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Teicoplanin

CAS# 61036-62-2

Teicoplanin

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Chemical structure

Teicoplanin

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Chemical Properties of Teicoplanin

Cas No. 61036-62-2 SDF Download SDF
PubChem ID 16129701 Appearance Powder
Formula C88H97Cl2N9O33 M.Wt 1879.7
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Antibiotic MDL-507; MDL-507
Solubility Soluble to 100 mg/mL (58.5 mM) in Water
Chemical Name (1S,2R,19R,22S,34S,37R,40R,52R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[(2S,3R,4R,5S,6R)-3-(decanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
SMILES CCCCCCCCCC(=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)C1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)Cl)CO)O)O
Standard InChIKey BJNLLBUOHPVGFT-VPMXZCLFSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Teicoplanin

DescriptionTeicoplanin 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.

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Preparing Stock Solutions of Teicoplanin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.532 mL 2.66 mL 5.32 mL 10.64 mL 13.3 mL
5 mM 0.1064 mL 0.532 mL 1.064 mL 2.128 mL 2.66 mL
10 mM 0.0532 mL 0.266 mL 0.532 mL 1.064 mL 1.33 mL
50 mM 0.0106 mL 0.0532 mL 0.1064 mL 0.2128 mL 0.266 mL
100 mM 0.0053 mL 0.0266 mL 0.0532 mL 0.1064 mL 0.133 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Teicoplanin

Effects of bone cement loaded with teicoplanin, N-acetylcysteine or their combination on Staphylococcus aureus biofilm formation: an in vitro study.[Pubmed:28291433]

Eklem Hastalik Cerrahisi. 2017 Apr;28(1):13-8.

OBJECTIVES: This study aims to demonstrate the antibiofilm effects of Teicoplanin alone, N-acetyl cysteine (NAC) alone, or combination of both compounds when mixed with bone cement. MATERIALS AND METHODS: A total of four groups were formed by using six cement samples in each, prepared with bone cement having different contents in each group. Group 1 (control group): cement alone without any drugs added. Group 2: 40 g cement, 400 mg Teicoplanin. Group 3: 40 g cement, 6 g NAC. Group 4: 40 g cement, 6 g NAC, 400 mg Teicoplanin. All cement samples were infected with Staphylococcus aureus for 48 hours at 36.5 degrees C. Bacterial colonies were then counted by serial dilution method. Bacteria were counted using scanning electron microscopic (SEM) images. RESULTS: Counts of bacteria colonies were 5.83+/-1.60 [mean colony forming unit (cfu) x 105+/-standard deviation (SD)] in group 1, 0.12+/-0.56 in group 2, 0.11+/-0.65 in group 3, and 0.01+/-0.001 in group 4. Significant difference was found between group 1 and all other groups (p<0.05), and between group 4 and all other groups (p<0.05). According to SEM analysis, counts of bacteria (mean+/-SD) were 1.88+/-0.45, 0.75+/-0.26, 0.21+/-0.22, and 0.13+/-0.25 in groups 1, 2, 3, and 4, respectively. Significant difference was found between group 1 and all other groups (p<0.05), and between group 4 and all other groups (p<0.05). CONCLUSION: N-acetyl cysteine, Teicoplanin, and their combination significantly reduced formation of biofilm compared to the control group. Also, combination of NAC and Teicoplanin had the highest antibiofilm effect.

Population pharmacokinetics of teicoplanin and attainment of pharmacokinetic/pharmacodynamic targets in adult patients with haematological malignancy.[Pubmed:28267636]

Clin Microbiol Infect. 2017 Sep;23(9):674.e7-674.e13.

OBJECTIVES: To describe the population pharmacokinetics of Teicoplanin in adult patients with haematological malignancies receiving higher than standard doses, and to perform Monte Carlo simulations to determine dosing regimens associated with optimal Teicoplanin concentrations. METHODS: This was a hospital-based clinical trial (EudraCT 2013-004535-72). Nine blood samples were collected on Day 3, plus single trough samples on Days 7 and 10, and 24 and 48 hours after the last dose. Teicoplanin minimum inhibitory concentrations were determined for Gram-positive isolates from study patients. Population pharmacokinetic analyses and Monte Carlo dosing simulations were undertaken using Pmetrics. RESULTS: Thirty adult haematological malignancy patients were recruited with a mean (SD) loading dose, age, total body weight, and creatinine clearance of 9.5 (1.9) mg/kg, 63 (12) years, 69.1 (15.8) kg, and 72 (41) mL/min, respectively. A three-compartment linear pharmacokinetic model best described the Teicoplanin concentration data. Covariates supported for inclusion in the final model were creatinine clearance for clearance and total body weight for volume of the central compartment. The median (IQR) area under the concentration-time curve from 48 to 72 hours (AUC48-72h) was 679 (319) mg.h/L. There was a strong correlation between the AUC48-72h and trough concentration at 72 hours (Pearson correlation coefficient 0.957, p <0.001). Dosing simulations showed that administration of five loading doses at 12-hourly intervals, stratified by total body weight and creatinine clearance, increased the probability of achieving target concentrations within 72 hours. CONCLUSIONS: To increase the number of patients achieving optimal Teicoplanin concentrations an individualized dosing approach, based on body weight and creatinine clearance, is recommended.

Variability in Trough Total and Unbound Teicoplanin Concentrations and Achievement of Therapeutic Drug Monitoring Targets in Adult Patients with Hematological Malignancy.[Pubmed:28320714]

Antimicrob Agents Chemother. 2017 May 24;61(6). pii: AAC.02466-16.

The objective of this study was to explore the following aspects of Teicoplanin use in patients with hematological malignancy: early attainment of target trough concentrations with current high-dose Teicoplanin regimens, variability in unbound Teicoplanin fractions, factors associated with observed total and unbound trough concentrations, efficacy and toxicity, and renal function estimation. This was a single-center, prospective study. Samples for determination of trough concentrations were taken on days 3, 4, 7, and 10. Total and unbound Teicoplanin concentrations were determined using validated high-performance liquid chromatography methods. Regression analyses were used to identify the factors associated with the trough concentration. Thirty Teicoplanin-treated adults with hematological malignancy were recruited. Despite the use of dosages higher than the conventional dosages, the proportions of patients with a trough concentration of >/=20 mg/liter at 48 h and at 72 h were 16.7% and 37.9%, respectively. Renal function was significantly negatively associated with total trough concentrations at 48 h and 72 h (P < 0.05). For an average hematological malignancy patient (creatinine clearance = 70 ml/min), sequential loading doses of at least 12 mg/kg of body weight may be needed to achieve early adequate exposure. In the absence of measured creatinine clearance, estimates obtained using the Cockcroft-Gault (total body weight) equation could prove to be an acceptable surrogate. The unbound fractions of Teicoplanin were highly variable (3.4 to 18.8%). Higher unbound fractions were observed in patients with low serum albumin concentrations. Teicoplanin was well tolerated. Teicoplanin loading doses higher than those in current use appear to be necessary. Increased dosing is needed in patients with increased renal function. The high variability in protein binding supports the contention for therapeutic drug monitoring of unbound Teicoplanin concentrations. (This study has been registered with EudraCT under registration no. 2013-004535-72.).

Description

Teicoplanin is a glycopeptide antibiotic, used to treat serious infections caused by Gram-positive bacteria.

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