Tobramycin

Athanor · official

C₁₈H₃₇N₅O₉ · 467.5 g/mol

IUPAC name: (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

Also called Tobrex, TOBI, aminoglycoside, nebcin

Drugs

Open in Athanor

Drawn from its SMILES with RDKit

DangerCauses skin irritation · May cause an allergic skin reaction · Causes serious eye irritation · May cause respiratory irritation · May damage fertility or the unborn child · Suspected of damaging fertility or the unborn child · Causes damage to organs through prolonged or repeated exposure · Very toxic to aquatic life · Toxic to aquatic life with long lasting effects

Names and identifiers

IUPAC name: (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
Synonyms: Tobrex, TOBI, aminoglycoside
+ 38 more
nebcin, Nebramycin VI, Nebramycin 6, Nebramycin factor 6, Deoxykanamycin B, Tobi, 3'-Deoxykanamycin B, Aktob, Tobralex, Tobramicina, Tobi Podhaler, vantobra, Tobramycine, Obramycin, 1-Epitobramycin, Tobramycetin, Tobramycinum, Bethkis, Nebicin, Kitabis Pak, Tobramitsetin, Tenebrimycin, Tenemycin, DTXSID8023680, VZ8RRZ51VK, (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, NSC-180514, 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
Molecular formula: C₁₈H₃₇N₅O₉
Empirical formula: C₁₈H₃₇N₅O₉
Molecular weight: 467.5 g/mol
Exact mass: 467.25913
CAS number: 32986-56-4
PubChem CID: 36294
Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N
Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N
InChI: InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChIKey: NLVFBUXFDBBNBW-PBSUHMDJSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 32
Rings: 3
Aromatic rings: 0
Fraction sp³ carbons (Fsp3): 1
H-bond donors: 10
H-bond acceptors: 14
Rotatable bonds: 6
TPSA (Å²): 268.2 computed here · PubChem 268
Formal charge: 0
XLogP3: -6.2 PubChem
Complexity: 609 PubChem
Stereocenters: 14 definedCIP: C3: R · C5: R · C7: R · C8: S · C11: R · C13: S · C15: S · C17: R · C20: S · C22: S · C24: R · C26: S
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C46.24%
H7.98%
N14.98%
O30.80%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -6.3 Crippen (Wildman and Crippen 1999)
log S (water solubility): 1.62 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 5.14 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 467.52
log P ≤ 5 (Crippen): -6.3
H-bond donors ≤ 5: 10
H-bond acceptors ≤ 10: 14

Breaks 2 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 15 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard
Environmental hazard

H315Causes skin irritation (46.7% of reports)
H317May cause an allergic skin reaction (13.3% of reports)
H319Causes serious eye irritation (40% of reports)
H335May cause respiratory irritation (40% of reports)
H360May damage fertility or the unborn child (20% of reports)
H361Suspected of damaging fertility or the unborn child (13.3% of reports)
H372Causes damage to organs through prolonged or repeated exposure (13.3% of reports)
H400Very toxic to aquatic life (20% of reports)
H411Toxic to aquatic life with long lasting effects (13.3% of reports)

Precautionary statements: P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501

View all classifications (3)

[2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 6.7% (1 of 15) of reports.
[2] European Chemicals Agency (ECHA) · 15 reports · DangerH315, H317, H319, H335, H360, H361, H372, H400, H411
[2] European Chemicals Agency (ECHA) · 6 reports · DangerH301, H302, H311, H312, H331, H332, H360, H361, H362, H373

Storage

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2 - 8 °C.[1]

Safety data sheets on the supplier’s page: Accela ChemBio Inc., eNovation Chemicals, Alfa Chemistry.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.