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Details

Stereochemistry RACEMIC
Molecular Formula C14H19N3O2
Molecular Weight 261.3196
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZILPATEROL

SMILES

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

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 261.3196
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

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
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
Beta-adrenergic receptor agonists induce the release of granulocyte chemotactic protein-2, oncostatin M, and vascular endothelial growth factor from macrophages.
2006 Jan
Dietary zilpaterol hydrochloride. I. Feedlot performance and carcass traits of steers and heifers.
2009 Apr
Dietary zilpaterol hydrochloride. II. Carcass composition and meat palatability of beef cattle.
2009 Apr
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
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
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
[Determination of fifteen beta-agonists in animal urine by high performance liquid chromatography-tandem mass spectrometry].
2010 Aug
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
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 Fri Dec 15 15:29:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:15 GMT 2023
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 Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
CFR 21 CFR 556.765
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID50904261
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
WIKIPEDIA
ZILPATEROL
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
FDA UNII
S384A1Y12J
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
PUBCHEM
3086576
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
CAS
119520-05-7
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
CAS
117827-79-9
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
SUPERSEDED
NCI_THESAURUS
C74221
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
EVMPD
SUB00158MIG
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL2218907
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
SMS_ID
100000079046
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
RXCUI
1727538
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY RxNorm
INN
6349
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY
MERCK INDEX
m11594
Created by admin on Fri Dec 15 15:29:15 GMT 2023 , Edited by admin on Fri Dec 15 15:29:15 GMT 2023
PRIMARY Merck Index
Related Record Type Details
Structure of ZILPATEROL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
BETA-2 ADRENERGIC RECEPTOR
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
Structure of ZILPATEROL
ACTIVE MOIETY
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