Amikacin supplier | CasNO.37517-28-5

Name
AMIKACIN
EINECS 253-538-5
CAS No. 37517-28-5
Article Data12
CAS DataBase
Density 1.6 g/cm³
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
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-N-[L-(-)-g-Amino-a-hydroxybutyryl]kanamycin A;Amukin;Antibiotic BB-K 8;Arikace;BB-K 8;Lukadin;Potentox;
PSA 331.94000
LogP -5.23210

Synthetic route

: C67H133N5O15Si10

: 37517-28-5
amikacin

Conditions

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

: C30H45N5O15

: 37517-28-5
amikacin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C51H124N4O11Si11

: 37517-28-5
amikacin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 37517-28-5
amikacin

: 134-81-6
benzil

: C78H75N5O17

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	92%

: 37517-28-5
amikacin

: 100-10-7
4-dimethylamino-benzaldehyde

: C58H79N9O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	92%

: 37517-28-5
amikacin

: 39831-55-5
amikacin sulfate

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 10℃; for 6h; Temperature;	91.5%

: 121-33-5
vanillin

: 37517-28-5
amikacin

: C54H67N5O21

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	91%

: 100-52-7
benzaldehyde

: 37517-28-5
amikacin

: C50H59N5O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	90%

: 119-61-9
benzophenone

: 37517-28-5
amikacin

: C74H75N5O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	90%

: 119-53-9
2-hydroxy-2-phenylacetophenone

: 37517-28-5
amikacin

: C78H83N5O17

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	89%

: 37517-28-5
amikacin

: 98-86-2
acetophenone

: C54H67N5O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	89%

: 37517-28-5
amikacin

: 67-64-1
acetone

: C34H59N5O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	89%

: 90-02-8
salicylaldehyde

: 37517-28-5
amikacin

: C50H59N5O17

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	88%

: 37517-28-5
amikacin

: 104-55-2
3-phenyl-propenal

: C58H67N5O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	87%

: 37517-28-5
amikacin

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: C34H63N9O13

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 3h; Reflux;	86%

: 24424-99-5
di-tert-butyl dicarbonate

: 37517-28-5
amikacin

: 3,6',3",1'"-tetra-N-(tert-butoxycarbonyl)-amikacin

Conditions

Conditions	Yield
With triethylamine In methanol	79%
With triethylamine In methanol

: 5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one

: 37517-28-5
amikacin

A: C29H47N5O14

B: C36H51N5O15

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 12h; Solvent;	A 77% B 14%

...Expand

: 37517-28-5
amikacin

: 79-06-1
2-propenamide

: 97856-35-4
N-succinimidyl p-vinylbenzoate

5\'\'\-(p-vinylbenzoyl)amikacin-acrylamide copolymer, ratio: 10/90, Mr = 90 KDa; Monomer(s): 5\'\'\-(p-vinylbenzoyl)amikacin; acrylamide: 5\'\'\-(p-vinylbenzoyl)amikacin-acrylamide copolymer, ratio: 10/90, Mr = 90 KDa; Monomer(s): 5\'\'\-(p-vinylbenzoyl)amikacin; acrylamide

Conditions

Conditions	Yield
Stage #1: amikacin; N-succinimidyl p-vinylbenzoate With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h; Stage #2: 2-propenamide With α,α'-azodiizobutyramidine-dihydrochloride In water at 60℃; for 4h;	70%

...Expand

: 619-66-9
4-Carboxybenzaldehyde

: 37517-28-5
amikacin

: C30H47N5O15

Conditions

Conditions	Yield
With pyridine In dimethyl sulfoxide at 60℃; for 20h;	70%

: 3-(cyclopent-1-en-1-yl)-5-(4-methoxybenzoyl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one

: 37517-28-5
amikacin

A: C30H49N5O15

B: C38H55N5O17

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 16h;	A 70% B 23%

...Expand

: 375-22-4
heptafluorobutyric Acid

: 37517-28-5
amikacin

: C-3-azidoamikacin tri(heptafluorobutyric acid)

Conditions

Conditions	Yield
Stage #1: amikacin With 1H-imidazole-1-sulfonyl azide hydrochloride; sodium hydroxide In aq. phosphate buffer at 20℃; for 18h; pH=8; Stage #2: heptafluorobutyric Acid In acetone at 40℃; regioselective reaction;	65%

: 37517-28-5
amikacin

: C22H35N13O13

Conditions

Conditions	Yield
With triflic azide; triethylamine; zinc(II) chloride In methanol; water at 20℃; Inert atmosphere;	64%

: azidoacetic acid succinimidyl ester

: 37517-28-5
amikacin

: C26H45N11O15

Conditions

Conditions	Yield
With potassium carbonate In methanol; water for 20h;	26%

: 37517-28-5
amikacin

: 56-65-5
ATP

: C32H55N10O19P

Conditions

Conditions	Yield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);

: 37517-28-5
amikacin

: 97856-35-4
N-succinimidyl p-vinylbenzoate

A: N-{3-[5-amino-2-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-(6-aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexylcarbamoyl]-3-hydroxy-propyl}-4-vinyl-benzamide

B: N-{6-[6-amino-3-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-(4-amino-2-hydroxy-butyrylamino)-2-hydroxy-cyclohexyloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl}-4-vinyl-benzamide

C: C40H55N5O15

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h; Title compound not separated from byproducts;

...Expand

: 37517-28-5
amikacin

: 97856-35-4
N-succinimidyl p-vinylbenzoate

poly[5''-(p-vinylbenzoyl)amikacin], Mr = 150 KDa; Monomer(s): 5''-(p-vinylbenzoyl)amikacin: poly[5''-(p-vinylbenzoyl)amikacin], Mr = 150 KDa; Monomer(s): 5''-(p-vinylbenzoyl)amikacin

Conditions

Conditions	Yield
Stage #1: amikacin; N-succinimidyl p-vinylbenzoate With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With α,α'-azodiizobutyramidine-dihydrochloride In water at 60℃; for 8h;

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: Xi Irritant
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- .

Product Name

AMIKACIN

Synthetic route

Amikacin Chemical Properties

Amikacin Uses

Amikacin Toxicity Data With Reference

Amikacin Safety Profile

Amikacin Specification

Related Products

Hot Products