Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H18Cl2N2O |
| Molecular Weight | 277.19 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1
InChI
InChIKey=STJMRWALKKWQGH-UHFFFAOYSA-N
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
| Molecular Formula | C12H18Cl2N2O |
| Molecular Weight | 277.19 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Clenbuterol is agonist of beta2 adrenergic receptor. In some countries it is used as bronchodilator for treatment of asthma, but is not approved in USA. The drug is abused by bodybuilders and athletes for its ability to increase lean muscle mass and to reduce body fat. In 1998 FDA approved the clenbuterol-based Ventipulmin Syrup as a prescription-only drug for treatment of airway obstruction in horses.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Novel quantitative assessment of the tremorogenic effects of the beta 2-mimetics clenbuterol and salbutamol after oral administration]. | 1985 |
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| Clenbuterol-induced tardive dyskinesia. | 1991 Oct |
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| Effect of clenbuterol on skeletal muscle atrophy in mice induced by the glucocorticoid dexamethasone. | 1992 May |
|
| Is the "atypical" beta-receptor in the rat stomach fundus the rat beta 3 receptor? | 1995 Jan |
|
| Adrenergic agents inhibit rapid increases in cerebellar Purkinje cell glutamic acid decarboxylase (GAD67) mRNA levels after climbing fiber lesions or reserpine treatment. | 1996 Mar 1 |
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| Clenbuterol and anabolic steroids: a previously unreported cause of myocardial infarction with normal coronary arteriograms. | 1998 Aug |
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| Early alterations of polyamine metabolism induced after acute administration of clenbuterol in mouse heart. | 1999 |
|
| beta1 to beta3 switch in control of cyclic adenosine monophosphate during brown adipocyte development explains distinct beta-adrenoceptor subtype mediation of proliferation and differentiation. | 1999 Sep |
|
| The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors. | 2000 Jun |
|
| [A case of immotile-dyskinetic cilia syndrome responding to clenbuterol hydrochloride and azithromycin]. | 2002 Jul |
|
| Role of myometrial activity in sperm transport through the genital tract and in fertilization in sows. | 2002 May |
|
| Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB. | 2004 Jun 25 |
|
| Endotoxin-induced liver damage in rats is minimized by beta 2-adrenoceptor stimulation. | 2004 Mar |
|
| Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro. | 2004 Nov |
|
| Dose-dependent apoptotic and necrotic myocyte death induced by the beta2-adrenergic receptor agonist, clenbuterol. | 2005 Dec |
|
| [Resolution of clenbuterol hydrochloride enantiomers by thin-layer chromatography on silica gel impregnated with beta-cyclodextrin]. | 2005 Jul |
|
| Beta-adrenergic receptor modulation of the LPS-mediated depression in CYP1A activity in astrocytes. | 2005 Mar 1 |
|
| [Enantiomeric resolution of clenbuterol hydrochloride using (2R, 3R)-Dicyclohexyl tartrate impregnated thin layer chromatography]. | 2005 Nov |
|
| Adrenergic receptor agonists prevent bile duct injury induced by adrenergic denervation by increased cAMP levels and activation of Akt. | 2006 Apr |
|
| [Use of ultrasensitive time-resolved fluoroimmunoassay for rapid detection of clenbuterol hydrochloride in urine]. | 2006 Nov |
|
| Left ventricular assist device and drug therapy for the reversal of heart failure. | 2006 Nov 2 |
|
| An increase in murine skeletal muscle peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1alpha) mRNA in response to exercise is mediated by beta-adrenergic receptor activation. | 2007 Jul |
|
| Pulmonary edema after electroconvulsive therapy in a patient treated for long-standing asthma with a beta2 stimulant. | 2007 Mar |
|
| Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms. | 2008 Oct |
|
| Solid substrate-room temperature phosphorimetry for the determination of residual clenbuterol hydrochloride based on the catalysis of sodium periodate oxidizing eosine Y. | 2009 Apr 6 |
|
| Accumulation of the beta(2)-adrenergic agonist clenbuterol in mouse dark hair. | 2009 Nov |
|
| Beta2-adrenergic agonist-induced hypertrophy of the quadriceps skeletal muscle does not modulate disease severity in the rodent meniscectomy model of osteoarthritis. | 2010 Apr |
|
| Beta(2)-adrenoceptor agonist clenbuterol reduces infarct size and myocardial apoptosis after myocardial ischaemia/reperfusion in anaesthetized rats. | 2010 Jul |
|
| Antitussive effects of the leukotriene receptor antagonist montelukast in patients with cough variant asthma and atopic cough. | 2010 Jun |
|
| Blocking beta2-adrenergic receptor attenuates acute stress-induced amyloid beta peptides production. | 2010 Mar 4 |
Sample Use Guides
For treatmen of airways obstruction the clenbuterol is administered orally, 15ml of syrop 2-3 times a day.
Route of Administration:
Oral
Affinity towards beta2 adrenergic receptors was measured using the recombinant receptor expressed in Sf-9 cells. Cell membrane homogenates were incubated with 0.15 nM of radioligand [3H]CGP1217 in the absence of presence of the clenbuterol. Following incubation, the samples were filtered rapidly under vacuum through through glass fiber filters, the filters were dried, and counted for radioactivity in a scintillation counter. Clenbuterol was binding to beta2 receptor with Ki of 0.58 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 00:26:56 UTC 2019
by
admin
on
Tue Oct 22 00:26:56 UTC 2019
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| Record UNII |
XTZ6AXU7KN
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| Record Status |
Validated (UNII)
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| Record Version |
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Code | English | ||
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| Classification Tree | Code System | Code | ||
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WHO-VATC |
QR03CC13
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WHO-VATC |
QR03AC14
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WHO-VATC |
QR03CC90
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WHO-ATC |
R03CC13
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admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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CFR |
21 CFR 530.41
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CFR |
21 CFR 520.452
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FDA ORPHAN DRUG |
451614
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NCI_THESAURUS |
C319
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admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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FDA ORPHAN DRUG |
546316
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admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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WHO-ATC |
R03CC63
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admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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WHO-ATC |
R03AC14
Created by
admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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FDA ORPHAN DRUG |
653918
Created by
admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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WHO-VATC |
QG02CA91
Created by
admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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NCI_THESAURUS |
C48149
Created by
admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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| Code System | Code | Type | Description | ||
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SUB06651MIG
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PRIMARY | |||
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37148-27-9
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PRIMARY | |||
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D002976
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PRIMARY | |||
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37148-27-9
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PRIMARY | |||
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2783
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PRIMARY | |||
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3264
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PRIMARY | |||
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CLENBUTEROL
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DB01407
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PRIMARY | |||
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2580
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PRIMARY | RxNorm | ||
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M3615
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PRIMARY | Merck Index | ||
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253-366-0
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PRIMARY | |||
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CHEMBL49080
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admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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PRIMARY | |||
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C65335
Created by
admin on Tue Oct 22 00:26:56 UTC 2019 , Edited by admin on Tue Oct 22 00:26:56 UTC 2019
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> AGONIST |
SHORT-ACTING
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ACTIVE MOIETY |
