U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H50N4O9S
Molecular Weight 690.8496
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DALFOPRISTIN

SMILES

CCN(CC)CCS(=O)(=O)[C@]1([H])CCN2[C@@]1([H])C(=O)O[C@]([H])(C(C)C)[C@]([H])(C)/C(/[H])=C(\[H])/C(=NC/C(/[H])=C(\[H])/C(=C(\[H])/[C@]([H])(CC(=O)Cc3nc(co3)C2=O)O)/C)O

InChI

InChIKey=SUYRLXYYZQTJHF-VMBLUXKRSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9511075

Dalfopristin is a pristinamycin-like component of anti-bacterial drug called Synercid which also containes quinupristin (quinupristin:dalfopristin ratio is 30:70 (w/w)). The drug was approved by FDA and used for the treatment of skin diseases caused by Staphylococcus aureus or Streptococcus pyogenes. Dalfopristin binds to the RNA of the 50S ribosomal subunit and thus inhibits the late phase of protein synthesis.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SYNERCID

Approved Use

Synercid is indicated in adults for the treatment of the following infections when caused by susceptible strains of the designated microorganisms. Complicated skin and skin structure infections caused by Staphylococcus aureus (methicillin susceptible) or Streptococcus pyogenes.

Launch Date

9.37872E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.96 μg/mL
5.25 mg/kg bw 3 times / day steady-state, intravenous
dose: 5.25 mg/kg bw
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: QUINUPRISTIN
DALFOPRISTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10.57 μg × h/mL
5.25 mg/kg bw 3 times / day steady-state, intravenous
dose: 5.25 mg/kg bw
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: QUINUPRISTIN
DALFOPRISTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.04 h
5.25 mg/kg bw 3 times / day steady-state, intravenous
dose: 5.25 mg/kg bw
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: QUINUPRISTIN
DALFOPRISTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Disc. AE: Arthralgia, Myalgia...
AEs leading to
discontinuation/dose reduction:
Arthralgia (3%)
Myalgia (2.6%)
Nausea (1.1%)
Myasthenia (0.7%)
Flatulence (0.3%)
Pain (0.3%)
Pharyngitis (0.3%)
Dysphagia (0.3%)
Dizziness (0.3%)
Chest pain (0.3%)
Asthenia (0.3%)
Rash (0.3%)
Vomiting (0.3%)
Anorexia (0.3%)
Sources: Page: Study 301
AEs

AEs

AESignificanceDosePopulation
Anorexia 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Asthenia 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Chest pain 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Dizziness 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Dysphagia 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Flatulence 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Pain 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Pharyngitis 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Rash 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Vomiting 0.3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Myasthenia 0.7%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Nausea 1.1%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Myalgia 2.6%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Arthralgia 3%
Disc. AE
5 mg/kg 3 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 3 times / day
Co-administed with::
QUINUPRISTIN(2.5 mg/kg, IV, Q8H15)
Sources: Page: Study 301
unhealthy, 52.9
n = 263
Health Status: unhealthy
Condition: Infection
Age Group: 52.9
Sex: M+F
Population Size: 263
Sources: Page: Study 301
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Quinupristin-dalfopristin is active against Toxoplasma gondii.
1999 Aug
Patents

Patents

Sample Use Guides

The recommended dosage for the treatment of complicated skin and skin structure infections is 7.5 mg/kg q12h.
Route of Administration: Intravenous
The combination of quinupristin and dalfopristin (Synercid) exhibits in vitro minimum inhibitory concentrations (MIC's) of ≤1.0 ug/mL against most (≥90%) isolates of the following microorganisms: Corynebacterium jeikeium, Staphylococcus aureus (methicillin-resistant isolates), Staphylococcus epidermidis (including methicillin-resistant isolates, Streptococcus agalactiae.
Name Type Language
DALFOPRISTIN
INN   JAN   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
DALFOPRISTIN COMPONENT OF SYNERCID
Common Name English
DALFOPRISTIN [VANDF]
Common Name English
SYNERCID COMPONENT DALFOPRISTIN
Common Name English
(3R,4R,5E,10E,12E,14S,26R,26AS)-26-((2-(DIETHYLAMINO)ETHYL)SULFONYL)-8,9,14,15,24,25,26,26A-OCTAHYDRO-14-HYDROXY-3-ISOPROPYL-4,12-DIMETHYL-3H-21,18-NITRILO-1H,22H-PYRROLO(2,1-C)(1,8,4,19)DIOXADIAZACYCLOTETRACOSINE-1,7,16,22(4H,17H)-TETRONE
Common Name English
RP 54476
Code English
DALFOPRISTIN [JAN]
Common Name English
DALFOPRISTIN [USAN]
Common Name English
DALFOPRISTIN [WHO-DD]
Common Name English
DALFOPRISTIN [ORANGE BOOK]
Common Name English
DALFOPRISTIN [INN]
Common Name English
DALFOPRISTIN [MI]
Common Name English
RP-54476
Code English
Classification Tree Code System Code
WHO-VATC QJ01FG02
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
NDF-RT N0000011418
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
LIVERTOX 260
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
WHO-ATC J01FG02
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
NDF-RT N0000175502
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
NCI_THESAURUS C258
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
NDF-RT N0000011418
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
Code System Code Type Description
DRUG CENTRAL
778
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200937
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
RXCUI
229369
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY RxNorm
MESH
C113826
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
EVMPD
SUB06892MIG
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
HSDB
8068
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
LACTMED
Quniupristin-Dalfopristin
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
CAS
112362-50-2
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
DRUG BANK
DB01764
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
NCI_THESAURUS
C47468
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
WIKIPEDIA
DALFOPRISTIN
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
INN
6581
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
FDA UNII
R9M4FJE48E
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
PUBCHEM
6323289
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY
MERCK INDEX
M4073
Created by admin on Sat Jun 26 03:01:12 UTC 2021 , Edited by admin on Sat Jun 26 03:01:12 UTC 2021
PRIMARY Merck Index