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;
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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