Search summary:
Session ID: 63d22dfaaa826c6705d6bc39966376eb
Search Type: drug
Started at: 2010-02-15 01:42:46
Finished at: 2010-02-15 01:45:16
| Field | Result | Source |
|---|---|---|
| Name | ||
| abelcet | External | |
| Drugbank ID | ||
| DB00681 | DrugBank | |
| Description | ||
| AmBisome is a liposomal formulation of amphotericin B for injection, developed by NeXstar Pharmaceuticals (acquired by Gilead Sciences in 1999). It is marketed by Gilead in Europe and licensed to Astellas Pharma (formerly Fujisawa Pharmaceuticals) for marketing in the USA, and Sumitomo Pharmaceuticals in Japan. | Wikipedia | |
| Ampholip is a lipid complex formulation of Amphotericin B marketed by Bharat Serums & Vaccines Ltd, Mumbai, India. | Wikipedia | |
| Amphotericin B (Fungilin, Fungizone, Abelcet, AmBisome, Fungisome, Amphocil, Amphotec) is a polyene antifungal drug, often used intravenously for systemic fungal infections. It was originally extracted from Streptomyces nodosus, a filamentous bacterium, in 1955 at the Squibb Institute for Medical Research from cultures of an undescribed streptomycete isolated from the soil collected in the Orinoco River region of Venezuela. Its name originates from the chemical's amphoteric properties. Two amphotericins, Amphotericin A and Amphotericin B are known, but only B is used clinically because it is significantly more active in vivo. Currently the drug is available as plain Amphotericin B, as cholesteryl sulfate complex, as lipid complex, and as liposomal formulation. The latter formulations have been developed to improve tolerability for the patient but may show considerably different pharmacokinetic characteristics compared to plain Amphotericin B. | Wikipedia | |
| Amphotericin B is well-known for its severe and potentially lethal side effects. Very often a serious acute reaction after the infusion (1 to 3 hours later) is noted consisting of high fever, shaking chills, hypotension, anorexia, nausea, vomiting, headache, dyspnea, and tachypnea, drowsiness, generalised weakness. This reaction sometimes subsides with later applications of the drug and may in part be due to histamine liberation. An increase in prostaglandin-synthesis may also play a role. This nearly universal febrile response necessitates a critical (and diagnostically difficult) professional determination as to whether the onset of high fever is a novel symptom of a fast-progressing disease, or merely the induced effect of the drug. In order to decrease the likelihood and severity of the symptoms, initial doses should be low and increased slowly. Acetaminophen, pethidine, diphenhydramine and/or hydrocortisone have all been used to treat or prevent the syndrome, but the prophylactic use of these drugs is often limited by the patient's condition. | Wikipedia | |
| Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses. | DrugBank | |
| Fungisome is a liposomal complex of Amphotericin B and being the latest and cheapest addition to the lipid formulations of Amphotericin B has many advantages. It is marketed by Lifecare Innovations of India. Other formulations include Amphotec (Intermune) and Abelcet (Enzon Pharmaceuticals). | Wikipedia | |
| Intravenously administered Amphotericin B has also been associated with multiple organ damage in therapeutic doses. Nephrotoxicity (kidney damage) is a frequently reported side-effect, and can be severe and/or irreversible. It is much milder when delivered via liposomes (AmBisome) if possible. Electrolyte imbalances (e.g. hypokalemia and hypomagnesemia) may also result. In the liver, increased liver enzymes and hepatotoxicity (up to and including fulminant liver failure) are common. In the circulatory system, several forms of anemia and other blood dyscrasias (leukopenia, thrombopenia), serious cardiac arrhythmias (including ventricular fibrillation), and even frank cardiac failure have been reported. Skin reactions, including serious forms, are also possible. | Wikipedia | |
| Chemical Kingdom | ||
| Organic | BioSpider | |
| Chemical Class | ||
| Not Available | Not Applicable | |
| Chemical Species | ||
| 1,2-aminoalcohol | Checkmol | |
| 1,2-diol | Checkmol | |
| acetal | Checkmol | |
| alkene | Checkmol | |
| carboxylic acid | Checkmol | |
| carboxylic acid ester | Checkmol | |
| hemiacetal | Checkmol | |
| heterocyclic compound | Checkmol | |
| lactone | Checkmol | |
| primary aliphatic amine (alkylamine) | Checkmol | |
| primary amine | Checkmol | |
| secondary alcohol | Checkmol | |
| Synonym | ||
| AMB | Pubchem | |
| Amb/liposomal | Pubchem | |
| Ambiosone | Pubchem | |
| Ampho-moronal | NCI | |
| Amphocin | Pubchem | |
| Amphotec | Pubchem | |
| Amphotericin β | NCI | |
| Amphotericin b | Pubchem | |
| Amphotericin b & nyotran | Pubchem | |
| Amphotericin b & nyotran(liposomal nystatin) | Pubchem | |
| Amphotericin b (van) | NCI | |
| Amphotericine b | NCI | |
| Amphozone | Pubchem | |
| Colloidal dispersion of cholesteryl sulfate and amphotericin b | Pubchem | |
| Fungilin | NCI | |
| Fungisone | NCI | |
| Fungizone | Pubchem | |
| IAB | NCI | |
| Lipid nanosphere that incorporates amphotericin b | Pubchem | |
| Liposomal amphotericin b | Pubchem | |
| Mysteclin-f | Pubchem | |
| Ribbon form of lipid-stabilized amphotericin b aggregates | Pubchem | |
| Tegopen | NCI | |
| Brand Mixture | ||
| Not Available | Not Applicable | |
| CAS | ||
| 1397-89-3 | PubChem | |
| InChI Identifier | ||
InChI=1/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34( 64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47( 61,65-38)25-33(51)21-31(49)19-20-35(52)36(53)22-32(50)23-39(55)62 -29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48 H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t 27-,28+,29-,30+,31-,32+,33-,34-,35-,36-,37-,38-,40+,41-,42+,43+,4 4-,46-,47+/m0/s1 |
World Wide Molecular Matrix | |
| IUPAC | ||
| (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]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 | DrugBank | |
| Chemical Formula | ||
| C47H73NO17 | PubChem | |
| Chemical Structure | ||
 |
PubChem | |
| Average Molecular Weight (g/mol) | ||
| 924.079020 | BioSpider | |
| Monoisotopic Molecular Weight (g/mol) | ||
| 923.487850 | BioSpider | |
| SMILES (Isomeric) | ||
C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[ C@](O2)(C[C@H](C[C@H](CC[C@@H]([C@H](C[C@H](CC(=O)O[C@H]([C@H]([C @@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O 3)C)O)N)O |
PubChem | |
| SMILES (Canonical) | ||
CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CCC(C(CC(CC(=O)OC(C (C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O |
PubChem | |
| Kegg Drug | ||
| D00203 | DrugBank | |
| Kegg Compound | ||
| C06573 | DrugBank | |
| Pubchem Compound ID | ||
| 6473721 | PubChem | |
| Pubchem Substance ID | ||
| 16568627 | Pubchem | |
| 55512583 | Pubchem | |
| 595981 | Pubchem | |
| 613710 | Pubchem | |
| 636503 | Pubchem | |
| 637400 | Pubchem | |
| 640216 | Pubchem | |
| 640217 | Pubchem | |
| 76394939 | Pubchem | |
| 8802 | Kegg | |
| OMIM ID | ||
| Not Available | Not Applicable | |
| ChEBI | ||
| 2682 | Kegg | |
| BioCyc | ||
| Not Available | Not Applicable | |
| PharmGKB | ||
| PA448415 | DrugBank | |
| HET ID | ||
| Not Available | Not Applicable | |
| DPD ID | ||
| Not Available | Not Applicable | |
| Rxlist Link | ||
| http://www.rxlist.com/cgi/generic2/amphoter.htm | DrugBank | |
| Wikipedia | ||
| abelcet | Wikipedia | |
| Pdr Health Link | ||
| Not Available | Not Applicable | |
| Melting Point | ||
| Not Available | Not Applicable | |
| State | ||
| Not Available | Not Applicable | |
| MSDS Link | ||
| Not Available | Not Applicable | |
| FDA Label | ||
| Not Available | Not Applicable | |
| Experimental Water Solubility | ||
| 0.75 mg/mL at 28 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | |
| Predicted Water Solubility | ||
| 0.0805 mg/mL [Predicted by ALOGPS] | Alogps | |
| Experimental LogP | ||
| Not Available | Not Applicable | |
| Predicted LogP | ||
| -0.67 [Predicted by ALOGPS] | Alogps | |
| -2.80 [MEYLAN,WM & HOWARD,PH (1995)] | PhysProp | |
| pKa | ||
| Not Available | Not Applicable | |
| SDF File | ||
| 1266223394.sdf | Pubchem | |
| Mol File | ||
| 1266223379.mol | Molconvert | |
| Pdb File | ||
| 1266223431.pdb | Molconvert | |
| Mass Spec File | ||
| Not Available | Not Applicable | |
| Associated Disorder | ||
| Not Available | Not Applicable | |
| Pathway | ||
| map01052 - Type I polyketide structures | Kegg Compound | |
| Category | ||
| Not Available | Not Applicable | |
| ATC Code | ||
| Not Available | Not Applicable | |
| AHFS Code | ||
| Not Available | Not Applicable | |
| Schedule | ||
| Not Available | Not Applicable | |
| Indication | ||
| Amphotericin B is well-known for its severe and potentially lethal side effects. Very often a serious acute reaction after the infusion (1 to 3 hours later) is noted consisting of high fever, shaking chills, hypotension, anorexia, nausea, vomiting, headache, dyspnea, and tachypnea, drowsiness, generalised weakness. This reaction sometimes subsides with later applications of the drug and may in part be due to histamine liberation. An increase in prostaglandin-synthesis may also play a role. This nearly universal febrile response necessitates a critical (and diagnostically difficult) professional determination as to whether the onset of high fever is a novel symptom of a fast-progressing disease, or merely the induced effect of the drug. In order to decrease the likelihood and severity of the symptoms, initial doses should be low and increased slowly. Acetaminophen, pethidine, diphenhydramine and/or hydrocortisone have all been used to treat or prevent the syndrome, but the prophylactic use of these drugs is often limited by the patient's condition. | Wikipedia | |
| Crystalline amphotericin B is insoluble in water; therefore, the antibiotic is solubilized by the addition of sodium desoxycholate to form a mixture which provides a colloidal dispersion for intravenous infusion following reconstitution. At the time of manufacture the air in the vial is replaced by nitrogen.Last updated on RxList: 4/8/2009 | RxList | |
| Oral preparations of Amphotericin B are used to treat thrush; these are virtually nontoxic, in contrast to typical IV doses. | Wikipedia | |
| Used to treat potentially life threatening fungal infections. | DrugBank | |
| Pharmacology | ||
| Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses. | DrugBank | |
| Mechanism Of Action | ||
| 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. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. | DrugBank | |
| Another IV use is as a drug of last resort in otherwise untreatable parasitic protozoan infections such as visceral leishmaniasis and primary amoebic meningoencephalitis. Mechanism of action | Wikipedia | |
| As with other polyene antifungals, amphotericin B associates with ergosterol, the main component of fungal cell membranes, forming a transmembrane channel that leads to K+ leakage and fungal cell death. Recently, however, researchers found evidence that pore formation is not necessarily linked to cell death (i.e. Angewandte Chemie Int. Ed. Engl. 2004). The actual mechanism of action may be more complex and multi-faceted. Side effects | Wikipedia | |
| Absorption | ||
| 100% (IV) | Wikipedia | |
| Bioavailability is 100% for intravenous infusion. | DrugBank | |
| Protein Binding | ||
| Highly bound (>90%) to plasma proteins. | DrugBank | |
| Half Life | ||
| An elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours. | DrugBank | |
| initial phase : 24 hours, second phase : approx. 15 days | Wikipedia | |
| Biotransformation | ||
| Exclusively renal | DrugBank | |
| Toxicity | ||
| Amphotericin B may also facilitate entry of Flucystosine into the fungal cell by interfering with the permeability of the fungal cell membrane. Diuretics or Cisplatin : Increased renal toxicity and incrised risk of hypokalemia Corticosteroids : Increased risk of hypokalemia Cytostatic drugs : Increased risk of kidney damage, hypotension and bronchospasms. Other nephrotoxic drugs : Increased risk of serious renal damage | Wikipedia | |
| In the liver, increased liver enzymes and hepatotoxicity (up to and including fulminant liver failure) are common | Wikipedia | |
| It is usually sold in a concentrated solution, either on its own or in combination with the antibiotics penicillin and streptomycin. Antiprotozoan Another IV use is as a drug of last resort in otherwise untreatable parasitic protozoan infections such as visceral leishmaniasis and primary amoebic meningoencephalitis. Mechanism of action As with other polyene antifungals, amphotericin B associates with ergosterol, the main component of fungal cell membranes, forming a transmembrane channel that leads to K+ leakage and fungal cell death | Wikipedia | |
| Nephrotoxicity (kidney damage) is a frequently reported side-effect, and can be severe and/or irreversible | Wikipedia | |
| Oral, rat: LD50 = >5 gm/kg. Amphotericin B overdoses can result in cardio-respiratory arrest. | DrugBank | |
| Recently, however, researchers found evidence that pore formation is not necessarily linked to cell death (i.e | Wikipedia | |
| Skin reactions, including serious forms, are also possible. Interactions Flucytosine : Toxicity of Flucytosine increased | Wikipedia | |
| The actual mechanism of action may be more complex and multi-faceted. Side effects Amphotericin B is well-known for its severe and potentially lethal side effects | Wikipedia | |
| Dosage | ||
| Not Available | Not Applicable | |
| Patient Information | ||
| 1266223509.html | RxList | |
| Interactions | ||
| Not Available | Not Applicable | |
| Contraindications | ||
| Not Available | Not Applicable | |
| Targets | ||
P40030[ UniProt | Analyze ] |
DrugBank |