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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=CC=CC([C@H]1O)=C23

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
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 C14H19N3O2
Molecular Weight 261.3196
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Frechet, D. et al.
4
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

2006
178
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 1.1 µM [Ki]
Binding Agent
1064
 10.0 µM [Ki]
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Simultaneous determination of Zilpaterol and other beta agonists in calf eye by gas chromatography/tandem mass spectrometry.
2003 Jan-Feb
Inhibitory effects of the beta-adrenergic receptor agonist zilpaterol on the LPS-induced production of TNF-alpha in vitro and in vivo.
2005 Dec
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005 May 4
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 Nov-Dec
Beta-adrenergic receptor agonists induce the release of granulocyte chemotactic protein-2, oncostatin M, and vascular endothelial growth factor from macrophages.
2006 Jan
Tissue residues and urinary excretion of zilpaterol in sheep treated for 10 days with dietary zilpaterol.
2006 Jun 14
Effects of feeding zilpaterol hydrochloride with and without monensin and tylosin on carcass cutability and meat palatability of beef steers.
2009 Apr
Dietary zilpaterol hydrochloride. II. Carcass composition and meat palatability of beef cattle.
2009 Apr
Development, validation and implementation of a receptor based bioassay capable of detecting a broad range of beta-agonist drugs in animal feedingstuffs.
2009 Apr 1
Influence of beta-agonists (ractopamine HCl and zilpaterol HCl) on fecal shedding of Escherichia coli O157:H7 in feedlot cattle.
2009 Dec
Effects of implanting and feeding zilpaterol hydrochloride on performance, carcass characteristics, and subprimal beef yields of fed cows.
2009 Feb
Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.
2009 Mar 26
Effects of zilpaterol hydrochloride and zilpaterol hydrochloride withdrawal time on beef carcass cutability, composition, and tenderness.
2009 Nov
Effect of zilpaterol hydrochloride supplementation of beef steers and calf-fed Holstein steers on the color stability of top sirloin butt steaks.
2009 Nov
The effect of zilpaterol hydrochloride on meat quality of calf-fed Holstein steers.
2009 Nov
Feeding zilpaterol hydrochloride to calf-fed Holsteins has minimal effects on semimembranosus steak color.
2009 Nov
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 Nov
Effects of duration of zilpaterol hydrochloride supplementation on growth performance, carcass traits and meat quality of grain-fed cull cows.
2010 Apr
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.
2010 Apr
Depletion of urinary zilpaterol residues in horses as measured by ELISA and UPLC-MS/MS.
2010 Apr 14
[Determination of fifteen beta-agonists in animal urine by high performance liquid chromatography-tandem mass spectrometry].
2010 Aug
The effects of zilpaterol hydrochloride on carcass cutability and tenderness of calf-fed Holstein steers.
2010 Jul
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 Jun
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 Jun
Effects of zilpaterol hydrochloride feeding duration on beef and calf-fed Holstein strip loin steak color.
2010 Mar
Effect of zilpaterol hydrochloride supplementation on cutability and subprimal yield of beef steer carcasses.
2010 May
Moisture enhancement and blade tenderization effects on the shear force and palatability of strip loin steaks from beef cattle fed zilpaterol hydrochloride.
2010 May
Comparative effects of ractopamine hydrochloride and zilpaterol hydrochloride on growth performance, carcass traits, and longissimus tenderness of finishing steers.
2010 May
The efficiency of electrical stimulation to counteract the negative effects of β-agonists on meat tenderness of feedlot cattle.
2010 Nov
Patents

Patents

20120058189
4
US20100022490
4
US5731028A
4
US8268813
4
US8343956B2
4

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:58:13 GMT 2023
Edited
by admin
on Sat Dec 16 08:58:13 GMT 2023
Record UNII
90J4TG861K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZILPATEROL HYDROCHLORIDE MONOHYDRATE
MI  
Common 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
ZILPATEROL HYDROCHLORIDE MONOHYDRATE [MI]
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 Sat Dec 16 08:58:13 GMT 2023 , Edited by admin on Sat Dec 16 08:58:13 GMT 2023
PRIMARY
CAS
186046-04-8
Created by admin on Sat Dec 16 08:58:13 GMT 2023 , Edited by admin on Sat Dec 16 08:58:13 GMT 2023
PRIMARY
PUBCHEM
66603288
Created by admin on Sat Dec 16 08:58:13 GMT 2023 , Edited by admin on Sat Dec 16 08:58:13 GMT 2023
PRIMARY
FDA UNII
90J4TG861K
Created by admin on Sat Dec 16 08:58:13 GMT 2023 , Edited by admin on Sat Dec 16 08:58:13 GMT 2023
PRIMARY
Related Record Type Details
Structure of ZILPATEROL HYDROCHLORIDE
ANHYDROUS->SOLVATE
NIH
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