Dalfopristin
Identification
- Summary
Dalfopristin is an antibiotic used with quinupristin to treat severe or life-threatening infections of vancomycin-resistant Enterococcus faecium (VREF), and skin infections caused by methicillin susceptible staphylococcus aureus or streptococcus pyogenes.
- Brand Names
- Synercid
- Generic Name
- Dalfopristin
- DrugBank Accession Number
- DB01764
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 690.85
Monoisotopic: 690.32985038 - Chemical Formula
- C34H50N4O9S
- Synonyms
- Dalfopristin
- Dalfopristina
- Dalfopristine
- Dalfopristinum
- External IDs
- RP 54476
- RP-54476
Pharmacology
- Indication
For the treatment of bacterial infections (usually in combination with quinupristin).
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: Quinupristin (DB01369) •••••••••••• Used in combination to treat Methicillin-resistant staphylococcus aureus infection Combination Product in combination with: Quinupristin (DB01369) ••• ••••• Used in combination to treat Complicated skin and subcutaneous tissue bacterial infection Combination Product in combination with: Quinupristin (DB01369) •••••••••••• - 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
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.
Target Actions Organism AStreptogramin A acetyltransferase inhibitorEnterococcus faecium - 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
- 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 Dalfopristin. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Dalfopristin. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Dalfopristin. Albendazole The metabolism of Albendazole can be decreased when combined with Dalfopristin. Alectinib The metabolism of Alectinib can be decreased when combined with Dalfopristin. - 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 Dalfopristin mesylate R5U9EZY06G Not Available ZUBXFMSQBHKVNC-ODOOVVHSSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Synercid Dalfopristin (350 mg/5mL) + Quinupristin (150 mg/5mL) Injection, powder, lyophilized, for solution Intravenous Pfizer Laboratories Div Pfizer Inc 1999-09-21 Not applicable US Synercid Dalfopristin (420 mg/6mL) + Quinupristin (180 mg/6mL) Injection Intravenous Monarch Pharmaceuticals, Inc. 2006-11-22 2006-11-22 US Synercid Dalfopristin (350 mg / vial) + Quinupristin (150 mg / vial) Powder, for solution Intravenous Monarch Pharmaceuticals, Inc. 2000-07-05 2008-05-28 Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolide lactams
- Sub Class
- Not Available
- Direct Parent
- Macrolide lactams
- Alternative Parents
- Alpha amino acid esters / Macrolactams / 2-heteroaryl carboxamides / Tertiary carboxylic acid amides / Heteroaromatic compounds / Sulfones / Oxazoles / Pyrrolidines / Lactones / Lactams show 11 more
- Substituents
- 2-heteroaryl carboxamide / Alcohol / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Enterococcus faecalis
Chemical Identifiers
- UNII
- R9M4FJE48E
- CAS number
- 112362-50-2
- InChI Key
- SUYRLXYYZQTJHF-VMBLUXKRSA-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
- IUPAC Name
- (6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethanesulfonyl]-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]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
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
- D00853
- KEGG Compound
- C08033
- PubChem Compound
- 6323289
- PubChem Substance
- 46506561
- ChemSpider
- 16736919
- 229369
- ChEMBL
- CHEMBL1200937
- ZINC
- ZINC000003917540
- Therapeutic Targets Database
- DAP001294
- PharmGKB
- PA164746234
- PDBe Ligand
- DOL
- Wikipedia
- Dalfopristin
- PDB Entries
- 1mrl / 1sm1 / 2z2p / 4u24 / 4u26 / 6zs9 / 6zsa / 6zsb / 6zsc / 6zsd … show 3 more
- 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
- Not Available
- 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 0.0716 mg/mL ALOGPS logP 2.57 ALOGPS logP 1.58 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 13.17 Chemaxon pKa (Strongest Basic) 7.09 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 176.42 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 182.84 m3·mol-1 Chemaxon Polarizability 72.41 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 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 + 0.6544 Blood Brain Barrier - 0.9286 Caco-2 permeable - 0.6574 P-glycoprotein substrate Substrate 0.7988 P-glycoprotein inhibitor I Non-inhibitor 0.6395 P-glycoprotein inhibitor II Non-inhibitor 0.9399 Renal organic cation transporter Non-inhibitor 0.9011 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.8118 CYP450 2C9 inhibitor Non-inhibitor 0.7261 CYP450 2D6 inhibitor Non-inhibitor 0.8606 CYP450 2C19 inhibitor Non-inhibitor 0.6834 CYP450 3A4 inhibitor Non-inhibitor 0.7363 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9392 Ames test Non AMES toxic 0.6184 Carcinogenicity Non-carcinogens 0.6071 Biodegradation Not ready biodegradable 0.6975 Rat acute toxicity 2.6096 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9396 hERG inhibition (predictor II) Non-inhibitor 0.7254
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 285.1376231 predictedDarkChem Lite v0.1.0 [M-H]- 245.13002 predictedDeepCCS 1.0 (2019) [M+H]+ 288.2304231 predictedDarkChem Lite v0.1.0 [M+H]+ 247.0254 predictedDeepCCS 1.0 (2019) [M+Na]+ 287.8949231 predictedDarkChem Lite v0.1.0 [M+Na]+ 252.64883 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Enterococcus faecium
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Inactivates the A compounds of streptogramin antibiotics by acetylation, thus providing resistance to these antibiotics.
- Gene Name
- vatD
- Uniprot ID
- P50870
- Uniprot Name
- Streptogramin A acetyltransferase
- Molecular Weight
- 23649.22 Da
References
- Manfredi R, Sabbatani S: Novel pharmaceutical molecules against emerging resistant gram-positive cocci. Braz J Infect Dis. 2010 Jan-Feb;14(1):96-108. [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]
- 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]
- 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]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51