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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DENAGARD

Approved Use

For the treatment of swine dysentery associated with Treponema hyodysenteriae and swine pneumonia due to Actinobacillus pleuropneumoniae susceptible to tiamulin.

Launch Date

7.2826559E11
Curative
DENAGARD

Approved Use

For the treatment of swine dysentery associated with Treponema hyodysenteriae and swine pneumonia due to Actinobacillus pleuropneumoniae susceptible to tiamulin.

Launch Date

7.2826559E11
PubMed

PubMed

TitleDatePubMed
The inhibitory effect of tiamulin on high K(+)-induced contraction in guinea pig intestinal smooth muscle.
1991 Dec
Comparative susceptibilities of various animal-pathogenic mycoplasmas to fluoroquinolones.
1997 Sep
Change in antimicrobial susceptibility of Mycoplasma gallisepticum field isolates.
2011 Jun 2
Pharmacokinetic/Pharmacodynamic Profiles of Tiamulin in an Experimental Intratracheal Infection Model of Mycoplasma gallisepticum.
2016
Patents

Sample Use Guides

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
Created
by admin
on Fri Dec 15 15:52:48 UTC 2023
Edited
by admin
on Fri Dec 15 15:52:48 UTC 2023
Record UNII
E38WZ4U54R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIAMULIN
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS  
USAN   INN  
Official Name English
[[2-(Diethylamino)ethyl]thio]acetic acid 8-ester with (3aS,4R,5S,6S,8R,9R,9aR,10R)-octahydro-5,8-dihydroxy-4,6,9,10)-tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopentacycloocten-1(4H)-one
Common Name English
SQ 14055
Code English
TIAMULIN [HSDB]
Common Name English
TIAMULIN [USAN]
Common Name English
SQ-14055
Code English
TIAMULIN [GREEN BOOK]
Common Name English
TIAMULIN [USP-RS]
Common Name English
TIAMULIN [MI]
Common Name English
tiamulin [INN]
Common Name English
DENAGARD
Brand Name English
TIAMULIN [USP MONOGRAPH]
Common Name English
TIAMULIN [MART.]
Common Name English
((2-(DIETHYLAMINO)ETHYL)THIO)-, 6-ETHENYLDECAHYDRO-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-8-YL ESTER (3AS-(3A.ALPHA.,4.BETA.,5.ALPHA.,6.ALPHA.,8.BETA.,9.ALPHA.,9A.BETA.,10S*))-
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.2455
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
WHO-VATC QJ01XQ01
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
CFR 21 CFR 556.732
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
CFR 21 CFR 558.612
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
Code System Code Type Description
FDA UNII
E38WZ4U54R
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID2046701
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
INN
3932
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
MESH
C014224
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
WIKIPEDIA
TIAMULIN
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
EVMPD
SUB11005MIG
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
RXCUI
1546410
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1667355
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
HSDB
7026
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
CHEBI
44137
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
CAS
55297-95-5
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
NCI_THESAURUS
C84207
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
259-580-0
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
DRUG BANK
DB11468
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
MERCK INDEX
m10844
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY Merck Index
SMS_ID
100000082177
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL498466
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
DAILYMED
E38WZ4U54R
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
PUBCHEM
656958
Created by admin on Fri Dec 15 15:52:48 UTC 2023 , Edited by admin on Fri Dec 15 15:52:48 UTC 2023
PRIMARY
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