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Details

Stereochemistry RACEMIC
Molecular Formula C14H19N3O2
Molecular Weight 261.3201
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZILPATEROL

SMILES

CC(C)N[C@]1([H])CCn2c3c(cccc3nc2O)[C@@]1([H])O

InChI

InChIKey=ZSTCZWJCLIRCOJ-DGCLKSJQSA-N
InChI=1S/C14H19N3O2/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)/t11-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula C14H19N3O2
Molecular Weight 261.3201
Charge 0
Count
Stereochemistry ABSOLUTE
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
Pharmaceuticals, direct-fed microbials, and enzymes for enhancing growth and feed efficiency of beef.
2003 Nov
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.
2004 Apr 21
Characterization of anti-inflammatory compounds using transcriptomics, proteomics, and metabolomics in combination with multivariate data analysis.
2004 Nov
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
Integration of two-dimensional LC-MS with multivariate statistics for comparative analysis of proteomic samples.
2006 Apr 1
Effects of two beta-adrenergic agonists on finishing performance, carcass characteristics, and meat quality of feedlot steers.
2006 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
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 implanting and feeding zilpaterol hydrochloride on performance, carcass characteristics, and subprimal beef yields of fed cows.
2009 Feb
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
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
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
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
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

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 Fri Jun 25 22:31:56 UTC 2021
Edited
by admin
on Fri Jun 25 22:31:56 UTC 2021
Record UNII
S384A1Y12J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZILPATEROL
GREEN BOOK   INN   MI  
INN  
Official Name English
(+/-)-TRANS-4,5,6,7-TETRAHYDRO-7-HYDROXY-6-(ISOPROPYLAMINO)IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE
Systematic Name English
IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE, 4,5,6,7-TETRAHYDRO-7-HYDROXY-6-((1-METHYLETHYL)AMINO)-, TRANS-(+/-)-
Systematic Name English
ZILPATEROL [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
Common Name English
ZILPATEROL [GREEN BOOK]
Common Name English
IMIDAZO(4,5,1-JK)(1)BENZAZEPIN-2(1H)-ONE, 4,5,6,7-TETRAHYDRO-7-HYDROXY-6-((1-METHYLETHYL)AMINO)-, (6R,7R)-REL-
Systematic Name English
RU-42173
Code English
TRANS-(+/-)-ZILPATEROL
Common Name English
ZILPATEROL [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 558.665
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
CFR 21 CFR 556.765
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
Code System Code Type Description
WIKIPEDIA
ZILPATEROL
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
FDA UNII
S384A1Y12J
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
PUBCHEM
3086576
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
CAS
119520-05-7
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
CAS
117827-79-9
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
SUPERSEDED
NCI_THESAURUS
C74221
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
EVMPD
SUB00158MIG
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL2218907
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
RXCUI
1727538
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY RxNorm
INN
6349
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY
MERCK INDEX
M11594
Created by admin on Fri Jun 25 22:31:56 UTC 2021 , Edited by admin on Fri Jun 25 22:31:56 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
ACTIVE MOIETY