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Details

Stereochemistry RACEMIC
Molecular Formula C12H18Cl2N2O.ClH
Molecular Weight 313.651
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLENBUTEROL HYDROCHLORIDE

SMILES

Cl.CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1

InChI

InChIKey=OPXKTCUYRHXSBK-UHFFFAOYSA-N
InChI=1S/C12H18Cl2N2O.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C12H18Cl2N2O
Molecular Weight 277.19
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
570.0 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
[Novel quantitative assessment of the tremorogenic effects of the beta 2-mimetics clenbuterol and salbutamol after oral administration].
1985
Clenbuterol-induced tardive dyskinesia.
1991 Oct
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
Clenbuterol and anabolic steroids: a previously unreported cause of myocardial infarction with normal coronary arteriograms.
1998 Aug
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
Patents

Sample Use Guides

In Vivo Use Guide
For treatmen of airways obstruction the clenbuterol is administered orally, 15ml of syrop 2-3 times a day.
Route of Administration: Oral
In Vitro Use Guide
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 Tue Oct 22 00:26:55 UTC 2019
Edited
by admin
on Tue Oct 22 00:26:55 UTC 2019
Record UNII
GOR5747GWU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLENBUTEROL HYDROCHLORIDE
EP   GREEN BOOK   JAN   MART.   MI   USP   USP-RS   WHO-DD  
Common Name English
NAB-365
Code English
VENTIPULMIN
Brand Name English
NAB 365 CL
Code English
NAB-365CL
Code English
CLENBUTEROL HYDROCHLORIDE [GREEN BOOK]
Common Name English
CLENBUTEROL HYDROCHLORIDE [JAN]
Common Name English
CLENBUTEROL HYDROCHLORIDE [WHO-DD]
Common Name English
CLENBUTEROL HCL
Common Name English
4-AMINO-.ALPHA.-((TERT-BUTYLAMINO)METHYL)-3,5-DICHLOROBENZYL ALCOHOL
Systematic Name English
CLENBUTEROL HYDROCHLORIDE [USP]
Common Name English
CLENBUTEROL HYDROCHLORIDE [MART.]
Common Name English
CLENBUTEROL HYDROCHLORIDE [MI]
Common Name English
CLENASMA
Brand Name English
SPIROPENT
Brand Name English
CLENBUTEROL HYDROCHLORIDE [EP]
Common Name English
CLENBUTEROL HYDROCHLORIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
Code System Code Type Description
RXCUI
235955
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY RxNorm
EVMPD
SUB01339MIG
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY
NCI_THESAURUS
C87473
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY
CAS
21898-19-1
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY
ChEMBL
CHEMBL49080
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
244-643-7
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY
MERCK INDEX
M3615
Created by admin on Tue Oct 22 00:26:55 UTC 2019 , Edited by admin on Tue Oct 22 00:26:55 UTC 2019
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY