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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
Structure of CLENBUTEROL

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

HIDE SMILES / InChI

Molecular Formula C12H18Cl2N2O
Molecular Weight 277.19
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://www.deadiversion.usdoj.gov/drug_chem_info/clenbuterol.pdf

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
570.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SPIROPENT

Approved Use

Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.
Primary
CLENBUTEROL

Approved Use

Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.
PubMed

PubMed

TitleDatePubMed
Effect of clenbuterol on skeletal muscle atrophy in mice induced by the glucocorticoid dexamethasone.
1992 May
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
Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB.
2004 Jun 25
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
Left ventricular assist device and drug therapy for the reversal of heart failure.
2006 Nov 2
Pulmonary edema after electroconvulsive therapy in a patient treated for long-standing asthma with a beta2 stimulant.
2007 Mar
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
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
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 Wed Jul 05 23:09:51 UTC 2023
Edited
by admin
on Wed Jul 05 23:09:51 UTC 2023
Record UNII
XTZ6AXU7KN
Record Status Validated (UNII)
Record Version
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Name Type Language
CLENBUTEROL
INN   MI   WHO-DD  
INN  
Official Name English
CLENBUTEROL [MI]
Common Name English
Clenbuterol [WHO-DD]
Common Name English
clenbuterol [INN]
Common Name English
PLANIPART
Brand Name English
NAB 365
Code English
CONTRASPASMIN
Brand Name English
NSC-758633
Code English
Classification Tree Code System Code
WHO-VATC QR03CC13
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-VATC QR03AC14
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-VATC QR03CC90
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-ATC R03CC13
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
CFR 21 CFR 530.41
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
CFR 21 CFR 520.452
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
FDA ORPHAN DRUG 451614
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
NCI_THESAURUS C319
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
FDA ORPHAN DRUG 546316
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-ATC R03CC63
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-ATC R03AC14
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
FDA ORPHAN DRUG 653918
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
WHO-VATC QG02CA91
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
NCI_THESAURUS C48149
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
Code System Code Type Description
DRUG CENTRAL
673
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
EVMPD
SUB06651MIG
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
DAILYMED
XTZ6AXU7KN
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
CAS
37148-27-9
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
SMS_ID
100000080213
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
MESH
D002976
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
FDA UNII
XTZ6AXU7KN
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID7022833
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
PUBCHEM
2783
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
INN
3264
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
WIKIPEDIA
CLENBUTEROL
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
DRUG BANK
DB01407
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
CHEBI
174690
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
RXCUI
2580
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M3615
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
253-366-0
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
NSC
758633
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL49080
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
NCI_THESAURUS
C65335
Created by admin on Wed Jul 05 23:09:51 UTC 2023 , Edited by admin on Wed Jul 05 23:09:51 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY