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Substance Name: Gentamicin [INN:BAN]
RN: 1403-66-3
UNII: T6Z9V48IKG
InChIKey: CEAZRRDELHUEMR-UHFFFAOYSA-N

Note

  • A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1(subA), obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis ( GENETIC TRANSLATION).

Molecular Weight

  • 477.599
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Gentamicin [INN:BAN]
  • Gentamicin [INN]
  • Gentamycin

MeSH Heading

  • Gentamicins

Synonyms

  • Centicin
  • Cidomycin
  • EINECS 215-765-8
  • Garamycin
  • Garasol
  • Gentacycol
  • Gentalline
  • Gentamicin
  • Gentamicina
  • Gentamicina [INN-Spanish]
  • Gentamicine
  • Gentamicine [INN-French]
  • Gentamicinum
  • Gentamicinum [INN-Latin]
  • Gentamycin
  • Gentamycin-creme
  • Gentamycin-creme [German]
  • Gentamycins
  • Gentamycinum
  • Gentavet
  • Gentocin
  • HSDB 3087
  • Lyramycin
  • Oksitselanim
  • Refobacin
  • Refobacin TM
  • Septigen
  • UNII-T6Z9V48IKG
  • Uromycine

Systematic Name

  • Gentamicin

Registry Numbers

CAS Registry Number

  • 1403-66-3

FDA UNII

  • T6Z9V48IKG

System Generated Number

  • 0001403663

Structure Descriptors

InChI

1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3

InChIKey

CEAZRRDELHUEMR-UHFFFAOYSA-N

Smiles

O([C@@H]1[C@@H]([C@@H](O[C@@H]2O[C@@H](CC[C@@H]2N)[C@@H](NC)C)[C@@H](N)C[C@@H]1N)O)[C@@H]1[C@@H]([C@@H]([C@@](C)(O)CO1)NC)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intramuscular 430mg/kg (430mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
cat LD50 intraperitoneal 304mg/kg (304mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
cat LD50 intravenous 88mg/kg (88mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intramuscular 750mg/kg (750mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intraperitoneal 710mg/kg (710mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intravenous 184mg/kg (184mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
guinea pig LD50 intraperitoneal 530mg/kg (530mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
guinea pig LD50 subcutaneous 740mg/kg (740mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
human TDLo intravenous 2mg/kg (2mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES New England Journal of Medicine. Vol. 303, Pg. 1002, 1980.
human TDLo intravenous 23mg/kg/1Y-I (23mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING TRIGEMINAL NERVE Archives of Internal Medicine. Vol. 138, Pg. 1621, 1978.
infant TDLo intramuscular 20mg/kg (20mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Pediatrics. Vol. 77, Pg. 848, 1986.
man TDLo intramuscular 8mg/kg/2W-I (8mg/kg) SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
JAMA, Journal of the American Medical Association. Vol. 211, Pg. 123, 1970.
mouse LD50 intramuscular 167mg/kg (167mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 intraperitoneal 235mg/kg (235mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
mouse LD50 intravenous 43500ug/kg (43.5mg/kg)   Antibiotiki. Vol. 21, Pg. 532, 1976.
mouse LD50 oral 10gm/kg (10000mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Japanese Journal of Antibiotics. Vol. 30, Pg. 386, 1977.
mouse LD50 subcutaneous 274mg/kg (274mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
rabbit LD50 intramuscular 780mg/kg (780mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 intraperitoneal 1350mg/kg (1350mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 intravenous 81mg/kg (81mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 subcutaneous 1230mg/kg (1230mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rat LD50 intramuscular 463mg/kg (463mg/kg)   Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intraperitoneal 735mg/kg (735mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 intravenous 70mg/kg (70mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 oral 6600mg/kg (6600mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 39, Pg. 259, 1978.
rat LD50 subcutaneous 710mg/kg (710mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
women TDLo intravenous 8200ug/kg/12D (8.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGES IN VESTIBULAR FUNCTIONS: EAR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Acta Pathologica et Microbiologica Scandinavica, Section B: Microbiology and Immunology. Vol. 81(Suppl,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105 deg C   EXP
log P (octanol-water) -1.880 (none)   EST
Atmospheric OH Rate Constant 4.05E-10 cm3/molecule-sec 25 EST

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