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Substance Name: Amikacin [USP:INN:BAN]
RN: 37517-28-5
UNII: 84319SGC3C
InChIKey: LKCWBDHBTVXHDL-RMDFUYIESA-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

Molecular Weight

  • 585.6037
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Amikacin
  • Amikacin [USP:INN:BAN]

MeSH Heading

  • Amikacin

Synonyms

  • 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A
  • Amicacin
  • Amiglyde-V
  • Amikacillin
  • Amikacin
  • Amikacin Inhalation Solution
  • Amikacina
  • Amikacina [INN-Spanish]
  • Amikacine
  • Amikacine [INN-French]
  • Amikacinum
  • Amikacinum [INN-Latin]
  • Amikavet
  • Amikozit
  • Amukin
  • Antibiotic BB-K 8
  • Arikace
  • BAY 41-6551
  • BAY41-6551
  • BB-K 8
  • 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)-
  • EINECS 253-538-5
  • HSDB 3583
  • Kaminax
  • Lukadin
  • MAT2501
  • Mikavir
  • NSC 177001
  • 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
  • Pierami
  • Potentox
  • UNII-84319SGC3C

Systematic Names

  • Amikacin
  • D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-
  • 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)-
  • 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-

Registry Numbers

CAS Registry Number

  • 37517-28-5

FDA UNII

  • 84319SGC3C

Other Registry Numbers

  • 1079316-47-4
  • 108914-65-4
  • 110660-81-6
  • 110660-83-8
  • 111319-93-8
  • 38859-32-4

Related Registry Number

  • 110660-83-8

System Generated Number

  • 0037517285

Structure Descriptors

InChI

InChI=1S/C22H43N5O13/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/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1

InChIKey

LKCWBDHBTVXHDL-RMDFUYIESA-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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 6200mg/kg (6200mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Antimicrobial Agents and Chemotherapy. Vol. 13, Pg. 41, 1978.
mouse LD50 intravenous 280mg/kg (280mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 858, 1990.
mouse LD50 oral > 6gm/kg (6000mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.
mouse LD50 subcutaneous 6200mg/kg (6200mg/kg)   Japanese Journal of Antibiotics. Vol. 28, Pg. 415, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 203-204 deg C   EXP
log P (octanol-water) -8.780 (none)   EST
Water Solubility 1.85E+05 mg/L 25 EXP
Vapor Pressure 8.59E-30 mm Hg 25 EST
Henry's Law Constant 2.67E-42 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.46E-10 cm3/molecule-sec 25 EST

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