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Details

Stereochemistry RACEMIC
Molecular Formula C14H19N3O2.ClH.3H2O
Molecular Weight 351.826
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZILPATEROL HYDROCHLORIDE TRIHYDRATE

SMILES

O.O.O.Cl.CC(C)N[C@@H]1CCN2C(=O)NC3=CC=CC([C@H]1O)=C23

InChI

InChIKey=PPHVDXUEHDNCNF-OFZMQQONSA-N
InChI=1S/C14H19N3O2.ClH.3H2O/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;3*1H2/t11-,13-;;;;/m1..../s1

HIDE SMILES / InChI

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

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

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
Extraction, clean-up and gas chromatography-mass spectrometry characterization of zilpaterol as feed additive in fattening cattle.
2003 Jan 5
Simultaneous determination of Zilpaterol and other beta agonists in calf eye by gas chromatography/tandem mass spectrometry.
2003 Jan-Feb
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
Identification of a probable new adrenergic agonist by nuclear magnetic resonance and mass spectrometry.
2007 Mar 14
Effects of duration of zilpaterol hydrochloride feeding and days on the finishing diet on feedlot cattle performance and carcass traits.
2008 Aug
Dietary zilpaterol hydrochloride. I. Feedlot performance and carcass traits of steers and heifers.
2009 Apr
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 zilpaterol hydrochloride on growth rates, feed conversion, and carcass traits in calf-fed Holstein steers.
2009 Dec
Effects of implanting and feeding zilpaterol hydrochloride on performance, carcass characteristics, and subprimal beef yields of fed cows.
2009 Feb
Effect of zilpaterol hydrochloride duration of feeding on performance and carcass characteristics of feedlot cattle.
2009 Jun
Effects of dietary zilpaterol hydrochloride on feedlot performance and carcass characteristics of beef steers fed with and without monensin and tylosin.
2009 Mar
Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.
2009 Mar 26
Effects of preslaughter withdrawal period on response of feedlot heifers to zilpaterol hydrochloride supplementation: growth performance and carcass characteristics.
2009 May
Effect of feeding zilpaterol hydrochloride to beef and calf-fed Holstein cattle on consumer palatability ratings.
2009 Nov
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
Effects of zilpaterol hydrochloride feeding duration and postmortem aging on Warner-Bratzler shear force of three muscles from beef steers and heifers.
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 feeding zilpaterol hydrochloride for twenty to forty days on carcass cutability and subprimal yield of calf-fed Holstein steers.
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 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 Nov
Effects of zilpaterol hydrochloride feeding duration on crossbred beef semimembranosus steak color in aerobic or modified atmosphere packaging.
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
[Determination of fifteen beta-agonists in animal urine by high performance liquid chromatography-tandem mass spectrometry].
2010 Aug
Perspectives on the application of zilpaterol hydrochloride in the United States beef industry.
2010 Aug
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 Jan
Effect of extended withdrawal of zilpaterol hydrochloride on performance and carcass traits in finishing beef steers.
2010 Jan
Effects of zilpaterol hydrochloride feeding duration on beef and calf-fed Holstein strip loin steak color.
2010 Mar
Moisture enhancement and blade tenderization effects on the shear force and palatability of strip loin steaks from beef cattle fed zilpaterol hydrochloride.
2010 May
The efficiency of electrical stimulation to counteract the negative effects of β-agonists on meat tenderness of feedlot cattle.
2010 Nov
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.
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
4KT1VE9Y64
Record Status Validated (UNII)
Record Version
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Name Type Language
ZILPATEROL HYDROCHLORIDE TRIHYDRATE
MI  
Common Name English
ZILPATEROL HYDROCHLORIDE TRIHYDRATE [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, HYDROCHLORIDE, TRIHYDRATE
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, TRIHYDRATE, TRANS-
Systematic Name English
ZILPATEROL HYDROCHLORIDE TRIHYDRATE, (±)-
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 (1:1:3), (6R,7R)-REL-
Systematic Name English
Code System Code Type Description
CAS
186046-05-9
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
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
PUBCHEM
66603768
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
4KT1VE9Y64
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
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