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Details

Stereochemistry RACEMIC
Molecular Formula C14H19N3O2.ClH.H2O
Molecular Weight 315.796
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZILPATEROL HYDROCHLORIDE MONOHYDRATE

SMILES

O.Cl.CC(C)N[C@@H]1CCN2C(=O)NC3=C2C(=CC=C3)[C@H]1O

InChI

InChIKey=FYUVMEDPENROOK-IZUPTLQPSA-N
InChI=1S/C14H19N3O2.ClH.H2O/c1-8(2)15-11-6-7-17-12-9(13(11)18)4-3-5-10(12)16-14(17)19;;/h3-5,8,11,13,15,18H,6-7H2,1-2H3,(H,16,19);1H;1H2/t11-,13-;;/m1../s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3240917

Zilpaterol is an agonist of β2-adrenergic receptor. Zilpaterol exerts bronchospasmolytic action. Zilmax® (4.8% Zilpaterol hydrochloride) is used to increase rate of bodyweight gain, improve feed efficiency, and increase carcass leanness in cattle fed in confinement for a period of 20-40 consecutive days at the end of the feeding period before slaughter.

Originator

Sources: Frechet D., Plassard G., Brown N.L., Cltmence F., Nhdelec L. & Worcel M. (1984) Proceedings of the VlIIth International Symposium on Medicinal Chemistry, Swedish Pharmaceutical Press, Stockholm. Vol. I , pp. 90-93
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/3240917

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The efficiency of electrical stimulation to counteract the negative effects of β-agonists on meat tenderness of feedlot cattle.
2010-11
[Determination of fifteen beta-agonists in animal urine by high performance liquid chromatography-tandem mass spectrometry].
2010-08
Perspectives on the application of zilpaterol hydrochloride in the United States beef industry.
2010-08
The effects of zilpaterol hydrochloride on carcass cutability and tenderness of calf-fed Holstein steers.
2010-07
Effects of supplementing feedlot steers and heifers with zilpaterol hydrochloride on Warner-Bratzler shear force interrelationships of steer and heifer longissimus lumborum and heifer triceps brachii and gluteus medius muscles aged for 7, 14 and 21d.
2010-06
Predicting red meat yields in carcasses from beef-type and calf-fed Holstein steers using the United States Department of Agriculture calculated yield grade.
2010-06
Effect of zilpaterol hydrochloride supplementation on cutability and subprimal yield of beef steer carcasses.
2010-05
Moisture enhancement and blade tenderization effects on the shear force and palatability of strip loin steaks from beef cattle fed zilpaterol hydrochloride.
2010-05
Comparative effects of ractopamine hydrochloride and zilpaterol hydrochloride on growth performance, carcass traits, and longissimus tenderness of finishing steers.
2010-05
Depletion of urinary zilpaterol residues in horses as measured by ELISA and UPLC-MS/MS.
2010-04-14
Effects of duration of zilpaterol hydrochloride supplementation on growth performance, carcass traits and meat quality of grain-fed cull cows.
2010-04
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.
2010-04
Effects of zilpaterol hydrochloride feeding duration on beef and calf-fed Holstein strip loin steak color.
2010-03
Additive effects of a steroidal implant and zilpaterol hydrochloride on feedlot performance, carcass characteristics, and skeletal muscle messenger ribonucleic acid abundance in finishing steers.
2010-01
Effect of extended withdrawal of zilpaterol hydrochloride on performance and carcass traits in finishing beef steers.
2010-01
Influence of beta-agonists (ractopamine HCl and zilpaterol HCl) on fecal shedding of Escherichia coli O157:H7 in feedlot cattle.
2009-12
Effects of zilpaterol hydrochloride on growth rates, feed conversion, and carcass traits in calf-fed Holstein steers.
2009-12
Effect of feeding zilpaterol hydrochloride to beef and calf-fed Holstein cattle on consumer palatability ratings.
2009-11
Effects of zilpaterol hydrochloride and zilpaterol hydrochloride withdrawal time on beef carcass cutability, composition, and tenderness.
2009-11
Effect of zilpaterol hydrochloride supplementation of beef steers and calf-fed Holstein steers on the color stability of top sirloin butt steaks.
2009-11
Effects of zilpaterol hydrochloride feeding duration and postmortem aging on Warner-Bratzler shear force of three muscles from beef steers and heifers.
2009-11
The effect of zilpaterol hydrochloride on meat quality of calf-fed Holstein steers.
2009-11
Feeding zilpaterol hydrochloride to calf-fed Holsteins has minimal effects on semimembranosus steak color.
2009-11
Effects of feeding zilpaterol hydrochloride for twenty to forty days on carcass cutability and subprimal yield of calf-fed Holstein steers.
2009-11
Effects of duration of zilpaterol hydrochloride and days on the finishing diet on carcass cutability, composition, tenderness, and skeletal muscle gene expression in feedlot steers.
2009-11
Effects of zilpaterol hydrochloride with or without an estrogen-trenbolone acetate terminal implant on carcass traits, retail cutout, tenderness, and muscle fiber diameter in finishing steers.
2009-11
Effects of zilpaterol hydrochloride feeding duration on crossbred beef semimembranosus steak color in aerobic or modified atmosphere packaging.
2009-11
Effect of zilpaterol hydrochloride duration of feeding on performance and carcass characteristics of feedlot cattle.
2009-06
Effects of preslaughter withdrawal period on response of feedlot heifers to zilpaterol hydrochloride supplementation: growth performance and carcass characteristics.
2009-05
Development, validation and implementation of a receptor based bioassay capable of detecting a broad range of beta-agonist drugs in animal feedingstuffs.
2009-04-01
Dietary zilpaterol hydrochloride. I. Feedlot performance and carcass traits of steers and heifers.
2009-04
Effects of feeding zilpaterol hydrochloride with and without monensin and tylosin on carcass cutability and meat palatability of beef steers.
2009-04
Dietary zilpaterol hydrochloride. II. Carcass composition and meat palatability of beef cattle.
2009-04
Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.
2009-03-26
Effects of dietary zilpaterol hydrochloride on feedlot performance and carcass characteristics of beef steers fed with and without monensin and tylosin.
2009-03
Effects of implanting and feeding zilpaterol hydrochloride on performance, carcass characteristics, and subprimal beef yields of fed cows.
2009-02
Effects of duration of zilpaterol hydrochloride feeding and days on the finishing diet on feedlot cattle performance and carcass traits.
2008-08
Identification of a probable new adrenergic agonist by nuclear magnetic resonance and mass spectrometry.
2007-03-14
Effects of two beta-adrenergic agonists on finishing performance, carcass characteristics, and meat quality of feedlot steers.
2006-12
Tissue residues and urinary excretion of zilpaterol in sheep treated for 10 days with dietary zilpaterol.
2006-06-14
Integration of two-dimensional LC-MS with multivariate statistics for comparative analysis of proteomic samples.
2006-04-01
Beta-adrenergic receptor agonists induce the release of granulocyte chemotactic protein-2, oncostatin M, and vascular endothelial growth factor from macrophages.
2006-01
In search of secreted protein biomarkers for the anti-inflammatory effect of beta2-adrenergic receptor agonists: application of DIGE technology in combination with multivariate and univariate data analysis tools.
2005-12-13
Inhibitory effects of the beta-adrenergic receptor agonist zilpaterol on the LPS-induced production of TNF-alpha in vitro and in vivo.
2005-12
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005-05-04
Characterization of anti-inflammatory compounds using transcriptomics, proteomics, and metabolomics in combination with multivariate data analysis.
2004-11
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.
2004-04-21
Pharmaceuticals, direct-fed microbials, and enzymes for enhancing growth and feed efficiency of beef.
2003-11
Simultaneous determination of Zilpaterol and other beta agonists in calf eye by gas chromatography/tandem mass spectrometry.
2003-02-28
Extraction, clean-up and gas chromatography-mass spectrometry characterization of zilpaterol as feed additive in fattening cattle.
2003-01-05
Patents

Sample Use Guides

Zilmax® (4.8% Zilpaterol hydrochloride) is used to increase rate of bodyweight gain, improve feed efficiency, and increase carcass leanness in cattle fed in confinement for a period of 20-40 consecutive days at the end of the feeding period before slaughter. Zilpaterol hydrochloride should be mixed into the feed at a level of 7.5 mg/kg on a 90% dry matter basis. This represents a dose of approximately 0.15 mg/kg bw or 60 to 90 mg zilpaterol hydrochloride per animal per day.
Route of Administration: Oral
Zilpaterol hydrochloride at 1 µM decreased β1-adrenergic receptor mRNA, and 0.01 and 1 µM Zilpaterol hydrochloride decreased β2-adrenergic receptor and β3-adrenergic receptor mRNA in bovine myoblasts.
Name Type Language
ZILPATEROL HYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
ZILPATEROL HYDROCHLORIDE MONOHYDRATE [MI]
Preferred Name English
IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE, 4,5,6,7-TETRAHYDRO-7-HYDROXY-6-((1-METHYLETHYL)AMINO)-, HYDROCHLORIDE, HYDRATE (1:1:1), (6R,7R)-REL-
Systematic Name English
IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE, 4,5,6,7-TETRAHYDRO-7-HYDROXY-6-((1-METHYLETHYL)AMINO)-, MONOHYDROCHLORIDE, MONOHYDRATE, TRANS-
Systematic Name English
ZILPATEROL HYDROCHLORIDE MONOHYDRATE, (±)-
Common Name English
REL-(6R,7R)-4,5,6,7-TETRAHYDRO-7-HYDROXY-6-((1-METHYLETHYL)AMINO)IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE, MONOHYDROCHLORIDE, MONOHYDRATE
Systematic Name English
Code System Code Type Description
MERCK INDEX
m11594
Created by admin on Mon Mar 31 22:24:38 GMT 2025 , Edited by admin on Mon Mar 31 22:24:38 GMT 2025
PRIMARY
CAS
186046-04-8
Created by admin on Mon Mar 31 22:24:38 GMT 2025 , Edited by admin on Mon Mar 31 22:24:38 GMT 2025
PRIMARY
PUBCHEM
66603288
Created by admin on Mon Mar 31 22:24:38 GMT 2025 , Edited by admin on Mon Mar 31 22:24:38 GMT 2025
PRIMARY
FDA UNII
90J4TG861K
Created by admin on Mon Mar 31 22:24:38 GMT 2025 , Edited by admin on Mon Mar 31 22:24:38 GMT 2025
PRIMARY