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Dalfopristin

CAS No.
112362-50-2
Chemical Name:
Dalfopristin
Synonyms
RP 54476;Dalfopristin;Dalfopristin Mesylate;RP-54476,RP 54476,Inhibitor,Dalfopristin,Antibiotic,Bacterial,inhibit;(3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(Diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadi;(3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(DiethylaMino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-diMethyl-3-(1-Methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetr;(3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(Diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone;3H-21,18-Nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone, 26-[[2-(diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-, (3R,4R,5E,10E,12E,14S,26R,26aS)-
CBNumber:
CB31075198
Molecular Formula:
C34H50N4O9S
Molecular Weight:
690.85
MDL Number:
MFCD00895414
MOL File:
112362-50-2.mol
MSDS File:
SDS
Last updated:2023-05-21 10:59:17

Dalfopristin Properties

Melting point ~150°
Boiling point 940.5±65.0 °C(Predicted)
Density 1.27±0.1 g/cm3(Predicted)
storage temp. Store at -20°C
solubility DMSO:113.0(Max Conc. mg/mL);163.57(Max Conc. mM)
Ethanol:100.0(Max Conc. mg/mL);144.75(Max Conc. mM)
pka 13.18±0.70(Predicted)
FDA UNII R9M4FJE48E

Dalfopristin price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 19762 Dalfopristin (mesylate) ≥98% 112362-50-2 1mg $335 2024-03-01 Buy
Cayman Chemical 19762 Dalfopristin (mesylate) ≥98% 112362-50-2 5mg $1091 2024-03-01 Buy
ApexBio Technology C5482 Dalfopristin(mesylate) 112362-50-2 5mg $1246 2021-12-16 Buy
ChemScene CS-6142 Dalfopristin 98.34% 112362-50-2 10mg $1800 2021-12-16 Buy
Biosynth Carbosynth FD20779 Dalfopristin 112362-50-2 1mg $1982 2021-12-16 Buy
Product number Packaging Price Buy
19762 1mg $335 Buy
19762 5mg $1091 Buy
C5482 5mg $1246 Buy
CS-6142 10mg $1800 Buy
FD20779 1mg $1982 Buy

Dalfopristin Chemical Properties,Uses,Production

Uses

A Viiginiamycin M1 (V672810) derivative. A streptogramin antibiotic used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

Uses

Dalfopristin is a semi-synthetic analogue of ostreogrycin A (virginiamycin M, pristinamycin IIA, streptogramin A) formed by addition of diethylaminoethylthiol to the 2-pyrroline group of ostreogrycin, followed by oxidation to the sulfone. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Dalfopristin is used commercially in synergistic combination with quinupristin (70:30). There is little published data on the synthesis, biological or antibiotic activity of dalfopristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.

Uses

Dalfopristin is a semi-synthetic analogue of ostreogyrcin A (virginiamycin M, pristinamycin IIA, streptogramin A) formed by addition of diethylaminoethylthiol to the 2-pyrroline group of ostreogyrcin, followed by oxidation to the sulphone. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Dalfopristin is used commercially in synergistic combination with quinupristin (70:30). There is little published data on the synthesis, biological or antibiotic activity of dalfopristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.

Definition

ChEBI: Dalfopristin is a macrolide that is pristinamycin IIA in which the double bond between positions 26 and 26a of the pyrroline ring has been reduced and position 26R carries a [2-(diethylamino)ethyl]sulfonyl group. It is a semi-synthetic streptogramin antibiotic and often used as a mixture with quinupristin for the treatment of vancomycin-resistant Enterococcus faecium. It has a role as an antibacterial drug and a protein synthesis inhibitor. It is a macrolide, a member of 1,3-oxazoles, a cyclic ketone, an enamide, a secondary alcohol, a secondary carboxamide, a tertiary carboxamide, a sulfone, a tertiary amino compound, a carboxylic ester and a macrolide antibiotic. It is functionally related to a pristinamycin IIA.

Dalfopristin Preparation Products And Raw materials

Raw materials

Preparation Products

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(3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(DiethylaMino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-diMethyl-3-(1-Methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetr Dalfopristin Mesylate RP 54476 Dalfopristin (3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(Diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadi 3H-21,18-Nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone, 26-[[2-(diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-, (3R,4R,5E,10E,12E,14S,26R,26aS)- (3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(Diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone RP-54476,RP 54476,Inhibitor,Dalfopristin,Antibiotic,Bacterial,inhibit 112362-50-2 C34H50N4O9S Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals