Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C40H76N2O12 |
| Molecular Weight | 777.0376 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 18 / 18 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN1C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@H]1C
InChI
InChIKey=VWAMTBXLZPEDQO-UZSBJOJWSA-N
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
| Molecular Formula | C40H76N2O12 |
| Molecular Weight | 777.0376 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 18 / 18 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20557439
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20557439
Gamithromycin, the active pharmaceutical ingredient of ZACTRAN is a novel 7a-azalide that has been developed for treatment and prevention of bovine respiratory disease (BRD). The compound belongs to the 15-membered semi-synthetic macrolide antibiotics of the azalide sub-class with a uniquely positioned alkylated nitrogen at the 7a-position of the lactone ring. Macrolide antibiotics in general have bacteriostatic action by inhibiting bacterial RNA dependent protein biosynthesis, but can also be bactericidal. They reversibly bind to 23S ribosomal RNA in the 50S-subunit of prokaryotic ribosomes and prevent protein elongation during the translocation process. In vitro data show that gamithromycin has both bactericidal and bacteriostatic actions at least at the higher concentrations found in lung tissue. The broad spectrum antimicrobial activity of gamithromycin includes Mannheimia haemolytica, Pasteurella multocida and Histophilus somni, the bacterial pathogens most commonly associated with BRD. Gamithromycin administered subcutaneously is well absorbed and fully bioavailable, and safe for the target animal receiving doses up to five times the recommended dose at 30 mg ⁄ kg body weight. Following s.c. administration, gamithromycin is extensively and rapidly distributed to lung tissue, the site of respiratory infection.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3932309 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Zactran Approved UseFor the treatment of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni in beef and non-lactating dairy cattle. For the control of respiratory disease in beef and non-lactating dairy cattle at high risk of developing BRD associated with Mannheimia haemolytica and Pasteurella multocida. Launch Date2011 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A mixed treatment comparison meta-analysis of metaphylaxis treatments for bovine respiratory disease in beef cattle. | 2017-02 |
|
| Multiplex PCR to identify macrolide resistance determinants in Mannheimia haemolytica and Pasteurella multocida. | 2012-07 |
|
| Increased MICs of gamithromycin and tildipirosin in the presence of the genes erm(42) and msr(E)-mph(E) for bovine Pasteurella multocida and Mannheimia haemolytica. | 2012-06 |
|
| Plasma pharmacokinetics, pulmonary distribution, and in vitro activity of gamithromycin in foals. | 2012-02 |
|
| Metaphylactic gamithromycin treatment for the management of lameness in ewes putatively caused by Bacteroides melaninogenicus. | 2011-11-19 |
|
| Demonstration of the metaphylactic use of gamithromycin against bacterial pathogens associated with bovine respiratory disease in a multicentre farm trial. | 2011-03-05 |
|
| Disposition of gamithromycin in plasma, pulmonary epithelial lining fluid, bronchoalveolar cells, and lung tissue in cattle. | 2011-03 |
|
| Determination of the duration of antibacterial efficacy following administration of gamithromycin using a bovine Mannheimia haemolytica challenge model. | 2011-02 |
|
| Pharmacokinetics of gamithromycin in cattle with comparison of plasma and lung tissue concentrations and plasma antibacterial activity. | 2010-06-01 |
Patents
Sample Use Guides
Administer ZACTRAN one time as a subcutaneous injection in the neck at 6 mg/kg (2 mL/110 lb) body weight (BW). If the total dose exceeds 10 mL, divide the dose so that no more than 10 mL is administered at each injection site.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20557439
In studies involving field strains isolated within different geographic European areas, gamithromycin has MIC90 values of 0.5, 1 and 1 ug ⁄ ml against M. haemolytica, P. multocida and H. somni, respectively, and corresponding minimum bactericidal concentrations’ (MBC90) values of 1, 2 and 2 ug ⁄ ml.
| Substance Class |
Chemical
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ZE856183S0
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EMA VETERINARY ASSESSMENT REPORTS |
ZACTRAN [AUTHORIZED]
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21 CFR 556.292
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EMA VETERINARY ASSESSMENT REPORTS |
ZACTRAN [AUTHORIZED]
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21 CFR 522.1014
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QJ01FA95
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EMA VETERINARY ASSESSMENT REPORTS |
ZACTRAN [AUTHORIZED]
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