Amphotericin B

Amphotericin B
Clinical data
Trade names	Fungizone, Mysteclin-F, AmBisome and other
AHFS/Drugs.com	Monograph
MedlinePlus	a682643
License data	US DailyMed: Amphotericin_B;
Pregnancy; category	AU: B2;
Routes of; administration	Intravenous infusion
ATC code	A01AB04 (WHO) A07AA07 (WHO), G01AA03 (WHO), J02AA01 (WHO);
Legal status
Legal status	US: WARNING Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (IV)
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;
Identifiers
	IUPAC name (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- β-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;
CAS Number	12633-72-6 ;
PubChem CID	14956;
DrugBank	DB00681 ;
ChemSpider	10237579 ;
UNII	7XU7A7DROE;
KEGG	D00203 ;
ChEBI	CHEBI:2682 ;
ChEMBL	ChEMBL267345 ;
NIAID ChemDB	000096;
CompTox Dashboard (EPA)	DTXSID9022601 ;
ECHA InfoCard	100.014.311
Chemical and physical data
Formula	C47H73NO17
Molar mass	924.091 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	170 °C (338 °F)
	SMILES O=C(O)[C@@H]3[C@@H](O)C[C@@]2(O)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)C=CC=CC=CC=CC=CC=CC=C[C@H](O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O)C[C@@H]3O2;
	InChI InChI=1S/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)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1 ; Key:APKFDSVGJQXUKY-INPOYWNPSA-N ;
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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. 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.

Amphotericin B was isolated from Streptomyces nodosus in 1955 at the Squibb Institute for Medical Research from cultures isolated from the streptomycete obtained from the river bed of Orinoco in that region of Venezuela and came into medical use in 1958. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.