Compound ID | 2056

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Quinupristin

Synonym(s): Pristinamycin IA  |  mikamycin B

Class: Streptogramin

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 50S ribosomal subunit to inhibit the elongation process of protein synthesis
Combined with other compounds:
Description: Component of the combination product quinupristin/dalfopristin
Year first mentioned: 1989
Highest development stage: Approved
Development status: Withdrawn
Reason dropped: Discontinued in most countries
Chemical structure(s):
Click here for structure editor
Molecular weight: 1022.22
Iso. SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
InChI Key: WTHRRGMBUAHGNI-LCYNINFDSA-N
Can. SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC3=CC=C(C=C3)N(C)C)C(=O)N4C[C@@H](CS[C@@H]5CN6CCC5CC6)C(=O)C[C@H]4C(=O)N[C@@H](C7=CC=CC=C7)C(=O)O[C@H](C)[C@@H](C(=O)N1)NC(=O)C8=NC=CC=C8O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5388937
Guide to Pharmacology: quinupristin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/11764864/
  • https://www.nature.com/articles/s41429-020-0312-7
  • https://pubmed.ncbi.nlm.nih.gov/1399955/

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