amphotericin B

Also known as APT370, AMPH-b, C-AmB, liposomal amphotericin B

chemical compound

Key facts

Trade names: Fungizone, Mysteclin-F, AmBisome and other
Ahfs drugs com: Monograph
Medlineplus: a682643
License data: United States</span>"}]]}'>US DailyMed : Amphotericin_B
Pregnancy category: Australia</span>"}]]}'>AU : B2
Routes of administration: Intravenous infusion
Atc code: A01AB04 ( WHO ) A07AA07 ( WHO ), G01AA03 ( WHO ), J02AA01 ( WHO )
Legal status: United States</span>"}]]}'>US : ℞-only In general: ℞ (Prescription only)
Bioavailability: 100% (IV) low (oral)
Metabolism: kidney
Elimination half life: Initial phase: 24 hours Second phase: approximately 15 days
Excretion: 40% found in urine after single cumulated over several days Biliary excretion is also important
Cas number: 1397-89-3
Drugbank: DB00681
Unii: 7XU7A7DROE
Kegg: D00203
Chebi: CHEBI:2682
Chembl: ChEMBL267345

via Wikipedia infobox

Chemical data

Formula: C47H73NO17
Molecular weight: 924.1 g/mol
IUPAC name: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-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-carboxylate
SMILES: 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]([C@@H](CC[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](O3)C)O)[NH3+])O
InChIKey: APKFDSVGJQXUKY-INPOYWNPSA-N
XLogP: 0.6
Polar surface area: 324 Å²
H-bond donors: 11
H-bond acceptors: 17
Formal charge: 0

via PubChem

Research

28,962 papers

Amphotericin B.Applied microbiology and biotechnology · 2005
Amphotericin B--specifics of administration.Modern treatment · 1970
[Clinical safety of liposomal amphotericin B].Revista iberoamericana de micologia · 2021
Amphotericin B lipid complex for the treatment of invasive fungal infections.Expert opinion on pharmacotherapy · 2003
Amphotericin B and its lipid formulations.Journal of pediatric oncology nursing : official journal of the Association of Pediatric Oncology Nurses · 1994

via PubMed

Wikidata facts

Mass: 923.488

Show 5 more facts

chemical formula: C₄₇H₇₃NO₁₇
World Health Organisation international non-proprietary name: amphotericin B
isomeric SMILES: 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]([C@@H](CC[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](O3)C)O)N)O
canonical SMILES: CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(C(CCC(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
defined daily dose: 0.4

Sources (6)

via Wikidata · CC0

~17 min read

Article

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis. It is sometimes used as a drug of last resort for primary amoebic meningoencephalitis. For certain infections it is given with flucytosine. It is typically given intravenously.

Common side effects include a reaction with fever, chills, and headaches soon after the medication is given, as well as kidney problems. Allergic symptoms including anaphylaxis may occur. Other serious side effects include low blood potassium and myocarditis (inflammation of the heart). It appears to be relatively safe in pregnancy. There is a lipid formulation that has a lower risk of side effects. It is in the polyene class of medications and works in part by interfering with the cell membrane of the fungus.