Quinupristin
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MedKoo CAT#: 318604

CAS#: 120138-50-3

Description: Quinupristin is an antibiotic, often used in combination with dalfopristin under the trade name Synercid. 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.


Price and Availability

Size
Price

100mg
USD 450
Size
Price

Size
Price

Quinupristin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318604
Name: Quinupristin
CAS#: 120138-50-3
Chemical Formula: C53H67N9O10S
Exact Mass: 1021.47316
Molecular Weight: 1022.22
Elemental Analysis: C, 62.27; H, 6.61; N, 12.33; O, 15.65; S, 3.14


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


Technical Data

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, not in water

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).

Harmonized System Code:
293490


References

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.