Drug Information

Drug (ID: DG00424) and It's Reported Resistant Information

• Name: Pentisomicin
• Synonyms: Pentisomicin; 5-Episisomicin; Sch 22591; UNII-L5BS6WSR0E; 55870-64-9; L5BS6WSR0E; SCH-22591; Mutamicin 6; Mutamycin 6; 5-epi-Sisomicin; (2R,3R,4R,5R)-2-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; Pentisomicina; Pentisomicine; Pentisomicinum; Pentisomicin [USAN:INN]; Pentisomicine [INN-French]; Pentisomicinum [INN-Latin]; Pentisomicina [INN-Spanish]; Pentisomicin (USAN/INN); O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->1)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1->3))-4,6-diamino-4,5,6-trideoxy-D-myo-inositol; SCHEMBL380284; CHEMBL2105403; DTXSID7046887; D-myo-Inositol, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->1)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1->3))-4,6-diamino-4,5,6-trideoxy-; D-myo-Inositol, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-1)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-3))-4,6-diamino-4,5,6-trideoxy-; O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-1)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-3))-4,6-diamino-4,5,6-trideoxy-D-myo-inositol; D05425; Q27282733
• Drug Resistance Disease(s):
  Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
  Escherichia coli intestinal infection [ICD-11: 1A03]; [1]
• Formula: C19H37N5O7
• IsoSMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
• InChI: 1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12-,13-,14-,15+,16-,17-,18-,19+/m1/s1
• InChIKey: URWAJWIAIPFPJE-VHLNBGGKSA-N
• PubChem CID: 65453

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

Escherichia coli intestinal infection [ICD-11: 1A03]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Drug Inactivation by Structure Modification (DISM)

Key Molecule: Aminoglycoside 2'-N-acetyltransferase (A2NA) [1]

• Molecule Alteration: Expression; Acquired
• Resistant Disease: Escherichia coli infection [ICD-11: 1A03.0]
• Experimental Note: Discovered Using In-vivo Testing Model
• In Vitro Model: Escherichia coli strain DH5a; 668369
• In Vitro Model: Escherichia coli strain XLI-Blue; 562
• In Vitro Model: Providencia stuartii strain PR50; 588
• In Vitro Model: Providencia stuartii strain SCH75082831A; 588
• Experiment for Molecule Alteration: DNA sequencing assay
• Experiment for Drug Resistance: Microdilution plates assay
• Mechanism Description: E.coli DH5alpha/pR 1000 demonstrated an AAC(2')-Ia resistance profile,with gentamicin, tobramycin, netilmicin, and 6'-Nethylnetilmicin MICs increased over those seen with E.coli DH5alpha. In addition, E.coli DH5alpha/pR 1000 did not show an elevated 2'-N-ethylnetilmicin MIC (MIC was 0.25ug/ml). Therefore, pR1000 encoded an enzyme capable of acetylating 6'-N-ethylnetilmicin but not 2'-N-ethylnetilmicin, suggesting 2'-N-acetyltransferase activity. DH5alpha/pSCH4500, which contains a subcloned 1.3-kb fragment, also demonstrated an AAC(2')-Ia resistance profile.

References

• Ref 1: Characterization and transcriptional regulation of the 2'-N-acetyltransferase gene from Providencia stuartii. J Bacteriol. 1993 Oct;175(20):6492-8. doi: 10.1128/jb.175.20.6492-6498.1993.