Amphotericin B
- CAS No.
- 1397-89-3
- Chemical Name:
- Amphotericin B
- Synonyms
- AMPHOTERICIN;FUNGIZONE;AMBISOME;ABELCET;fungilin;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,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;ns718;Halizon;LNS-AmB
- CBNumber:
- CB3425912
- Molecular Formula:
- C47H73NO17
- Molecular Weight:
- 924.08
- MOL File:
- 1397-89-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/27 20:28:20
| Melting point | >170°C |
|---|---|
| Boiling point | 804.34°C (rough estimate) |
| alpha | D24 +333° (acidic DMF); -33.6° (0.1N methanolic HCl) |
| Density | 1.34 |
| refractive index | 1.5280 (estimate) |
| storage temp. | 2-8°C |
| solubility | sterile water: 20 mg/mL as a stock solution. Stock solutions should be stored at −20°C. Stable at 37°C for 3 days. |
| form | powder |
| pka | pKa ～5.7(DMF/H2O) (Uncertain) |
| color | yellow |
| Water Solubility | <0.1 g/100 mL at 21 ºC |
| Sensitive | Moisture & Light Sensitive |
| Merck | 13,590 |
| BRN | 78342 |
| Stability | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| InChIKey | APKFDSVGJQXUKY-INPOYWNPSA-N |
| CAS DataBase Reference | 1397-89-3(CAS DataBase Reference) |
| EPA Substance Registry System | Amphotericin B (1397-89-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H372 | |||||||||
| Precautionary statements | P260-P264-P270-P314-P501 | |||||||||
| Hazard Codes | C,Xi,Xn,T | |||||||||
| Risk Statements | 36/37/38-22-40-23/24/25 | |||||||||
| Safety Statements | 26-36/37/39-45-36-60-37 | |||||||||
| RIDADR | UN 1759 8/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | BU2625000 | |||||||||
| F | 8-10-21 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29419090 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 88 i.p., 4 i.v. (Keim) | |||||||||
| NFPA 704 |
|
Amphotericin B price More Price(24)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A9528 | Amphotericin B solubilized powder, γ-irradiated, BioXtra, suitable for cell culture | 1397-89-3 | 50MG | ₹4968.68 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9528 | Amphotericin B solubilized powder, γ-irradiated, BioXtra, suitable for cell culture | 1397-89-3 | 100MG | ₹9493.53 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9528 | Amphotericin B solubilized powder, γ-irradiated, BioXtra, suitable for cell culture | 1397-89-3 | 500MG | ₹44696.43 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9528 | Amphotericin B solubilized powder, γ-irradiated, BioXtra, suitable for cell culture | 1397-89-3 | 1G | ₹83677.25 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1662 | Amphotericin B Pharmaceutical Secondary Standard; Certified Reference Material | 1397-89-3 | 500MG | ₹31901.28 | 2022-06-14 | Buy |
Amphotericin B Chemical Properties,Uses,Production
Chemical Properties
Crystalline Yellow Solid
Uses
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.
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: Amphotericin B is a macrolide antibiotic used to treat potentially life-threatening fungal infections.
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.
Pharmaceutical Applications
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.
Pharmacology
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.
Pharmacokinetics
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.
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.
Side effects
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.
Safety Profile
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.
Amphotericin B Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4542 | 58 | Inquiry |
| Varanous Labs Pvt Ltd | +91-7036248882 +91-7036248882 | Hyderabad, India | 1541 | 58 | Inquiry |
| Bajaj Healthcare Ltd | +91-2266177400 +91-2266177400 | Maharashtra, India | 86 | 58 | Inquiry |
| Synbiotics Limited | +91-9909001737 +91-9099978530 | Gujarat, India | 1 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| PROTECH TELELINKS | +91-8571891912 +91-9855060837 | Himachal Pradesh, India | 62 | 58 | Inquiry |
| BDR Pharmaceuticals International Pvt Ltd | +91-2240560560 +91-7718884418 | Maharashtra, India | 206 | 58 | Inquiry |
| Century Pharmaceuticals Ltd | +91-2652361581 +91-2652361581 | Gujarat, India | 53 | 58 | Inquiry |
| Asence Pharma Pvt Ltd | +91-265228317 +91-265228317 | Gujarat, India | 16 | 58 | Inquiry |
| AKASH PHARMA EXPORTS | +91-9388123451 +91-9846039283 | Kerela, India | 470 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| GLR Innovations | 58 |
| Varanous Labs Pvt Ltd | 58 |
| Bajaj Healthcare Ltd | 58 |
| Synbiotics Limited | 58 |
| Ralington Pharma | 58 |
| PROTECH TELELINKS | 58 |
| BDR Pharmaceuticals International Pvt Ltd | 58 |
| Century Pharmaceuticals Ltd | 58 |
| Asence Pharma Pvt Ltd | 58 |
| AKASH PHARMA EXPORTS | 58 |
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