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Amikacin

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Name

Amikacin

EINECS 253-538-5
CAS No. 37517-28-5 Density 1.6 g/cm3
PSA 331.94000 LogP -5.23210
Solubility water: 50 mg/mL, clear, colorless Melting Point 203-204oC (sesquihydrate)
Formula C22H43N5O13 Boiling Point 981.8 °C at 760 mmHg
Molecular Weight 585.609 Flash Point 547.6 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 37517-28-5 (AMIKACIN) Hazard Symbols IrritantXi
Synonyms

1-N-[L-(-)-g-Amino-a-hydroxybutyryl]kanamycin A;Amukin;Antibiotic BB-K 8;Arikace;BB-K 8;Lukadin;Potentox;

Article Data 12

Amikacin Synthetic route

C67H133N5O15Si10

37517-28-5

amikacin

Conditions
ConditionsYield
With hydrogen bromide In water pH=2 - 3;99.5%

C30H45N5O15

37517-28-5

amikacin

Conditions
ConditionsYield
With hydrazine hydrate for 4h; Reflux;99%
With hydrazine hydrate In water at 20℃; for 3h; Reflux;71.3%
With ammonium hydroxide
40732-91-0

γ-phthalimidoimino-α-hydroxybutyric acid

silyl kanamycin A

silyl kanamycin A

37517-28-5

amikacin

Conditions
ConditionsYield
Stage #1: γ-phthalimidoimino-α-hydroxybutyric acid With 2-Mercaptobenzothiazole; triethylamine In dichloromethane at 20℃; for 3h;
Stage #2: silyl kanamycin A In dichloromethane at 0 - 5℃; for 5h; Further stages;
93.6%

C16H20N2O4S2

59-01-8

kanamycin A

37517-28-5

amikacin

Conditions
ConditionsYield
Stage #1: kanamycin A With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile Reflux;
Stage #2: C16H20N2O4S2 In acetone; acetonitrile at 0 - 5℃; for 1h;
Stage #3: With hydrogenchloride In water; acetone; acetonitrile for 1h; pH=2 - 3; Solvent; Reagent/catalyst; Temperature;
83%

C23H43N5O14

37517-28-5

amikacin

Conditions
ConditionsYield
Stage #1: C23H43N5O14 With sodium hydroxide at -16 - 15℃; for 0.25h; Green chemistry;
Stage #2: With sodium hypochlorite In water at -16 - -10℃; for 2h; Temperature; Hofmann Rearrangement; Green chemistry;
65.2%
39831-55-5

amikacin sulfate

37517-28-5

amikacin

Conditions
ConditionsYield
With Amberlite ion exchange resin (OH-form) In water for 1h;

C51H124N4O11Si11

37517-28-5

amikacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetone / 0.5 h
1.2: 0.5 h / 0 °C
2.1: hydrogenchloride / water / 1 h / pH 2.34
3.1: hydrazine hydrate / water / 3 h / 20 °C / Reflux
View Scheme

C54H109N5O15Si8

37517-28-5

amikacin

Conditions
ConditionsYield
Stage #1: C54H109N5O15Si8 With hydrogenchloride In water for 1h; pH=3;
Stage #2: With hydrazine hydrate for 3h; Reflux;

C22H41BrN4O13

37517-28-5

amikacin

Conditions
ConditionsYield
With ammonia; potassium carbonate In acetone at 30℃; Temperature;
24424-99-5

di-tert-butyl dicarbonate

37517-28-5

amikacin

tetra-N-Boc-amikacin

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; dichloromethane; water at 20℃;99%

Amikacin Chemical Properties

Product Name: Amikacin (CAS NO.37517-28-5)


Molecular Formula: C22H43N5O13
Molecular Weight: 585.6g/mol
Mol File: 37517-28-5.mol
Einecs: 253-538-5
Boiling point: 981.8 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 547.6 °C
Density: 1.6 g/cm3
Water Solubility: 50 mg/mL, clear, colorless
Surface Tension: 103.2 dyne/cm
Enthalpy of Vaporization: 162.21 kJ/mol
Structure Descriptors of Amikacin (CAS NO.37517-28-5):
  InChI : InChI=1/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 
  Smiles: O([C@H]1[C@@H](C[C@H](N)[C@H]([C@@H]1O)O[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CN)NC([C@H](CCN)O)=O)[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)N)CO

Amikacin Uses

 Amikacin (CAS NO.37517-28-5) is most often used for treating severe, hospital-acquired infections with multidrug resistant Gram negative bacteria such as Pseudomonas aeruginosa, Acinetobacter, and Enterobacter.
Amikacin may be combined with a beta-lactam antibiotic for empiric therapy for people with neutropenia and fever.

Amikacin Toxicity Data With Reference

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.

Amikacin Safety Profile

Safety Information of Amikacin (CAS NO.37517-28-5):
Hazard Codes: XiIrritant
Risk Statements: 36/37/38
36:  Irritating to the eyes 
37:  Irritating to the respiratory system 
38:  Irritating to the skin 
Safety Statements: 26-36
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 

Amikacin Specification

 Amikacin ,its CAS NO. is 37517-28-5,the synonyms is 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A ; Amiglyde-V ; Amikacin Inhalation Solution ; Amikacinum ; Amikavet ; Antibiotic BB-K 8 ; 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 ; 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 ; UNII-84319SGC3C ; 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- .

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