Zilpaterol
Star0
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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- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Zilpaterol hydrochloride EX8IEP25JU 119520-06-8 GIEFXLLRTJNFGT-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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 2343170
- BindingDB
- 27955
- 1727538
- ChEMBL
- CHEMBL462313
- ZINC
- ZINC000003785294
- Wikipedia
- Zilpaterol
Clinical Trials
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
Property Value Source Water Solubility 2.01 mg/mL ALOGPS logP 0.3 ALOGPS logP 0.84 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 12.8 Chemaxon pKa (Strongest Basic) 9.14 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 64.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 74.06 m3·mol-1 Chemaxon Polarizability 27.87 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000y-8190000000-580ed8cdfadd9f02671b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-956ed86c857306affcac Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-f239de526de0e6cea249 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0090000000-835ab46e89dd8b05ba39 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0190000000-df0e0c41385c1771d3b5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0551-3910000000-d60fef8fb6c1804784d1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9510000000-348edf6a4ccebde35eba Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.9976 predictedDeepCCS 1.0 (2019) [M+H]+ 165.3556 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.9066 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 19:06 / Updated at February 21, 2021 18:53