Basic information
- CAS
32986-56-4- Standard SMILES
NCC1OC(OC2C(N)CC(N)C(OC3OC(CO)C(O)C(N)C3O)C2O)C(N)CC1O- InChIKey
NLVFBUXFDBBNBW-UHFFFAOYSA-N- Molecular formula
- C18H37N5O9
- Average molar mass
- 467.5 g/mol
- Monoisotopic mass
- 467.25912777
Overview
See also: Tobramycin (annotation moved to); Tobramycin Sulfate (annotation moved to); Fluorometholone acetate; tobramycin (annotation moved to) ... View More ...
Names & identifiers
- Preferred name
- Tobracin
- IUPAC
- 4-amino-2-[4,6-diamino-3-[3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
- English name
- Tobramycin
- Molecular formula
- C18H37N5O9
- Molecular weight
- 467.52
Names & synonyms
TobramaxinNF 6Lilly 47663Tobracin(1S,3R)-4,6-diamino-3-[(2,6-diamino-2,3,6-trideoxy-alpha-L-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-allopyranoside1173106-27-8C18H37N5O9Nebramycin Factor 6;Deoxykanamycin BNSC 180514O-[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-streptaminePrestwick_850Obracine (Salt/Mix)
Show more names
Tobramycin BaseTobramycinetobranebcintobrexTobramaxnf6obracinnebicina
Distobram (Salt/Mix)Gernebcin (Salt/Mix)Prestwick0_000544Prestwick1_000544Prestwick2_000544CHEMBL14440SPBio_002508SCHEMBL2736461
Database identifiers
Properties
Computed structural properties
- XLogP
- -6.2
- Topological polar surface area
- 268 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 609
Experimental & physicochemical properties
DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 178 °C · 178 °C
- Boiling point
- 570.01 °C · 570.01°C (rough estimate)
- alpha
- 20 · D20 +129° (c = 1 in water)
- Density
- 1.3458 · 1.3458 (rough estimate)
- refractive index
- 143 ° · 143 ° (C=4, H2O)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, faintly yellow
- pka
- 6.7 · pKa 6.7 (Uncertain);8.3 (Uncertain);9.9 (Uncertain)
- form
- White to off-white solid
- color
- white to off-white
- Water Solubility
- Soluble in water
- Merck
- 14 · 14,9490
- BRN
- 1357507 · 1357507
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- wgk
- 2
- rtecs
- WK2100000
- hs_code
- 29419090
- Toxicity
- LD50 in mice, rats (mg/kg): 441, 969 s.c. (Welles)
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361f
- Hazard Classifications
- Repr. 2
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
- Hazardous Substances Data
- 32986-56-4(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionTobramycin is one component (factor 6) of a mixture produced by fermentation of Streptomyces tenebrari us. Lacking the C-3′ hydroxyl group, it is not a substrate for APH(3′)-1 and APH(3′)-II and so has an intrinsically broader spectrum than kanamycin. It is a substrate, however, for adenylation at C-2′ by ANT (2′) and acetylation at C-3 by AAC(3)-I and AAC(3)-II and at C-2′ by AAC(2′).
Usesantibacterial, inhibits protein synthesis
UsesAntihypertensive
UsesTobramycin is an aminoglycoside antibiotic.
UsesSingle factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. Antibacterial
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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