Amikacin

Details

• Internal ID: 6df1e369-ff4d-4e2e-8038-5e876f1f4810
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > 2-deoxystreptamine aminoglycosides > 4,6-disubstituted 2-deoxystreptamines
• IUPAC Name: (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
• InChI: 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
• InChI Key: LKCWBDHBTVXHDL-RMDFUYIESA-N
• Popularity: 21,742 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₄₃N₅O₁₃
• Molecular Weight: 585.60 g/mol
• Exact Mass: 585.28573644 g/mol
• Topological Polar Surface Area (TPSA): 332.00 Ų
• XlogP: -7.90
• Atomic LogP (AlogP): -8.42
• H-Bond Acceptor: 17
• H-Bond Donor: 13
• Rotatable Bonds: 10

Synonyms

• 37517-28-5
• Amikacinum
• Amicacin
• Lukadin
• Amikin
• amikacine
• Amikacina
• Amikavet
• Arikace
• Amikacillin
• Mikavir
• Potentox
• Antibiotic BB-K 8
• Amukin
• Amikacine [INN-French]
• Amikacinum [INN-Latin]
• Amikacina [INN-Spanish]
• Amikacin Base
• BB-K8
• Kaminax
• Amikozit
• 1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin A
• CHEBI:2637
• BAY 41-6551
• HSDB 3583
• Arikayce liposomal
• Amikacin free base
• EINECS 253-538-5
• Briclin
• NSC 177001
• UNII-84319SGC3C
• Amikacin hydrate
• DTXSID3022586
• Amiglyde-V
• 84319SGC3C
• NSC-177001
• Amikacin [USP:INN:BAN]
• ANTIBIOTIC BB-K8
• DTXCID002586
• (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
• 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
• MAT2501
• N1-[(S)-4-Amino-2-hydroxybutyryl]kanamycin A
• 37517-28-5 (free base)
• Amikacin Dihydrate
• NSC177001
• (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
• AMK
• BB-K 8
• Amikacin disulfate
• NCGC00093350-02
• Amikacine (INN-French)
• Amikacinum (INN-Latin)
• Amikacina (INN-Spanish)
• AMIKACIN (MART.)
• AMIKACIN [MART.]
• AMIKACIN (USP-RS)
• AMIKACIN [USP-RS]
• Amikacin (USP:INN:BAN)
• (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
• 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
• AMIKACIN (EP MONOGRAPH)
• AMIKACIN [EP MONOGRAPH]
• AMIKACIN (USP MONOGRAPH)
• AMIKACIN [USP MONOGRAPH]
• (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
• Amikacin (USP/INN)
• SR-01000722004
• 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
• Amikacin; 6-O-(3-Amino-3-deoxy-?-d-glucopyranosyl)-4-O-(6-amino-6-deoxy-?-d-glucopyranosyl)-1-N-[(2S)-4-amino-2-hydroxybutanoyl]-2-deoxy-d-streptamine
• Amikacinum (Latin)
• Amikin (Disulfate)
• MFCD00883675
• AT03 - Amikacin
• BAY41-6551
• Amikacin (free base)
• nktr-061
• AMIKACIN [HSDB]
• AMIKACIN [INN]
• AMIKACIN [JAN]
• AMIKACIN [MI]
• AMIKACIN [VANDF]
• Prestwick3_000395
• AMIKACIN [WHO-DD]
• AMIKACIN [WHO-IP]
• 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
• TD1 - Therapeutic Drug mixture
• GTPL10894
• HY-B0509A
• D06AX12
• J01GB06
• S01AA21
• AMIKACINUM [WHO-IP LATIN]
• Tox21_111201
• BDBM50237603
• AKOS005383276
• Tox21_111201_1
• DB00479
• 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
• AS-76985
• 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)-
• 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
• AB00513828
• C06820
• D02543
• AB00513828_06
• Amikacin, Antibiotic for Culture Media Use Only
• EN300-7481440
• A823716
• Q408529
• SR-01000722004-6
• 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)-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
• ,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide
• 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)]-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-
• 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
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9766	97.66%
Caco-2	-	0.8940	89.40%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Mitochondria	0.3940	39.40%
OATP2B1 inhibitior	-	0.8646	86.46%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7334	73.34%
P-glycoprotein inhibitior	-	0.7230	72.30%
P-glycoprotein substrate	-	0.8400	84.00%
CYP3A4 substrate	+	0.6347	63.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8256	82.56%
CYP3A4 inhibition	-	0.9434	94.34%
CYP2C9 inhibition	-	0.9237	92.37%
CYP2C19 inhibition	-	0.9128	91.28%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	-	0.9381	93.81%
CYP2C8 inhibition	-	0.5983	59.83%
CYP inhibitory promiscuity	-	0.8866	88.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7062	70.62%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8000	80.00%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3648	36.48%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.5049	50.49%
skin sensitisation	-	0.9112	91.12%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.7837	78.37%
Acute Oral Toxicity (c)	IV	0.5094	50.94%
Estrogen receptor binding	+	0.5744	57.44%
Androgen receptor binding	-	0.5405	54.05%
Thyroid receptor binding	+	0.5327	53.27%
Glucocorticoid receptor binding	+	0.6946	69.46%
Aromatase binding	+	0.5906	59.06%
PPAR gamma	+	0.6257	62.57%
Honey bee toxicity	-	0.7204	72.04%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.9803	98.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	158.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	98.77%	95.58%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL2094135	Q96BI3	Gamma-secretase	96.59%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.45%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.60%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.87%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.46%	99.17%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	89.28%	82.86%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.14%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.12%	91.24%
CHEMBL4581	P52732	Kinesin-like protein 1	86.79%	93.18%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.59%	94.33%
CHEMBL226	P30542	Adenosine A1 receptor	85.97%	95.93%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.68%	92.29%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.43%	95.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.55%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.45%	96.95%
CHEMBL2514	O95665	Neurotensin receptor 2	83.36%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.82%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.51%	96.21%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.13%	94.00%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	82.06%	88.42%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.02%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.95%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.66%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.05%	90.71%
CHEMBL5255	O00206	Toll-like receptor 4	80.92%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.91%	91.19%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.91%	97.29%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.59%	89.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 37768
• LOTUS: LTS0089808
• wikiData: Q408529