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

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H52N2O5S.ClH
Molecular Weight 601.281
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALNEMULIN HYDROCHLORIDE

SMILES

Cl.[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)CSC(C)(C)CNC(=O)[C@H](N)C(C)C

InChI

InChIKey=MFBPRQKHDIVLOJ-AFFLPQGKSA-N
InChI=1S/C31H52N2O5S.ClH/c1-10-29(8)15-22(38-23(35)16-39-28(6,7)17-33-27(37)24(32)18(2)3)30(9)19(4)11-13-31(20(5)26(29)36)14-12-21(34)25(30)31;/h10,18-20,22,24-26,36H,1,11-17,32H2,2-9H3,(H,33,37);1H/t19-,20+,22-,24-,25+,26+,29-,30+,31+;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C31H52N2O5S
Molecular Weight 564.82
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Valnemulin (marketed under the trade name Econor) is a pleuromutilin antibiotic used to treat swine dysentery, ileitis, colitis and pneumonia. It is approved for veterinary use only. Valnemulin is an antibiotic belonging to the pleuromutilin group, which acts by the inhibition of the initiation of protein synthesis at the level of the bacterial ribosome. Valnemulin has activity against a range of bacteria including those responsible for enteric and respiratory disease in pigs. Valnemulin shows high activity against Mycoplasma spp. and spirochaetes such as Brachyspira hyodysenteriae and Brachyspira pilosicoli. Valnemulin has little activity against Enterobacteriaceae, such as Salmonella spp. and Escherichia coli. There appears to be no resistance development to valnemulin to date by M. hyopneumoniae and L. intracellularis. There have been some increases of MICs of valnemulin against B. hyodysenteriae and to a lesser degree B. pilosicoli, some of which appear to have developed resistance. Valnemulin binds to the ribosome and inhibits bacterial protein synthesis. Resistance development primarily occurs because of changes at the binding site associated with mutations of the ribosomal DNA genes. Econor 10% and 50% is indicated for: The treatment and prevention of swine dysentery. The treatment of clinical signs of porcine proliferative enteropathy (ileitis). The prevention of clinical signs of porcine colonic spirochaetosis (colitis) when the disease has been diagnosed in the herd. Treatment and prevention of swine enzootic pneumonia. At the recommended dosage of 10 - 12 mg/kg bodyweight lung lesions and weight loss are reduced, but infection with Mycoplasma hyopneumoniae is not eliminated. Econor 0.5% and 1% is indicated: For the treatment and prevention of swine dysentery. The treatment of clinical signs of porcine proliferative enteropathy (ileitis). The prevention of clinical signs of porcine colonic spirochaetosis (colitis) when the disease has been diagnosed in the herd.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Econor

Approved Use

Econor 10% and 50%: The treatment and prevention of swine dysentery. The treatment of clinical signs of porcine proliferative enteropathy (ileitis). The prevention of clinical signs of porcine colonic spirochaetosis (colitis) when the disease has been diagnosed in the herd. Treatment and prevention of swine enzootic pneumonia. At the recommended dosage of 10 - 12 mg/kg bodyweight lung lesions and weight loss are reduced, but infection with Mycoplasma hyopneumoniae is not eliminated. Econor 0.5% and 1%: For the treatment and prevention of swine dysentery. The treatment of clinical signs of porcine proliferative enteropathy (ileitis). The prevention of clinical signs of porcine colonic spirochaetosis (colitis) when the disease has been diagnosed in the herd.

Launch Date

9.4417918E11
PubMed

PubMed

TitleDatePubMed
The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome.
2001 Sep
Efficacy and tolerability of early administration of valnemulin hydrochloride premix on epizootic rabbit enteropathy.
2015 Jun
A novel method to determine valnemulin in feedingstuffs for several animal species by liquid chromatography-electrospray tandem mass spectrometry.
2016 Nov
Determination of the Mutant Selection Window and Evaluation of the Killing of Mycoplasma gallisepticum by Danofloxacin, Doxycycline, Tilmicosin, Tylvalosin and Valnemulin.
2017
Pharmacokinetics of valnemulin after intravenous, intramuscular, and oral administration in layer chickens.
2017 Aug
Antimicrobial susceptibility monitoring of Mycoplasma hyopneumoniae and Mycoplasma bovis isolated in Europe.
2017 May
Patents

Sample Use Guides

Pigs:Treatment and prevention of swine enzootic pneumonia. At the recommended dosage of 10–12 mg/kg bodyweight lung lesions and weight loss are reduced, but infection with Mycoplasma hyopneumoniae is not eliminated.
Route of Administration: Oral
MIC50/MIC90 values for valnemulin against M. hyopneumoniae were ≤0.001/ ≤0.001mg/L respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:49:10 UTC 2023
Edited
by admin
on Fri Dec 15 16:49:10 UTC 2023
Record UNII
W1GDP58BNQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALNEMULIN HYDROCHLORIDE
MI  
Common Name English
VALNEMULIN HYDROCHLORIDE [MI]
Common Name English
((2-((R)-2-AMINO-3-METHYLBUTYRAMIDO)-1,1-DIMETHYLETHYL)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 HYDROCHLORIDE
Common Name English
ECONOR
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
Code System Code Type Description
FDA UNII
W1GDP58BNQ
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
CAS
133868-46-9
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
SMS_ID
300000023799
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
NCI_THESAURUS
C132065
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
RXCUI
2604037
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
DAILYMED
W1GDP58BNQ
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
MERCK INDEX
m11367
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID30158407
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
PUBCHEM
60195218
Created by admin on Fri Dec 15 16:49:11 UTC 2023 , Edited by admin on Fri Dec 15 16:49:11 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY