Drug Information

Drug (ID: DG00572) and It's Reported Resistant Information

• Name: Amphotericin B
• Synonyms: Amphotericin b; 1397-89-3; Amphotericin; Amphotericine B; Fungizone; Amfotericina B; Amphotericinum B; AMPH-B; Liposomal Amphotericin B; Amphotericin-B; Abelcet; Ambisome; Fungilin; Ampho-Moronal; UNII-7XU7A7DROE; Amphotec; Halizon; MFCD00877763; 7XU7A7DROE; NSC 527017; NCGC00090808-01; Abelecet; C47H73NO17; 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; Amphortericin B; Anfotericine B; (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; IAB; 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); (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 (85%); 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.; 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,; (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; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,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-carbo; (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
• Indication:
  In total 3 Indication(s)
  Fungal infection [ICD-11: 1F29-1F2F]; Approved; [1]
  Fungal infection [ICD-11: 1F29-1F2F]; Approved; [1]
  Mycoses [ICD-11: MB47]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (1 diseases)
  Leishmaniasis [ICD-11: 1F54]; [2]
  Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
  Candidosis [ICD-11: 1F23]; [1]
• Target: Fungal Cell membrane ergosterol (Fung CME); NOUNIPROTAC; [1]
• Formula: C47H73NO17
• IsoSMILES: C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](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
• PubChem CID: 5280965
• TTD Drug ID: D02DWM
• VARIDT ID: DR01468
• INTEDE ID: DR2632
• DrugBank ID: DB00681

Type(s) of Resistant Mechanism of This Drug

  UAPP: Unusual Activation of Pro-survival Pathway

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-01: Infectious/parasitic diseases

Candidosis [ICD-11: 1F23]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Unusual Activation of Pro-survival Pathway (UAPP)

Key Molecule: Heat shock protein HSP 90 (HSP90 ) [1]

• Molecule Alteration: Expression; Up-regulation
• Resistant Disease: Recurrent oropharyngeal candidiasis [ICD-11: 1F23.6]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Candida albicans strain; 5476
• Mechanism Description: The fitness and survival of amphotericin B-resistant Candida isolates are critically dependent upon Hsp90 expression and function. As a consequence, pharmacological inhibition of Hsp90 in resistant C. albicans or C. tropicalis strains abolished amphotericin B resistance.

Key Molecule: Lanosterol 14-alpha demethylase (ERG11) [1]

• Molecule Alteration: Missense mutation; p.A114S
• Resistant Disease: Recurrent oropharyngeal candidiasis [ICD-11: 1F23.6]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Candida albicans strain; 5476
• Mechanism Description: In C. albicans, reduced amphotericin B susceptibility can occur through mutations in several ergosterol biosynthesis enzymes, including ERG2,ERG3, ERG5, ERG11.

Key Molecule: Delta(7)-sterol 5(6)-desaturase ERG3 (ERG3) [1]

• Molecule Alteration: Mutation; p.H243N+p.T330A+p.D147G
• Resistant Disease: Recurrent oropharyngeal candidiasis [ICD-11: 1F23.6]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Candida albicans strain; 5476
• Mechanism Description: In C. albicans, reduced amphotericin B susceptibility can occur through mutations in several ergosterol biosynthesis enzymes, including ERG2,ERG3, ERG5, ERG11.

Key Molecule: C-22 sterol desaturase ERG5 (ERG5) [1]

• Molecule Alteration: SNP; p.CA108
• Resistant Disease: Recurrent oropharyngeal candidiasis [ICD-11: 1F23.6]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Candida albicans strain; 5476
• Mechanism Description: In C. albicans, reduced amphotericin B susceptibility can occur through mutations in several ergosterol biosynthesis enzymes, including ERG2,ERG3, ERG5, ERG11.

References

• Ref 1: Antifungal Drug Resistance: Molecular Mechanisms in Candida albicans and Beyond .Chem Rev. 2021 Mar 24;121(6):3390-3411. doi: 10.1021/acs.chemrev.0c00199. Epub 2020 May 22. 10.1021/acs.chemrev.0c00199
• Ref 2: Drug resistance in visceral leishmaniasis .J Biomed Biotechnol. 2010;2010:617521. doi: 10.1155/2010/617521. Epub 2009 Nov 1. 10.1155/2010/617521