Drug Information

Drug (ID: DG00455) and It's Reported Resistant Information

• Name: Lankamycin
• Synonyms: Lankamycin; UNII-68DQY2P51C; 30042-37-6; 68DQY2P51C; Kujimycin B; Lankavamycin; (2R,3S,4S,5R,7S,9S,10S,11R,12S,13R)-12-(((2R,4R,5R,6S)-5-acetoxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-hydroxy-10-(((2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-((2S,3S)-3-hydroxybutan-2-yl)-3,5,7,9,11,13-hexamethyl-6,14-dioxooxacyclotetradecan-4-yl acetate; Antibiotic A-20338-N2; A-20338-N2; CHEBI:80017; Q27149163; [(2R,3S,4S,5R,7S,9S,10S,11R,12S,13R)-12-[(2R,4R,5R,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-hydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-10-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-6,14-dioxo-oxacyclotetradec-4-yl] acetate
• Drug Resistance Disease(s):
  Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
  Actinomycetoma [ICD-11: 1C43]; [1]
• Formula: C42H72O16
• IsoSMILES: C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@](C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]3C[C@@]([C@@H]([C@@H](O3)C)OC(=O)C)(C)OC)C)[C@@H](C)[C@H](C)O)C)OC(=O)C)C)(C)O)C)O)OC
• InChI: 1S/C42H72O16/c1-19-17-41(12,49)37(47)24(6)35(54-28(10)44)23(5)34(21(3)26(8)43)57-39(48)25(7)36(22(4)33(19)58-40-32(46)30(50-14)16-20(2)52-40)56-31-18-42(13,51-15)38(27(9)53-31)55-29(11)45/h19-27,30-36,38,40,43,46,49H,16-18H2,1-15H3/t19-,20+,21-,22+,23-,24+,25+,26-,27-,30-,31-,32+,33-,34+,35-,36-,38+,40-,41-,42+/m0/s1
• InChIKey: JQMACDQCTNFQMM-QAOHEUSVSA-N
• PubChem CID: 15560071

Type(s) of Resistant Mechanism of This Drug

  DISM: Drug Inactivation by Structure Modification

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-01: Infectious/parasitic diseases

Actinomycetoma [ICD-11: 1C43]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Drug Inactivation by Structure Modification (DISM)

Key Molecule: srmA open reading frame gimA (GIMA) [1]

• Molecule Alteration: Expression; Inherence
• Resistant Disease: Streptomyces ambbyaciens infection [ICD-11: 1C43.0]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Escherichia coli; 668369
• In Vitro Model: Escherichia coli strain S17.1; 1227813
• In Vitro Model: Micrococcus luteus strain Cgr; 1270
• In Vitro Model: Micrococcus luteus strain DSM1790; 1270
• In Vitro Model: Streptomyces ambofaciens strain ATCC 23877; 278992
• In Vitro Model: Streptomyces ambofaciens strain OS41.99; 1954
• In Vitro Model: Streptomyces ambofaciens strain OS41.99NP; 1954
• In Vitro Model: Streptomyces ambofaciens strain OS81; 1954
• In Vitro Model: Streptomyces lividans strain OS456; 1916
• Experiment for Molecule Alteration: DNA sequencing assay
• Experiment for Drug Resistance: Observation of growth inhibition zones assay
• Mechanism Description: With UDP-[14C]glucose as the cofactor, crude S30 extracts from OS456(pOS41.90) were tested on various macrolides. Among those, chalcomycin was the most active substrate. Methymycin, tylosin, pikromycin, and rosaramicin were four of the best substrates. Oleandomycin, josamycin, and carbomycin were glycosylated to a lesser extent. Macrolides that were found to be as poor substrates of GimA as lankamycin were erythromycin and angolamycin. Spiramycin was also a very poor substrate.

References

• Ref 1: Characterization of a glycosyl transferase inactivating macrolides, encoded by gimA from Streptomyces ambofaciens. Antimicrob Agents Chemother. 1998 Oct;42(10):2612-9. doi: 10.1128/AAC.42.10.2612.