Banner
targets (5) enzymes (2)
for drugs
Identification
Name Clenbuterol
Accession Number DB01407
Type small molecule
Groups approved
Description

A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Clenbuterolum [inn-latin]
Salts Not Available
Brand names
Name Company
Planipart
Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
CAS number 37148-27-9
Weight Average: 277.19
Monoisotopic: 276.079618622
Chemical Formula C12H18Cl2N2O
InChI Key InChIKey=STJMRWALKKWQGH-UHFFFAOYSA-N
InChI
InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3
Plain Text
IUPAC Name
1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol
SMILES
CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Anilines
Pharmacology
Indication Used as a bronchodilator in the treatment of asthma patients.
Pharmacodynamics Clenbuterol is a substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma. Although approved for use in some countries, as of fall, 2006, clenbuterol is not an ingredient of any therapeutic drug approved by the U.S. Food and Drug Administration.
Mechanism of action Clenbuterol is a Beta(2) agonist similar in some structural respects to salbutamol. Agonism of the beta(2) receptor stimulates adenylyl cyclase activity which ultimately leads to downstream effects of smooth muscle relaxation in the bronchioles.
Absorption 89-98% orally
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life 36-39 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.12e-01 g/l ALOGPS
logP 2.94 ALOGPS
logP 2.33 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 14.06 ChemAxon
pKa (strongest basic) 9.63 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 58.28 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 73.38 ChemAxon
polarizability 28.81 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 2783 Link_out
PubChem Substance 46508373 Link_out
ChemSpider 2681 Link_out
BindingDB 27958 Link_out
ChEBI 174690 Link_out
ChEMBL 174690 Link_out
Therapeutic Targets Database DAP000945 Link_out
PharmGKB PA164745640 Link_out
Wikipedia http://en.wikipedia.org/wiki/Clenbuterol Link_out
ATC Codes
  • R03CC13
  • R03AC14
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Zhu Y, Culmsee C, Roth-Eichhorn S, Krieglstein J: Beta(2)-adrenoceptor stimulation enhances latent transforming growth factor-beta-binding protein-1 and transforming growth factor-beta1 expression in rat hippocampus after transient forebrain ischemia. Neuroscience. 2001;107(4):593-602. Pubmed
  2. Ryall JG, Gregorevic P, Plant DR, Sillence MN, Lynch GS: Beta 2-agonist fenoterol has greater effects on contractile function of rat skeletal muscles than clenbuterol. Am J Physiol Regul Integr Comp Physiol. 2002 Dec;283(6):R1386-94. Epub 2002 Sep 5. Pubmed
  3. Choo JJ, Horan MA, Little RA, Rothwell NJ: Anabolic effects of clenbuterol on skeletal muscle are mediated by beta 2-adrenoceptor activation. Am J Physiol. 1992 Jul;263(1 Pt 1):E50-6. Pubmed
  4. Sillence MN, Matthews ML, Spiers WG, Pegg GG, Lindsay DB: Effects of clenbuterol, ICI118551 and sotalol on the growth of cardiac and skeletal muscle and on beta 2-adrenoceptor density in female rats. Naunyn Schmiedebergs Arch Pharmacol. 1991 Oct;344(4):449-53. Pubmed
  5. Mazzanti G, Di Sotto A, Daniele C, Battinelli L, Brambilla G, Fiori M, Loizzo S, Loizzo A: A pharmacodynamic study on clenbuterol-induced toxicity: beta1- and beta2-adrenoceptors involvement in guinea-pig tachycardia in an in vitro model. Food Chem Toxicol. 2007 Sep;45(9):1694-9. Epub 2007 Mar 12. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Baker JG: The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. Br J Pharmacol. 2010 Jul;160(5):1048-61. Pubmed

3. Beta-3 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis

Organism class: human
UniProt ID: P13945 Link_out
Gene: ADRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Baker JG: The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. Br J Pharmacol. 2010 Jul;160(5):1048-61. Pubmed

4. Beta-nerve growth factor

Pharmacological action: unknown
Actions: stimulator

Nerve growth factor is important for the development and maintenance of the sympathetic and sensory nervous systems. It stimulates division and differentiation of sympathetic and embryonic sensory neurons

Organism class: human
UniProt ID: P01138 Link_out
Gene: NGFB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Culmsee C, Semkova I, Krieglstein J: NGF mediates the neuroprotective effect of the beta2-adrenoceptor agonist clenbuterol in vitro and in vivo: evidence from an NGF-antisense study. Neurochem Int. 1999 Jul;35(1):47-57. Pubmed
  2. Semkova I, Krieglstein J: Neuroprotection mediated via neurotrophic factors and induction of neurotrophic factors. Brain Res Brain Res Rev. 1999 Aug;30(2):176-88. Pubmed
  3. Puls I, Beck M, Giess R, Magnus T, Ochs G, Toyka KV: [Clenbuterol in amyotrophic lateral sclerosis. No indication for a positive effect] Nervenarzt. 1999 Dec;70(12):1112-5. Pubmed
  4. Samina Riaz S, Tomlinson DR: Pharmacological modulation of nerve growth factor synthesis: a mechanistic comparison of vitamin D receptor and beta(2)-adrenoceptor agonists. Brain Res Mol Brain Res. 2000 Dec 28;85(1-2):179-88. Pubmed
  5. Riaz SS, Tomlinson DR: Clenbuterol stimulates neurotrophic support in streptozotocin-diabetic rats. Diabetes Obes Metab. 1999 Jan;1(1):43-51. Pubmed

5. Tumor necrosis factor

Pharmacological action: unknown
Actions: other/unknown

Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin 1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation

Organism class: human
UniProt ID: P01375 Link_out
Gene: TNF Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Izeboud CA, Mocking JA, Monshouwer M, van Miert AS, Witkamp RF: Participation of beta-adrenergic receptors on macrophages in modulation of LPS-induced cytokine release. J Recept Signal Transduct Res. 1999 Jan-Jul;19(1-4):191-202. Pubmed
  2. Yoshimura T: [Modulation of cytokine production from human mononuclear cells by several agents] Yakugaku Zasshi. 2000 Dec;120(12):1277-90. Pubmed
  3. Izeboud CA, Hoebe KH, Grootendorst AF, Nijmeijer SM, van Miert AS, Witkamp RR, Rodenburg RJ: Endotoxin-induced liver damage in rats is minimized by beta 2-adrenoceptor stimulation. Inflamm Res. 2004 Mar;53(3):93-9. Epub 2004 Feb 16. Pubmed
  4. Laan TT, Bull S, Pirie RS, Fink-Gremmels J: Evaluation of cytokine production by equine alveolar macrophages exposed to lipopolysaccharide, Aspergillus fumigatus, and a suspension of hay dust. Am J Vet Res. 2005 Sep;66(9):1584-9. Pubmed
  5. van den Hoven R, Duvigneau JC, Hartl RT, Gemeiner M: Clenbuterol affects the expression of messenger RNA for interleukin 10 in peripheral leukocytes from horses challenged intrabronchially with lipopolysaccharides. Vet Res Commun. 2006 Nov;30(8):921-8. Pubmed
Enzymes

1. Cytochrome P450 1A1

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on July 17, 2007 06:33 / Updated on February 08, 2013 16:20