ISOETHARINE

US Previously Marketed

First approved in 1961

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@H](NC(C)C)[C@@H](O)C1=CC(O)=C(O)C=C1

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

Description
Sources: ISBN-13: 9781449638641, '2012 Nurse's Drug Handbook' (2011), p. 566, Retrieved from https://books.google.com/books?id=yJ9K8_aMNSEC&dq

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 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	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic bronchitis 51 Sources: (2011) '2012 Nurse's Drug Handbook', p. 566, retrieved from https://books.google.com/books?id=yJ9K8_aMNSEC&dq	Palliative		Approved 8429	BRONKOSOL Approved Use To prevent and treat reversible bronchospasm from chronic bronchitis or emphysema.
Emphysema 13 Sources: (2011) '2012 Nurse's Drug Handbook', p. 566, retrieved from https://books.google.com/books?id=yJ9K8_aMNSEC&dq	Palliative		Approved 8429	BRONKOSOL Approved Use To prevent and treat reversible bronchospasm from chronic bronchitis or emphysema.

C_max

Value	Dose	Co-administered	Analyte	Population
162 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7120101/	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

Value	Dose	Co-administered	Analyte	Population
498 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7120101/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7120101/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/799980	unhealthy, 29-72 years n = 39 Health Status: unhealthy Age Group: 29-72 years Sex: M+F Population Size: 39 Sources: https://pubmed.ncbi.nlm.nih.gov/799980	Other AEs: Tremor, Tremor... Other AEs: Tremor (1 patient) Tremor (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/799980
5 mg 1 times / hour multiple, respiratory Dose: 5 mg, 1 times / hour Route: respiratory Route: multiple Dose: 5 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/8629678/	unhealthy, 35 ± 3.31 years Health Status: unhealthy Age Group: 35 ± 3.31 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8629678/	Disc. AE: Nervousness... AEs leading to discontinuation/dose reduction: Nervousness (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8629678/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/799980	unhealthy, 29-72 years n = 39 Health Status: unhealthy Age Group: 29-72 years Sex: M+F Population Size: 39 Sources: https://pubmed.ncbi.nlm.nih.gov/799980
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: https://pubmed.ncbi.nlm.nih.gov/799980	unhealthy, 29-72 years n = 39 Health Status: unhealthy Age Group: 29-72 years Sex: M+F Population Size: 39 Sources: https://pubmed.ncbi.nlm.nih.gov/799980
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: https://pubmed.ncbi.nlm.nih.gov/8629678/	unhealthy, 35 ± 3.31 years Health Status: unhealthy Age Group: 35 ± 3.31 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8629678/

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	2481AH
Alfa Chemistry	113891
Alfa Chemistry	7279-75-6
Alfa Chemistry	ACM2576923
BOC Sciences	2576-92-3
BOC Sciences	530-08-5
BOC Sciences	7279-75-6
Compound Cloud	23702
Compound Cloud	3762
Compound Cloud	5791
Hangzhou Yuhao Chemical Technology	LQ2260
HongKong Chemhere	SCE20226
MolPort	MolPort-003-941-811
MuseChem	I007378
MuseChem	R023080
Sigma Aldrich	I3639
Sigma Aldrich	I3639\|SIGMA
TargetMol	T4983
Tetrahedron	TS63980
Toronto Research Chemicals	I815703
ZINC	ZINC000000402981	http://zinc15.docking.org/substances/ZINC000000402981
eMolecules	300012659
eMolecules	539639

PubMed

Title	Date	PubMed
Hypomania related to phenelzine and isoetharine interaction in one patient.	1987 Apr	3558333
A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma.	1991 Oct	1928879
Pharmacological treatment of chronic obstructive pulmonary disease.	2006	18044097
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

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

Official Name

English

ISOETHARINE [USP IMPURITY]

Common Name

English

ETYPRENALINE

Common Name

English

ISOETHARINE [VANDF]

Common Name

English

WIN-3046

Code

English

Isoetarine [WHO-DD]

Common Name

English

NEOISUPREL

Brand 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-α-[1-(isopropylamino)propyl]benzyl alcohol

Systematic Name

English

ISOETHARINE [USAN]

Common Name

English

(±)-ISOETHARINE

Common Name

English

ISOETARINE

Official Name

English

Classification Tree Code System Code

WHO-ATC

R03CC06