Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C88H95Cl2N9O33 |
Molecular Weight | 1877.642 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 23 / 23 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]%14(O[C@H]1[C@@H]2NC(=O)[C@]([H])(NC(=O)[C@]3([H])NC(=O)[C@@]4([H])NC(=O)[C@@H](CC5=CC=C(OC6=C(O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7NC(=O)CC\C=C/CCCCC)C(OC8=C(Cl)C=C1C=C8)=CC3=C6)C(Cl)=C5)NC(=O)[C@H](N)C9=CC(OC%10=CC4=CC(O)=C%10)=C(O)C=C9)C%11=CC(=C(O)C=C%11)C%12=C(C=C(O)C=C%12O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O)[C@H](NC2=O)C(O)=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%14NC(C)=O
InChI
InChIKey=YMWQIYMUNZBOOV-CFYXQOLXSA-N
InChI=1S/C88H95Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h7-8,11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-6,9-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/b8-7-/t48-,57-,58-,59-,62-,63-,64+,65-,66+,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88+/m1/s1
Molecular Formula | C88H95Cl2N9O33 |
Molecular Weight | 1877.642 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 23 / 23 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
Teicoplanin A2-1 is one of the main components of a lipoglycopeptide antibiotic, teicoplanin. Teicoplanin was first approved for marketing in Italy as Targocid, consisting of six closely related glycopeptide subcomponents (A2-1 to A2-5 and A3). Targocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital-acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Teicoplanin inhibits the growth of susceptible organisms by interfering with cell-wall biosynthesis at a site different from that affected by beta-lactams, by binding to the D-Ala-D-Ala C-terminus of peptidoglycan precursors.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: D-Ala-D-Ala C-terminus of peptidoglycan precursor Sources: https://www.ncbi.nlm.nih.gov/pubmed/24805824 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents. Launch Date1987 |
|||
Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents. Launch Date1987 |
|||
Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents. Launch Date1987 |
|||
Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents. Launch Date1987 |
|||
Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the following infections: complicated skin and soft tissue infections, bone and joint infections, hospital acquired pneumonia, community acquired pneumonia, complicated urinary tract infections, infective endocarditis, peritonitis associated with continuous ambulatory peritoneal dialysis (CAPD), bacteraemia that occurs in association with any of the indications listed above. Targocid is also indicated as an alternative oral treatment for Clostridium difficile infection-associated diarrhoea and colitis. Where appropriate, teicoplanin should be administered in combination with other antibacterial agents. Consideration should be given to official guidance on the appropriate use of antibacterial agents. Launch Date1987 |
PubMed
Title | Date | PubMed |
---|---|---|
Teicoplanin, a new antibiotic from Actinoplanes teichomyceticus nov. sp. | 1984 Dec |
|
Teicoplanin metabolism in humans. | 1992 Aug |
|
Improved quantitative determination of total and unbound concentrations of six teicoplanin components in human plasma by high performance liquid chromatography. | 2005 Oct |
|
New insights into glycopeptide antibiotic binding to cell wall precursors using SPR and NMR spectroscopy. | 2014 Jun 10 |
|
Direct injection LC-MS/MS method for the determination of teicoplanin in human plasma. | 2016 Jan 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/27321
Curator's Comment: teicoplanin A2-1 is one of the main components of a lipoglycopeptide antibiotic, teicoplanin
Complicated skin and soft tissue infections; Pneumonia; Complicated urinary tract infections: loading dose regimen: 6 mg/kg body weight every 12 hours for 3 intravenous or intramuscular administrations. maintenance dose: 6 mg/kg body weight intravenous or intramuscular once a day.
Bone and joint infections: loading dose regimen: 12 mg/kg body weight every 12 hours for 3 to 5 intravenous administrations. Maintenance dose: 12 mg/kg body weight intravenous or intramuscular once a day.
Infective endocarditis: loading dose regimen: 12 mg/kg body weight every 12 hours for 3 to 5 intravenous administrations. Maintenance dose: 12 mg/kg body weight intravenous or intramuscular once a day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6240963
A cell-free system from Bacillus stearothermophilus, capable of synthesizing peptidoglycan, is 50% inhibited by teicoplanin (teicoplanin A2-1 is one of the main components teicoplanin) at 40 micrograms/ml and 100% inhibited at 100 micrograms/ml; suppression of peptidoglycan synthesis is accompanied by parallel accumulation of the lipid intermediate. Teicoplanin binds to cell walls and forms a complex with N,N'-diacetyl-L-lysyl-D-alanyl-D-alanine. The association constant of this complex is 2.56 X 10(6) liters mol-1, calculated by spectrophotometric titration.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:39:02 GMT 2023
by
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on
Fri Dec 15 19:39:02 GMT 2023
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Record UNII |
36DYU0VKRK
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Record Status |
Validated (UNII)
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Record Version |
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CHEMBL1908353
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m10525
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