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

General Information of Drug (ID: DR0130)
Drug Name
Arbekacin
Synonyms
Arbekacin; Arbekacin (INN); Arbekacin [INN]; Arbekacina; Arbekacina [Spanish]; Arbekacine; Arbekacine [French]; Arbekacinum; Arbekacinum [Latin]; Haberacin; NPC-14; 51025-85-5; CHEBI:37922; G7V6SLI20L; O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-6))-N'-((2S)-4-amino-2-hydroxybutyryl)-2-deoxy-L-streptamine; UNII-G7V6SLI20L
Indication Pneumocystis pneumonia [ICD11: CA40] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 552.6 Topological Polar Surface Area 297
Heavy Atom Count 38 Rotatable Bond Count 10
Hydrogen Bond Donor Count 11 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
68682
PubChem SID
8192273 ; 12012746 ; 15012131 ; 24434905 ; 43125217 ; 50047867 ; 50112783 ; 50764410 ; 51091793 ; 57317006 ; 99443250 ; 103027235 ; 103069356 ; 103080181 ; 103508341 ; 104342778 ; 117570307 ; 124766131 ; 126671210 ; 134223846 ; 135027886 ; 136290748 ; 137248758 ; 164788050 ; 178103917 ; 179150519 ; 184544961 ; 198976904 ; 226408426 ; 241090282 ; 252358771 ; 252671973
ChEBI ID
ChEBI:37922
CAS Number
51025-85-5
TTD Drug ID
D07JPC
Formula
C22H44N6O10
Canonical SMILES
C1CC(C(OC1CN)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CO)O)N)O)NC(=O)C(CCN)O)N)N
InChI
1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
InChIKey
MKKYBZZTJQGVCD-XTCKQBCOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2'-N-acetyl ABK DM001575 N. A. Conjugation - N-Acetylation 1 [3]
3"-N-Acetylarbekacin DM001577
10257909
Conjugation - 3"-N-Acetylation 1 [2]
2',6'-di-N-acetyl ABK DM001576 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000282 Arbekacin 2'-N-acetyl ABK Conjugation - N-Acetylation aac [3]
MR000283 Arbekacin 3"-N-Acetylarbekacin Conjugation - 3"-N-Acetylation Unclear [2]
MR000281 2'-N-acetyl ABK 2',6'-di-N-acetyl ABK Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[2]
References
1 Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1994;20(6):233-9.
2 The novel enzymatic 3''-N-acetylation of arbekacin by an aminoglycoside 3-N-acetyltransferase of Streptomyces origin and the resulting activity. J Antibiot (Tokyo). 1998 Aug;51(8):735-42.
3 Enzymatic 2'-N-acetylation of arbekacin and antibiotic activity of its product J Antibiot (Tokyo). 1996 May;49(5):458-64. doi: 10.7164/antibiotics.49.458.

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