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Amikacin
AMK · amikacin hydrate · Amikacin base · amikin · amicacin · Amikacine · Amikacina · Amikacinum
Identifikatoren & physikalische Daten
| CAS No. | 37517-28-5 |
|---|---|
| Summenformel | C22H43N5O13 |
| Durchschnittliche Molmasse | 585,6 g/mol |
| Monoisotopische Masse | 585,28573644 g/mol |
| 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]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O |
| InChIKey | LKCWBDHBTVXHDL-RMDFUYIESA-N |
| PubChem CID | 37768 |
| ChEMBL | CHEMBL177 |
| ChEBI | CHEBI:2637 |
| EC No. | 253-538-5 |
| DTXSID | DTXSID3022586 |
| Lokaler Name | Amikacin |
Chemische & physikalische Eigenschaften
| XLogP | -7,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 332 |
| H-Brücken-Donoren | 13 |
| H-Brücken-Akzeptoren | 17 |
| Frei drehbare Bindungen | 10 |
| Schwere Atome | 40 |
| Formalladung | 0 |
| Komplexität | 819 |
| LogP (Verteilungskoeffizient) | -7.4 |
| LogS | -0.5 |
| Color/Form | White crystalline powder from methanol-isopropanol |
| Löslichkeit | 50In water, 1.85X10+5 mg/L at 25 °C4.97e+01 g/LH2O: 50 mg/mL, clear, colorlessSoluble in water (partly). |
| Siedepunkt | 632.23642.23°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/./Sulfate/ melts at ... about 225 °C with decomp. /Amikacin sulfate/ |
| Schmelzpunkt | 214203-204 °C (sesquihydrate)203 - 204 °C203℃ |
| Optical Rotation | Amorphous form, dec 220-230 °C,Specific optical rotation: +74.75 deg at 22 °C/D (in water), Freely soluble in water /Amikacin sulfate/Specific optical rotation: +99 deg at 23 °C/D (c = 1.0 in water) |
| Physical Description | Solid |
| Dissociation Constants | 8.1pKa1 = 6.7 (primary amine)pKa2 = 8.4 (primary amine)pKa3 = 8.4 (primary amine)pKa4 = 9.7 (primary amine) |
| Collision Cross Section | 235.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]233.7 Ų [M+Na]+ [CCS Type: TW |
| Dichte | 1.3764 (rough estimate) |
| Brechungsindex | 1.7500 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pKa 8.1 (Uncertain) |
| Aggregatzustand | solid |
| Farbe | white to off-white |
| Merck | 13,404 |
| BRN | 1445422 |
| Stabilität | Hygroscopic |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChIKey | LKCWBDHBTVXHDL-RMDFUYIESA-N |
| SMILES | N([C@H]1[C@@H]([C@H]([C@@H]([C@H](C1)N)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CN)O)O[C@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)N)O)CO)C(=O)[C@@H](O)CCN |
| EPA chemische Informationen | Amikacin (37517-28-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH317 (75%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (25%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H332 (25%): Harmful if inhaled [Warning Acute toxicity, inhalation]H360 (25%): May damage fertility or the unborn child [Danger Reproductive toxicity]H372 (25%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]P203, P260, P261, P264, P264+P265, P270, P271, P272, P280, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 15-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21141 |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including amikacin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including amikacin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Amikacin sulfate/The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Amikacin sulfate is included on this list. /Amikacin sulfate/Implantation or injectable dosage form new animal drugs. Amikacin. ... Indications for use. For treatment of genitourinary tract infections (cystitis) caused by susceptible strains of Escherichia coli and Proteus spp. and skin and soft tissue infections caused by susceptible strains of Pseudomonas spp. and E. coli. ... Limitations. Do not use in horses intended for human consumption. Federal law restricts this drug to use by or on the order of a licensed veterinarian. |
Anwendungen & Verwendung
Beschreibung
Amikacin is made semisynthetically from kanamycin A. Interestingly, the L-hydroxyaminobutyryl amide (HABA) moiety attached to N-3 inhibits adenylation and phosphorylation in the distant amino sugar ring (at C-2′and C-3′), even though the HABA substituent is not where the enzymatic reaction takes place. This effect is attributed to decreased binding to the R factor–mediated enzymes.
Verwenden
Amikacin is a semi-synthetic derivative of kanamycin. It is much less sensitive to the enzymes that inactivate aminoglycoside antibiotics. The spectrum is similar to that of gentamicin. Amikacin principally finds use in the treatment of infections arising from bacteria that are resistant to gentamicin and/or tobramycin.