Zilpaterol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Zilpaterol
DrugBank Accession Number
DB11479
Background

Zilpaterol is a β2 adrenergic agonist sold under the trade name, Zilmax, produced by Intervet, a subsidiary of Merck & Co. Zilpaterol is typically fed to cattle in the last three to six weeks of life with a brief washout period to clear the drug from the tissues before slaughter.

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 261.325
Monoisotopic: 261.147726864
Chemical Formula
C14H19N3O2
Synonyms
  • Zilpaterol
External IDs
  • RU-42173

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Zilpaterol hydrochlorideEX8IEP25JU119520-06-8GIEFXLLRTJNFGT-LOCPCMAASA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
Benzimidazoles / Azepines / Aralkylamines / N-substituted imidazoles / Benzenoids / Heteroaromatic compounds / Ureas / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines
show 4 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Azole / Benzazepine / Benzenoid
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
S384A1Y12J
CAS number
119520-05-7
InChI Key
ZSTCZWJCLIRCOJ-DGCLKSJQSA-N
InChI
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
IUPAC Name
(9R,10R)-9-hydroxy-10-[(propan-2-yl)amino]-1,3-diazatricyclo[6.4.1.0^{4,13}]trideca-4,6,8(13)-trien-2-one
SMILES
CC(C)N[C@@H]1CCN2C(=O)NC3=CC=CC([C@H]1O)=C23

References

General References
  1. Shelver WL, Smith DJ: Tissue residues and urinary excretion of zilpaterol in sheep treated for 10 days with dietary zilpaterol. J Agric Food Chem. 2006 Jun 14;54(12):4155-61. [Article]
  2. Shook JN, VanOverbeke DL, Kinman LA, Krehbiel CR, Holland BP, Streeter MN, Yates DA, Hilton GG: Effects of zilpaterol hydrochloride and zilpaterol hydrochloride withdrawal time on beef carcass cutability, composition, and tenderness. J Anim Sci. 2009 Nov;87(11):3677-85. doi: 10.2527/jas.2009-1816. Epub 2009 Aug 14. [Article]
  3. Kern C, Meyer T, Droux S, Schollmeyer D, Miculka C: Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol. J Med Chem. 2009 Mar 26;52(6):1773-7. doi: 10.1021/jm801211c. [Article]
  4. Leheska JM, Montgomery JL, Krehbiel CR, Yates DA, Hutcheson JP, Nichols WT, Streeter M, Blanton JR Jr, Miller MF: Dietary zilpaterol hydrochloride. II. Carcass composition and meat palatability of beef cattle. J Anim Sci. 2009 Apr;87(4):1384-93. doi: 10.2527/jas.2008-1168. Epub 2008 Oct 10. [Article]
  5. Lawrence TE, Gasch CA, Hutcheson JP, Hodgen JM: Zilpaterol improves feeding performance and fabrication yield of concentrate-finished cull cows. J Anim Sci. 2011 Jul;89(7):2170-5. doi: 10.2527/jas.2010-3422. Epub 2011 Jan 28. [Article]
  6. Macias-Cruz U, Alvarez-Valenzuela FD, Soto-Navarro SA, Aguila-Tepato E, Avendano-Reyes L: Effect of zilpaterol hydrochloride on feedlot performance, nutrient intake, and digestibility in hair-breed sheep. J Anim Sci. 2013 Apr;91(4):1844-9. doi: 10.2527/jas.2011-4911. Epub 2013 Jan 23. [Article]
  7. Shelver WL, Smith DJ: Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol. J Agric Food Chem. 2004 Apr 21;52(8):2159-66. [Article]
  8. Garmyn AJ, Shook JN, VanOverbeke DL, Beckett JL, Delmore RJ, Yates DA, Allen DM, Hilton GG: The effects of zilpaterol hydrochloride on carcass cutability and tenderness of calf-fed Holstein steers. J Anim Sci. 2010 Jul;88(7):2476-85. doi: 10.2527/jas.2009-2635. Epub 2010 Apr 9. [Article]
  9. Parr SL, Chung KY, Galyean ML, Hutcheson JP, DiLorenzo N, Hales KE, May ML, Quinn MJ, Smith DR, Johnson BJ: Performance of finishing beef steers in response to anabolic implant and zilpaterol hydrochloride supplementation. J Anim Sci. 2011 Feb;89(2):560-70. doi: 10.2527/jas.2010-3101. Epub 2010 Oct 8. [Article]
  10. Shelver WL, Thorson JF, Hammer CJ, Smith DJ: Depletion of urinary zilpaterol residues in horses as measured by ELISA and UPLC-MS/MS. J Agric Food Chem. 2010 Apr 14;58(7):4077-83. doi: 10.1021/jf904253t. [Article]
ChemSpider
2343170
BindingDB
27955
RxNav
1727538
ChEMBL
CHEMBL462313
ZINC
ZINC000003785294
Wikipedia
Zilpaterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.01 mg/mLALOGPS
logP0.3ALOGPS
logP0.84Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.8Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area64.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity74.06 m3·mol-1Chemaxon
Polarizability27.87 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000y-8190000000-580ed8cdfadd9f02671b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-956ed86c857306affcac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-f239de526de0e6cea249
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0090000000-835ab46e89dd8b05ba39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0190000000-df0e0c41385c1771d3b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0551-3910000000-d60fef8fb6c1804784d1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9510000000-348edf6a4ccebde35eba
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.9976
predicted
DeepCCS 1.0 (2019)
[M+H]+165.3556
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.9066
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 19:06 / Updated at February 21, 2021 18:53