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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
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 Weight 777.0 g/mol
Molecular Formula C40H76N2O12
XLogP34.9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count9
Exact Mass776.53982586 g/mol
Monoisotopic Mass776.53982586 g/mol
Topological Polar Surface Area180 Ų
Heavy Atom Count54
Formal Charge0
Complexity1180
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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