Teicoplanin

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Teicoplanin
Category New Products
Catalog number BBF-03495
CAS 61036-62-2
Molecular Weight 1879.65
Molecular Formula C88H97Cl2N9O33
Purity Assay: 900 IU/mg (anhydrous and sodium-free substance)

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BBF-03495 1 g $299 In stock

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Description

Teichomycin is a glycopeptide antibiotic produced by Actinoplanes teichomyceticus nov. sp. (ATTCC 31121). Activity against gram-positive bacteria.

Specification

Synonyms Targocid; Teichomycin; Teichomycin A2; Teicoplanin
Storage -20°C
IUPAC Name (1S,2R,19R,22R,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
Canonical 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
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
InChI Key BJNLLBUOHPVGFT-QRZIFLFXSA-N
Source Actinoplanes sp.

Properties

Appearance White Powder
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 310°C (dec.)
Density 1.69 g/cm3
Solubility Soluble in DMSO, ethanol, methanol, DMF

Reference Reading

1.Pharmacokinetic/pharmacodynamic analysis of teicoplanin in patients with MRSA infections.
Matsumoto K1, Watanabe E1, Kanazawa N1, Fukamizu T1, Shigemi A1, Yokoyama Y2, Ikawa K3, Morikawa N3, Takeda Y1. Clin Pharmacol. 2016 Mar 30;8:15-8. doi: 10.2147/CPAA.S96143. eCollection 2016.
BACKGROUND: Teicoplanin is a glycopeptide antibiotic that has been used to treat serious, invasive infections caused by Gram-positive bacteria. The area under the drug concentration-time curve (AUC)/minimum inhibitory concentration (MIC) was identified as a pharmacokinetic-pharmacodynamic (PK-PD) parameter of glycopeptide antibiotics that correlated with bacteriological responses and clinical outcomes. Although optimized dosing regimens based on PK-PD are needed, a PK-PD analysis of teicoplanin against methicillin-resistant Staphylococcus aureus (MRSA) infections has not yet been performed. Thus, this study examined patients with MRSA infections, who were administered with teicoplanin in order to determine the target AUC/MIC ratio.
2.Change of teicoplanin loading dose requirement for incremental increases of systemic inflammatory response syndrome score in the setting of sepsis.
Nakano T1,2, Nakamura Y3, Takata T4, Irie K5, Sano K5, Imakyure O6, Mishima K5, Futagami K6. Int J Clin Pharm. 2016 Apr 28. [Epub ahead of print]
Background Target trough concentrations are recommended for teicoplanin (TEIC) to minimize its adverse effects and to maximize efficacy in sepsis caused by grampositive cocci, including methicillin-resistant Staphylococcus aureus infection. However, optimal doses to attain proper trough values in patients with sepsis have not yet been well established for TEIC. Objective This study investigated whether the systemic inflammatory response syndrome (SIRS) score could predict the pharmacokinetics of TEIC in patients with sepsis. Setting This study was conducted at Fukuoka University Hospital in Japan. Methods We retrospectively reviewed the records of patients using TEIC between April 2012 and March 2015. SIRS positive was defined as infection with a SIRS score ≥2. Estimates of pharmacokinetic parameters were calculated using a Bayesian method. Creatinine clearance rates were estimated by the Cockcroft-Gault formula (eCcr). Main outcome measure Change of TEIC loading dose requirement for incremental increases of SIRS score.

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