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MedKoo Cat#: 317578 | Name: Dalfopristin
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Description:

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

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

Dalfopristin
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: 690.85

Elemental Analysis: C, 59.11; H, 7.30; N, 8.11; O, 20.84; S, 4.64

Price and Availability

Size Price Availability Quantity
5mg USD 1,250.00 2 Weeks
10mg USD 2,150.00 2 Weeks
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Related CAS #
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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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dalfopristin is a semi-synthetic streptogramin antibiotic. Quinupristin/Dalfopristin (Q/D) is a valuable alternative antibiotic to vancomycin for the treatment of multi-drug resistant Enterococcus faecium infections.
In vitro activity:
Quinupristin-dalfopristin (Q-D), which is active against bacteria and Toxoplasma gondii, was examined for its activity against Pneumocystis carinii. Q-D reduced the ATP pools in P. carinii in a dose- and time-dependent manner (Fig.1A). Maximal effect was seen at 72 h with an IC50 of 10.6 μg/ml, which amounts to slight to moderate activity on our scoring scale. Toxicity evaluation revealed that the IC50 of Q-D for A549 cells was 122.0 μg/ml, compared with an IC50 of 10.6 μg/ml for P. carinii at 72 h, a >10-fold difference (Fig.1B). The in vitro data in the present study suggest that Q-D is less active against P. carinii than against T. gondii in tissue culture and is also less active than standard anti-P. carinii drugs against the organism in the ATP assay. Reference: Antimicrob Agents Chemother. 2001 Nov; 45(11): 3234–3237. https://pubmed.ncbi.nlm.nih.gov/11600389/
In vivo activity:
The effects of Q-D on P. carinii were examined by in vivo techniques. Q-D was administered intraperitoneally at doses of 50 to 200 mg per kg of body weight per day in the treatment and 100 mg/kg/day three times per week in the prophylaxis of pneumocystosis in immunosuppressed mice. Q-D doses of 50 and 100 mg per kg of body weight per day in the treatment of pneumocystosis lowered the mean organism cyst count four- to fivefold, from log10 7.49 ± 0.57/lung in the C-S group to log10 6.82 ± 0.63 and log10 6.87 ± 0.37/lung, respectively (P < 0.01) (Fig.2A). Q-D at 200 mg/kg/day reduced the organism count 15-fold (moderate activity), to log10 6.32 ± 0.46/lung (P < 0.001). This was greater than the reduction with the 50- and 100-mg/kg/day doses (P < 0.05). It is concluded that Q-D has activity against P. carinii in vivo. Reference: Antimicrob Agents Chemother. 2001 Nov;45(11):3234-7. https://pubmed.ncbi.nlm.nih.gov/11600389/
Solvent mg/mL mM
Solubility
DMSO 113.0 163.57
Ethanol 100.0 144.75
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 690.85 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
Formulation protocol:
1. Walzer PD, Ashbaugh A, Collins M, Cushion MT. In vitro and in vivo effects of quinupristin-dalfopristin against Pneumocystis carinii. Antimicrob Agents Chemother. 2001 Nov;45(11):3234-7. doi: 10.1128/AAC.45.11.3234-3237.2001. PMID: 11600389; PMCID: PMC90815. 2. Khan AA, Slifer TR, Araujo FG, Remington JS. Quinupristin-dalfopristin is active against Toxoplasma gondii. Antimicrob Agents Chemother. 1999 Aug;43(8):2043-5. doi: 10.1128/AAC.43.8.2043. PMID: 10428933; PMCID: PMC89411.
In vitro protocol:
1. Walzer PD, Ashbaugh A, Collins M, Cushion MT. In vitro and in vivo effects of quinupristin-dalfopristin against Pneumocystis carinii. Antimicrob Agents Chemother. 2001 Nov;45(11):3234-7. doi: 10.1128/AAC.45.11.3234-3237.2001. PMID: 11600389; PMCID: PMC90815. 2. Khan AA, Slifer TR, Araujo FG, Remington JS. Quinupristin-dalfopristin is active against Toxoplasma gondii. Antimicrob Agents Chemother. 1999 Aug;43(8):2043-5. doi: 10.1128/AAC.43.8.2043. PMID: 10428933; PMCID: PMC89411.
In vivo protocol:
1. Walzer PD, Ashbaugh A, Collins M, Cushion MT. In vitro and in vivo effects of quinupristin-dalfopristin against Pneumocystis carinii. Antimicrob Agents Chemother. 2001 Nov;45(11):3234-7. doi: 10.1128/AAC.45.11.3234-3237.2001. PMID: 11600389; PMCID: PMC90815. 2. Khan AA, Slifer TR, Araujo FG, Remington JS. Quinupristin-dalfopristin is active against Toxoplasma gondii. Antimicrob Agents Chemother. 1999 Aug;43(8):2043-5. doi: 10.1128/AAC.43.8.2043. PMID: 10428933; PMCID: PMC89411.
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.