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Chemistry

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Also known as: 145435-72-9, Ml-1709460, Ml-1,709,460, Ml-460, Ze856183s0, (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-11-(((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one

Molecular Formula

C₄₀H₇₆N₂O₁₂

Molecular Weight

777.0 g/mol

InChI Key

VWAMTBXLZPEDQO-UZSBJOJWSA-N

FDA UNII

ZE856183S0

Gamithromycin is an antibiotic used in cattle.

1 2D Structure

Gamithromycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one

2.1.2 InChI

InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1

2.1.3 InChI Key

VWAMTBXLZPEDQO-UZSBJOJWSA-N

2.1.4 Canonical SMILES

CCCN1CC(C(C(C(OC(=O)C(C(C(C(C(CC1C)(C)O)OC2C(C(CC(O2)C)N(C)C)O)C)OC3CC(C(C(O3)C)O)(C)OC)C)CC)(C)O)O)C

2.1.5 Isomeric SMILES

CCCN1C[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H]1C)(C)O)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)CC)(C)O)O)C

2.2 Other Identifiers

2.2.1 UNII

ZE856183S0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Zactran

2.3.2 Depositor-Supplied Synonyms

1. 145435-72-9

2. Ml-1709460

3. Ml-1,709,460

4. Ml-460

5. Ze856183s0

6. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-11-(((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one

7. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one

8. Gamithromycin [usan:inn]

9. Unii-ze856183s0

10. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8

11. Gamithromycin [mi]

12. Gamithromycin [inn]

13. Gamithromycin [usan]

14. Chembl2107342

15. Dtxsid90904260

16. Gamithromycin [green Book]

17. Ex-a1349

18. Mfcd09954125

19. S5328

20. Zinc169292837

21. Cs-7858

22. Db11416

23. Ds-4441

24. Gamithromycin 100 Microg/ml In Methanol

25. Ac-32611

26. Gamithromycin [ema Epar Veterinary]

27. Hy-108365

28. C72760

29. 435g729

30. A884620

31. J-008105

32. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-13-((2,6-dideoxy-3-c-methyl-3-o-methyl-.alpha.-l-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-((3,4,6-trideoxy-3-(dimethylamino)-.beta.-d-xylo-hexopyranosyl)oxy)-1-oxa-7-azacyclopentadecan-15-one

33. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-13-[(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranosyl)

34. (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-13-[(2,6-dideoxy-3-cmethyl-3-o-methyl-a-l-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-d-xylo-hexopyranosyl]oxy]-1-oxa-7-azacyclopentadecan-15-one

35. 1-oxa-7-azacyclopentadecan-15-one, 13-((2,6-dideoxy-3-c-methyl-3-o-methyl-.alpha.-l-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-((3,4,6-trideoxy-3-(dimethylamino)-.beta.-d-xylo-hexopyranosyl)oxy)-, (2r,3s,4r,5s,8r,10r,11r,12s,13s,14r)-

36. 1-oxa-7-azacyclopentadecan-15-one,13-[(2,6-dideoxy-3-c-methyl-3-o-methyl-a-l-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-b-d-xylo-hexopyranosyl]oxy]-,[2r-(2r*,3s*,4r*,5s*,8r*,10r*,11r*,12s*,13s*,14r*)]-

2.4 Create Date

2012-08-20

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₇₆N₂O₁₂
Molecular Weight	777.0 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	9
Exact Mass	776.53982586 g/mol
Monoisotopic Mass	776.53982586 g/mol
Topological Polar Surface Area	180 Å²
Heavy Atom Count	54
Formal Charge	0
Complexity	1180
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

* Cattle:

Treatment and metaphylaxis of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida and Histophilus somni. The presence of the disease in the herd should be established before metaphylactic use.

* Pigs:

Treatment of swine respiratory disease (SRD) associated with Actinobacillus pleuropneumoniae, Pasteurella multocida, Haemophilus parasuis and Bordetella bronchiseptica.

* Sheep:

Treatment of infectious pododermatitis (foot rot) associated with virulent Dichelobacter nodosus and Fusobacterium necrophorum requiring systemic treatment.

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 ATC Code

QJ01FA95

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