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Also known as: 49842-07-1, Tobramycin sulphate, Nebcin, Tobramycinsulfate, 79645-27-5, Mls000069826

Molecular Formula

C₁₈H₃₉N₅O₁₃S

Molecular Weight

565.6 g/mol

InChI Key

ZEUUPKVZFKBXPW-TWDWGCDDSA-N

An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.

1 2D Structure

Nebicina

2 Identification

2.1 Computed Descriptors

2.1.1 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;sulfuric acid

2.1.2 InChI

InChI=1S/C18H37N5O9.H2O4S/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;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1

2.1.3 InChI Key

ZEUUPKVZFKBXPW-TWDWGCDDSA-N

2.1.4 Canonical SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N.OS(=O)(=O)O

2.1.5 Isomeric SMILES

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.OS(=O)(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Brulamycin

2. Nebcin

3. Nebicin

4. Nebramycin Factor 6

5. Obracin

6. Sulfate, Tobramycin

7. Tobracin

8. Tobramycin

2.2.2 Depositor-Supplied Synonyms

1. 49842-07-1

2. Tobramycin Sulphate

3. Nebcin

4. Tobramycinsulfate

5. 79645-27-5

6. Mls000069826

7. Smr000058891

8. Dartobcin

9. Nebcine

10. Tobraneg

11. Tobrasix

12. (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 Sulfate

13. Opera_id_1050

14. Schembl2837

15. Chembl1200780

16. Hms2230j04

17. Mfcd00133864

18. Akos025310614

19. 842t071

20. A923784

21. Tobramycin Sulfate Salt, Aminoglycoside Antibiotic

22. Q-201838

23. 2-ethoxy-5-[(morpholine-4-carbonyl)-amino]-benzenesulfonylchloride

24. (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 Sulfate

25. (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 Sulfate

26. (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,sulfuric Acid

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₉N₅O₁₃S
Molecular Weight	565.6 g/mol
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	6
Exact Mass	565.22650749 g/mol
Monoisotopic Mass	565.22650749 g/mol
Topological Polar Surface Area	351 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	691
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 3
Drug Name	TOBRAMYCIN SULFATE
Active Ingredient	TOBRAMYCIN SULFATE
Company	AKORN (Application Number: A205179); BAXTER HLTHCARE CORP (Application Number: A206965); FRESENIUS KABI USA (Application Number: A065122); FRESENIUS KABI USA (Application Number: N050789); HOSPIRA (Application Number: A063111); HOSPIRA (Application Number: A063112); MYLAN LABS LTD (Application Number: A065407); TEVA PHARMS USA (Application Number: A063100); WEST-WARD PHARMS INT (Application Number: A063117); X GEN PHARMS (Application Number: A065013); XELLIA PHARMS APS (Application Number: A205685)

2 of 3
Drug Name	TOBRAMYCIN SULFATE (PHARMACY BULK)
Active Ingredient	TOBRAMYCIN SULFATE
Company	FRESENIUS KABI USA (Application Number: A065120)

3 of 3
Drug Name	TOBRAMYCIN SULFATE IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER
Active Ingredient	TOBRAMYCIN SULFATE
Company	HOSPIRA (Application Number: A063081)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Aminoglycosides [CS]; Aminoglycoside Antibacterial [EPC]

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