Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C88H97Cl2N9O33 |
Molecular Weight | 1879.658 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 23 / 23 |
E/Z Centers | 0 |
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)CCCCCCCCC)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=BJNLLBUOHPVGFT-PKMGYIMSSA-N
InChI=1S/C88H97Cl2N9O33/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/h11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-10,20,31-33,91H2,1-2H3,(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)/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 | C88H97Cl2N9O33 |
Molecular Weight | 1879.658 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 23 / 23 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Teicoplanin A2-3 is a major component of the teicoplanin complex, a glycopeptide antibiotic produced by A. teichomyceticus that is broadly effective against Gram-positive bacteria in vitro. Bacteria treated with the drug failed to incorporate GlcNAc, a peptidoglycan precursor, whereas they continued to synthesize DNA, RNA, and protein. The cell wall inhibition was accompanied by an accumulation of UDP-MurNAc-pentapeptide, thus indicating that the antibiotic interferes with the polymerization of the peptidoglycan but not with the synthesis of soluble precursors. Teicoplanin 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; complicated urinary tract infections; infective endocarditis; bacteremia that occurs in association with any of the indications listed above. The following side-effects may occur -- nausea, vomiting, diarrhea and stomach pain, skin rash and pruritus, bronchospasm, renal impairment. Teicoplanin should be administrated with caution in patients receiving concurrent nephrotoxic or ototoxic drugs, such as aminoglycosides, amphotericin B, cyclosporine, and frusemide.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0009273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6240963 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the bacteraemia/septicemia. Launch Date1987 |
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Curative | Teicoplanin Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the infective endocarditis. Launch Date1987 |
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Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the complicated urinary tract infections. Launch Date1987 |
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Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the bone and joint infections. Launch Date1987 |
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Curative | Targocid Approved UseTargocid is indicated in adults and in children from birth for the parenteral treatment of the complicated skin and soft tissue infections. Launch Date1987 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Teicoplanin for clinical administration is a mixture of five teicoplanins (A2-1, A2-2, A2-3, A2-4 and A2-5)
Urinary tract infections, skin and soft tissue infections. Loading dose: single injection of 400 mg on the first day; Maintenance dose: single injection of 200 mg/ml daily.
Endocarditis, septicemia, joint and bone infections. Loading dose: for the first three doses – 400 mg every 12 hours; Maintenance dose: single injection of 400 mg daily.
An intramuscular injection of Targocid should not exceed 3 ml (400 mg) at a single site.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6235204
Minimal inhibitory concentration (MIC) was read as the lowest concentration, which showed no visible growth after 18-24 h incubation at 37° C. The obtained results are: Staphylococcus aureus – 0.2-0.8 ug/ml, Staphylococcus epidermidis – 0.2-0.8 ug/ml, Streptococcus pyogenes – 0.006-0.05 ug/ml, Streptococcus pneumoniae – 0.05-0.1 ug/ml, Streptococcus faecalis – 0.1-0.4 ug/ml, Streptococcus mitis – 0.025 ug/ml, Streptococcus solivarius – 0.05 ug/ml, Streptococcus sanguis – 0.05 ug/ml, Streptococcus bovis – 0.4 ug/ml, Streptococcus agalactiae – 0.1 ug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:39:03 GMT 2023
by
admin
on
Fri Dec 15 19:39:03 GMT 2023
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Record UNII |
6LN24Z7AMM
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Record Status |
Validated (UNII)
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Record Version |
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17748671
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CHEMBL2103913
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m10525
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DTXSID70872357
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