Teicoplanin

Teicoplanin (trade name Targocid) is a semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-104

CAS No:61036-62-2

Synonyms/Alias:Targocid; Teichomycin; Teichomycin A2; Teicoplanin

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M.F/Formula
C88H95Cl2N9O33
M.W/Mr.
1879.66
Labeling Target
D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Application
Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Biological Activity
Teicoplanin is a semisynthetic glycopeptide antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including Methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.
Areas of Interest
Cardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
Target
Bacterial
Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
InChI
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
InChI Key
YMWQIYMUNZBOOV-DOZYEWNNSA-N
Isomeric SMILES
CCCCC/C=C\CCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@H](C7=CC(=CC(=C7C8=C(C=CC(=C8)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]9C1=CC(=CC(=C1)O)OC1=C(C=CC(=C1)[C@@H](C(=O)N[C@H](CC1=CC(=C(O3)C=C1)Cl)C(=O)N9)N)O)O)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)Cl)CO)O)O
BoilingPoint
N/A
ShelfLife
>2 years if stored properly
References

Intravenous teicoplanin has been used to treat 23 cases of gram-positive-bacterial endocarditis, usually with 3 to 7 mg/kg every 12 h on the first day, followed by 3 to 7 mg/kg every 24 h. For some cases (staphylococcal and enterococcal endocarditis), the dosage was 8 to 14.4 mg/kg per day and/or other antibiotics were given. The mean duration was 48.2 days (range, 23 to 130 days). Of 23 patients, 21 (91.3%) had negative cultures or were cured. A total of 18 patients were treated with teicoplanin alone; of these, 4 had surgery, and all (except 2 who relapsed) were cured. Teicoplanin was combined with one or more antibiotics in five cases; in all cases appropriate cultures were negative, but three patients died during therapy or follow-up. Mild renal impairment was seen in two patients; both were receiving teicoplanin in combination with an aminoglycoside. We conclude that intravenous teicoplanin administered once a day at doses of 7 to 14 mg/kg per day is well tolerated, easy to administer, and may represent an efficacious therapy for gram-positive-bacterial endocarditis.

Martino, P., Venditti, M., Micozzi, A., Brandimarte, C., Gentile, G., Santini, C., & Serra, P. (1989). Teicoplanin in the treatment of gram-positive-bacterial endocarditis. Antimicrobial agents and chemotherapy, 33(8), 1329-1334.

The merits and dosing regimens for teicoplanin in the treatment of endocarditis, bacteremia, bone and joint infections, pediatric use, non in-patient use and in the ICU are discussed. Teicoplanin has several advantages over vancomycin in the treatment of serious infections: long half-life, lower nephrotoxicity, and lack of requirement for serum assays. The recommended regimen for teicoplanin is three loading doses of 6 mg/kg (400 mg) q12h, then 6 mg/kg (400 mg) q24h. There is no significant difference in efficacy between teicoplanin and vancomycin when at least 6 mg/kg teicoplanin is used or, in the case of staphylococcal endocarditis, it is given in combination with another antimicrobial. Teicoplanin is effective and safe in staphylococcal infections including endocarditis, osteomyelitis and septic arthritis. The once daily or alternate daily dosage allows home administration of treatment of infections caused by Staphylococcus aureus, including methicillin-resistant strains and enterococci with appreciable savings in hospital costs and improvement in the quality of life.

Schaison, G., Graninger, W., & Bouza, E. (2000). Teicoplanin in the treatment of serious infection. Journal of Chemotherapy, 12(sup5), 26-33.

Melting Point
N/A

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