CLENBUTEROL HYDROCHLORIDE

Possibly Marketed Outside US

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 Search

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	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: http://rmtcnet.com/wp-content/uploads/2015/07/RMTC-Position-Paper-on-Clenbuterol.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19245211	Agonist 2752		570.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8583	SPIROPENT Approved Use Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.
Chronic obstructive pulmonary disease 175 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8583	CLENBUTEROL Approved Use Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.

C_max

Value	Dose	Co-administered	Analyte	Population
133.2 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg single, oral dose: 40 μg route of administration: Oral experiment type: SINGLE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
329.7 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg 1 times / day steady-state, oral dose: 40 μg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
4889.4 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg single, oral dose: 40 μg route of administration: Oral experiment type: SINGLE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14164.8 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg 1 times / day steady-state, oral dose: 40 μg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
26.56 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg single, oral dose: 40 μg route of administration: Oral experiment type: SINGLE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
33.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26770490/	40 μg 1 times / day steady-state, oral dose: 40 μg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://www.jstage.jst.go.jp/article/bpb1978/8/5/8_5_385/_article/-char/en	80 μg single, oral dose: 80 μg route of administration: Oral experiment type: SINGLE co-administered:		CLENBUTEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Overdose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22633759/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/22633759/	Disc. AE: Myocardial ischemia... AEs leading to discontinuation/dose reduction: Myocardial ischemia (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/22633759/
108.75 ug single, oral Overdose Dose: 108.75 ug Route: oral Route: single Dose: 108.75 ug Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/	Other AEs: Supraventricular tachycardia, Atrial fibrillation... Other AEs: Supraventricular tachycardia (1 pt) Atrial fibrillation (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/
40 ug 1 times / day multiple, oral Recommended Dose: 40 ug, 1 times / day Route: oral Route: multiple Dose: 40 ug, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32908823/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/32908823/	Disc. AE: Myocarditis... AEs leading to discontinuation/dose reduction: Myocarditis (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/32908823/

AEs

AE	Significance	Dose	Population
Myocardial ischemia	1 pt Disc. AE	30 mg 1 times / day multiple, oral Overdose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22633759/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/22633759/
Atrial fibrillation	1 pt	108.75 ug single, oral Overdose Dose: 108.75 ug Route: oral Route: single Dose: 108.75 ug Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/
Supraventricular tachycardia	1 pt	108.75 ug single, oral Overdose Dose: 108.75 ug Route: oral Route: single Dose: 108.75 ug Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18072161/
Myocarditis	1 pt Disc. AE	40 ug 1 times / day multiple, oral Recommended Dose: 40 ug, 1 times / day Route: oral Route: multiple Dose: 40 ug, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32908823/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/32908823/

PubMed

Title	Date	PubMed
Beta(2)-adrenoceptor agonist clenbuterol reduces infarct size and myocardial apoptosis after myocardial ischaemia/reperfusion in anaesthetized rats.	2010-07	20590644
Antitussive effects of the leukotriene receptor antagonist montelukast in patients with cough variant asthma and atopic cough.	2010-06	20299826
Beta2-adrenergic agonist-induced hypertrophy of the quadriceps skeletal muscle does not modulate disease severity in the rodent meniscectomy model of osteoarthritis.	2010-04	20060953
Blocking beta2-adrenergic receptor attenuates acute stress-induced amyloid beta peptides production.	2010-03-04	20059989
Accumulation of the beta(2)-adrenergic agonist clenbuterol in mouse dark hair.	2009-11	19533101
Solid substrate-room temperature phosphorimetry for the determination of residual clenbuterol hydrochloride based on the catalysis of sodium periodate oxidizing eosine Y.	2009-04-06	19298881
Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms.	2008-10	18552870
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.	2007-07	17446185
Pulmonary edema after electroconvulsive therapy in a patient treated for long-standing asthma with a beta2 stimulant.	2007-03	17435570
Left ventricular assist device and drug therapy for the reversal of heart failure.	2006-11-02	17079761
[Use of ultrasensitive time-resolved fluoroimmunoassay for rapid detection of clenbuterol hydrochloride in urine].	2006-11	17290771
Adrenergic receptor agonists prevent bile duct injury induced by adrenergic denervation by increased cAMP levels and activation of Akt.	2006-04	16339297
Dose-dependent apoptotic and necrotic myocyte death induced by the beta2-adrenergic receptor agonist, clenbuterol.	2005-12	16007677
[Enantiomeric resolution of clenbuterol hydrochloride using (2R, 3R)-Dicyclohexyl tartrate impregnated thin layer chromatography].	2005-11	16499011
[Resolution of clenbuterol hydrochloride enantiomers by thin-layer chromatography on silica gel impregnated with beta-cyclodextrin].	2005-07	16250460
Beta-adrenergic receptor modulation of the LPS-mediated depression in CYP1A activity in astrocytes.	2005-03-01	15710352
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.	2004-11	15502056
Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB.	2004-06-25	15178407
Endotoxin-induced liver damage in rats is minimized by beta 2-adrenoceptor stimulation.	2004-03	15021963
[A case of immotile-dyskinetic cilia syndrome responding to clenbuterol hydrochloride and azithromycin].	2002-07	12382429
Role of myometrial activity in sperm transport through the genital tract and in fertilization in sows.	2002-05	12006096
The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors.	2000-06	10898105
beta1 to beta3 switch in control of cyclic adenosine monophosphate during brown adipocyte development explains distinct beta-adrenoceptor subtype mediation of proliferation and differentiation.	1999-09	10465291
Early alterations of polyamine metabolism induced after acute administration of clenbuterol in mouse heart.	1999	10353628
Clenbuterol and anabolic steroids: a previously unreported cause of myocardial infarction with normal coronary arteriograms.	1998-08	9715231
Adrenergic agents inhibit rapid increases in cerebellar Purkinje cell glutamic acid decarboxylase (GAD67) mRNA levels after climbing fiber lesions or reserpine treatment.	1996-03-01	8774452
Is the "atypical" beta-receptor in the rat stomach fundus the rat beta 3 receptor?	1995-01	7815362
Effect of clenbuterol on skeletal muscle atrophy in mice induced by the glucocorticoid dexamethasone.	1992-05	1351811
Clenbuterol-induced tardive dyskinesia.	1991-10	1742751
[Novel quantitative assessment of the tremorogenic effects of the beta 2-mimetics clenbuterol and salbutamol after oral administration].	1985	3907640

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 `Mon Mar 31 18:13:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:36 GMT 2025`
Record UNII	GOR5747GWU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLENBUTEROL HYDROCHLORIDE

Common Name

English

SPIROPENT

Preferred Name

English

CLENBUTEROL HYDROCHLORIDE [EP IMPURITY]

Common Name

English

Clenbuterol hydrochloride [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 [USP MONOGRAPH]

Common Name

English

CLENBUTEROL HCL

Common Name

English

4-AMINO-.ALPHA.-((TERT-BUTYLAMINO)METHYL)-3,5-DICHLOROBENZYL ALCOHOL

Systematic Name

English

CLENBUTEROL HYDROCHLORIDE [MART.]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [MI]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149