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Chemistry

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Also known as: Rickamicin, Sisomycin, 32385-11-8, Sissomicin, Antibiotic 6640, Antibiotic 66-40

Molecular Formula

C₁₉H₃₇N₅O₇

Molecular Weight

447.5 g/mol

InChI Key

URWAJWIAIPFPJE-YFMIWBNJSA-N

FDA UNII

X55XSL74YQ

Antibiotic produced by Micromonospora inyoensis. It is closely related to gentamicin C1A, one of the components of the gentamicin complex (GENTAMICINS).

1 2D Structure

Sisomicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

2.1.2 InChI

InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1

2.1.3 InChI Key

URWAJWIAIPFPJE-YFMIWBNJSA-N

2.1.4 Canonical SMILES

CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O

2.1.5 Isomeric SMILES

C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O

2.2 Other Identifiers

2.2.1 UNII

X55XSL74YQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,5 Dehydrogentamicin

2. 4,5-dehydrogentamicin

3. Antibiotic 6640

4. Extramycin

5. Pathomycin

6. Rickamicin

7. Sch 13475

8. Sch-13475

9. Sch13475

10. Siseptin

11. Sisomicin Sulfate

12. Sisomicin Sulfate (2:5) Salt

13. Sisomycin

14. Sissomicin

15. Sizomycin

2.3.2 Depositor-Supplied Synonyms

1. Rickamicin

2. Sisomycin

3. 32385-11-8

4. Sissomicin

5. Antibiotic 6640

6. Antibiotic 66-40

7. Sch 13475

8. Dehydrogentamicin Cla

9. Sch-13475

10. X55xsl74yq

11. Chebi:9169

12. Sisomin

13. D-streptamine, O-3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-

14. Sisomicinum

15. Sisomicina

16. Sisomicine

17. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

18. Sisomicine [inn-french]

19. Sisomicinum [inn-latin]

20. Salvamina

21. Sisomicina [inn-spanish]

22. Siseptin Sulfate

23. (1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranoside

24. (1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranoside

25. (2r,3r,4r,5r)-2-(((1s,2s,3r,4s,6r)-4,6-diamino-3-(((2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2h-pyran-3,5-diol

26. O-2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy-d-streptamine

27. Einecs 251-018-2

28. Unii-x55xsl74yq

29. Brn 1357913

30. Sisomicin [usan:inn:ban]

31. Sch13475

32. Sisomicin-sulfate

33. Sis

34. Siso

35. Sisomicin [inn]

36. Sisomicin [mi]

37. Sisomicin (usan/inn)

38. Sisomicin [usan]

39. Sisomicin [who-dd]

40. Schembl49395

41. O-2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6)-2-deoxy-d-streptamine

42. O-3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-l-streptamine

43. Chembl221886

44. Gtpl10858

45. (2s-cis)-4-o-(3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)-2-deoxy-6-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl)-d-streptamine

46. Zinc56870809

47. Akos015895179

48. Db12604

49. (2s-cis)-4-o-(3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)-2-deoxy-6-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl)-d-streptamine

50. 85s118

51. C00494

52. D02544

53. Gentamicin Sulfate Impurity A [ep Impurity]

54. Q3962119

55. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol

56. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

57. 2-deoxy-4-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl)-6-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-glycero-hex-4-enopyranosyl)-l-streptamine

58. O-3-deoxy-4-c-methyl-3-(methylamino)-.beta-l-arabinopyranosyl-(1->4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-glycero-hex-4-enopyranosyl-(1->6))-2-deoxy-l-streptamine

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₇N₅O₇
Molecular Weight	447.5 g/mol
XLogP3	-5.1
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	447.26929854 g/mol
Monoisotopic Mass	447.26929854 g/mol
Topological Polar Surface Area	214 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	643
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Anti-Bacterial Agents

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

4.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01G - Aminoglycoside antibacterials

J01GB - Other aminoglycosides

J01GB08 - Sisomicin

NDC API