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Daptomycin

Daptomycin Struktur
103060-53-3
CAS-Nr.
103060-53-3
Englisch Name:
Daptomycin
Synonyma:
Cubicin;N-[N-(1-Oxodecyl)-L-Trp-D-Asn-L-Asp-]-cyclo[L-Thr*-Gly-L-Orn-L-Asp-D-Ala-L-Asp-Gly-D-Ser-[(3R)-3-methyl-L-Glu-]-4-(2-aminophenyl)-4-oxo-L-Abu-];Dapcin;Cidecin;Ly-146032;aptomycin;datomycin;daptomycin;Dattomycin;DAPTOMYCINE
CBNumber:
CB8855073
Summenformel:
C72H101N17O26
Molgewicht:
1620.67
MOL-Datei:
103060-53-3.mol

Daptomycin Eigenschaften

Schmelzpunkt:
202-204?C
Siedepunkt:
2078.2±65.0 °C(Predicted)
Dichte
1.45±0.1 g/cm3(Predicted)
Flammpunkt:
87℃
storage temp. 
Sealed in dry,Store in freezer, under -20°C
L?slichkeit
methanol: soluble5mg/mL
pka
4.00±0.10(Predicted)
Aggregatzustand
powder
Farbe
colorless to faint yellow
maximale Wellenl?nge (λmax)
260nm(EtOH)(lit.)
Merck 
14,2823
Stabilit?t:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey
DOAKLVKFURWEDJ-RWDRXURGSA-N
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
WGK Germany  3
RTECS-Nr. HB5626000
HS Code  29419090
Toxizit?t LD50 i.v. in mice: 600 mg/kg (Debono)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

Daptomycin Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften

Off-White to Light Yellow Solid

Verwenden

Daptomycin is a member of the A 21978 complex of high molecular weight cyclic lipopeptides with potent antibiotic activity, notably against MRSA, VISA and VRSA bacterial strains. Originally isolated from Streptomyces roseosprous by Eli Lily in the 1980s, daptomycin was selected and developed by Cubist Pharmaceticals for human use. Daptomycin exhibits Ca-dependent depolarisation of the bacterial membrane resulting in loss of membrane potential leading to inhibition of DNA, RNA and protein synthesis which results in cell death.

Definition

ChEBI: A polypeptide comprising N-decanoyltryptophan, asparagine, aspartic acid, threonine, glycine, ornithine, aspartic acid, D-alanine, aspartic acid, glycine, D-serine, threo-3-methylglutamic ac d and 3-anthraniloylalanine (also known as kynurinine) coupled in sequence and lactonised by condensation of the carboxylic acid group of the 3-anthraniloylalanine with the alcohol group of the threonine residue.

Pharmazeutische Anwendungen

A semisynthetic lipopeptide derived from a fermentation product of Streptomyces roseosporus.
Daptomycin is a cyclic peptide with a lipophilic tail and thus resembles the polymyxins structurally. Its useful activity is restricted to Gram-positive cocci, notably Staph. aureus and its chief attraction is that it retains activity against multiresistant strains. Its activity in vitro is greatly potentiated by the presence of calcium (but not magnesium) ions and in these conditions it is more potently bactericidal than the glycopeptides.

Pharmakokinetik

Oral absorption: Poor
Cmax 4 mg/kg intravenous infusion :55 mg/L end infusion
Plasma half-life: 8–9 h
Volume of distribution:c.0.1 L/kg
Plasma protein binding: 92–95%
Oral absorption is poor and it is administered intravenously. It is eliminated predominantly by the kidneys, about half the dose being excreted unchanged within 24 h. The plasma halflife increases in patients with impaired renal function so that the dosage interval should be extended. Around 10% of an administered dose is removed by peritoneal and hemodialysis.

Clinical Use

Daptomycin is a fermentation product having a cyclic lipopeptide structure. It is primarily active against Gram-positive infections, especially those involved in skin/skin structure infections. It is given IV but must be administered over a period of 30 minutes or more. It binds to cell membranes and causes depolarization, which interrupts protein, DNA, and RNA synthesis. Daptomycin is bactericidal. Although resistance can be achieved in vitro, resistance has been slow to emerge in the clinic. Patients should be monitored for muscle pain or weakness, because some incidence of elevated serum creatinine phosphokinase is associated with its use. A small number of clinical trial patients also developed conditions related to decreases in nerve conduction (e.g., paresthesias and Bell's palsy). Daptomycin is eliminated primarily by the kidney, so dose adjustment may be necessary in cases of renal insufficiency.

Nebenwirkungen

It is generally well-tolerated, but gastrointestinal side effects, headache and various other adverse reactions occur with varying frequency. Less commonly, but more seriously, myalgia, muscle weakness and myositis may occur requiring regular monitoring of creatine kinase during treatment. Rhabdomyolysis has been reported, but is very rare.

Arzneimittelwechselwirkung

In vitro experiments using human hepatocytes demonstrated that daptomycin has no effects on hepatic CYP450-mediated drug metabolism and, therefore, suggest that daptomycin is unlikely to show potential for pharmacokinetic interactions with concomitantly administered drugs that are metabolized by CYP450 isoforms. Drug interaction single- and multiple-dose studies were performed in healthy subjects. No clinically relevant interactions were found when daptomycin 2–6 mg/kg was administered with aztreonam, tobramycin, warfarin, simvastatin, and probenecid. Although no specific drug interactions have been detected when daptomycin is co-administered with HMG-CoA reductase inhibitors (e.g. simvastatin), a number of patients who developed creatine phosphokinase (CPK) increases in a study of daptomycin efficacy in S. aureus bacteremia/endocarditis were receiving concomitant HMGCoA reductase inhibitors. Thus, monitoring of CPK levels is probably warranted in patients with risk factors and timely cessation of potential agents if myopathy is noted.

Daptomycin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Daptomycin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 521)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hubei Ipure Biology Co., Ltd
+8613367258412
ada@ipurechemical.com China 10319 58
AFINE CHEMICALS LIMITED
+86-0571-85134551
sales@afinechem.com China 15352 58
BOC Sciences
16314854226; +16314854226
inquiry@bocsci.com United States 19741 58
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325
sales1@chuanghaibio.com China 5889 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714
FandaChem@Gmail.com China 9087 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3009 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
bruce@xrdchem.cn CHINA 566 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795
ivan@atkchemical.com China 32957 60
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58

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