amikacin
An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.
Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.
Classification
aminoglycoside antibioticARO:0000016
-
CHEBI:22390 -
CHEBI:22479 -
CHEBI:37622 -
CHEBI:47779 - aminoglycoside antibiotic
ARO:0000016
Chemical structure
| Molecular formula | C22H43N5O13 |
|---|---|
| Charge | 0 |
| Average mass | 585.608 Da |
| Monoisotopic mass | 585.28574 Da |
| Source | ChEBI |
| InChIKey | LKCWBDHBTVXHDL-RMDFUYIESA-N |
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
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
Also called
- amikacina
- amikacine
- amikacinum
- (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-α-D-glucopyranosyloxy)-4-(6-amino-6-deoxy-α-D-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide
- 1-N-(L(−)-γ-amino-α-hydroxybutyryl)kanamycin A
- Amikacin
- O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→4)-O-(6-amino-6-deoxy-α-D-glucopyranosyl-(1→6))-N3-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine
- AMK
- Amicacin
- Amikacina
- Amikacinum
- Amikavet
- Arikace
- Kaminax
- Lukadin
- Mikavir
- mikacin
Cross-references
- amikacin
ARO:0000013 - cas:37517-28-5
- hmdb:HMDB0014622
- kegg.compound:C06820
- lincs.smallmolecule:LSM-5935
- metacyc.compound:CPD-14197
- reaxys:5915117
- chembl:CHEMBL177
- pubchem.compound:37768
Drug registries
Patents and articles
Activity roles
- antimicrobial agent
CHEBI:33281 - antibacterial drug
CHEBI:36047
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:0000013 |
amikacin | antibioticmech:aro-78030ec7ba |
2026-08-30 |
| CHEBI | CHEBI:2637 |
amikacin | antibioticmech:chebi-cc9bb9e534 |
2026-08-30 |
Molecular targets
antibiotic sensitive 16S rRNA NUCLEIC_ACID DIRECT_BINDING_TARGET
Activity spectrum
| Organism | Activity | MIC | Disk diffusion | Assay | Strain | Sample/genome | Evidence |
|---|---|---|---|---|---|---|---|
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 | — |
270 source isolates 270 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 | — |
4066 source isolates 4066 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; not specified | — |
2 source isolates 2 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2020; not specified | — |
3 source isolates 3 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; solid media | — |
24 source isolates 24 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2020; solid media | — |
225 source isolates 225 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | INTERMEDIATE | — | — | CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 | — |
1 source isolates 1 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 | — |
46 source isolates 46 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 | — |
850 source isolates 850 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2023; not specified | — |
1 source isolates 1 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
1323 source isolates 1323 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
93 source isolates 93 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
302 source isolates 302 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
117 source isolates 117 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
38 source isolates 38 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
29 source isolates 29 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | 2.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
18 source isolates 18 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | 2.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
17 source isolates 17 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | 2.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
8 source isolates 8 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | 4.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
20 source isolates 20 measurements |
EvidencePage data (JSON.gz) |
Resistance mechanisms
ANTIBIOTIC_INACTIVATION 79
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| AAC(3)-Ib/AAC(6')-Ib3 bifunctional protein | ARO:3002600 | — | ||
| AAC(6')-29a | ARO:3002583 | — | ||
| AAC(6')-29b | ARO:3002584 | — | ||
| AAC(6')-31 | ARO:3002585 | — | ||
| AAC(6')-32 | ARO:3002586 | — | ||
| AAC(6')-I-48 | ARO:3004638 | — | ||
| AAC(6')-I30 | ARO:3002588 | — | ||
| AAC(6')-I33 | ARO:3002587 | — | ||
| AAC(6')-Ia | ARO:3002545 | — | ||
| AAC(6')-Iaa | ARO:3002571 | — | ||
| AAC(6')-Iad | ARO:3002572 | — | ||
| AAC(6')-Iae | ARO:3002573 | — | ||
| AAC(6')-Iaf | ARO:3002574 | — | ||
| AAC(6')-Iai | ARO:3002575 | — | ||
| AAC(6')-Iaj | ARO:3003677 | — | ||
| AAC(6')-Iak | ARO:3003199 | — | ||
| AAC(6')-Ian | ARO:3003200 | — | ||
| AAC(6')-Iap | ARO:3007204 | — | ||
| AAC(6')-Ib | ARO:3002546 | — | ||
| AAC(6')-Ib' | ARO:3003676 | — | ||
| AAC(6')-Ib-Hangzhou | ARO:3002592 | — | ||
| AAC(6')-Ib-SK | ARO:3002593 | — | ||
| AAC(6')-Ib-Suzhou | ARO:3002591 | — | ||
| AAC(6')-Ib-cr1 | ARO:3002547 | — | ||
| AAC(6')-Ib-cr3 | ARO:3005112 | — | ||
| AAC(6')-Ib-cr4 | ARO:3005114 | — | ||
| AAC(6')-Ib-cr5 | ARO:3005115 | — | ||
| AAC(6')-Ib-cr6 | ARO:3005116 | — | ||
| AAC(6')-Ib-cr7 | ARO:3005117 | — | ||
| AAC(6')-Ib-cr8 | ARO:3005118 | — | ||
| AAC(6')-Ib-cr9 | ARO:3005119 | — | ||
| AAC(6')-Ib10 | ARO:3002581 | — | ||
| AAC(6')-Ib11 | ARO:3002582 | — | ||
| AAC(6')-Ib3 | ARO:3002576 | — | ||
| AAC(6')-Ib4 | ARO:3002577 | — | ||
| AAC(6')-Ib7 | ARO:3002578 | — | ||
| AAC(6')-Ib8 | ARO:3002579 | — | ||
| AAC(6')-Ib9 | ARO:3002580 | — | ||
| AAC(6')-Ic | ARO:3002549 | — | ||
| AAC(6')-Ie-APH(2'')-Ia bifunctional protein | ARO:3002597 | — | ||
| AAC(6')-If | ARO:3002553 | — | ||
| AAC(6')-Ig | ARO:3002554 | — | ||
| AAC(6')-Ih | ARO:3002555 | — | ||
| AAC(6')-Ii | ARO:3002556 | — | ||
| AAC(6')-Iid | ARO:3002589 | — | ||
| AAC(6')-Iih | ARO:3002590 | — | ||
| AAC(6')-Ij | ARO:3002557 | — | ||
| AAC(6')-Ik | ARO:3002558 | — | ||
| AAC(6')-Il | ARO:3004635 | — | ||
| AAC(6')-Im | ARO:3004629 | — | ||
| AAC(6')-Ip | ARO:3002559 | — | ||
| AAC(6')-Iq | ARO:3002560 | — | ||
| AAC(6')-Ir | ARO:3002561 | — | ||
| AAC(6')-Is | ARO:3002562 | — | ||
| AAC(6')-Isa | ARO:3002563 | — | ||
| AAC(6')-It | ARO:3002564 | — | ||
| AAC(6')-Iu | ARO:3002565 | — | ||
| AAC(6')-Iv | ARO:3002566 | — | ||
| AAC(6')-Iw | ARO:3002567 | — | ||
| AAC(6')-Ix | ARO:3002568 | — | ||
| AAC(6')-Iy | ARO:3002569 | — | ||
| AAC(6')-Iz | ARO:3002570 | — | ||
| ANT(4')-IIa | ARO:3002624 | — | ||
| ANT(4')-IIb | ARO:3002625 | — | ||
| ANT(4')-Ia | ARO:3002623 | — | ||
| ANT(4')-Ib | ARO:3003905 | — | ||
| APH(2'')-IIIa | ARO:3002636 | — | ||
| APH(2'')-IVa | ARO:3002637 | — | ||
| APH(2'')-Ie | ARO:3002634 | — | ||
| APH(2'')-Ig | ARO:3002669 | — | ||
| APH(3')-IIIa | ARO:3002647 | — | ||
| APH(3')-IXa | ARO:3004087 | — | ||
| APH(3')-VIIIa | ARO:3004680 | — | ||
| APH(3')-VIIIb | ARO:3004086 | — | ||
| APH(3')-VIa | ARO:3002652 | — | ||
| APH(3')-VIb | ARO:3002653 | — | ||
| aac(6')-Ib-cr10 | ARO:3007770 | — | ||
| aac(6')-Ib-cr11 | ARO:3007771 | — | ||
| aphA15 | ARO:3004675 | — |
ANTIBIOTIC_TARGET_ALTERATION 17
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Mycobacterium tuberculosis 16S rRNA (rrnS) mutation conferring resistance to kanamycin | ARO:3007537 | — | ||
| Mycobacterium tuberculosis 16S rRNA mutation conferring resistance to amikacin | ARO:3003481 | — | ||
| Mycobacterium tuberculosis eis with mutation conferring resistance to amikacin | ARO:3009333 | — | ||
| Mycobacteroides abscessus 16S rRNA mutation conferring resistance to amikacin | ARO:3003239 | — | ||
| Mycobacteroides chelonae 16S rRNA mutation conferring resistance to amikacin | ARO:3003514 | — | ||
| armA | ARO:3000858 | — | ||
| npmA | ARO:3002665 | — | ||
| rmtA | ARO:3000859 | — | ||
| rmtB | ARO:3000860 | — | ||
| rmtC | ARO:3000861 | — | ||
| rmtD | ARO:3002667 | — | ||
| rmtD2 | ARO:3004677 | — | ||
| rmtE | ARO:3004678 | — | ||
| rmtE2 | ARO:3004679 | — | ||
| rmtG | ARO:3002668 | — | ||
| rmtH | ARO:3003198 | — | ||
| sgm | ARO:3000862 | — |
ANTIBIOTIC_EFFLUX 5
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Acinetobacter baumannii AbuO | ARO:3004578 | — | ||
| AcrAD-TolC | ARO:3004082 | — | ||
| MexXY-OprA | ARO:3003038 | — | ||
| MexXY-OprM | ARO:3003032 | — | ||
| acrD | ARO:3000491 | — |
UNKNOWN 1
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| PvrR | ARO:3003688 | — |
Curation history
-
SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank amikacin-resistant Klebsiella pneumoniae isolate MIC observation.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank amikacin-resistant Escherichia coli MIC observation from isolate 0346.
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CURATED_RESISTANT_TAXA
Added 8 stable-URL CDC/FDA AR Isolate Bank amikacin-resistant Multi-Mechanism panel MIC observations for AR-1153, AR-1155, AR-1156, AR-1157, AR-1158, AR-1159, AR-1161, and AR-1163.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1268.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1269.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1270.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1328.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 amikacin-resistant Acinetobacter baumannii MIC observation for AR-0083; preserved source Unknown, BioSample SAMN04014924, Study ID CarbaNP-52, and MLST ST1(Pasteur)/ST231/1604(Oxford) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 amikacin-resistant Acinetobacter baumannii MIC observation for AR-0078; preserved source Pus, BioSample SAMN04014919, Study ID CarbaNP-47, and MLST ST229(Pasteur)/ST203(Oxford) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1332; preserved source Urine, Study ID IMP-10, unavailable BioSample accession, and MLST ST357(Pasteur) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 amikacin-resistant Pseudomonas aeruginosa MIC observation for AR-1333; preserved source Urine, Study ID IMP-11, unavailable BioSample accession, and MLST ST2731(Pasteur) in evidence notes.
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STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS
Structured BioSample accessions on 16 activity_spectrum observation(s) where evidence notes already named exactly one accession.
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RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
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RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.