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Substance Name: Amikacin sulfate [USAN:USP:JAN]
RN: 39831-55-5
UNII: N6M33094FD
InChIKey: FXKSEJFHKVNEFI-GCZBSULCSA-N

Note

  • A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.

Molecular Formula

  • C22-H43-N5-O13.2H2-O4-S

Molecular Weight

  • 781.7593
 

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Amikacin sulfate [USAN:USP:JAN]

Synonyms

  • Amikacin disulfate
  • Amikacin sulfate
  • Amikacin sulfate in sodium chloride 0.9% in plastic container
  • Amikafur
  • Amikin
  • Amikin in sodium chloride 0.9% in plastic container
  • Amitrex
  • Antibiotic BB-K8 sulfate
  • BB-K8
  • Biklin
  • Biodacyn
  • Chemacin
  • EINECS 254-648-6
  • Fabianol
  • Kaminax
  • Kancin-Gap
  • Likacin
  • Lukadin
  • NN-K 8
  • NSC 755846
  • O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-6))-N(sup 3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine sulfate (1:2)
  • Pierami
  • UNII-N6M33094FD

Systematic Names

  • Amikacin bis(sulphate)
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-, sulfate (1:2)(salt)
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-N1-((2S)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, sulfate (1:2) (salt)

Superlist Name

  • Amikacin sulfate

Registry Numbers

CAS Registry Number

  • 39831-55-5

FDA UNII

  • N6M33094FD

Other Registry Number

  • 37357-52-1

System Generated Number

  • 0039831555

Molecular Formulas

Molecular Formula

  • C22-H43-N5-O13.2H2-O4-S

Molecular Formula Fragments

  • C22-H43-N5-O13
  • COMPONENT
  • H2-O4-S

Structure Descriptors

InChI

InChI=1S/C22H43N5O13.2H2O4S/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1

InChIKey

FXKSEJFHKVNEFI-GCZBSULCSA-N

Smiles

NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O.OS(=O)(=O)O.OS(=O)(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intramuscular > 667mg/kg (667mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
dog LD50 intravenous 383mg/kg (383mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
monkey LD50 intramuscular > 1335mg/kg (1335mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
mouse LD50 intramuscular 1247mg/kg (1247mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986.
mouse LD50 intraperitoneal 2930mg/kg (2930mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
mouse LD50 intravenous 181mg/kg (181mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986.
mouse LD50 oral > 10679mg/kg (10679mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
mouse LD50 subcutaneous 2470mg/kg (2470mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
rabbit LD50 intramuscular > 3gm/kg (3000mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
rabbit LD50 intravenous 248mg/kg (248mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
rabbit LD50 oral > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. -, Pg. 45, 1990.
rat LD50 intramuscular 2244mg/kg (2244mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986.
rat LD50 intraperitoneal 3500mg/kg (3500mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
rat LD50 intravenous 234mg/kg (234mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.
rat LD50 oral > 4gm/kg (4000mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
rat LD50 subcutaneous 3604mg/kg (3604mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 1, Pg. 125, 1977.