Identification
- Summary
Quinupristin is an antibiotic agent used in the treatment of serious vancomycin-resistant Enterococcus faecium bacteremia as well as complicated skin and skin structure infections.
- Brand Names
- Synercid
- Generic Name
- Quinupristin
- DrugBank Accession Number
- DB01369
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Quinupristin (DB01369)
- Weight
- Average: 1022.23
Monoisotopic: 1021.473160567 - Chemical Formula
- C53H67N9O10S
- Synonyms
- Quinupristin
- External IDs
- RP 57669
Pharmacology
- Indication
For the treatment of bacterial infections (usually in combination with dalfopristin).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Bacterial infections Combination Product in combination with: Dalfopristin (DB01764) •••••••••••• Used in combination to treat Methicillin-resistant staphylococcus aureus infection Combination Product in combination with: Dalfopristin (DB01764) ••• ••••• Used in combination to treat Complicated skin and subcutaneous tissue bacterial infection Combination Product in combination with: Dalfopristin (DB01764) •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Quinupristin is a streptogramin antibiotic, derived from pristinamycin I. By inhibiting the bacterial ribosomal subunits, protein synthesis is inhibited thus leading to eventual bacterial cell death or stasis.
- Mechanism of action
Quinupristin inhibits the late phase of protein synthesis in the bacterial ribosome. Dalfopristin binds to the 23S portion of the 50S ribosomal subunit, and changes the conformation it, enhancing the binding of quinupristin by a factor of about 100. In addition, it inhibits peptidyl transferase. Quinupristin binds to a nearby site on the 50S ribosomal subunit and prevents elongation of the polypeptide as well as causing incomplete chains to be released.
Target Actions Organism A23S ribosomal RNA inhibitorEnteric bacteria and other eubacteria A50S ribosomal protein L10 inhibitorShigella flexneri A50S ribosomal protein L22 inhibitorEscherichia coli O157:H7 - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Moderate.
- Metabolism
Quinupristin is converted to two conjugated active major metabolites, one with glutathione and one with cysteine.
- Route of elimination
Not Available
- Half-life
3.1 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be decreased when combined with Quinupristin. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Quinupristin. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Quinupristin. Albendazole The metabolism of Albendazole can be decreased when combined with Quinupristin. Alectinib The metabolism of Alectinib can be decreased when combined with Quinupristin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Quinupristin mesylate 91VAC8654E Not Available ZNQOUMVWYLNQRW-FDQSXSIVSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Synercid Quinupristin (150 mg/5mL) + Dalfopristin (350 mg/5mL) Injection, powder, lyophilized, for solution Intravenous Pfizer Laboratories Div Pfizer Inc 1999-09-21 Not applicable US 
Synercid Quinupristin (180 mg/6mL) + Dalfopristin (420 mg/6mL) Injection Intravenous Monarch Pharmaceuticals, Inc. 2006-11-22 2006-11-22 US Synercid Quinupristin (150 mg / vial) + Dalfopristin (350 mg / vial) Powder, for solution Intravenous Monarch Pharmaceuticals, Inc. 2000-07-05 2008-05-28 Canada 
Categories
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Peptides
- Peptides, Cyclic
- Streptogramin Antibacterial
- Streptogramins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Peptidomimetics
- Sub Class
- Depsipeptides
- Direct Parent
- Cyclic depsipeptides
- Alternative Parents
- Macrolide lactams / Alpha amino acid esters / Macrolactams / N-acyl-alpha amino acids and derivatives / Pyridinecarboxamides / Quinuclidines / 2-heteroaryl carboxamides / Aniline and substituted anilines / Dialkylarylamines / Piperidinones show 19 more
- Substituents
- 2-heteroaryl carboxamide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group show 42 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Enterococcus faecalis
Chemical Identifiers
- UNII
- 23OW28RS7P
- CAS number
- 120138-50-3
- InChI Key
- WTHRRGMBUAHGNI-LCYNINFDSA-N
- InChI
- InChI=1S/C53H67N9O10S/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/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)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1
- IUPAC Name
- N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
- SMILES
- [H][C@@]12CCCN1C(=O)[C@@H](CC)NC(=O)[C@@H](NC(=O)C1=NC=CC=C1O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@]1([H])CC(=O)[C@]([H])(CS[C@@H]3CN4CCC3CC4)CN1C(=O)[C@H](CC1=CC=C(C=C1)N(C)C)N(C)C2=O)C1=CC=CC=C1
References
- General References
- Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. [Article]
- 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. [Article]
- Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. [Article]
- Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. [Article]
- External Links
- KEGG Drug
- D00852
- KEGG Compound
- C08032
- PubChem Compound
- 5388937
- PubChem Substance
- 46505148
- ChemSpider
- 4470884
- 229367
- ChEMBL
- CHEMBL1200649
- ZINC
- ZINC000150338707
- Therapeutic Targets Database
- DAP001288
- PharmGKB
- PA164749647
- Wikipedia
- Quinupristin
- FDA label
- Download (67.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Treatment Gram Positive Bacterial Infections 1 0 Terminated Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- DSM Corp.
- Gruppo Lepetit SPA
- Monarch Pharmacy
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Injection Intravenous Injection, powder, lyophilized, for solution Intravenous Powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0445 mg/mL ALOGPS logP 2.99 ALOGPS logP 2.18 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 7.45 Chemaxon pKa (Strongest Basic) 8.28 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 231.2 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 272.84 m3·mol-1 Chemaxon Polarizability 107.45 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6848 Blood Brain Barrier - 0.9972 Caco-2 permeable - 0.648 P-glycoprotein substrate Substrate 0.8607 P-glycoprotein inhibitor I Non-inhibitor 0.5298 P-glycoprotein inhibitor II Non-inhibitor 0.6803 Renal organic cation transporter Non-inhibitor 0.8877 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6413 CYP450 1A2 substrate Non-inhibitor 0.8804 CYP450 2C9 inhibitor Non-inhibitor 0.803 CYP450 2D6 inhibitor Non-inhibitor 0.8539 CYP450 2C19 inhibitor Non-inhibitor 0.7776 CYP450 3A4 inhibitor Non-inhibitor 0.8954 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9155 Ames test Non AMES toxic 0.7484 Carcinogenicity Non-carcinogens 0.8552 Biodegradation Not ready biodegradable 0.9816 Rat acute toxicity 2.9306 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9575 hERG inhibition (predictor II) Inhibitor 0.7598
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 345.3941782 predictedDarkChem Lite v0.1.0 [M-H]- 302.34 predictedDeepCCS 1.0 (2019) [M+H]+ 339.3821782 predictedDarkChem Lite v0.1.0 [M+H]+ 304.0637 predictedDeepCCS 1.0 (2019) [M+Na]+ 339.9016782 predictedDarkChem Lite v0.1.0 [M+Na]+ 310.24228 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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Yes
Inhibitor
References
- Barthel D, Schlitzer M, Pradel G: Telithromycin and quinupristin-dalfopristin induce delayed death in Plasmodium falciparum. Antimicrob Agents Chemother. 2008 Feb;52(2):774-7. Epub 2007 Dec 3. [Article]
- Beyer D, Pepper K: The streptogramin antibiotics: update on their mechanism of action. Expert Opin Investig Drugs. 1998 Apr;7(4):591-9. [Article]
- Harms JM, Schlunzen F, Fucini P, Bartels H, Yonath A: Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin. BMC Biol. 2004 Apr 1;2:4. [Article]
- Dang V, Nanda N, Cooper TW, Greenfield RA, Bronze MS: Part VII. Macrolides, azalides, ketolides, lincosamides, and streptogramins. J Okla State Med Assoc. 2007 Mar;100(3):75-81. [Article]
- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Structural constituent of ribosome
- Specific Function
- Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a cent...
- Gene Name
- rplJ
- Uniprot ID
- P0A7J6
- Uniprot Name
- 50S ribosomal protein L10
- Molecular Weight
- 17711.38 Da
References
- Barthel D, Schlitzer M, Pradel G: Telithromycin and quinupristin-dalfopristin induce delayed death in Plasmodium falciparum. Antimicrob Agents Chemother. 2008 Feb;52(2):774-7. Epub 2007 Dec 3. [Article]
- Harms JM, Schlunzen F, Fucini P, Bartels H, Yonath A: Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin. BMC Biol. 2004 Apr 1;2:4. [Article]
- Dang V, Nanda N, Cooper TW, Greenfield RA, Bronze MS: Part VII. Macrolides, azalides, ketolides, lincosamides, and streptogramins. J Okla State Med Assoc. 2007 Mar;100(3):75-81. [Article]
- Kind
- Protein
- Organism
- Escherichia coli O157:H7
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Structural constituent of ribosome
- Specific Function
- This protein binds specifically to 23S rRNA; its binding is stimulated by other ribosomal proteins, e.g. L4, L17, and L20. It is important during the early stages of 50S assembly. It makes multiple...
- Gene Name
- rplV
- Uniprot ID
- P61177
- Uniprot Name
- 50S ribosomal protein L22
- Molecular Weight
- 12226.165 Da
References
- Barthel D, Schlitzer M, Pradel G: Telithromycin and quinupristin-dalfopristin induce delayed death in Plasmodium falciparum. Antimicrob Agents Chemother. 2008 Feb;52(2):774-7. Epub 2007 Dec 3. [Article]
- Harms JM, Schlunzen F, Fucini P, Bartels H, Yonath A: Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin. BMC Biol. 2004 Apr 1;2:4. [Article]
- Dang V, Nanda N, Cooper TW, Greenfield RA, Bronze MS: Part VII. Macrolides, azalides, ketolides, lincosamides, and streptogramins. J Okla State Med Assoc. 2007 Mar;100(3):75-81. [Article]
- Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. [Article]
- Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. [Article]
- Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. [Article]
- Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [Article]
- Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rubinstein E, Prokocimer P, Talbot GH: Safety and tolerability of quinupristin/dalfopristin: administration guidelines. J Antimicrob Chemother. 1999 Sep;44 Suppl A:37-46. [Article]
- Bearden DT: Clinical pharmacokinetics of quinupristin/dalfopristin. Clin Pharmacokinet. 2004;43(4):239-52. [Article]
- Delgado G Jr, Neuhauser MM, Bearden DT, Danziger LH: Quinupristin-dalfopristin: an overview. Pharmacotherapy. 2000 Dec;20(12):1469-85. [Article]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Quinupristin FDA label [Link]
Drug created at July 06, 2007 20:25 / Updated at April 16, 2021 04:47