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Details

Stereochemistry RACEMIC
Molecular Formula C13H21NO3
Molecular Weight 239.3112
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOETHARINE

SMILES

CC[C@]([H])([C@]([H])(c1ccc(c(c1)O)O)O)NC(C)C

InChI

InChIKey=HUYWAWARQUIQLE-MFKMUULPSA-N
InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3/t10-,13+/m1/s1

HIDE SMILES / InChI
Isoetharine is a beta-2 adrenergic receptor agonist, which was developed by Max Bockmuhl, Gustav Erhart and Leonhard Stein at the Hochst laboratories of I.G. Farbenindustrie in 1934. By binding to beta-2 adrenergic receptors on bronchial cell membranes, isoetharine increases the level of cAMP and thus stimulates the relaxation of smooth-muscle cells, stabilizes mast cells and inhibits histamine release. Isoetharine was approved by FDA for the symptomatic relief of bronchiospasms in patients with chronic bronchitis or emphysema (aerosol and solution for inhalation), however, later on the drug was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
Sources: www.ncbi.nlm.nih.gov/pubmed/11283
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BRONKOSOL

Approved Use

To prevent and treat reversible bronchospasm from chronic bronchitis or emphysema.
Palliative
BRONKOSOL

Approved Use

To prevent and treat reversible bronchospasm from chronic bronchitis or emphysema.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
162 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOETHARINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
498 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOETHARINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.3 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOETHARINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 4 times / day multiple, oral
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, 29-72 years
n = 39
Health Status: unhealthy
Age Group: 29-72 years
Sex: M+F
Population Size: 39
Sources:
Other AEs: Tremor, Tremor...
Other AEs:
Tremor (1 patient)
Tremor (2 patients)
Sources:
5 mg 1 times / hour multiple, respiratory
Dose: 5 mg, 1 times / hour
Route: respiratory
Route: multiple
Dose: 5 mg, 1 times / hour
Sources:
unhealthy, 35 ± 3.31 years
Health Status: unhealthy
Age Group: 35 ± 3.31 years
Sex: M+F
Sources:
Disc. AE: Nervousness...
AEs leading to
discontinuation/dose reduction:
Nervousness (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Tremor 1 patient
20 mg 4 times / day multiple, oral
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, 29-72 years
n = 39
Health Status: unhealthy
Age Group: 29-72 years
Sex: M+F
Population Size: 39
Sources:
Tremor 2 patients
20 mg 4 times / day multiple, oral
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, 29-72 years
n = 39
Health Status: unhealthy
Age Group: 29-72 years
Sex: M+F
Population Size: 39
Sources:
Nervousness 1 patient
Disc. AE
5 mg 1 times / hour multiple, respiratory
Dose: 5 mg, 1 times / hour
Route: respiratory
Route: multiple
Dose: 5 mg, 1 times / hour
Sources:
unhealthy, 35 ± 3.31 years
Health Status: unhealthy
Age Group: 35 ± 3.31 years
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma.
1991 Oct
Pharmacological treatment of chronic obstructive pulmonary disease.
2006
Patents

Sample Use Guides

1 or 2 inhalations (340 or 680 ug) every 4 h (aerosol); 3 to 7 inhalations of undiluted 0.5 or 1% solution every 4 h (inhalation solution for hand-bulb nebulizer); 2.5 to 10 mg over 15 to 20 min, repeated every 4 h.
Route of Administration: Respiratory
In Vitro Use Guide
Unknown
Name Type Language
ISOETHARINE
MI   USAN   USP   VANDF  
USAN  
Official Name English
ETYPRENALINE
Common Name English
ISOETHARINE [VANDF]
Common Name English
WIN-3046
Code English
NEOISUPREL
Brand Name English
ISOETHARINE [USP]
Common Name English
DILABRON
Brand Name English
ISOETARINE [INN]
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((1-METHYLETHYL)AMINO)BUTYL)-
Systematic Name English
ISOETARINE [MART.]
Common Name English
ISOETHARINE [MI]
Common Name English
WIN3406
Code English
3,4-DIHYDROXY-.ALPHA.-(1-(ISOPROPYLAMINO)PROPYL)BENZYL ALCOHOL
Systematic Name English
ISOETHARINE [USAN]
Common Name English
(+/-)-ISOETHARINE
Common Name English
ISOETARINE
INN   MART.   WHO-DD  
INN  
Official Name English
ISOETARINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC R03CC06
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
WHO-ATC R03AC07
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
WHO-VATC QR03AC07
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
WHO-VATC QR03CC06
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
NCI_THESAURUS C48149
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1491
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
LACTMED
Isoetharine
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-472-1
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
IUPHAR
7205
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
WIKIPEDIA
ISOETARINE
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
CAS
530-08-5
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
EPA CompTox
530-08-5
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
INN
1384
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
MERCK INDEX
M6485
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201213
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
MESH
D007528
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
FDA UNII
YV0SN3276Q
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
DRUG BANK
DB00221
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
RXCUI
6023
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY RxNorm
CAS
79490-84-9
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
NCI_THESAURUS
C65974
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY
EVMPD
SUB08316MIG
Created by admin on Fri Jun 25 20:36:28 UTC 2021 , Edited by admin on Fri Jun 25 20:36:28 UTC 2021
PRIMARY