DALFOPRISTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H50N4O9S
Molecular Weight	690.847
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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)CC3=NC(=CO3)C2=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

Molecular Formula	C34H50N4O9S
Molecular Weight	690.847
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050747s014,050748s013lbl.pdf
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050747s014,050748s013lbl.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Complicated skin and skin structure infections caused by Staphylococcus aureus or Streptococcus pyogenes 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050747s014,050748s013lbl.pdf	Curative		Approved 8583	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 1999

C_max

Value	Dose	Co-administered	Analyte	Population
7.96 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	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	QUINUPRISTIN	DALFOPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
10.57 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	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	QUINUPRISTIN	DALFOPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.04 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	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	QUINUPRISTIN	DALFOPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf

AEs

AE	Significance	Dose	Population
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf	unhealthy, 52.9 Health Status: unhealthy Age Group: 52.9 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf#page=9 Page: 9.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34389	https://www.001chemical.com/chem/112362-50-2
AA Blocks	AA008T0Y	https://www.aablocks.com/goods/Goods/detail?id=AA008T0Y
AbMole Bioscience	M6129	http://www.abmole.com/products/dalfopristin.html
Alfa Chemistry	112362-50-2	https://www.alfa-chemistry.com/cas_112362-50-2.htm
Ambeed	A271356	https://www.ambeed.com/products/112362-50-2.html
BenchChem	B524967	https://www.benchchem.com/product/b524967
BioChemPartner	BCP22325	http://www.biochempartner.com/112362-50-2-BCP22325
BLD Pharm	BD123362	http://www.bldpharm.com/products/112362-50-2.html
Chem Scene	CS-6142	http://www.chemscene.com/112362-50-2.html
Chemspace	CSSS00161189721	https://chem-space.com/CSSS00161189721
CSNpharm	CSN10739	https://www.csnpharm.com/products/dalfopristin.html
Finetech	FT-0665456	http://www.finetechnology-ind.com/prod/detail/pub/112362-50-2.html
Glentham Life Sciences	GA0156	http://www.glentham.com/products/product/GA0156/
Lab Network	LN01270720	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01270720
MedChem Express	HY-A0241	https://www.medchemexpress.com/Dalfopristin.html
Molcore	MC34389	https://www.molcore.com/product/112362-50-2
MolPort	MolPort-046-702-035	https://www.molport.com/shop/molecule-link/MolPort-046-702-035
MuseChem	I000465	https://www.musechem.com/product/I000465.html
Selleck Chemicals	S6761	http://www.selleckchem.com/products/dalfopristin.html
Smolecule	S524967	http://www.smolecule.com/products/s524967
THE BioTek	bt-266951	https://www.thebiotek.com/product/inhibitors/bt-266951
Yuhao Chemical	YH25114	http://www.chemyuhao.com/112362-50-2.html

PubMed

Title	Date	PubMed
Quinupristin-dalfopristin is active against Toxoplasma gondii.	1999-08	10428933

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage for the treatment of complicated skin and skin structure infections is 7.5 mg/kg q12h.

Route of Administration: Intravenous

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:35 GMT 2025`
Record UNII	R9M4FJE48E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SYNERCID COMPONENT DALFOPRISTIN

Preferred Name

English

DALFOPRISTIN

Official Name

English

DALFOPRISTIN [VANDF]

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 [WHO-DD]

Common Name

English

DALFOPRISTIN [USAN]

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