Tobramycin

Details

• Internal ID: 4e9551d5-a79c-4f06-b1ed-de345fdf3459
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > 2-deoxystreptamine aminoglycosides > 4,6-disubstituted 2-deoxystreptamines
• IUPAC Name: (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
• SMILES (Canonical): C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N
• SMILES (Isomeric): C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)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[C@@H]([C@H](O3)CN)O)N)N
• InChI: InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
• InChI Key: NLVFBUXFDBBNBW-PBSUHMDJSA-N
• Popularity: 16,272 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₇N₅O₉
• Molecular Weight: 467.50 g/mol
• Exact Mass: 467.25912777 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: -6.20
• Atomic LogP (AlogP): -6.30
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 32986-56-4
• Nebramycin factor 6
• Nebramycin VI
• Nebramycin 6
• Tobi
• Tobramicin
• 3'-Deoxykanamycin B
• Aktob
• Deoxykanamycin B
• Tobrex
• Tobi Podhaler
• Nebcin
• vantobra
• Tobralex
• Tobramycin Base
• 1-Epitobramycin
• Tobramycetin
• Tobramycinum
• Gotabiotic
• Tobradistin
• Tobramicina
• Tobramycine
• Tobrased
• Bethkis
• Tobacin
• Kitabis Pak
• Tobramitsetin
• Tenebrimycin
• Tenemycin
• Tobramaxin
• TOBRAMYCIN SULFATE
• NEBRAMYCIN
• Distobram
• Nebramycin factir 6
• Kitabis
• NSC 180514
• HSDB 3259
• UNII-VZ8RRZ51VK
• VZ8RRZ51VK
• Tobramycine [INN-French]
• Tobramycinum [INN-Latin]
• Tobramicina [INN-Spanish]
• EINECS 251-322-5
• Lilly 47663
• Tobracin (TN)
• Tobrex (TN)
• BRN 1357507
• DTXSID8023680
• CHEBI:28864
• NSC-180514
• DTXCID903680
• (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
• Obramycin
• ZYLET COMPONENT TOBRAMYCIN
• TOBRADEX COMPONENT TOBRAMYCIN
• TOBRAMYCIN COMPONENT OF ZYLET
• TOBRASONE COMPONENT TOBRAMYCIN
• TOBRADEX ST COMPONENT TOBRAMYCIN
• Tobramycin [USAN:USP:INN:BAN:JAN]
• TOBRAMYCIN COMPONENT OF TOBRADEX
• TOBRAMYCIN COMPONENT OF TOBRASONE
• Nebicin
• TOBRAMYCIN COMPONENT OF TOBRADEX ST
• Tobramycine (INN-French)
• Tobramycinum (INN-Latin)
• Tobramicina (INN-Spanish)
• TOBRAMYCIN (MART.)
• TOBRAMYCIN [MART.]
• TOBRAMYCIN (USP-RS)
• TOBRAMYCIN [USP-RS]
• (2S,3R,4S,5S,6R)-4-amino-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol
• O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-6))-2-deoxy-L-streptamine
• O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine
• C18H37N5O9
• TOBRAMYCIN (EP MONOGRAPH)
• TOBRAMYCIN [EP MONOGRAPH]
• TOBRAMYCIN (USP MONOGRAPH)
• TOBRAMYCIN [USP MONOGRAPH]
• Tobramycin (USAN:USP:INN:BAN:JAN)
• (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside
• (2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
• O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine
• TOB
• TOY
• SR-05000001726
• SPRC-AB01
• torbamycin
• Nebramycin Factor 6;Deoxykanamycin B
• Tobramycin,(S)
• Nebcin (Sulfate)
• NCGC00016814-01
• (2S,3R,4S,5S,6R)-4-amino-2-((1S,2S,3R,4S,6R)-4,6-diamino-3-((2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol
• D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-.ALPHA.-D-RIBO-HEXOPYRANOSYL-(1->4))-2-DEOXY-
• D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribo-hexopyranosyl-(1->4)]-2-deoxy-
• O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-[2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4)]-2-deoxy-D-streptamine
• Bethkis (TN)
• CAS-32986-56-4
• Tobramycin Deuterated
• Tobramycin Inhalation
• Tobramycinum (Latin)
• AT02 - Tobramycin
• D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-4))-2-deoxy-
• Tobi (TN)
• Spectrum_001072
• TOBRAMYCIN [MI]
• TOBRAMYCIN [INN]
• TOBRAMYCIN [JAN]
• Prestwick3_000544
• Spectrum2_000078
• Spectrum3_000588
• Spectrum4_000752
• Spectrum5_001038
• TOBRAMYCIN [HSDB]
• TOBRAMYCIN [USAN]
• TOBRAMYCIN [VANDF]
• Tobramycin (JP17/USP)
• SCHEMBL2838
• CHEMBL1747
• TOBRAMYCIN [WHO-DD]
• BSPBio_000587
• BSPBio_002036
• KBioGR_001104
• KBioSS_001552
• 4-(2,6-Diamino-2,3,6-trideoxy-alpha-D-glycopyranosyl)-6-(3-amino-3-deoxy-alpha-D-glycopyranosyl)-2-deoxystreptamine
• MLS000069544
• Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-tyrideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D-
• BIDD:GT0503
• SPECTRUM1500579
• Tobramycin Inhalation Solution
• Tobramycin Ophthalmic Solution
• SPBio_000295
• BPBio1_000647
• TOBRAMYCIN [ORANGE BOOK]
• GTPL10930
• KBio2_001552
• KBio2_004120
• KBio2_006688
• KBio3_001536
• TobramycinInhalation Solution Pak
• J01GB01
• S01AA12
• HMS2090B16
• HMS2092M17
• HMS2096N09
• HMS3713N09
• Pharmakon1600-01500579
• HY-B0441
• Tox21_110626
• BDBM50366778
• CCG-39936
• HB4564
• NSC757352
• s2514
• Tobradex (tobramycin + dexamethasone)
• AKOS016339662
• DB00684
• KS-1405
• NSC-757352
• NCGC00178852-01
• NCGC00178852-02
• (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxy-tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]-6-(hydroxymethyl)tetrahydropyran-3,5-diol
• SMR000058793
• Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D-
• SBI-0051915.P003
• AB00513858
• T2503
• C00397
• D00063
• AB00052438-12
• AB00052438_13
• AB00052438_14
• EN300-7480857
• SR-01000721898
• Tobramycin, Antibiotic for Culture Media Use Only
• Q-201837
• Q1758380
• SR-01000721898-2
• SR-05000001726-1
• SR-05000001726-2
• BRD-K05619559-001-12-7
• (1S,2S,3R,4S,6R)-4,6-diamino-3-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside
• D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribohexopyranosyl-(1->4)]-2-deoxy-
• D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1?6)-O-[2,6-diamino-2,3,6-trideoxy-.alpha.-D-ribo-hexopyranosyl-(1?4)]-2-deoxy-
• O-[3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)]-O-[2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1->4)]-2-deoxy-D-streptamine
• O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-.ALPHA.-D-RIBO-HEXOPYRANOSYL-(1.ALPHA.6))-2-DEOXY-L-STREPTAMINE
• O-3-Amino-3-deoxy-?-D-glucopyranosyl-(1-6)-O-[2,6-diamino-2,3,6-trideoxy-?-D-ribohexopyranosyl-(1-4)]-2-deoxy-D-streptamine
• O-3-AMINO-3-DEOXY-alpha-D-GLUCOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,6-TRIDEOXY-alpha-D-RIBO-HEXOPYRANOSYL-(1alpha6))-2-DEOXY-L-STREPTAMINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9849	98.49%
Caco-2	-	0.8837	88.37%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Lysosomes	0.5127	51.27%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9777	97.77%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9200	92.00%
CYP3A4 substrate	+	0.5497	54.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6873	68.73%
CYP3A4 inhibition	-	0.9728	97.28%
CYP2C9 inhibition	-	0.9359	93.59%
CYP2C19 inhibition	-	0.9117	91.17%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9052	90.52%
CYP2C8 inhibition	-	0.7502	75.02%
CYP inhibitory promiscuity	-	0.9398	93.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6546	65.46%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9310	93.10%
Skin irritation	-	0.7932	79.32%
Skin corrosion	-	0.9232	92.32%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7073	70.73%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.8855	88.55%
skin sensitisation	-	0.9316	93.16%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	IV	0.6190	61.90%
Estrogen receptor binding	-	0.5467	54.67%
Androgen receptor binding	-	0.7471	74.71%
Thyroid receptor binding	+	0.5317	53.17%
Glucocorticoid receptor binding	+	0.6178	61.78%
Aromatase binding	-	0.7017	70.17%
PPAR gamma	+	0.5361	53.61%
Honey bee toxicity	-	0.7406	74.06%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.9480	94.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	97.49%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.06%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.98%	95.93%
CHEMBL3589	P55263	Adenosine kinase	86.18%	98.05%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.18%	95.58%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.79%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.17%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.84%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.26%	94.45%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	81.01%	82.86%
CHEMBL4581	P52732	Kinesin-like protein 1	80.16%	93.18%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 36294
• LOTUS: LTS0197343
• wikiData: Q1758380