Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00832)
Name
Amikacin
Synonyms    Click to Show/Hide the Synonyms of This API
amikacin; 37517-28-5; Amicacin; Amikin; amikacine; Amikacina; Amikacinum; Amikacillin; Antibiotic BB-K 8; Amukin; Lukadin; Amikacine [INN-French]; Amikacinum [INN-Latin]; Amikacina [INN-Spanish]; Amikacin Base; BB-K8; Kaminax; 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A; Amikacin free base; Briclin; UNII-84319SGC3C; Amikavet; BAY 41-6551; CHEBI:2637; Amiglyde-V; Arikace; ANTIBIOTIC BB-K8; (2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide; Mikavir; N1-[(S)-4-Amino-2-hydroxybutyryl]kanamycin A; 84319SGC3C; 37517-28-5 (free base); BAY416651; NSC177001; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide; BB-K 8; NCGC00093350-02; DSSTox_CID_2586; Amikacin Dihydrate; DSSTox_RID_76645; DSSTox_GSID_22586; (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide; AMK; Amikozit; Potentox; HSDB 3583; Amikacin (USP/INN); C22H43N5O13; EINECS 253-538-5; NSC 177001; Amikacin [USP:INN:BAN]; Amikacin Inhalation Solution; Arikayce liposomal; NSC-177001; NCGC00093350-05; Amikacin,(S); (2s)-N-[(1r,2s,3s,4r,5s)-4-[(2r,3r,4s,5s,6r)-6-(Aminomethyl)-3,4,5-Tris(Oxidanyl)oxan-2-Yl]oxy-5-Azanyl-2-[(2s,3r,4s,5s,6r)-4-Azanyl-6-(Hydroxymethyl)-3,5-Bis(Oxidanyl)oxan-2-Yl]oxy-3-Oxidanyl-Cyclohexyl]-4-Azanyl-2-Oxidanyl-Butanamide; AKN; Amikin (Disulfate); MFCD00883675; BAY41-6551; 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; nktr-061; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]; Prestwick3_000395; CHEMBL177; SCHEMBL2985; CAS-37517-28-5; BSPBio_000609; 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)-; BPBio1_000671; DTXSID3022586; 37517-28-5 (anhydr; GTPL10894; HY-B0509A; MAT2501; ZINC8214483; Tox21_111201; BDBM50237603; MFCD11045969; STK039706; AKOS005383276; Tox21_111201_1; BAY 416651; DB00479; MCULE-6148260173; NCGC00093350-03; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-4-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide; 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-(1-6)-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-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-; H978; O-3-Amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine; AB00513828; 6462-EP1441224A2; 6462-EP2292612A2; 6462-EP2295402A2; 6462-EP2301544A1; C06820; D02543; AB00513828_06; Amikacin, Antibiotic for Culture Media Use Only; 517A285; Q408529; W-106531; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide; (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide; (2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S; (2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S ,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide; (S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4-((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide; D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-; 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-
Clinical Status
Approved
PubChem CID
37768
Formula
C22H43N5O13
Canonical SMILES
C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=37768"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 585.6 Topological Polar Surface Area 332
XlogP -7.9 Complexity 819
Heavy Atom Count 40 Rotatable Bond Count 10
Hydrogen Bond Donor Count 13 Hydrogen Bond Acceptor Count 17
Full List of Drug Formulations (DFMs) Containing This API
          Amikacin eq 250mg injectable Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium Metabisulfite; Sodium Citrate; Sulfuric Acid
                   Dosage Form Injectable
                   Company Heritage Pharmaceuticals D/B/A Avet Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [1]
Sulfuric acid DIG Info Carbonic anhydrase V (Ki = 680 nM) [2]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Trisodium Citrate Dihydrate; Sodium Metabisulfite; Water; Sulfuric Acid; Sodium Hydroxide
                   Dosage Form Injectable
                   Company Teva Parenteral Medicines
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sulfuric acid DIG Info Carbonic anhydrase V (Ki = 680 nM) [2]
          Amikacin 590 mg/8.4 ml injectable Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Dipalmitoylphosphatidylcholine (Dppc); Cholesterol; Sodium Chloride; Sodium Hydroxide; Water
                   Dosage Form Injectable
                   Company Insmed orporated
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Cholesterol DIG Info Nuclear receptor ROR-gamma (EC50 = 20 nM) [3]
References
1 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
2 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
3 Retinoic Acid Receptor-Related Orphan Receptor t (RORt) Agonists as Potential Small Molecule Therapeutics for Cancer Immunotherapy. J Med Chem. 2018 Jul 26; 61(14):5794-5804.

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