Compound: amikacin
SMILES: O=C(N[C@H]1[C@H](O[C@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)N)CO)[C@@H](O)[C@H](O[C@H]3O[C@@H]([C@@H](O)[C@@H]([C@H]3O)O)CN)[C@H](C1)N)[C@@H](O)CCN
InChIKey: LKCWBDHBTVXHDL-RMDFUYIESA-N
Synonyms: amikacin, 37517-28-5, Lukadin, amikacine, Amikacina, Amikacinum, Potentox, 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A, BAY 41-6551, CHEBI:2637, DTXSID3022586, 84319SGC3C, NSC-177001, DTXCID002586, (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-{[(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, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-, Amiklin, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-N1-((2S)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, Biclin, Normon, Amikacina, Medical, Amikacina, (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-((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, RefChem:5541, D06AX12, J01GB06, S01AA21, 253-538-5, 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, Amikacillin, Amikacine [INN-French], Amikacinum [INN-Latin], Amikacina [INN-Spanish], Amikacin Base, Kaminax, Amikacin Dihydrate, Amicacin, Briclin, Amikavet, Arikace, ANTIBIOTIC BB-K8, Mikavir, Antibiotic BB-K 8, (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, (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide, NCGC00093350-02, Amukin, BB-K 8, MFCD00883675, Amikozit, N1-[(S)-4-Amino-2-hydroxybutyryl]kanamycin A, MLS002207279, C22H43N5O13, Amikacin free base, (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide, HSDB 3583, Amikacin (USP/INN), SMR001306795, EINECS 253-538-5, NSC 177001, Amikacin [USP:INN:BAN], UNII-84319SGC3C, SR-01000722004, Amikacin CRS, Amikacin anhydrous, Arikayce liposomal, Amikacin & Tumor Necrosis Factor, NCGC00093350-05, 37517-28-5 (free base), (2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S ,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide, AKN, Amikacin; 6-O-(3-Amino-3-deoxy-?-d-glucopyranosyl)-4-O-(6-amino-6-deoxy-?-d-glucopyranosyl)-1-N-[(2S)-4-amino-2-hydroxybutanoyl]-2-deoxy-d-streptamine, Amikacin; 6-O-(3-Amino-3-deoxy-a-d-glucopyranosyl)-4-O-(6-amino-6-deoxy-a-d-glucopyranosyl)-1-N-[(2S)-4-amino-2-hydroxybutanoyl]-2-deoxy-d-streptamine, Amikin (Disulfate), Amikacin (Standard), AT03 - Amikacin, BAY41-6551, Amikacin (free base), 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, nktr-061, AMIKACIN [HSDB], AMIKACIN [INN], AMIKACIN [JAN], AMIKACIN [MI], AMIKACIN [VANDF], Prestwick3_000395, AMIKACIN [MART.], AMIKACIN [USP-RS], AMIKACIN [WHO-DD], AMIKACIN [WHO-IP], CHEMBL177, SCHEMBL2985, CAS-37517-28-5, BSPBio_000609, BPBio1_000671, HY-B0509AR, orb1310051, AMIKACIN [EP MONOGRAPH], AMIKACIN [USP MONOGRAPH], TD1 - Therapeutic Drug mixture, BDBM91426, GTPL10894, HY-B0509A, MAT2501, MSK7705, AMIKACINUM [WHO-IP LATIN], cid_16218899, MSK7705-100MW, MSK7705-1000MW, Tox21_111201, BDBM50237603, EBC-27355, MFCD11045969, MSK7705-100W, STK039706, AKOS005383276, MSK7705-1000W, Tox21_111201_1, AA29724, Amikacin Solution in Water, 100ug/mL, DB00479, Amikacin Solution in Water, 1000ug/mL, NCGC00093350-03, (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, AS-76985, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-, 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(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine, AB00513828, NS00006181, Amikacin Solution in Methanol/Water, 100ug/mL, C06820, D02543, AB00513828_06, Amikacin Solution in Methanol/Water, 1000ug/mL, EN300-7481440, Q408529, SR-01000722004-6, an-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide, BRD-K88043978-315-02-8, (2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S, (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyr, ,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide, D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-N(SUP 1)-(4-AMINO-2-HYDROXY-1-OXOBUTYL)-2-DEOXY-, (S)-, D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-, 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
Theoretical properties:
molecular_formula: C22H43N5O13
molecular_weight: 585.6 g/mol
exact_mass: 585.28573644 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 13
hydrogen_bond_acceptor_count: 17
rotatable_bond_count: 10
heavy_atom_count: 40
topological_polar_surface_area: 332 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White crystalline powder from methanol-isopropanol
color: White crystalline powder from methanol-isopropanol
Descriptions:
pubchem: Amikacin is an amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group. It has a role as an antimicrobial agent, an antibacterial drug and a nephrotoxic agent. It is an alpha-D-glucoside, an amino cyclitol glycoside, a carboxamide and an aminoglycoside. It is functionally related to a kanamycin A. It is a conjugate base of an amikacin(4+).
chebi: An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.
chembl: AMIKACIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Amikacin is an antibiotic medication used for a number of bacterial infections. This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used by injection into a vein using an IV or into a muscle.
Amikacin, like other aminoglycoside antibiotics, can cause hearing loss, balance problems, and kidney problems. Other side effects include paralysis, resulting in the inability to breathe. If used during pregnancy it may cause permanent deafness in the baby. Amikacin works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to produce proteins.
Amikacin was patented in 1971, and came into commercial use in 1976. It is on the World Health Organization's List of Essential Medicines. It is derived from kanamycin.