Drug Details

General Information of the Drug (ID: DR5598)
Name
Amphotericin B
Synonyms
amphotericin b; 1397-89-3; Amphotericine B; Amphotericin; Fungizone; Amfotericina B; Amphotericinum B; AMPH-B; Liposomal Amphotericin B; Amphotericin-B; Ambisome; Fungilin; Abelcet; Ampho-Moronal; UNII-7XU7A7DROE; Amphotec; MFCD00877763; 7XU7A7DROE; NCGC00090808-01; Abelecet; Halizon; DSSTox_CID_2601; DSSTox_RID_76653; DSSTox_GSID_22601; (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-beta-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; Amphotericin B trihydrate; C47H73NO17; Amphortericin B; Anfotericine B; Amphotericin b deoxycholate; IAB; NSC 527017; Fungisome; Amfotericina B [INN-Spanish]; Amphotericine B [INN-French]; Amphotericinum B [INN-Latin]; CCRIS 5963; HSDB 3008; Amphotericin B [USP:INN:JAN]; Fungizone (TN); Amphotec (TN); (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-methyltetrahydro-2H-pyran-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; (1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20R,21S,25R,27R,30R,31R,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid; AmBisome (TN); Amp B; CAS-1397-89-3; EINECS 215-742-2; NS 718; BRN 0078342; AI3-26528; Prestwick3_000410; Amphotericin B solubilized; SCHEMBL17973; BSPBio_000340; 5-18-10-00525 (Beilstein Handbook Reference); BIDD:GT0351; BPBio1_000374; NKTR-024; Amphotericin B and cinnamon oil; DTXSID9022601; HMS2096A22; HMS3713A22; Amphotericin B (JP17/USP/INN); HY-B0221; Amphotericin B, Streptomyces nodosus; Tox21_111027; Tox21_202484; Amphotericin B from Streptomyces sp.; BRL-49594; LMPK06000002; s1636; AKOS024464746; ZINC253387843; CCG-220410; DB00681; NCGC00260033-01; (1R-(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-beta-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; 14,39-Dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,2 7,29,31-heptaene-36-carboxylic acid, 33-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E, 25E-27E,29E,31E,33R*,35S*,36R*,37S*))-; AB00513832; C06573; D00203; J10140; AB00513832_02; 397A893; Q412223; 1397-89-3, C47H73NO17; Amphotericin B from Streptomyces sp., ~80% (HPLC), powder; Amphotericin B from Streptomyces sp., BioReagent, suitable for cell culture, ~80% (HPLC); Amphotericin B solubilized, powder, gamma-irradiated, BioXtra, suitable for cell culture; (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; (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-?-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; (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-beta-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-he; (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-beta-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-hept; (1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20R,21S,25R,27R,30R,31R,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-; 23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid; Amphotericin B from Streptomyces sp., Vetec(TM) reagent grade, BioReagent, suitable for cell culture, ~80%; Amphotericin B solution, 250 mug/mL in deionized water, sterile-filtered, BioReagent, suitable for cell culture
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Molecular Type
Small molecule
Disease Fungal infection [ICD-11: 1F29-1F2F] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C47H73NO17
PubChem CID
5280965
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
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
CAS Number
CAS 1397-89-3
TTD Drug ID
D02DWM
DrugBank ID
DB00681
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Acorus calamus      Acorus calamus     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida species Microorganism model Candida species
                    Experimental
                    Result(s)		 The combined effects of asarones and drugs principally recorded substantial synergistic activity (fractional inhibitory concentration index (FICI) <0.5).
          Anidulafungin      Aspergillus nidulans     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Anidulafungin with amphotericin B results in a synergistic effect against C. albicans and C. glabrata biofilms at serum concentrations of the drugs, but showed no interaction against C. tropicalis and C. parapsilosis complex.
          Caspofungin acetate      Glarea lozoyensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model For a xenograft model, mice were rendered diabetic with a single intraperitoneal injection of 210 mg of streptozocin per kg of body weight.
                    Experimental
                    Result(s)		 Combination therapy improved survival compared to that of mice given monotherapy and that of untreated controls (P < 0.05) but did not improve organ clearance.
          Echinocandin      Glarea lozoyensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model C57BL/6N female mice, immunosuppressed with cyclophosphamide, were challenged intravenously via the tail vein with 1.0 * 107 C. glabrata.
                    Experimental
                    Result(s)		 The combination of liposomal amphotericin B with an echinocandin markedly improved the therapeutic outcome in murine C. glabrata systemic infection.
          Ergosterol      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Disruption Cell membrane integrity
                    In-vitro Model Hep 3B2.1-7 CVCL_0326 Childhood hepatocellular carcinoma Homo sapiens
HepJ5 CVCL_RW48 Hepatoblastoma Homo sapiens
                    Experimental
                    Result(s)		 Combination treatment of ergosterol followed by amphotericin B induces necrotic cell death in human hepatocellular carcinoma cells.
          Xanthotoxin      Cullen corylifolium     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida albicans ATCC 22972 Microorganism model Candida albicans
Candida glabrata ATCC 90525 Microorganism model Candida glabrata
Candida guilliermondii ATCC 20216 Microorganism model Candida guilliermondii
Candida krusei ATCC 6258 Microorganism model Candida krusei
Candida parapsilosis ATCC 7330 Microorganism model Candida parapsilosis
Candida tropicalis ATCC 42678 Microorganism model Candida tropicalis
                    Experimental
                    Result(s)		 1/2 MIC dose of xanthorrhizol in combination with 1/2 MIC dose of ketoconazole or 1/2 MIC dose of amphotericin B exhibited growth inhibition of all Candida species tested and reduced viable cells by several logs within 4 h.
Target and Pathway
Target(s) Fungal Cell membrane ergosterol (Fung CME)  Molecule Info  [8]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050724.
Reference 2 Asarones from Acorus calamus in combination with azoles and amphotericin B: a novel synergistic combination to compete against human pathogenic Candida species in vitro. Appl Biochem Biotechnol. 2015 Apr;175(8):3683-95.
Reference 3 In vitro activity of anidulafungin in combination with amphotericin B or voriconazole against biofilms of five Candida species. J Antimicrob Chemother. 2016 Dec;71(12):3449-3452.
Reference 4 Combination therapy with amphotericin B lipid complex and caspofungin acetate of disseminated zygomycosis in diabetic ketoacidotic mice. Antimicrob Agents Chemother. 2005 Feb;49(2):830-2.
Reference 5 Treatment of Candida glabrata infection in immunosuppressed mice by using a combination of liposomal amphotericin B with caspofungin or micafungin. Antimicrob Agents Chemother. 2005 Dec;49(12):4895-902.
Reference 6 Combination treatment of ergosterol followed by amphotericin B induces necrotic cell death in human hepatocellular carcinoma cells. Oncotarget. 2017 Aug 16;8(42):72727-72738.
Reference 7 Synergistic anticandidal activity of xanthorrhizol in combination with ketoconazole or amphotericin B. FEMS Yeast Res. 2009 Dec;9(8):1302-11.
Reference 8 Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels. Biochim Biophys Acta. 2002 Dec 23;1567(1-2):63-78.
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