Drug Information
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
Click to Show/Hide
|
||||
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 |
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
Bacterial infection [ICD-11: 1A00-1C4Z]
Drug Resistance Data Categorized by Their Corresponding Mechanisms | ||||
Drug Inactivation by Structure Modification (DISM) | ||||
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]
Drug Resistance Data Categorized by Their Corresponding Mechanisms | ||||
Drug Inactivation by Structure Modification (DISM) | ||||
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
Pneumonia [ICD-11: CA40]
Drug Resistance Data Categorized by Their Corresponding Mechanisms | ||||
Drug Inactivation by Structure Modification (DISM) | ||||
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
If you find any error in data or bug in web service, please kindly report it to Dr. Sun and Dr. Zhang.