2011 Mar 31;5:130. doi: 10.1186/1752-1947-5-130. PubMed PMID: 21453475; PubMed Central PMCID: PMC3077336. 9: Hwang IY, Ku HO, Lim SK, Lee KJ, Park CK, Jung GS, Jung SC, Park YH, Nam HM. Distribution of streptogramin resistance genes and genetic relatedness among quinupristin/dalfopristin-resistant Enterococcus faecium recovered from pigs and chickens in Korea. Res Vet Sci. 2010 Aug;89(1):1-4. doi: 10.1016/j.rvsc.2010.01.011. Epub 2010 Mar 5. PubMed PMID: 20206952. 10: Chong YP, Lee SO, Song EH, Lee EJ, Jang EY, Kim SH, Choi SH, Kim MN, Jeong JY, Woo JH, Kim YS. Quinupristin-dalfopristin versus linezolid for the treatment of vancomycin-resistant Enterococcus faecium bacteraemia: efficacy and development of resistance. Scand J Infect Dis. 2010 Jul;42(6-7):491-9. doi: 10.3109/00365541003699623. PubMed PMID: 20524781. 11: Baudoux P, Lemaire S, Denis O, Tulkens PM, Van Bambeke F, Glupczynski Y. Activity of quinupristin/dalfopristin against extracellular and intracellular Staphylococcus aureus with various resistance phenotypes. J Antimicrob Chemother. 2010 Jun;65(6):1228-36. doi: 10.1093/jac/dkq110. Epub 2010 Apr 8. PubMed PMID: 20378672. 12: López F, Culebras E, Betriú C, Rodríguez-Avial I, Gómez M, Picazo JJ. Antimicrobial susceptibility and macrolide resistance genes in Enterococcus faecium with reduced susceptibility to quinupristin-dalfopristin: level of quinupristin-dalfopristin resistance is not dependent on erm(B) attenuator region sequence. Diagn Microbiol Infect Dis. 2010 Jan;66(1):73-7. doi: 10.1016/j.diagmicrobio.2008.06.004. Epub 2008 Jul 23. PubMed PMID: 18653303. 13: Nailor MD, Sobel JD. Antibiotics for gram-positive bacterial infections: vancomycin, teicoplanin, quinupristin/dalfopristin, oxazolidinones, daptomycin, dalbavancin, and telavancin. Infect Dis Clin North Am. 2009 Dec;23(4):965-82, ix. doi: 10.1016/j.idc.2009.06.010. Review. PubMed PMID: 19909893. 14: Hammerum AM, Agersø Y, Garcia-Migura L, Mette Seyfarth A, Porsbo LJ, Emborg HD, Bogø Jensen L. Evaluation of the quinupristin/dalfopristin breakpoints for Enterococcus faecium. Int J Antimicrob Agents. 2009 Sep;34(3):288-90. doi: 10.1016/j.ijantimicag.2009.03.018. Epub 2009 May 5. PubMed PMID: 19409762. 15: Drago L, Nicola L, De Vecchi E. A comparative in-vitro evaluation of resistance selection after exposure to teicoplanin, vancomycin, linezolid and quinupristin-dalfopristin in Staphylococcus aureus and Enterococcus spp. Clin Microbiol Infect. 2008 Jun;14(6):608-11. doi: 10.1111/j.1469-0691.2008.01993.x. Epub 2008 Apr 5. PubMed PMID: 18397336. 16: Nam HR, Lee HM, Lee Y. Isolation of quinupristin/dalfopristin-resistant Streptococcus agalactiae from asymptomatic Korean women. J Microbiol. 2008 Feb;46(1):108-11. doi: 10.1007/s12275-007-0217-1. PubMed PMID: 18337702. 17: Barthel D, Schlitzer M, Pradel G. Telithromycin and quinupristin-dalfopristin induce delayed death in Plasmodium falciparum. Antimicrob Agents Chemother. 2008 Feb;52(2):774-7. Epub 2007 Dec 3. PubMed PMID: 18056275; PubMed Central PMCID: PMC2224768. 18: Lee do K, Kim Y, Park KS, Yang JW, Kim K, Ha NJ. Antimicrobial activity of mupirocin, daptomycin, linezolid, quinupristin/dalfopristin and tigecycline against vancomycin-resistant enterococci (VRE) from clinical isolates in Korea (1998 and 2005). J Biochem Mol Biol. 2007 Nov 30;40(6):881-7. PubMed PMID: 18047782. 19: Jørgen B, Merckoll P, Melby KK. Susceptibility to daptomycin, quinupristin-dalfopristin and linezolid and some other antibiotics in clinical isolates of methicillin resistant and methicillin sensitive S.aureus from the Oslo area. Scand J Infect Dis. 2007;39(11-12):1059-62. Epub 2007 Jul 30. PubMed PMID: 17852934. 20: Młynarczyk G, Młynarczyk A, Szymanek K, Bilewska A, Pupek J, Luczak M. [MIC and MBC of quinupristin/dalfopristin of erythromycin-resistant MRSA strains isolated from clinical specimens]. Med Dosw Mikrobiol. 2006;58(3):199-205. Polish. PubMed PMID: 17340994.