QUINUPRISTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C53H67N9O10S
Molecular Weight	1022.218
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)[C@@H](CC)NC(=O)[C@@H](NC(=O)C3=NC=CC=C3O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@]4([H])CC(=O)[C@H](CS[C@@H]5CN6CCC5CC6)CN4C(=O)[C@H](CC7=CC=C(C=C7)N(C)C)N(C)C2=O)C8=CC=CC=C8

InChI

InChIKey=WTHRRGMBUAHGNI-LCYNINFDSA-N

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

HIDE SMILES / InChI

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: http://www.drugbank.ca/drugs/DB01369 http://www.ncbi.nlm.nih.gov/pubmed/15059283

Quinupristin is an antibiotic compound and a semisynthetic derivative of pristinamycin Ia. Quinupristin is a combination of three peptide macrolactones. Quinupristin is used in combination with dalfopristin, another antibiotic, under the trade name Synercid. Synercid is indicated for treatment of complicated skin and skin structure infections caused by methicillin-susceptible Staphylococcus aureus or Streptococcus pyogenes. The mechanism of action of quinupristin is inhibition of the late phase of protein synthesis in the bacterial ribosome. Quinupristin binds to 23S rRNA within the 50S ribosomal subunit and prevents elongation of the polypeptide as well as causing incomplete chains to be released. Adverse reactions to Synercid include inflammation at infusion site, rash, nausea, vomiting and others.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: http://www.drugbank.ca/drugs/DB01369	Inhibitor 8297		0.22 µM [IC50]

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 8429	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. (See CLINICAL STUDIES. ) Launch Date 1999

C_max

Value	Dose	Co-administered	Analyte	Population
3.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	2.25 mg/kg bw 3 times / day steady-state, intravenous dose: 2.25 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: DALFOPRISTIN	DALFOPRISTIN	QUINUPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
7.2 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	2.25 mg/kg bw 3 times / day steady-state, intravenous dose: 2.25 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: DALFOPRISTIN	DALFOPRISTIN	QUINUPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.07 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050747s015,050748s014lbl.pdf	2.25 mg/kg bw 3 times / day steady-state, intravenous dose: 2.25 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: DALFOPRISTIN	DALFOPRISTIN	QUINUPRISTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301

AEs

AE	Significance	Dose	Population
Anorexia	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Asthenia	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Chest pain	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Dizziness	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Dysphagia	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Flatulence	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Pain	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Pharyngitis	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Rash	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Vomiting	0.3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Myasthenia	0.7% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Nausea	1.1% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Myalgia	2.6% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301
Arthralgia	3% Disc. AE	2.5 mg/kg 3 times / day multiple, intravenous Recommended Dose: 2.5 mg/kg, 3 times / day Route: intravenous Route: multiple Dose: 2.5 mg/kg, 3 times / day Co-administed with:: DALFOPRISTIN(5 mg/kg, IV, Q8H15) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301	unhealthy, 52.9 n = 263 Health Status: unhealthy Condition: Infection Age Group: 52.9 Sex: M+F Population Size: 263 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_medr_P1.pdf Page: Study 301

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	yes
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	yes
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/99/50747_Synercid_biopharmr.pdf#page=37 Page: 37.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific, Inc. (AKSCI)	X7262	http://www.aksci.com/item_detail.php?cat=X7262
Alfa Chemistry	120138-50-3	https://www.alfa-chemistry.com/quinupristin-cas-120138-50-3-item-289800.htm
BOC Sciences	120138-50-3	https://www.bocsci.com/quinupristin-cas-120138-50-3-item-241774.html
BioChemPartner	BCP22328	http://www.biochempartner.com/120138-50-3-BCP22328
BioSynth	J-004265	https://www.biosynth.com/en/products/all-products/products/J-004265.html
Chem Scene	CS-0017494	http://www.chemscene.com/120138-50-3.html
DC Chemicals	DC12365	http://www.dcchemicals.com/product_show-Quinupristin.html
Finetech	FT-0674292	http://www.finetechnology-ind.com/prod/detail/pub/120138-50-3.html
Glentham Life Sciences	GA5430	http://www.glentham.com/products/product/GA5430/
Hairui	HR109471	http://www.hairuichem.com/en/product/120138-50-3.html
MedChem Express	HY-A0162	https://www.medchemexpress.com/quinupristin.html
Molcore	MC510891	https://www.molcore.com/product/120138-50-3
Smolecule	S540878	http://www.smolecule.com/products/s540878
Smolecule	S572454	https://www.smolecule.com/products/s572454
THE BioTek	bt-281376	https://www.thebiotek.com/product/inhibitors/bt-281376
Yuhao Chemical	RT5168	http://www.chemyuhao.com/120138-50-3.html
eNovation Chemicals	D674708	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674708
iChemical	EBD2202102	http://www.ichemical.com/products/120138-50-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin.	2004 Apr 1	15059283

Patents

Sample Use Guides

In Vivo Use Guide

7.5 mg/kg q12h

Route of Administration: Intravenous

In Vitro Use Guide

Quinupristin-dalfopristin inhibited protein synthesis of Staphylococcus aureus with IC50=0.22 μg/mL

Name

Type

Language

QUINUPRISTIN

Official Name

English

VIRGINIAMYCIN S1, 4-(4-(DIMETHYLAMINO)-N-METHYL-L-PHENYLALANINE)-5-(5-(1-AZABICYCLO(2.2.2)OCT-3-YLTHIO)METHYL)-4-OXO-L-2-PIPERIDINECARBOXYLIC ACID)-, (S)-

Common Name

English

QUINUPRISTIN [USAN]

Common Name

English

QUINUPRISTIN [JAN]

Common Name

English

quinupristin [INN]

Common Name

English

QUINUPRISTIN [ORANGE BOOK]

Common Name

English

SYNERCID COMPONENT QUINUPRISTIN

Common Name

English

QUINUPRISTIN [VANDF]

Common Name

English

RP 57669

Code

English

QUINUPRISTIN COMPONENT OF SYNERCID

Common Name

English

Quinupristin [WHO-DD]

Common Name

English

RP-57669

Code

English

QUINUPRISTIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01FG02