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| CAS No.: | 37517-28-5 |
|---|---|
| Name: | AMIKACIN |
| Molecular Structure: | |
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|
|
| Formula: | C22H43N5O13 |
| Molecular Weight: | 585.609 |
| Synonyms: | 1-N-[L-(-)-g-Amino-a-hydroxybutyryl]kanamycin A;Amukin;Antibiotic BB-K 8;Arikace;BB-K 8;Lukadin;Potentox; |
| EINECS: | 253-538-5 |
| Density: | 1.6 g/cm3 |
| Melting Point: | 203-204oC (sesquihydrate) |
| Boiling Point: | 981.8 °C at 760 mmHg |
| Flash Point: | 547.6 °C |
| Solubility: | water: 50 mg/mL, clear, colorless |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 331.94000 |
| LogP: | -5.23210 |
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- 37517-28-5
amikacin
| Conditions | Yield |
|---|---|
| With hydrogen bromide In water pH=2 - 3; | 99.5% |
- 37517-28-5
amikacin
| 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
- 37517-28-5
amikacin
| 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% |
| 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% |
- 37517-28-5
amikacin
| 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 | Yield |
|---|---|
| With Amberlite ion exchange resin (OH-form) In water for 1h; |
- 37517-28-5
amikacin
| 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 |
- 37517-28-5
amikacin
| Conditions | Yield |
|---|---|
| Stage #1: C54H109N5O15Si8 With hydrogenchloride In water for 1h; pH=3; Stage #2: With hydrazine hydrate for 3h; Reflux; |
- 37517-28-5
amikacin
| Conditions | Yield |
|---|---|
| With ammonia; potassium carbonate In acetone at 30℃; Temperature; |
| Conditions | Yield |
|---|---|
| With triethylamine In 1,4-dioxane; dichloromethane; water at 20℃; | 99% |
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Chemistry
Product Name: Amikacin (CAS NO.37517-28-5)
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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
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.
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. |
Safety Profile
Safety Information of Amikacin (CAS NO.37517-28-5):
Hazard Codes: Xi
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
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- .