Compound ID | 400

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Mideplanin

Synonym(s): CTA A1  |  MDL 62,873  |  MDL 62873  |  CTA-A-1

Class: Glycopeptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against oxacillin-resistant and -susceptible Staphylococcus aureus
Description: Semisynthetic compound; an amide derivative of teicoplanin A2-2
Institute where first reported: Biosearch Italia (Pfizer, US); Aventis (Sanofi Aventis, France)
Year first mentioned: 1988
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Literature papers stop at 1992 which concludes with a need to carry out more pharmacological studies to progress to clinical trials. The study on PMN activity shows that for interference, a dosage higher than proposed human dosage is required. There may be a cross resistance issue but not stated.
Chemical structure(s):
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Molecular weight: 1963.82
Iso. SMILES: CC(C)CCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C%10C%11=CC(=CC(=C%11)OC%12=C(C=CC(=C%12)C(C(=O)NC(CC%13=CC(=C(O3)C=C%13)Cl)C(=O)N%10)N)O)O)O)C(=O)NCCCN(C)C)OC%14C(C(C(C(O%14)CO)O)O)NC(=O)C)Cl)CO)O)O
InChI Key: KVZUWEFUEGGULL-UHFFFAOYSA-N
Can. SMILES: CC(C)CCCCCCC(=O)NC1C(C(C(CO)OC1OC2=C3C=C4C=C2OC5=CC=C(C=C5Cl)CC6C(=O)NC(C7=CC(=CC(=C7)O)OC8=CC(=CC=C8O)C(C(=O)N6)N)C(=O)NC4C(=O)NC9C%10=CC=C(C(=C%10)C%11=C(C=C(C=C%11C(C(=O)NCCCN(C)C)NC(=O)C(C(C%12=CC=C(C(=C%12)Cl)O3)OC%13C(C(C(C(CO)O%13)O)O)NC(=O)C)NC9=O)O)OC%14C(C(C(C(CO)O%14)O)O)O)O)O)O
InChI: InChI=1S/C93H109Cl2N11O32/c1-38(2)11-8-6-7-9-12-65(115)100-73-79(120)76(117)63(36-108)135-92(73)138-83-60-30-45-31-61(83)132-57-20-16-43(28-52(57)95)82(137-91-72(98-39(3)110)78(119)75(116)62(35-107)134-91)74-90(129)104-71(86(125)97-21-10-22-106(4)5)50-33-47(112)34-59(133-93-81(122)80(121)77(118)64(37-109)136-93)66(50)49-27-42(15-17-54(49)113)68(87(126)105-74)102-89(128)70(45)103-88(127)69-44-25-46(111)32-48(26-44)130-58-29-41(14-18-55(58)114)67(96)85(124)99-53(84(123)101-69)24-40-13-19-56(131-60)51(94)23-40/h13-20,23,25-34,38,53,62-64,67-82,91-93,107-109,111-114,116-122H,6-12,21-22,24,35-37,96H2,1-5H3,(H,97,125)(H,98,110)(H,99,124)(H,100,115)(H,101,123)(H,102,128)(H,103,127)(H,104,129)(H,105,126)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16132175
Guide to Pharmacology: mideplanin
Citations:
  • http://www.ncbi.nlm.nih.gov/pubmed/1832144
  • https://doi.org/10.1128/aac.36.2.446

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