Dalfopristin
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MedKoo CAT#: 317578

CAS#: 112362-50-2

Description: Dalfopristin is a semi-synthetic derivative of streptogramin A produced by streptomycetes. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome by binding to the 70S subunit, and also alters the configuration of the ribosome to make it more susceptible for streptogramin B binding. Dalfopristin is used in combination with quinopristin, a streptogramin B derivative. This combination is active against most gram-positive organisms, including Enterococcus faecium, and is also active against some gram-negative organisms and mycoplasma.


Chemical Structure

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Dalfopristin
CAS# 112362-50-2

Theoretical Analysis

MedKoo Cat#: 317578
Name: Dalfopristin
CAS#: 112362-50-2
Chemical Formula: C34H50N4O9S
Exact Mass: 690.3298
Molecular Weight: 690.853
Elemental Analysis: C, 59.11; H, 7.30; N, 8.11; O, 20.84; S, 4.64

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Synonym: Dalfopristine; Dalfopristinum; Dalfopristina; Dalfopristina

IUPAC/Chemical Name: (12Z,32S,33R,6R,7R,8E,13E,15E,17S)-33-((2-(diethylamino)ethyl)sulfonyl)-17-hydroxy-6-isopropyl-7,15-dimethyl-5-oxa-11-aza-1(4,2)-oxazola-3(1,2)-pyrrolidinacycloicosaphane-8,13,15-triene-2,4,10,19-tetraone

InChi Key: SUYRLXYYZQTJHF-VMBLUXKRSA-N

InChi Code: InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1

SMILES Code: CCN(CCS(=O)([C@@H]1CCN2[C@H]1C(O[C@@H]([C@@H](/C=C/C(NC/C=C/C(C)=C/[C@H](CC(CC3=NC(C2=O)=CO3)=O)O)=O)C)C(C)C)=O)=O)CC

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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 690.853 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.

Recalculate based on batch purity %
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

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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: 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.

5: 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.

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: Bhatawadekar S, Chattopadhyay A. Quinpristin-Dalfopristin resistance among methicillin-resistant strains of staphylococci. Indian J Pharmacol. 2010 Feb;42(1):56. doi: 10.4103/0253-7613.62403. PubMed PMID: 20606841; PubMed Central PMCID: PMC2885644.

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.