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Substance Name: Tobramycin [USAN:USP:INN:BAN:JAN]
RN: 32986-56-4
UNII: VZ8RRZ51VK
InChIKey: NLVFBUXFDBBNBW-PBSUHMDJSA-N

Note

  • An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.

Molecular Formula

  • C18-H37-N5-O9

Molecular Weight

  • 467.516
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Natural Product
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Tobramycin
  • Tobramycin [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Tobramycin

Synonyms

  • 1-Epitobramycin
  • 3'-Deoxykanamycin B
  • 4-(2,6-Diamino-2,3,6-trideoxy-alpha-D-glycopyranosyl)-6-(3-amino-3-deoxy-alpha-D-glycopyranosyl)-2-deoxystreptamine
  • 47663
  • Aktob
  • Bethkis
  • BRN 1357507
  • 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-
  • Deoxykanamycin B
  • EINECS 251-322-5
  • Gotabiotic
  • HSDB 3259
  • Kitabis Pak
  • Lilly 47663
  • Nebramycin
  • Nebramycin 6
  • Nebramycin factor 6
  • Nebramycin VI
  • NF 6
  • NSC 180514
  • 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
  • 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-
  • Tenebrimycin
  • Tenemycin
  • Tobacin
  • Tobi
  • TOBI Podhaler
  • Tobracin
  • Tobradistin
  • Tobralex
  • Tobramaxin
  • Tobramicin
  • Tobramicina
  • Tobramicina [INN-Spanish]
  • Tobramitsetin
  • Tobramycetin
  • Tobramycin
  • Tobramycine
  • Tobramycine [INN-French]
  • Tobramycinum
  • Tobramycinum [INN-Latin]
  • Tobrased
  • Tobrex
  • UNII-VZ8RRZ51VK

Systematic Names

  • 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-
  • 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-
  • Tobramycin

Mixture Names

  • Tobradex
  • Tobrasone

Registry Numbers

CAS Registry Number

  • 32986-56-4

FDA UNII

  • VZ8RRZ51VK

Other Registry Numbers

  • 11098-01-4
  • 11111-45-8
  • 34337-51-4
  • 37321-13-4
  • 54330-95-9
  • 70322-33-7

Related Registry Number

  • 49842-07-1 (Sulfate)

System Generated Number

  • 0032986564

Structure Descriptors

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

Smiles

NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 37714ug/kg (37.714mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED American Journal of Kidney Diseases. Vol. 23, Pg. 118, 1994.
mouse LD50 intramuscular 440mg/kg (440mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
mouse LD50 intraperitoneal 445mg/kg (445mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
mouse LD50 intravenous 72500ug/kg (72.5mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Antibiotiki. Vol. 29, Pg. 361, 1984.
mouse LD50 oral > 11500mg/kg (11500mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
mouse LD50 subcutaneous 367mg/kg (367mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
pig LD50 subcutaneous 676mg/kg (676mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE		 Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
rat LD50 intramuscular 913mg/kg (913mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 107, 1977.
rat LD50 intraperitoneal 1030mg/kg (1030mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 intravenous 104mg/kg (104mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 oral > 7500mg/kg (7500mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
rat LD50 subcutaneous 969mg/kg (969mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Toxicology and Applied Pharmacology. Vol. 22, Pg. 332, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -5.760 (none)   EST
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 2.37E-21 mm Hg 25 EST
Henry's Law Constant 2.24E-39 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.63E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.