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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H47NO4S
Molecular Weight 493.742
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIAMULIN

SMILES

[H][C@@]12C(=O)CC[C@]13CC[C@@H](C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSCCN(CC)CC

InChI

InChIKey=UURAUHCOJAIIRQ-QGLSALSOSA-N
InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H47NO4S
Molecular Weight 493.742
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Tiamulin is a diterpene antimicrobial with a pleuromutilin chemical structure similar to that of valnemulin. The activity of tiamulin is largely confined to gram-positive micro-organisms and mycoplasma. Tiamulin acts by inhibiting protein synthesis at the ribosomal level. In veterinary medicine, tiamulin is used for treatment and prophylaxis of dysentery, pneumonia and mycoplasmal infections in pigs and poultry. Tiamulin is available as a 2, 10 or 20% premix for pigs and poultry, a 12.5% solution or 45% water soluble powder for addition to drinking water for pigs and poultry, or a 10% injectable formulation for pigs. Tiamulin inhibits protein synthesis by targeting the 50S bacterial ribosomal subunit and binding to peptidyl transferase, the enzyme responsible for forming peptide bonds between amino acids.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DENAGARD
Curative
DENAGARD

PubMed

Sample Use Guides

In Vivo Use Guide
Pigs and poultry: Dietary doses are 100 to 200 mg/kg feed for 5 to 10 days, and up to 6 weeks at 50 mg/kg feed for pigs, and 160 to 320 mg/kg feed for poultry. In drinking water, doses of 4 to 25 mg/kg bw for up to 1 week are used for pigs, and doses of 30 to 60 mg/kg bw for 3 to 5 days in poultry. Intramuscular doses of 10 to 20 mg/kg bw may be given daily for up to 5 days.
Route of Administration: Other
In Vitro Use Guide
Tiamulin was most active against mycoplasma strains of eight species isolated from poultry (MICs at which 90% of the isolates were inhibited [MIC90s], 0.025 to 0.25 ug/ml).
Substance Class Chemical
Record UNII
E38WZ4U54R
Record Status Validated (UNII)
Record Version