(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-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

• ChemBase ID: 563
• Molecular Formular: C47H73NO17
• Molecular Mass: 924.07902
• Monoisotopic Mass: 923.48784988
• SMILES: [C@H]12[C@@H]([C@H](C[C@](O1)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]([C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C2)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O)C)O)C)C)O)O)O)O)O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
• 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
• InChIKey: APKFDSVGJQXUKY-INPOYWNPSA-N

NAMES AND DATABASE IDS

Names

• 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-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
• IUPAC Traditional name: amphotericin B
• Brand Name: ABLC; Abelcet; AmB; AmBisome; Ampho-Moronal; Amphocin; Amphotec; Amphotericin; Amphozone; Fungilin; Fungisone; Fungizone; Fungizone Intravenous; HSDB 3008 IAB; Halizon; IAB; LNS-AmB; Mysteclin-F; Tegopen; SinuNase
• Synonyms: AMPH-B; Amphortericin B; Amphotericine B; Liposomal Amphotericin B; amphotericin B; Amphotericin B; Amphomoronal; Amphozone; Fungilin; Fungisone; Fungizone

Database IDs

• CAS Number: 1397-89-3
• EC Number: 215-742-2
• PubChem SID: 46505473; 160964026
• PubChem CID: 14956; 5280965
• CHEBI ID: 2682
• ATC CODE: A01AB04; A07AA07; G01AA03; J02AA01
• CHEMBL: 267345
• Chemspider ID: 10237579
• DrugBank ID: DB00681
• KEGG ID: D00203
• Wikipedia Title: Amphotericin_B

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5797393
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -2.3028812
• LogD (pH = 7.4): -2.3064086
• Log P: -2.3001616
• Molar Refractivity: 244.6705 cm^3
• Polarizability: 94.662575 Å^3
• Polar Surface Area: 319.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.66
• LOG S: -4.05
• Solubility (Water): 8.19e-02 g/l

PROPERTIES

Physical Property

• Solubility: 750 mg/L
• Melting Point: >170°C
• Hydrophobicity(logP): 0.8

Safety Information

• Storage Condition: 2-8°C
• RTECS: BU2625000

Pharmacology Properties

• Admin Routes: slow i.v.-infusion only
• Bioavailability: 100% (IV)
• Excretion: 40% found in urine after single cumulated over several days ; biliar excretion also important
• Half Life: initial phase : 24 hours, ; second phase : approx. 15 days
• Metabolism: renal
• Legal Status: Rx-only, hospitalization recommended.
• Pregnancy Category: B (US)

DETAILS

MP Biomedicals - 02195043

An Antifungal agent produced by Streptomyces species.

DrugBank - DB00681

• Drug Groups: approved; investigational
• Description: 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.
• Indication: Used to treat potentially life threatening fungal infections.
• 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.
• Toxicity: Oral, rat: LD₅₀ = >5 gm/kg. Amphotericin B overdoses can result in cardio-respiratory arrest.
• Affected Organisms: Various Fungus Species
• Biotransformation: Exclusively renal
• Absorption: Bioavailability is 100% for intravenous infusion.
• Half Life: An elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.
• Protein Binding: Highly bound (>90%) to plasma proteins.
• Clearance: * 39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]; * 17 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day 3-20 days later]; * 51 +/- 44 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day at Day 1]; * 22 +/- 15 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day 3-20 days later]; * 21 +/- 14 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day at Day 1]; * 11 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day 3-20 days later]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• R.C. Pandey, K.L. Rinehart, J. Antibiot., 29: 1035, (1976)
• Mechlinski, et al., Tetrahedron Letters, 3873, (1970).