quinupristin

Small moleculeapproved

Approved

Sep 21, 1999

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. — NCATS

Clinical trial activity

1 trials · 3 clinical orgs · 1 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Jun 1, 2000 (NCT00240747)

Timeline

1990s

Sep 21, 1999
King Pharmaceuticals — Earliest FDA Approval
Sep 21, 1999
King Pharmaceuticals — NDA Secondary Org
Sep 21, 1999
King Pharmaceuticals — NDA Organization

2000s

Jan 1, 2000
Earliest Phase 3 Sponsor(trial)

Indications

Approved for

Skin Diseases, Infectious (approved 1999)

Studied for

Gram-Positive Bacterial Infections · Phase 3

Mechanism of action

Bacterial 70S ribosomeINHIBITOR
Bacterial 70S ribosome inhibitor
23S RRNA

Combination products

synerci
with dalfopristin
Also known as dalfopristin/quinupristin

Approval history

approvedPriority reviewAcceleratedSep 21, 1999

Chemistry & pharmacology

Loading structure…

SMILES

CC[C@H]1NC(=O)[C@@H](NC(=O)C2=C(O)C=CC=N2)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]3CC(=O)[C@H](CS[C@@H]4CN5CCC4CC5)CN3C(=O)[C@H](CC6=CC=C(C=C6)N(C)C)N(C)C(=O)[C@@H]7CCCN7C1=O)C8=CC=CC=C8

Mol. weight: 1022.218 g/mol
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Parenteral
Availability: Discontinued

Oral

Parenteral

Yes

Topical

Sources

Also known as

5delta-(3-quinuclidinyl)thiomethylpristinamycin ia
quinupristin
quinupristin
quinupristin
quinupristin
quinupristin
quinupristin
quinupristin
quinupristin
quinupristin mesilate
quinupristin mesilate
quinupristin mesilate
quinupristin mesilate
quinupristin mesilate
quinupristin mesylate
rp 57669
rp-57669
rp-57669
rp-57669

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT00240747	Phase 3	Jun 1, 2000	Aventis, Pfizer, Yale University

Showing 1 of 1 trials

Page 1 / 1

Organizations

Research & Development (3)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Aventis	For profit	1	0	1	2000
Pfizer	For profit	1	1	1	2000
Yale University	Academic/Hospital	1	0	1	2000

3 organizations

Page 1 / 1

Marketing (2)

Organization	Org type	Relationship	Date
King Pharmaceuticals	For profit	NDA2	Sep 21, 1999
King Pharmaceuticals	For profit	NDA	Sep 21, 1999