Amphotericin

Amphotericin B

Clinical data
Trade names	Fungizone, Mysteclin-F, others
AHFS/Drugs.com	Monograph
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	usually I.V. (slow infusion only)
ATC code	A01AB04 (WHO) A07AA07 (WHO), G01AA03 (WHO), J02AA01 (WHO)
Legal status
Legal status	Rx-only, hospitalization recommended
Pharmacokinetic data
Bioavailability	100% (IV)
Metabolism	kidney
Biological half-life	initial phase : 24 hours, second phase : approx. 15 days
Excretion	40% found in urine after single cumulated over several days biliar excretion 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	1397-89-3 Y
PubChem CID	14956
DrugBank	DB00681 Y
ChemSpider	10237579 Y
KEGG	D00203 Y
ChEBI	CHEBI:2682 Y
ChEMBL	CHEMBL267345 Y
NIAID ChemDB	000096
ECHA InfoCard	100.014.311
Chemical and physical data
Formula	C47H73NO17
Molar mass	924.091
3D model (Jmol)	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 Y Key:APKFDSVGJQXUKY-INPOYWNPSA-N Y

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include aspergillosis, blastomycosis, candida, coccidioidomycosis, and . For certain infections it is given with flucytosine. It is typically given by injection into a vein

Common side effects include a reaction with fever, chills, and headaches soon after the medication is give, as well as kidney problems. Allergic symptoms including anaphylaxis may occur. Other serious side effects include low blood potassium and 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 originally made from Streptomyces nodosus in 1955. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The cost in the developing world of a course of treatment as of 2010 is between 162 and 229 USD.