U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of GAMITHROMYCIN

SMILES

[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)N(CCC)C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

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

HIDE SMILES / InChI

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Zactran

Approved Use

For 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 Date

2011
PubMed

PubMed

TitleDatePubMed
Determination of the duration of antibacterial efficacy following administration of gamithromycin using a bovine Mannheimia haemolytica challenge model.
2011 Feb
Plasma pharmacokinetics, pulmonary distribution, and in vitro activity of gamithromycin in foals.
2012 Feb
A mixed treatment comparison meta-analysis of metaphylaxis treatments for bovine respiratory disease in beef cattle.
2017 Feb
Patents

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 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
Created
by admin
on Sat Dec 16 16:50:47 GMT 2023
Edited
by admin
on Sat Dec 16 16:50:47 GMT 2023
Record UNII
ZE856183S0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GAMITHROMYCIN
INN   USAN  
INN   USAN  
Official Name English
GAMITHROMYCIN [GREEN BOOK]
Common Name English
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
Common Name English
ML-1,709,460
Code English
ML-1709460
Code English
GAMITHROMYCIN [MI]
Common Name English
(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-AZAC
Common Name English
GAMITHROMYCIN [USAN]
Common Name English
gamithromycin [INN]
Common Name English
ML-460
Code English
GAMITHROMYCIN [EMA EPAR VETERINARY]
Official Name English
ZACTRAN
Common Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS ZACTRAN [AUTHORIZED]
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
CFR 21 CFR 556.292
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS ZACTRAN [AUTHORIZED]
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
CFR 21 CFR 522.1014
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
WHO-VATC QJ01FA95
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS ZACTRAN [AUTHORIZED]
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
Code System Code Type Description
INN
8754
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107342
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
FDA UNII
ZE856183S0
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
CAS
145435-72-9
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
MERCK INDEX
m11761
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
DRUG BANK
DB11416
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
PUBCHEM
59364992
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
RXCUI
1113697
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY RxNorm
DAILYMED
ZE856183S0
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID90904260
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
SMS_ID
300000023798
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
NCI_THESAURUS
C170019
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
USAN
RR-124
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
MESH
C552399
Created by admin on Sat Dec 16 16:50:47 GMT 2023 , Edited by admin on Sat Dec 16 16:50:47 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY