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Showing drug card for Quinupristin (DB01369)

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Version 2.5
Creation Date 2007-07-06 20:25:11
Update Date 2009-04-16 16:48:23
Primary Accession Number DB01369
Secondary Accession Number Not Available
Name Quinupristin
Drug Type
  • Approved
  • Small Molecule
Description Quinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone.
Synonyms Not Available
Brand Names Not Available
Brand Mixtures
  1. Synercid (Dalfopristin + Quinupristin)
Chemical IUPAC Name Not Available
Chemical Formula C87H117N13O19S2
Chemical Structure Structure
CAS Registry Number 120138-50-3
InChI Identifier InChI=1/C53H67N9O10S.C34H50N4O9S/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;1-7-37(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/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);9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b;10-9-,12-11-,23-18-/t31-,35+,37+,38+,39?,40+,43-,44+,45+;24-,25-,28-,31-,32-/m11/s1/f/h55-57H;35H
InChI Key PPKJUHVNTMYXOD-DXVBPLDJDX
KEGG Drug D00852 Link Image
KEGG Compound C08032 Link Image
PubChem Compound 11953896 Link Image
PubChem Substance 7847917 Link Image
ChEBI ID Not Available
PharmGKB ID PA451215 Link Image
HET ID SYB Link Image
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Quinupristin Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 1713.0660
Monoisotopic Molecular Weight 1711.8030
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCN(CC)CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@H](C(C)C)[C@H](C)\C=C/C(=O)NC\C=C/C(C)=C\[C@@H](O)CC(=O)CC1=NC(=CO1)C2=O.CC[C@@H]1NC(=O)[C@@H](NC(=O)C2=C(O)C=CC=N2)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)[C@H](CS[C@@H]3C[N@@]4CC[C@H]3CC4)CN2C(=O)[C@H](CC2=CC=C(C=C2)N(C)C)N(C)C(=O)[C@@H]2CCCN2C1=O)C1=CC=CC=C1
Canonical SMILES CCN(CC)CCS(=O)(=O)C1CCN2C1C(=O)OC(C(C)C)C(C)C=CC(=O)NCC=CC(C)=CC(O)CC(=O)CC1=NC(=CO1)C2=O.CCC1NC(=O)C(NC(=O)C2=C(O)C=CC=N2)C(C)OC(=O)C(NC(=O)C2CC(=O)C(CSC3CN4CCC3CC4)CN2C(=O)C(CC2=CC=C(C=C2)N(C)C)N(C)C(=O)C2CCCN2C1=O)C1=CC=CC=C1
Drug Category
  • Antibacterial Agents
ATC Codes Not Available
AHFS Codes Not Available
Indication For the treatment of bacterial infections (usually in combination with dalfopristin).
Pharmacology Quinupristin is a streptogramin antibiotic, derived from pristinamycin I.
Mechanism of Action Quinupristin inhibits the late phase of protein synthesis in the bacterial ribosome.
Absorption Not Available
Toxicity Not Available
Protein Binding Moderate.
Biotransformation Quinupristin is converted to two conjugated active major metabolites, one with glutathione and one with cysteine.
Half Life 3.1 hours
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions
Drug Interaction
Amlodipine This combination presents an increased risk of toxicity
Arsenic trioxide This combination presents an increased risk of toxicity
Astemizole This combination presents an increased risk of toxicity
Atorvastatin This combination presents an increased risk of toxicity
Carbamazepine This combination presents an increased risk of toxicity
Cerivastatin This combination presents an increased risk of toxicity
Cisapride This combination presents an increased risk of toxicity
Clarithromycin This combination presents an increased risk of toxicity
Cyclosporine Synercid increases the effect of cyclosporine
Delavirdine This combination presents an increased risk of toxicity
Diazepam This combination presents an increased risk of toxicity
Dihydroquinidine barbiturate This combination presents an increased risk of toxicity
Diltiazem This combination presents an increased risk of toxicity
Disopyramide This combination presents an increased risk of toxicity
Docetaxel This combination presents an increased risk of toxicity
Dofetilide This combination presents an increased risk of toxicity
Droperidol This combination presents an increased risk of toxicity
Erythromycin This combination presents an increased risk of toxicity
Etoposide This combination presents an increased risk of toxicity
Felbamate This combination presents an increased risk of toxicity
Felodipine This combination presents an increased risk of toxicity
Flecainide This combination presents an increased risk of toxicity
Foscarnet This combination presents an increased risk of toxicity
Fosphenytoin This combination presents an increased risk of toxicity
Gatifloxacin This combination presents an increased risk of toxicity
Grepafloxacin This combination presents an increased risk of toxicity
Halofantrine This combination presents an increased risk of toxicity
Indinavir This combination presents an increased risk of toxicity
Isradipine This combination presents an increased risk of toxicity
Lercanidipine This combination presents an increased risk of toxicity
Levofloxacin This combination presents an increased risk of toxicity
Levomethadyl Acetate This combination presents an increased risk of toxicity
Lidocaine This combination presents an increased risk of toxicity
Losartan This combination presents an increased risk of toxicity
Lovastatin This combination presents an increased risk of toxicity
Methylprednisolone This combination presents an increased risk of toxicity
Midazolam This combination presents an increased risk of toxicity
Moexipril This combination presents an increased risk of toxicity
Moxifloxacin This combination presents an increased risk of toxicity
Nevirapine This combination presents an increased risk of toxicity
Nicardipine This combination presents an increased risk of toxicity
Nifedipine Synercid increases the effect of ziprasidone
Nimodipine This combination presents an increased risk of toxicity
Nisoldipine This combination presents an increased risk of toxicity
Octreotide This combination presents an increased risk of toxicity
Paclitaxel This combination presents an increased risk of toxicity
Pentamidine This combination presents an increased risk of toxicity
Quetiapine This combination presents an increased risk of toxicity
Quinidine This combination presents an increased risk of toxicity
Quinidine barbiturate This combination presents an increased risk of toxicity
Ritonavir This combination presents an increased risk of toxicity
Salmeterol This combination presents an increased risk of toxicity
Simvastatin This combination presents an increased risk of toxicity
Tacrolimus This combination presents an increased risk of toxicity
Tamoxifen This combination presents an increased risk of toxicity
Teniposide This combination presents an increased risk of toxicity
Terfenadine This combination presents an increased risk of toxicity
Tizanidine This combination presents an increased risk of toxicity
Venlafaxine This combination presents an increased risk of toxicity
Verapamil This combination presents an increased risk of toxicity
Vinblastine This combination presents an increased risk of toxicity
Vincristine This combination presents an increased risk of toxicity
Vindesine This combination presents an increased risk of toxicity
Vinorelbine This combination presents an increased risk of toxicity
Food Interactions Not Available
Pathways Not Available
General References
  1. 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 Link Image]
  2. Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. [PubMed Link Image]
  3. Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. [PubMed Link Image]
  4. Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. [PubMed Link Image]
  5. Wikipedia Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.