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Details

Stereochemistry RACEMIC
Molecular Formula C17H27NO2.ClH
Molecular Weight 313.863
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Zenidolol hydrochloride

SMILES

Cl.CC(C)N[C@H](C)[C@@H](O)COC1=C2CCCC2=C(C)C=C1

InChI

InChIKey=KBXMBGWSOLBOQM-CACIRBSMSA-N
InChI=1S/C17H27NO2.ClH/c1-11(2)18-13(4)16(19)10-20-17-9-8-12(3)14-6-5-7-15(14)17;/h8-9,11,13,16,18-19H,5-7,10H2,1-4H3;1H/t13-,16+;/m1./s1

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 C17H27NO2
Molecular Weight 277.4018
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28064316 | https://www.ncbi.nlm.nih.gov/pubmed/26762097 | https://www.ncbi.nlm.nih.gov/pubmed/3320184 | https://www.ncbi.nlm.nih.gov/pubmed/2908820

ICI-118551 is a selective β2 adrenergic receptor antagonist, that was originally developed for the regulation of blood pressure. ICI-118551 crosses the blood-brain barrier and it was in phase I clinical trials for the treatment of chronic anxiety. Currently, ICI-118,551 has no known therapeutic use in humans although it has been used widely in research to understand the action of the β2 adrenergic receptor, as few other specific antagonists for this receptor are known.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 1.2 nM [IC50]
Antagonist
2849
 240.0 nM [Kd]
Antagonist
2849
 0.5 nM [IC50]
Beta-2 adrenergic receptor
209
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
Antagonist
2849
 2.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2564208/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2564208/
Other AEs: headache...
Other AEs:
headache (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2564208/
AEs

AEs

AESignificanceDosePopulation
headache 2 patients
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2564208/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2564208/
PubMed

PubMed

TitleDatePubMed
[Changes in the receptor activity of β2-adrenoreceptors of human T-lymphocytes under the effect of β2-agonists].
2015-10-21
beta(2)-adrenoceptor antagonist ICI 118,551 decreases pulmonary vascular tone in mice via a G(i/o) protein/nitric oxide-coupled pathway.
2009-07
A cell-based assay to assess the persistence of action of agonists acting at recombinant human beta(2) adrenoceptors.
2007-12-16
Functional characterization of the beta-adrenergic receptor subtypes expressed by CA1 pyramidal cells in the rat hippocampus.
2005-08
Nicotine-induced NO-mediated increase in cortical cerebral blood flow is blocked by beta2-adrenoceptor antagonists in the anesthetized rats.
2002-03-18
Beta-adrenoceptor subtypes and the opening of plasmalemmal K(+)-channels in trachealis muscle: electrophysiological and mechanical studies in guinea-pig tissue.
1993-08
Molecular characterization of the human beta 3-adrenergic receptor.
1989-09-08
Beta 1- and beta 2-adrenergic receptor-mediated adenylate cyclase stimulation in nonfailing and failing human ventricular myocardium.
1989-03
Human fat cell beta-adrenergic receptors: beta-agonist-dependent lipolytic responses and characterization of beta-adrenergic binding sites on human fat cell membranes with highly selective beta 1-antagonists.
1988-05
The pharmacology of a beta 2-selective adrenoceptor antagonist (ICI 118,551).
1983-05-01
Patents

Patents

20030152566
2
20040048286
2
20050130136
2
20060216755
2

Sample Use Guides

In Vivo Use Guide
ICI 118,551, 50 mg given thrice daily, in hypertensive patients known to respond to therapy with atenolol or propranolol.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/26762097
In cultured rat inner medullary collecting duct (IMCD) cells expressing beta-adrenoceptor subtype(s) ICI-118551 inhibited adenosine 3',5'-cyclic monophosphate (cAMP) accumulation by 50% at 1.7 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:15:11 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:11 GMT 2025
Record UNII
9GT820DINA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ICI-111581
Preferred Name English
Zenidolol hydrochloride
Common Name English
2-BUTANOL, 1-((2,3-DIHYDRO-7-METHYL-1H-INDEN-4-YL)OXY)-3-((1-METHYLETHYL)AMINO)-, HYDROCHLORIDE (1:1), (2R,3R)-REL-
Systematic Name English
ICI-118551 HYDROCHLORIDE
Code English
Code System Code Type Description
FDA UNII
9GT820DINA
Created by admin on Mon Mar 31 18:15:11 GMT 2025 , Edited by admin on Mon Mar 31 18:15:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID201339098
Created by admin on Mon Mar 31 18:15:11 GMT 2025 , Edited by admin on Mon Mar 31 18:15:11 GMT 2025
PRIMARY
PUBCHEM
46704050
Created by admin on Mon Mar 31 18:15:11 GMT 2025 , Edited by admin on Mon Mar 31 18:15:11 GMT 2025
PRIMARY
CAS
72795-01-8
Created by admin on Mon Mar 31 18:15:11 GMT 2025 , Edited by admin on Mon Mar 31 18:15:11 GMT 2025
PRIMARY
Related Record Type Details
Structure of Zenidolol
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Zenidolol
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