Tulathromycin

Tulathromycin, sold under the brand name Draxxin among others, is a macrolide antibiotic used to treat bovine respiratory disease in cattle and swine respiratory disease in pigs.^[2][7][8]

Tulathromycin

Clinical data
Trade names	Draxxin, others
AHFS/Drugs.com	International Drug Names
Routes of administration	Intramuscular, subcutaneous
ATCvet code	QJ01FA94 (WHO)
Legal status
Legal status	CA: ℞-only[1] US: ℞-only[2] EU: Rx-only[3][4][5][6]
Identifiers
IUPAC name (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-dideoxy-3-C-methyl-3-Ο-methyl-4-C-[(propylamino)methyl]-α-L-ribo-hexopyrano-syl]oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]-oxy]-1-oxa-6-azacyclopentadecan-15-one
CAS Number	217500-96-4
DrugBank	DB11474 Y
ChemSpider	24583287 Y
UNII	Q839I13422 897A3KN7AP
KEGG	D06258 Y C21788
CompTox Dashboard (EPA)	DTXSID60274184
ECHA InfoCard	100.166.454
Chemical and physical data
Formula	C41H79N3O12
Molar mass	806.092 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCNCC1(C(OC(CC1(C)OC)OC2C(C(C(CC(NC(C(C(C(OC(=O)C2C)CC)(C)O)O)C)C)(C)O)OC3C(C(CC(O3)C)N(C)C)O)C)C)O
InChI InChI=1S/C40H77N3O12/c1-15-17-41-21-40(49)27(8)52-30(20-38(40,10)50-14)54-32-24(5)34(55-36-31(44)28(43(12)13)18-23(4)51-36)37(9,47)19-22(3)42-26(7)33(45)39(11,48)29(16-2)53-35(46)25(32)6/h22-34,36,41-42,44-45,47-49H,15-21H2,1-14H3/t22-,23-,24+,25-,26-,27+,28+,29-,30+,31-,32+,33-,34-,36+,37-,38-,39-,40+/m1/s1 Y Key:HWATWVYEWMIMSO-FROLMUNOSA-N Y InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1 Key:GUARTUJKFNAVIK-QPTWMBCESA-N
(verify)

Medical uses

Tulathromycin is indicated for:

Cattle: Treatment and metaphylaxis of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida, Histophilus somni, and Mycoplasma bovis sensitive to tulathromycin.^[3]

Treatment of infectious bovine keratoconjunctivitis (IBK) associated with Moraxella bovis sensitive to tulathromycin.^[3]

Pigs: Treatment and metaphylaxis of swine respiratory disease (SRD) associated with Actinobacillus pleuropneumoniae, Pasteurella multocida, Mycoplasma hyopneumoniae, Haemophilus parasuis, and Bordetella bronchiseptica sensitive to tulathromycin.^[3]

Sheep: Treatment of the early stages of infectious pododermatitis (foot rot) associated with virulent Dichelobacter nodosus requiring systemic treatment.^[3]

Society and culture

Legal status

Tulathromycin (brand name Draxxin) was approved for medical use in the European Union in November 2003.^[3]

Tulathromycin (brand names Tulissin and Tulaven) was approved for medical use in the European Union in April 2020.^[9][10]

In July 2020, the Committee for Medicinal Products for Veterinary Use (CVMP) adopted positive opinions, recommending the granting of marketing authorizations for the veterinary medicinal products Increxxa and Tulinovet solutions for injection for cattle, pigs and sheep.^[11][12] The applicant for Increxxa is Elanco GmbH.^[11] The applicant for Tulinovet is VMD N.V.^[12] Increxxa was approved for veterinary use in the European Union in September 2020.^[5]

Brand names

It is marketed by Zoetis under the brand name Draxxin.^[2]

It is marketed by Bimeda Inc. under the brand name Macrosyn, and by Merck & Co. under the brand name Arovyn.^[13]

It is also sold under the brand name Increxxa.^[2][5] by Elanco