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

General Information of Drug (ID: DR2167)
Drug Name
Amikacin
Synonyms
Amiglyde-V; Amiglyde-V (TN); Amikacin & Tumor Necrosis Factor; Amikacin (USP); Amikacin (USP/INN); Amikacin Base; Amikacin Dihydrate; Amikacin [USAN:BAN:INN]; Amikacina; Amikacina [INN-Spanish]; Amikacine; Amikacine [INN-French]; Amikacinum; Amikacinum [INN-Latin]; Amikavet; Amikin; Amikin(Disulfate); AMIKACIN SULFATE; ANTIBIOTIC BB-K8; Amicacin; Antibiotic BB-K 8; Arikace; BB-K 8; Briclin; Kaminax; Lukadin; Mikavir; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-4-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide; (2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide; 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A; BB-K8; O-3-Amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptamine; O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-6))-N(sup 3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine
Indication Pseudomonas infection [ICD11: 1G40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 585.6 Topological Polar Surface Area 332
Heavy Atom Count 40 Rotatable Bond Count 10
Hydrogen Bond Donor Count 13 Hydrogen Bond Acceptor Count 17
Cross-matching ID
PubChem CID
37768
PubChem SID
9038 ; 602892 ; 7978685 ; 8140488 ; 8175188 ; 11533325 ; 14886882 ; 17396714 ; 26057066 ; 29215141 ; 34679028 ; 46506386 ; 47734200 ; 47734201 ; 48182834 ; 48415546 ; 49699077 ; 50047827 ; 50105695 ; 56314316 ; 57312091 ; 57691603 ; 79044930 ; 96099940 ; 104234226 ; 104327437 ; 117570306 ; 123080686 ; 124766001 ; 125263960 ; 127284329 ; 127284330 ; 127284331 ; 127284332 ; 131665903 ; 134337696 ; 134999046 ; 135988791 ; 137003403 ; 144204752 ; 160963825 ; 162177716 ; 164806376 ; 166265868 ; 170465345 ; 175268115 ; 176267073 ; 177013106 ; 179150401 ; 210279669
ChEBI ID
ChEBI:2637
CAS Number
37517-28-5
TTD Drug ID
D0Y3MO
Formula
C22H43N5O13
Canonical SMILES
C1C(C(C(C(C1NC(=O)C(CCN)O)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)O)N
InChI
1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
InChIKey
LKCWBDHBTVXHDL-RMDFUYIESA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Amikacin M1 PDM007079 N. A. Hydrolysis - Glycoside hydrolysis 1 Human
Amikacin M10 PDM007088 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M11 PDM007089 N. A. Conjugation - Sulfation of primary alcohol 1 Human
Amikacin M2 PDM007080
413054
Hydrolysis - Glycoside hydrolysis 1 Human
Amikacin M3 PDM007081 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M4 PDM007082 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M5 PDM007083 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M6 PDM007084 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M7 PDM007085 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M8 PDM007086 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Amikacin M9 PDM007087 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aminoglycoside O-phosphotransferase (aphA6) DME1068 Acinetobacter baumannii
KKA6_ACIBA
2.7.1.95
[2]
Endoglucanase A (EGA) DME1182 Lactobacillus gasseri
A0A660DUI5_9LACO
3.2.1.4
[3]
Endoglucanase Y (EGY) DME1642 Lactobacillus johnsonii
A0A256VAC0_LACRE
3.2.1.136
[3]
References
1 Amikacin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Relationship between antimicrobial resistance and aminoglycoside-modifying enzyme gene expressions in Acinetobacter baumannii. Chin Med J (Engl). 2005 Jan 20;118(2):141-5.
3 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.

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