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Identification
Name Dalfopristin
Accession Number DB01764 (EXPT01246)
Type small molecule
Groups approved
Description

Dalfopristin is a combination of two antibiotics (Dalfopristin and quinupristin) used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. It is not effective against Enterococcus faecalis infections. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dalfopristina [inn-spanish]
  • Dalfopristine [inn-french]
  • Dalfopristinum [inn-latin]
Synonyms
Dalfopristina [inn-spanish]
Dalfopristine [inn-french]
Dalfopristinum [inn-latin]
Salts Not Available
Brand names Not Available
Brand mixtures
Brand Name Ingredients
Synercid Dalfopristin + Quinupristin
Categories
  • Anti-Bacterial Agents
  • Antibacterial Agents
CAS number 112362-50-2
Weight Average: 690.847
Monoisotopic: 690.329849908
Chemical Formula C34H50N4O9S
InChI Key InChIKey=SUYRLXYYZQTJHF-FUODUHIRSA-N
InChI
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
Plain Text
IUPAC Name
(6R,10R,11R,12Z,17Z,19Z,21S)-6-{[2-(diethylamino)ethane]sulfonyl}-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
SMILES
CCN(CC)CCS(=O)(=O)[C@@H]1CCN2C(=O)C3=COC(=N3)CC(=O)C[C@H](O)\C=C(\C)/C=C\CNC(=O)\C=C/[C@@H](C)[C@@H](C(C)C)OC(=O)C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Amino Acids
  • Lactams
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Lactones
  • Amino Ketones
  • Sulfonyls
  • Pyrrolidines
  • Ethers
  • Aliphatic and Aryl Amines
  • Sulfones
  • Isoprenes
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Oxazoles
  • Amino Acids
  • Lactams
  • Imines
  • Alcohols and Polyols
  • Sulfoxides
  • Ketones
Pharmacology
Indication For the treatment of bacterial infections (usually in combination with quinupristin).
Pharmacodynamics Dalfopristin is a streptogramin antibiotic, derived from pristinamycin IIA.
Mechanism of action The site of action of dalfopristin is the bacterial ribosome. Dalfopristin has been shown to inhibit the early phase of protein synthesis.
Absorption Not Available
Volume of distribution Not Available
Protein binding Moderate
Metabolism Converted to an active non-conjugated metabolite by hydrolysis.
Route of elimination Not Available
Half life The elimination half-life is approximately 0.70 hours.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Solution Intravenous
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 7.16e-02 g/l ALOGPS
logP 2.57 ALOGPS
logP 1.58 ChemAxon Molconvert
logS -4 ALOGPS
pKa 14.65 ChemAxon Molconvert
hydrogen acceptor count 9 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 176.42 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 182.84 ChemAxon Molconvert
polarizability 73.8 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. Pubmed
  2. Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97. Pubmed
  3. Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. Pubmed
  4. Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. Pubmed
External Links
Resource Link
KEGG Drug D00853 Link_out
KEGG Compound C08033 Link_out
PubChem Compound 21943991 Link_out
PubChem Substance 46506561 Link_out
ChemSpider 4940480 Link_out
Therapeutic Targets Database DAP001294 Link_out
PharmGKB PA449200 Link_out
HET DOL Link_out
Drug Product Database 2241323 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dalfopristin Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label show (67.1 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Streptogramin A acetyltransferase

Pharmacological action: yes
Actions: inhibitor

Inactivates the A compounds of streptogramin antibiotics by acetylation, thus providing resistance to these antibiotics

Organism class: bacterial
UniProt ID: P50870 Link_out
Gene: vatD
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Manfredi R, Sabbatani S: Novel pharmaceutical molecules against emerging resistant gram-positive cocci. Braz J Infect Dis. 2010 Jan-Feb;14(1):96-108. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:49