Compound: tobramycin
SMILES: O1[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@@H]([C@@H](O)C[C@H]3N)CN)[C@@H](N)C[C@H]2N)[C@H](O)[C@@H](N)[C@@H]([C@H]1CO)O
InChIKey: NLVFBUXFDBBNBW-PBSUHMDJSA-N
Synonyms: tobramycin, 32986-56-4, Nebramycin VI, Nebramycin 6, Nebramycin factor 6, Tobrex, Tobi, Deoxykanamycin B, 3'-Deoxykanamycin B, Aktob, Tobralex, Tobi Podhaler, vantobra, Tobramicina, Tobramycine, Obramycin, 1-Epitobramycin, Tobramycetin, Tobramycinum, Bethkis, Kitabis Pak, Tobramitsetin, Tenebrimycin, Tenemycin, Nebicin, VZ8RRZ51VK, NSC-180514, DTXSID8023680, (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol, DTXCID903680, CHEBI:28864, 4-(2,6-Diamino-2,3,6-trideoxy-alpha-D-glycopyranosyl)-6-(3-amino-3-deoxy-alpha-D-glycopyranosyl)-2-deoxystreptamine, D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-4))-2-deoxy-, O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine, Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-tyrideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D-, O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine, Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D-, Bramitob, Tobravisc, Tymbrineb, Nebris, Tobramycin solution, (2S,3R,4S,5S,6R)-4-amino-2-((1S,2S,3R,4S,6R)-4,6-diamino-3-((2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl)oxy-2-hydroxycyclohexyl)oxy-6-(hydroxymethyl)oxane-3,5-diol, Tobramycin Inhalation, RefChem:6312, Tobramycin Inhalation Solution, Tobramycin Ophthalmic Solution, J01GB01, S01AA12, Tobramycin Inhalation Solution Pak, 251-322-5, 3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1->4))-2-deoxy-D-streptamine, Tobramicin, Tobramycin Base, Distobram, Tobracin (TN), Tobrex (TN), Tobramycin Deuterated, C18H37N5O9, NSC 180514, Gotabiotic, Tobacin, Tobrased, (2S,3R,4S,5S,6R)-4-amino-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol, (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxy-tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]-6-(hydroxymethyl)tetrahydropyran-3,5-diol, (2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol, Tobramycine [INN-French], Tobramycinum [INN-Latin], Tobramicina [INN-Spanish], (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside, O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-->6)-O-[2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-->4)]-2-deoxy-D-streptamine, TOY, Nebramycin factir 6, HSDB 3259, SR-05000001726, EINECS 251-322-5, UNII-VZ8RRZ51VK, MFCD00077885, SPRC-AB01, BRN 1357507, torbamycin, Kitabis, Nebramycin Factor 6;Deoxykanamycin B, Tobramycin CRS, Nebcin (Sulfate), NCGC00016814-01, D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-.ALPHA.-D-RIBO-HEXOPYRANOSYL-(1->4))-2-DEOXY-, D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribo-hexopyranosyl-(1->4)]-2-deoxy-, Bethkis (TN), CAS-32986-56-4, AT02 - Tobramycin, Tobramycin [USAN:USP:INN:BAN:JAN], Tobi (TN), Spectrum_001072, TOBRAMYCIN [MI], TOBRAMYCIN [INN], TOBRAMYCIN [JAN], Prestwick3_000544, Spectrum2_000078, Spectrum3_000588, Spectrum4_000752, Spectrum5_001038, Tobramycin - high purity, TOBRAMYCIN [HSDB], TOBRAMYCIN [USAN], TOBRAMYCIN [VANDF], Tobramycin (JP18/USP), SCHEMBL2838, TOBRAMYCIN [MART.], CHEMBL1747, TOBRAMYCIN [USP-RS], TOBRAMYCIN [WHO-DD], BSPBio_000587, BSPBio_002036, KBioGR_001104, KBioSS_001552, MLS000069544, BIDD:GT0503, SPECTRUM1500579, SPBio_000295, BPBio1_000647, orb1309215, orb3140193, Tobramycin Deuterated (>90%), TOBRAMYCIN [ORANGE BOOK], GTPL10930, KBio2_001552, KBio2_004120, KBio2_006688, KBio3_001536, ZYLET COMPONENT TOBRAMYCIN, MSK7708, TOBRAMYCIN [EP MONOGRAPH], Tobramycin for identification CRS, GLXC-06548, HMS2090B16, HMS2092M17, HMS2096N09, HMS3713N09, Pharmakon1600-01500579, TOBRAMYCIN [USP MONOGRAPH], HY-B0441, TOBRADEX COMPONENT TOBRAMYCIN, Tox21_110626, BDBM50366778, CCG-39936, EBC-27168, HB4564, MSK7708-100W, NSC757352, s2514, TOBRASONE COMPONENT TOBRAMYCIN, Tobradex (tobramycin + dexamethasone), AKOS016339662, MSK7708-1000W, DB00684, KS-1405, NSC-757352, TOBRADEX ST COMPONENT TOBRAMYCIN, NCGC00178852-01, NCGC00178852-02, Tobramycin Solution in Water, 100ug/mL, AT161114, O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-6))-2-deoxy-L-streptamine, SMR000058793, SBI-0051915.P003, Tobramycin Solution in Water, 1000ug/mL, Second International Standard for Tobramycin, AB00513858, NS00003131, T2503, C00397, D00063, AB00052438-12, AB00052438_13, AB00052438_14, EN300-7480857, SR-01000721898, Tobramycin, Antibiotic for Culture Media Use Only, Q-201837, Q1758380, SR-01000721898-2, SR-05000001726-1, SR-05000001726-2, BRD-K05619559-001-10-1, BRD-K05619559-001-12-7, (1S,2S,3R,4S,6R)-4,6-diamino-3-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside, D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribohexopyranosyl-(1->4)]-2-deoxy-, D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1?6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribo-hexopyranosyl-(1?4)]-2-deoxy-, O-[3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)]-O-[2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1->4)]-2-deoxy-D-streptamine, O-[3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1?6)]-O-[2,6-diamino-2,3 ,6-trideoxy-alpha-D-ribohexopyranosyl-(1?4)]-2-deoxy-D-streptamine, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-.ALPHA.-D-RIBO-HEXOPYRANOSYL-(1.ALPHA.6))-2-DEOXY-L-STREPTAMINE, O-3-Amino-3-deoxy-|A-D-glucopyranosyl-(1 inverted exclamation marku6)-O-[2,6-diamino-2,3,6-trideoxy-|A-D-ribo-hexopyranosyl-(1 inverted exclamation marku4)]-2-deoxy-D-streptamine
Theoretical properties:
molecular_formula: C18H37N5O9
molecular_weight: 467.5 g/mol
exact_mass: 467.25912777 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 10
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 6
heavy_atom_count: 32
topological_polar_surface_area: 268 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white powder
color: White to off-white powder
solubility: freely soluble
Descriptions:
pubchem: Tobramycin Sulfate can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.
chembl: TOBRAMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius that is used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas.
It was patented in 1965, and approved for medical use in 1974. It is on the World Health Organization's List of Essential Medicines. In 2023, it was the 298th most commonly prescribed medication in the United States, with more than 400,000 prescriptions.