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N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^{6,10}]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
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ChemBase ID:
1193
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Molecular Formular:
C53H67N9O10S
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Molecular Mass:
1022.21838
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Monoisotopic Mass:
1021.47316039
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SMILES and InChIs
SMILES:
N12C(C(=O)N[C@@H](c3ccccc3)C(=O)O[C@H]([C@H](NC(=O)c3c(cccn3)O)C(=O)N[C@@H](C(=O)N3[C@H](C(=O)N([C@H](C1=O)Cc1ccc(cc1)N(C)C)C)CCC3)CC)C)CC(=O)C(C2)CS[C@H]1C2CCN(C1)CC2
Canonical SMILES:
CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@H](C)OC(=O)[C@@H](NC(=O)C2N(C(=O)[C@@H](N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccc(cc1)N(C)C)CC(CS[C@@H]1CN3CCC1CC3)C(=O)C2)c1ccccc1
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
InChIKey:
WTHRRGMBUAHGNI-MJWHERSYSA-N
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Cite this record
CBID:1193 http://www.chembase.cn/molecule-1193.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^{6,10}]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
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IUPAC Traditional name
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N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^{6,10}]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
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Synonyms
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
Data Source
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Data ID
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Price
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CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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7.447674
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H Acceptors
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12
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H Donor
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4
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LogD (pH = 5.5)
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0.40517336
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LogD (pH = 7.4)
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2.0695662
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Log P
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2.1781592
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Molar Refractivity
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272.8403 cm3
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Polarizability
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105.59297 Å3
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Polar Surface Area
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231.2 Å2
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Rotatable Bonds
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10
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Lipinski's Rule of Five
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false
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Log P
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2.99
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LOG S
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-4.36
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Solubility (Water)
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4.45e-02 g/l
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PROPERTIES
PROPERTIES
Bioassay(PubChem)
DETAILS
DETAILS
DrugBank
DrugBank -
DB01369
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Item |
Information |
Drug Groups
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approved |
Description
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Quinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone. |
Indication |
For the treatment of bacterial infections (usually in combination with dalfopristin). |
Pharmacology |
Quinupristin is a streptogramin antibiotic, derived from pristinamycin I. By inhibiting the bacterial ribosomal subunits, protein synthesis is inhibited thus leading to eventual bacterial cell death or stasis. |
Affected Organisms |
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Enteric bacteria and other eubacteria |
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Biotransformation |
Quinupristin is converted to two conjugated active major metabolites, one with glutathione and one with cysteine. |
Half Life |
3.1 hours |
Protein Binding |
Moderate. |
References |
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Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44.
[Pubmed]
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Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97.
[Pubmed]
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Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6.
[Pubmed]
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Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17.
[Pubmed]
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External Links |
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PATENTS
PATENTS
PubChem Patent
Google Patent