Drug (ID: DG00377) and It's Reported Resistant Information
Name
Butirosina
Synonyms
Butirosina; Ambutyrosin; Butirosin; 12772-35-9; (2R)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-hydroxycyclohexyl]-2-hydroxybutanamide; Butirosin [INN]; Butirosine; Butirosinum; Butirosine [INN-French]; Butirosinum [INN-Latin]; Butirosina [INN-Spanish]; DTXSID60925967; 4-Amino-N-{5-amino-4-[(2,6-diamino-2,6-dideoxyhexopyranosyl)oxy]-2-hydroxy-3-(pentofuranosyloxy)cyclohexyl}-2-hydroxybutanimidic acid
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Structure
Drug Resistance Disease(s)
Disease(s) with Clinically Reported Resistance for This Drug (3 diseases)
Bacillus infection [ICD-11: 1C4Y]
[1]
Bacterial infection [ICD-11: 1A00-1C4Z]
[2]
Pneumonia [ICD-11: CA40]
[3]
Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
Bacterial infection [ICD-11: 1A00-1C4Z]
[4]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
C21H41N5O12
IsoSMILES
C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@@H](CCN)O)O)O[C@@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
InChI
1S/C21H41N5O12/c22-2-1-8(28)19(34)26-7-3-6(24)17(37-20-11(25)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34)/t6-,7+,8+,9+,10+,11+,12-,13+,14+,15+,16+,17+,18+,20+,21+/m0/s1
InChIKey
XEQLFNPSYWZPOW-NUOYRARPSA-N
PubChem CID
72393
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
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Bacterial infection [ICD-11: 1A00-1C4Z]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: Aminoglycoside 3'-phosphotransferase (A3AP) [2]
Molecule Alteration Expression
Inherence
Resistant Disease Stenotrophomonas maltophilia infection [ICD-11: 1A00-1C4Z]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli 668369
Experiment for
Molecule Alteration
PCR amplification assay
Experiment for
Drug Resistance
MIC assay
Mechanism Description Aph(3')-IIc significantly increases MICs of kanamycin, neomycin, butirosin, and paromomycin when expressed in Escherichia coli. Disruption of aph(3')-IIc results in decreased MICs of these drugs.
Key Molecule: Aminoglycoside 3'-phosphotransferase (A3AP) [4]
Molecule Alteration Expression
Inherence
Resistant Disease Streptococcus faecalis infection [ICD-11: 1A00-1C4Z]
Experimental Note Discovered Using In-vivo Testing Model
In Vitro Model Escherichia coli strain JM 10 562
Escherichia coli strain k802 562
Streptococcus faecnlis strain JHZ-15 1351
Experiment for
Molecule Alteration
Chemical sequencing method assay
Experiment for
Drug Resistance
Disc sensitivity tests assay
Mechanism Description Strain BM2182 was examined for aminoglyco- side-modifying activities. That kanamycin B was modified and tobramycin (3'-deoxykanamycin B) was not, indicates that the 3'-hydroxyl group is the site of phosphorylation. That butirosin, lividomycin A, and amikacin were phosphorylated indicates that the enzyme is APH-III.
Key Molecule: Aminoglycoside 3'-phosphotransferase (A3AP) [3]
Molecule Alteration Expression
Inherence
Resistant Disease Serratia marcescens infection [ICD-11: 1A00-1C4Z]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli C41(DE3) 469008
Escherichia coli DH5alpha 668369
Escherichia coli Ecmrs144 562
Escherichia coli Ecmrs150 562
Escherichia coli Ecmrs151 562
Escherichia coli strain 83-125 562
Escherichia coli strain 83-75 562
Escherichia coli strain JM83 562
Escherichia coli strain JM83(pRPG101) 562
Escherichia coli strain M8820Mu 562
Escherichia coli strain MC1065 562
Escherichia coli strain MC1065(pRPG101) 562
Escherichia coli strain POII1681 562
Escherichia coli strain PRC930(pAO43::Tn9O3) 562
Klebsiella pneumoniae strains 573
Serratia marcescens strains 615
Experiment for
Molecule Alteration
Restriction enzyme treating assay
Experiment for
Drug Resistance
Cation-supplemented Mueller-Hinton broth assay; agar dilution with MH agar assay
Mechanism Description Clinical isolates of Klebsiella pneumoniae and Serratia marcescens at a hospital that had used amikacin as its principal aminoglycoside for the preceding 42 months demonstrated high-level resistance to amikacin (greater than or equal to 256 micrograms/ml), kanamycin (greater than or equal to 256 micrograms/ml), gentamicin (greater than or equal to 64 micrograms/ml), netilmicin (64 micrograms/ml), and tobramycin (greater than or equal to 16 micrograms/ml). The clinical isolates and transformants produced a novel 3'-phosphotransferase, APH(3'), that modified amikacin and kanamycin in vitro.
Bacillus infection [ICD-11: 1C4Y]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: Aminoglycoside 3'-phosphotransferase (A3AP) [1]
Molecule Alteration Expression
Inherence
Resistant Disease Infection by Bacillus circulans [ICD-11: 1C4Y.12]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli HB101 634468
Escherichia coli strain JM103 83333
Bacillus circulans strain 1397
Streptomyces lividans strain 66 1200984
Streptomyces lividans strain M180 1916
Experiment for
Molecule Alteration
DNA sequencing assay
Experiment for
Drug Resistance
Semi-quantitative phosphocellulose-paper binding assay method assay
Mechanism Description We have elucidated the full nucleotide sequence of the aminoglycoside phosphotransferase (APH) gene from Bacillus circulans, which produces the aminoglycoside antibiotic butirosin.
ICD-12: Respiratory system diseases
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Pneumonia [ICD-11: CA40]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: Aminoglycoside 3'-phosphotransferase (A3AP) [3]
Molecule Alteration Expression
Inherence
Resistant Disease Klebsiella pneumoniae infection [ICD-11: CA40.1]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli C41(DE3) 469008
Escherichia coli DH5alpha 668369
Escherichia coli Ecmrs144 562
Escherichia coli Ecmrs150 562
Escherichia coli Ecmrs151 562
Escherichia coli strain 83-125 562
Escherichia coli strain 83-75 562
Escherichia coli strain JM83 562
Escherichia coli strain JM83(pRPG101) 562
Escherichia coli strain M8820Mu 562
Escherichia coli strain MC1065 562
Escherichia coli strain MC1065(pRPG101) 562
Escherichia coli strain POII1681 562
Escherichia coli strain PRC930(pAO43::Tn9O3) 562
Klebsiella pneumoniae strains 573
Serratia marcescens strains 615
Experiment for
Molecule Alteration
Restriction enzyme treating assay
Experiment for
Drug Resistance
Cation-supplemented Mueller-Hinton broth assay; agar dilution with MH agar assay
Mechanism Description Clinical isolates of Klebsiella pneumoniae and Serratia marcescens at a hospital that had used amikacin as its principal aminoglycoside for the preceding 42 months demonstrated high-level resistance to amikacin (greater than or equal to 256 micrograms/ml), kanamycin (greater than or equal to 256 micrograms/ml), gentamicin (greater than or equal to 64 micrograms/ml), netilmicin (64 micrograms/ml), and tobramycin (greater than or equal to 16 micrograms/ml). The clinical isolates and transformants produced a novel 3'-phosphotransferase, APH(3'), that modified amikacin and kanamycin in vitro.
References
Ref 1 Sequence and interspecies transfer of an aminoglycoside phosphotransferase gene (APH) of Bacillus circulans. Self-defence mechanism in antibiotic-producing organisms. Biochem J. 1986 Jan 15;233(2):383-93. doi: 10.1042/bj2330383.
Ref 2 Aph(3')-IIc, an aminoglycoside resistance determinant from Stenotrophomonas maltophilia. Antimicrob Agents Chemother. 2007 Jan;51(1):359-60. doi: 10.1128/AAC.00795-06. Epub 2006 Nov 6.
Ref 3 Isolation, characterization, and cloning of a plasmid-borne gene encoding a phosphotransferase that confers high-level amikacin resistance in enteric bacilli. Antimicrob Agents Chemother. 1988 Sep;32(9):1379-84. doi: 10.1128/AAC.32.9.1379.
Ref 4 Nucleotide sequence of the Streptococcus faecalis plasmid gene encoding the 3'5"-aminoglycoside phosphotransferase type III. Gene. 1983 Sep;23(3):331-41. doi: 10.1016/0378-1119(83)90022-7.

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