U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005 May 4
Tissue residues and urinary excretion of zilpaterol in sheep treated for 10 days with dietary zilpaterol.
2006 Jun 14
Effects of duration of zilpaterol hydrochloride feeding and days on the finishing diet on feedlot cattle performance and carcass traits.
2008 Aug
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
Effects of zilpaterol hydrochloride on growth rates, feed conversion, and carcass traits in calf-fed Holstein steers.
2009 Dec
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
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
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
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
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
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966