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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H47NO4S.C4H4O4
Molecular Weight 609.814
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TIAMULIN FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@]23CCC(=O)[C@H]2[C@@]1(C)[C@H](C)CC3

InChI

InChIKey=YXQXDXAHCSEVSD-GCYNEOGWSA-N
InChI=1S/C28H47NO4S.C4H4O4/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;5-3(6)1-2-4(7)8/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

1993
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

1993
Doses

Doses

DosePopulationAdverse events​
0.5 ug/mL single, respiratory
Studied dose
Dose: 0.5 ug/mL
Route: respiratory
Route: single
Dose: 0.5 ug/mL
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: QT interval prolonged, Ventricular tachyarrhythmia...
Other AEs:
QT interval prolonged
Ventricular tachyarrhythmia
Sources:
AEs

AEs

AESignificanceDosePopulation
QT interval prolonged
0.5 ug/mL single, respiratory
Studied dose
Dose: 0.5 ug/mL
Route: respiratory
Route: single
Dose: 0.5 ug/mL
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Ventricular tachyarrhythmia
0.5 ug/mL single, respiratory
Studied dose
Dose: 0.5 ug/mL
Route: respiratory
Route: single
Dose: 0.5 ug/mL
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Pharmacokinetic/Pharmacodynamic Profiles of Tiamulin in an Experimental Intratracheal Infection Model of Mycoplasma gallisepticum.
2016
Change in antimicrobial susceptibility of Mycoplasma gallisepticum field isolates.
2011-06-02
Comparative susceptibilities of various animal-pathogenic mycoplasmas to fluoroquinolones.
1997-09
Inhibitory effects of tiamulin on contractile and electrical responses in isolated thoracic aorta and cardiac muscle of guinea-pigs.
1992-09
The inhibitory effect of tiamulin on high K(+)-induced contraction in guinea pig intestinal smooth muscle.
1991-12
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 Mon Mar 31 18:09:19 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:19 GMT 2025
Record UNII
ION1Q02ZCX
Record Status Validated (UNII)
Record Version
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Name Type Language
TIAMULIN FUMARATE
MART.   MI   USAN   USP   USP-RS  
USAN  
Official Name English
TIAMULIN HYDROGEN FUMARATE
GREEN BOOK  
Preferred Name English
SQ 22947
Code English
TIAMULIN FUMARATE [USAN]
Common 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 FUMARATE (1:1) (SALT)
Common Name English
TIAMULIN HYDROGEN FUMARATE [GREEN BOOK]
Common Name English
TIAMULIN FUMARATE [MI]
Common Name English
TIAMULIN FUMARATE [USP-RS]
Common Name English
TIAMULIN FUMARATE [USP MONOGRAPH]
Common Name English
SQ-22947
Code 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*))-, (E)-2-BUTENEDIOATE (1:1) (SALT)
Common Name English
TIAMULIN FUMARATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
Code System Code Type Description
PUBCHEM
23725049
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL498466
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
MESH
C014224
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
MERCK INDEX
m10844
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY Merck Index
SMS_ID
300000029138
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
RXCUI
1314589
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY RxNorm
CAS
55297-96-6
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
DAILYMED
ION1Q02ZCX
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
NCI_THESAURUS
C84208
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
FDA UNII
ION1Q02ZCX
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
RS_ITEM_NUM
1667290
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID901020751
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
259-581-6
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
DRUG BANK
DBSALT001660
Created by admin on Mon Mar 31 18:09:19 GMT 2025 , Edited by admin on Mon Mar 31 18:09:19 GMT 2025
PRIMARY
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