Compound ID | 2053

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Pristinamycin

Class: Streptogramin

Agent Type: Natural product; 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
Description: Natural compound produced by Streptomyces. Mixture of pristinamycin IA (macrolide) and pristinamycin IIA (depsipeptide streptogramin A). Oral formulation.
Year first mentioned: 1962
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 1349.49
Iso. SMILES: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CCC(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=CC=C6)C.CC1/C=C\C(=O)NC/C=C\C(=C/C(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)OC1C(C)C)O)\C
InChI Key: MVTQIFVKRXBCHS-FHWPYUEJSA-N
Can. SMILES: CCC1C(=O)N2CCCC2C(=O)N(C)C(CC3=CC=CC=C3)C(=O)N4CCC(=O)CC4C(=O)NC(C5=CC=CC=C5)C(=O)OC(C)C(C(=O)N1)NC(=O)C6=NC=CC=C6O.CC(C)C1C(C)/C=C\C(=O)NC/C=C\C(=C/C(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O1)O)\C
InChI: InChI=1S/C43H49N7O10.C28H35N3O7/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36;1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53);5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b;7-5-,10-9-,18-13-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/11979535
Guide to Pharmacology: pristinamycin IIA pristinamycin IA
Citations:
  • https://journals.asm.org/doi/10.1128/aac.00212-10?permanently=true
  • https://academic.oup.com/jac/article/69/9/2319/2911234

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