Compound: kanamycin
SMILES: O1[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@@H]([C@@H](O)[C@@H]([C@H]3O)O)CN)[C@@H](N)C[C@H]2N)[C@H](O)[C@@H](N)[C@@H]([C@H]1CO)O
InChIKey: SBUJHOSQTJFQJX-NOAMYHISSA-N
Synonyms: kanamycin, Kanamicina, Kanamycine, Kanamycinum, 8063-07-8, Kanamycins, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy-, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol, Kanamycin Complex, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-2-hydroxycyclohexyl)oxy)oxane-3,4,5-triol, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-((1R,2R,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2-hydroxycyclohexyl)oxyoxane-3,4,5-triol, RefChem:5930, RUC37XUP2P, CHEBI:6104, DTXSID2041171, CHEBI:24951, A07AA08, J01GB04, S01AA24, 200-411-7, 232-512-7, KANAMYCIN A, 59-01-8, Kanamycin Base, KanamycinA, Kanamycin A Deuterated, 1174286-24-8, Kanamycin A monosulfate, 4,6-Diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-alpha-D-glucoside, EQK9Q303C5, KAN, CHEBI:17630, C18H36N4O11, Kanamycin (sulfate), Kanamicina [Italian], KM (the Antibiotic), Kanamycin [INN:BAN], Kanamycine [INN-French], Kanamycinum [INN-Latin], 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside, (1S,2R,3R,4S,6R)-4,6-diamino-3-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol, HSDB 3107, EINECS 200-411-7, BRN 0061647, UNII-EQK9Q303C5, DTXSID3023184, Liposomal Kanamycin, Prestwick3_000394, Kantrex (1:1 sulfate), Klebcil (1:1 sulfate), KANAMYCIN A [MI], KANAMYCIN A [HSDB], SCHEMBL2735, CHEMBL1384, Glucopyranoside, 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-, D-, BSPBio_000607, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1,4))-2-deoxy-, DivK1c_000024, KANAMYCIN A [WHO-IP], BPBio1_000669, orb1992991, orb2813903, GTPL12132, KBio1_000024, Kanamycin A Deuterated (>90%), MSK7706, NINDS_000024, 7227b, BDBM50031282, EBC-12280, MFCD00070289, T0793L, Amikacin EP Impurity D; Kanamycin A, AKOS025293505, AK30116, DB01172, IDI1_000024, SMP2_000007, NCGC00179506-01, NCGC00179506-05, 2-(aminomethyl)-6-[4,6-diamino-3-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol, AS-14003, D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.4)]-2-deoxy-, HY-16566, AB00513827, CS-0006792, NS00098990, C01822, EN300-19735925, BRD-K08327065-065-01-9, BRD-K08327065-065-04-3, Q27094615, (1S,2R,3R,4S,6R)-4,6-diamino-3-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside, (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triol, D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXY-, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-2-deoxy-, O-3-Amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-2-deoxy-D-streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-D-streptamine
Theoretical properties:
molecular_formula: C18H36N4O11
molecular_weight: 484.5 g/mol
exact_mass: 484.23805798 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 11
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 6
heavy_atom_count: 33
topological_polar_surface_area: 283 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethanol
color: Crystals from ethanol
solubility: 9.23e+01 g/L
Descriptions:
pubchem: Kanamycin A is a member of kanamycins. It has a role as a bacterial metabolite. It is a conjugate base of a kanamycin A(4+).
chembl: KANAMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Kanamycin A, often referred to simply as kanamycin, is an antibiotic used to treat severe bacterial infections and tuberculosis. It is not a first line treatment. It is used by mouth, injection into a vein, or injection into a muscle. Kanamycin is recommended for short-term use only, usually from 7 to 10 days. Since antibiotics only show activity against bacteria, it is ineffective in viral infections.
Common side effects include hearing and balance problems. Kidney problems may also occur. Kanamycin is not recommended during pregnancy as it may harm the baby. It is likely safe during breastfeeding. Kanamycin is in the aminoglycoside family of medications. It has the weakest antibacterial capabilities of all compounds in this family when used clinically, which is partially due to its increased toxicity in comparison to other aminoglycosides. It works by blocking the production of proteins that are required for bacterial survival.
Kanamycin was first isolated in 1957 by Hamao Umezawa from the bacterium Streptomyces kanamyceticus. It was removed from the World Health Organization's List of Essential Medicines in 2019. It is no longer marketed in the United States.