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Amphotericin B Produkt Beschreibung

Amphotericin B Struktur
1397-89-3
CAS-Nr.
1397-89-3
Bezeichnung:
Amphotericin B
Englisch Name:
Amphotericin B
Synonyma:
ns718;ABELCET;Halizon;LNS-AmB;AMBISOME;Abelecet;fungilin;Amphocin;AMPHOZONE;FUNGIZONE
CBNumber:
CB3425912
Summenformel:
C47H73NO17
Molgewicht:
924.08
MOL-Datei:
1397-89-3.mol

Amphotericin B Eigenschaften

Schmelzpunkt:
>170°C
Siedepunkt:
804.34°C (rough estimate)
alpha 
D24 +333° (acidic DMF); -33.6° (0.1N methanolic HCl)
Dichte
1.34
Brechungsindex
1.5280 (estimate)
storage temp. 
2-8°C
Löslichkeit
sterile water: 20 mg/mL as a stock solution. Stock solutions should be stored at −20?#x00b0;C. Stable at 37?#x00b0;C for 3 days.
Aggregatzustand
powder
pka
pKa ~5.7(DMF/H2O) (Uncertain)
Farbe
yellow
Wasserlöslichkeit
<0.1 g/100 mL at 21 ºC
Sensitive 
Moisture & Light Sensitive
Merck 
13,590
BRN 
78342
Stabilität:
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
InChIKey
APKFDSVGJQXUKY-INPOYWNPSA-N
CAS Datenbank
1397-89-3(CAS DataBase Reference)
EPA chemische Informationen
Amphotericin B (1397-89-3)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher C,Xi,Xn,T
R-Sätze: 36/37/38-22-40-23/24/25
S-Sätze: 26-36/37/39-45-36-60-37
RIDADR  UN 1759 8/PG 3
WGK Germany  3
RTECS-Nr. BU2625000
8-10-21
HazardClass  6.1(b)
PackingGroup  III
HS Code  29419090
Giftige Stoffe Daten 1397-89-3(Hazardous Substances Data)
Toxizität LD50 in mice (mg/kg): 88 i.p., 4 i.v. (Keim)
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
P261 Einatmen von Staub vermeiden.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P405 Unter Verschluss aufbewahren.

Amphotericin B Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

Crystalline Yellow Solid

Originator

Fungizone,Squibb,US,1958

Verwenden

Polypeptide antibiotic active against gram positive bacteria. Antifungal.

Verwenden

Amphotericin B is heptaene polyene antifungal originally discovered as a metabolite of Streptomyces nodosus in 1956. Amphotericin B acts by binding sterols in the cell membrane leading to the formation of transmembrane channels and subsequent ion leakage. Amphotericin B is poorly water soluble so has been developed for therapeutic use as a complex with desoxylate or in liposomes to improve bioavailability. Amphotericin B is widely used as a research reagent in diverse applications with over 15,000 literature citations.

Verwenden

Amphotericin B (Funizone) is an antifungal macrolide antibiotic produced by Streptomyces nodosus that has been used as an alternative, albeit more toxic, drug to the antimonials. See also Amebiasis (Amebic Dysentery) . It acts as a leishmanicide against the visceral and mucocutaneous forms of the disease. To overcome its potentially severe nephrotoxicity, the drug must be administered over an extended period of time.

Indications

Amphotericin B (Fungizone), a polyene antifungal drug produced by the actinomycete Streptomyces nodosus, consists of a large ring structure with both hydrophilic and lipophilic regions. Polyene antifungal drugs bind to the fungal cell membrane component ergosterol, leading to increased fungal cell membrane permeability and the loss of intracellular constituents. Amphotericin has a lesser affinity for the mammalian cell membrane component cholesterol, but this interaction does account for most adverse toxic effects associated with this drug.

Definition

ChEBI: A macrolide antibiotic used to treat potentially life-threatening fungal infections.

Manufacturing Process

The process for producing amphotericin comprises cultivating a strain of Streptomyces nodosus in an aqueous nutrient medium comprising an assimilable, fermentable carbohydrate and an assimilable organic nitrogen source, under submerged aerobic conditions, until substantial antifungal activity is imparted to the medium and recovering amphotericin from the medium.

Trademarks

Amphotec (Three Rivers); Fungizone (BristolMyers Squibb).

Therapeutic Function

Antifungal

Antimicrobial activity

The spectrum includes most fungi that cause human disease: A. fumigatus, Blast. dermatitidis, Candida spp., Coccidioides spp., Cryptococcus spp., Hist. capsulatum, Paracocc. brasiliensis and Spor. schenckii. Dermatophytes, Fusarium spp. and some other Aspergillus spp., including A. terreus and A. flavus, may be less susceptible, while Scedosporium spp., Trichosporon asahii (formerly T. beigelii) and some fungi that cause mucormycosis are resistant.

Acquired resistance

Resistant strains of C. tropicalis, C. lusitaniae, C. krusei and C. guilliermondii, with alterations in the cell membrane, including reduced amounts of ergosterol, have occasionally been isolated after prolonged treatment, particularly of infections in partially protected sites, such as the vegetations of endocarditis. Significant resistance in yeasts, including C. albicans and C. glabrata, has been reported in isolates from cancer patients with prolonged neutropenia. In some cases resistant strains have caused disseminated infection. There are a few reports of amphotericin-resistant strains of Cryp. neoformans recovered from AIDS patients with relapsed meningitis.

Hazard

May have undesirable side effects.

Pharmazeutische Anwendungen

A fermentation product of Streptomyces nodosus available for intravenous infusion or oral administration. The traditional micellar suspension formulation is often associated with serious toxic effects, in particular renal damage, and this has stimulated efforts to develop chemical modifications and new formulations.

Biochem/physiol Actions

Amphotericin B is used for primary treatment of acute invasive fungal infections, such as aspergillosis.

Pharmakokinetik

Less than 10% of a parenteral dose of the conventional micellar suspension of amphotericin B remains in the blood 12 h after administration. The remainder is thought to bind to tissue cell membranes, the highest concentrations being found in the liver (up to 40% of the dose). Levels in the CSF are less than 5% of the simultaneous blood concentration. The conventional formulation has a terminal half-life of about 2 weeks. About 75% of a given dose is excreted unchanged in the urine and feces. No metabolites have been identified.
The pharmacokinetics of lipid-based formulations are quite diverse. Maximal serum concentrations of the liposomal formulation are much higher than those of the conventional micellar formulation, while levels of colloidal dispersion and lipid complex formulations are lower due to more rapid distribution of the drug to tissue. Administration of lipid-associated formulations of amphotericin B results in much higher drug concentrations in the liver and spleen than are achieved with the conventional formulation. Renal concentrations of the drug are much lower and its nephrotoxic side effects are greatly reduced.
Blood concentrations are unchanged in hepatic or renal failure. Hemodialysis does not influence serum concentrations unless the patient is hyperlipidemic, in which case there is some drug loss due to adherence to the dialysis membrane.

Pharmakologie

This compound has a broad spectrum of antifungal activity, including Candida albicans, Leishmania brasiliensis, Mycobacterium leprae, Histoplasma capsulatum, Blastomyces dermatitidus, and Coccidioides immitis. It possesses fungistatic and fungicidal activity depending on the dose used. The antifungal activity of amphotericin B is exhibited because it binds with sterols, in particular with ergosterol in the cellular membrane of sensitive fungi. This reaction makes pores in the membrane and increases the permeability of the membrane to small molecules, thus reducing the function of the membrane as an osmotic barrier and making the cells more sensitive to being destroyed.
Amphotericin B is active against growing cells and cells that are dormant. However, this compound is not highly selective and reacts with host mammalian cells. Despite the many side effects, amphotericin B remains the primary drug for treating severe, acute systemic fungal infections. It is used for generalized fungal infections, such as candidomycosis, aspergillosis, histoplasmosis, cryptococcosis, coccidioidomycosis, blastomycosis, and pulmonary mycoses. Synonyms of this drug are amphocyclin, fungisone, fungilin, and others.

Clinical Use

Amphotericin B is most commonly used to treat serious disseminated yeast and dimorphic fungal infections in immunocompromised hospitalized patients. As additional experience has been gained in the treatment of fungal infections with the newer azoles, the use of amphotericin B has diminished; if azole drugs have equivalent efficacy, they are preferred to amphotericin B because of their reduced toxicity profile and ease of administration. For the unstable neutropenic patient with Candida albicans fungemia, amphotericin B is the drug of choice.
Amphotericin B remains the drug of choice in the treatment of invasive aspergillosis, locally invasive mucormycosis, and many disseminated fungal infections occurring in immunocompromised hosts (the patient population most at risk for serious fungal infections). For example, the febrile neutropenic oncology patient with persistent fever despite empirical antibacterial therapy is best treated with amphotericin B for possible Candida spp. sepsis.

Clinical Use

Aspergillosis
Systemic mycoses with dimorphic fungi (blastomycosis, coccidioidomycosis, histoplasmosis, paracoccidioidomycosis, penicilliosis)
Candidosis
Cryptococcosis
Hyalohyphomycosis, mucormycosis, phaeohyphomycosis
Visceral leishmaniasis

Nebenwirkungen

Fever, chills, and tachypnea commonly occur shortly after the initial intravenous doses of amphotericin B; this is not generally an allergic hypersensitivity to the drug, which is extremely rare. Continued administration of amphotericin B is accomplished by premedication with acetaminophen, aspirin, and/or diphenhydramine or the addition of hydrocortisone to the infusion bag.
Normochromic normocytic anemia is the most common hematological side effect of amphotericin B administration; thrombocytopenia and leukopenia are much less common. Infusion of the drug into a peripheral vein usually causes phlebitis or thrombophlebitis. Nausea, vomiting, and anorexia are a persistent problem for some patients.

Nebenwirkungen

Common side effects of conventional amphotericin B include hypotension, fever, rigors, chills, headache, backache, nausea, vomiting, anorexia, anemia, disturbances in renal function (including hypokalemia and hypomagnesemia), renal toxicity, abnormal liver function (discontinue treatment), rash and anaphylactoid reactions. Risk factors for nephrotoxicity include average daily dose, concomitant treatment with other nephrotoxic drugs and elevated baseline serum creatinine.
The lipid-associated formulations all lower the risk of amphotericin B-induced renal failure. However, infusionrelated side effects, such as fever, rigors and hypotension, develop in up to 40% of patients treated with the colloidal dispersion, and hypoxic events also occur; as a result this formulation is not widely used. In contrast, infusionrelated reactions are uncommon with liposomal amphotericin B or the lipid complex. Patients who have developed renal impairment while receiving the conventional formulation of amphotericin B have improved or stabilized when lipid-associated amphotericin B was substituted, even when the dose was increased. Renal function should be measured at regular intervals, particularly in patients receiving other nephrotoxic drugs.

Sicherheitsprofil

Poison by intravenous and intraperitoneal routes. Human systemic effects by intravenous route: leukopenia, lung changes, and cardiac changes.Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Amphotericin B, is a large polyene antibiotic made from the cultural fluid of the actinomycete Streptomyces nodosus.

Veterinary Drugs and Treatments

Amphotericin B has been used topically and subconjunctivally to treat cases of equine fungal keratitis. Amphotericin B is fungistatic or fungicidal depending on the concentration obtained in body fluids and the susceptibility of the fungus. The drug acts by binding to sterols in the cell membrane of susceptible fungi with a resultant change in membrane permeability allowing leakage of intracellular components. Mammalian cell membranes also contain sterols and it has been suggested that the damage to human cells and fungal cells may share common mechanisms. Amphotericin B has been shown to be effective against the following fungi: Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium spp. are often resistant to amphotericin B. The major action of amphotericin B is to bind ergosterol in the fungal plasma cell membrane, making the membrane more permeable and resulting in leakage of cell electrolytes and cell death. At high concentrations, amphotericin B is thought to cause oxidative damage to the fungal cell or disruption of fungal cell enzymes.

Amphotericin B Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Amphotericin B Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 405)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5941 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
+86 (576) 8169-6105 sales@frappschem.com China 886 50
Shanxi Naipu Import and Export Co.,Ltd
+8613734021967
kaia@neputrading.com CHINA 1011 58
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29954 58
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86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Shanghai Longyu Biotechnology Co., Ltd.
+8615821988213
+86 15821988213 info@longyupharma.com China 2500 58

1397-89-3(Amphotericin B)Verwandte Suche:


  • FUNGIZONE
  • FUNGIZONE(R)
  • ABELCET
  • AMBISOME
  • AMPHOTERCIN B
  • AMPHOTERICIN B
  • AMPHOTERICIN B SOLUBILIZED
  • AMPHOTERICIN B, SOLUBLE
  • AMPHOTERICIN B, STREPTOMYCES NODOSUS
  • AMPHOTERICIN B, STREPTOMYCES SPECIES
  • AMPHOZONE
  • 33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
  • ,16r*,17r*,18s*,19e,21e,23e,25e-27e,29e,31e,33r*,35s*,36r*,37s*))-
  • 14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbo
  • 17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1r-(1r*,3s*,5r*,6r*,9r*,11r*,15s*
  • Amphotericin B from Streptomyces sp
  • AmphotericinB from Streptomyces sp., Fungizone
  • (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-Amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
  • 1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E,25E,27E,29E,31E,33R*,35S*,36R*,37S*))-33-((3-Amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,2
  • AMPHOTERICIN B SOLUTION
  • AMPHOTERICIN B CELL CULTURE TESTED
  • mysteclin-f
  • ns718
  • nsc527017
  • B AMPHOTERICIN B
  • AMPHOTERICIN
  • Fungillin
  • AmphotericinB solubilized,AmphotericinB from Streptomyces sp., Fungizone
  • Amphotericin B (125 mg) (COLD SHIPMENT REQUIRED)
  • Amphotericin B (125 mg)J3C2461009ug/mg(dr)
  • Amphotericin B (125 mg)
  • Amphotericin B (125 mg) (INTERNATIONAL COLD CHAIN SHIPMENT REQUIRED)
  • AMphotericin B (Abelcet)
  • Abelecet
  • AMphotericin B (85%)
  • Apothecon
  • Fungizona
  • Amphotericin B for microbiological assay
  • 2-[2-[(4-amino-3,5-dihydroxy-6-methyl-2-oxanyl)oxy]-18-hydroxy-17,19-dimethyl-20-(3,5,8,9,11-pentahydroxy-1-oxododecoxy)heneicosa-3,5,7,9,11,13,15-heptaenyl]-4,6-dihydroxy-3-oxanecarboxylic acid
  • Amphotericin B (oral)
  • Amphotericin B, 750μg/mg
  • fungisone14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,2 7,29,31-heptaene-36-carbo
  • Amphocil 50mg and 100mg Vial (8450A/8455A)
  • Amphotericin B from Streptomyces sp. Vetec(TM) reagent grade, BioReagent, suitable for cell culture, ~80%
  • EZNA KIT ENDO-FREE PLASMID MEGA
  • 33-((3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy)-1,3,5,6,9,11,-xylicaci
  • amphomoronal
  • ampho-moronal
  • amphotericinbstandardsolution
  • amphotericineb
  • fungilin
  • fungisone
  • AMPHOTERICIN B FORM STREPTOMYCES SSP.
  • AMPHOTERICIN B-PLANT CELL CULTURETESTED
  • AMPHOTERICIN B FROM STREPTOMYCES SSP., F OR CELL BIOLOGY
  • AMPHOTERICIN B, PHARMA
  • B amphotericin B,trihydrate
  • AMPHOTERICINB,USP
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