Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2174)
Drug Name
Gentamicin
Synonyms
Garamycin; Garamycin (TN); Garamycin Otic Solution; Garasol; Genoptic Liquifilm; Genoptic S.O.P.; Gentacidin; Gentacycol; Gentafair; Gentak; Gentamar; Gentamcin Sulfate; Gentamicin (BAN); Gentamicin (TN); Gentamicin C1; Gentamicin sulphate sterile; Gentamicina; Gentamicina [INN-Spanish]; Gentamicine; Gentamicine [INN-French]; Gentamicins; Gentamicinum; Gentamycin-creme [German]; Gentamycinum; Gentavet; Gentocin; Jenamicin; Ocu-Mycin; Refobacin; Refobacin TM; Alcomicin; Apogen; Bristagen; Cidomycin; G-Mycin; G-Myticin; GENTAMYCIN; Spectro-Genta; U-Gencin; Uromycine; (1R,2S,3S,4R,6S)-4,6-diamino-3-[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyloxy]-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-beta-L-lyxo-heptopyranoside; (1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl (6x)-2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-alpha-D-erythro-heptopyranoside; (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; 4,6-diamino-3-{[3-deoxy-4-c-methyl-3-(methylamino)pentopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)heptopyranoside; Gentamicinum [INN-Latin];Gentamycin-creme; O-2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-alpha-D-ribo-heptopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine
Indication Acute upper respiratory infection [ICD11: CA07] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 477.6 Topological Polar Surface Area 200
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
3467
PubChem SID
4652583 ; 8152203 ; 29222600 ; 46506523 ; 49972189 ; 53787495 ; 57321817 ; 74460187 ; 92712501 ; 96024706 ; 103135455 ; 104303599 ; 117535962 ; 124766025 ; 126407615 ; 126625531 ; 126661266 ; 126691181 ; 127340104 ; 127340105 ; 127340106 ; 134337440 ; 134980500 ; 135650301 ; 137239444 ; 142147875 ; 152100630 ; 160964140 ; 196105377 ; 223658860 ; 226847630 ; 242084438 ; 246167234 ; 250134950
ChEBI ID
ChEBI:17833
CAS Number
1403-66-3
TTD Drug ID
D0L9UU
Formula
C21H43N5O7
Canonical SMILES
CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
InChI
1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
InChIKey
CEAZRRDELHUEMR-UHFFFAOYSA-N
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aminoglycoside 6'-N-acetyltransferase (aacA) DME2057 Klebsiella pneumoniae
C5MQW3_KLEPO
2.3.1.82
[2]
Aminoglycoside O-phosphotransferase (aphA6) DME1068 Acinetobacter baumannii
KKA6_ACIBA
2.7.1.95
[3]
Aminoglycoside phosphotransferase (aph-Ib) DME1090 Campylobacter jejuni
A0A075C7U3_CAMJU
2.7.1.190
[4]
Endoglucanase Y (EGY) DME1641 Lactobacillus gasseri
A0A256VAC0_LACRE
3.2.1.136
[5]
Endoglucanase Y (EGY) DME1642 Lactobacillus johnsonii
A0A256VAC0_LACRE
3.2.1.136
[5]
Kanamycin/gentamycin-resistance enzyme (aacA) DME1091 Campylobacter coli
J3S7E2_CAMCO
2.7.1.190
[4]
Unclear metabolic mechanism (DME-unclear) DME1279 Methanobrevibacter oralis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1280 Methanobrevibacter smithii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1281 Methanomassiliicoccus luminyensis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1282 Methanosphaera stadtmanae Not Available Not Available [6]
⏷ Show the Full List of 10  DME(s)
References
1 Gentamicin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Detection of multidrug-resistant Enterobacteriaceae isolated from river waters flowing to the Guanabara Bay and from clinical samples of hospitals in Rio de Janeiro, Brazil. Biomedica. 2019 May 1;39(s1):135-149.
3 Relationship between antimicrobial resistance and aminoglycoside-modifying enzyme gene expressions in Acinetobacter baumannii. Chin Med J (Engl). 2005 Jan 20;118(2):141-5.
4 Cloning and expression of novel aminoglycoside phosphotransferase genes from Campylobacter and their role in the resistance to six aminoglycosides. Antimicrob Agents Chemother. 2017 Dec 21;62(1). pii: e01682-17.
5 Expression of Clostridium thermocellum endoglucanase gene in Lactobacillus gasseri and Lactobacillus johnsonii and characterization of the genetically modified probiotic lactobacilli. Curr Microbiol. 2000 Apr;40(4):257-63.
6 The antimicrobial resistance pattern of cultured human methanogens reflects the unique phylogenetic position of archaea. J Antimicrob Chemother. 2011 Sep;66(9):2038-44.

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