U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C13H21NO3.CH4O3S
Molecular Weight 335.416
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOETHARINE MESYLATE

SMILES

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

InChI

InChIKey=SOYAGMVKMXZVNZ-HTKOBJQYSA-N
InChI=1S/C13H21NO3.CH4O3S/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9;1-5(2,3)4/h5-8,10,13-17H,4H2,1-3H3;1H3,(H,2,3,4)/t10-,13+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C13H21NO3
Molecular Weight 239.3107
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Hypomania related to phenelzine and isoetharine interaction in one patient.
1987 Apr
Pharmacological treatment of chronic obstructive pulmonary disease.
2006
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:11 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:11 GMT 2023
Record UNII
DV74WJ5PJB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOETHARINE MESYLATE
ORANGE BOOK   USP   VANDF  
Common Name English
BRONKOMETER
Brand Name English
ISOETHARINE MESYLATE [USP IMPURITY]
Common Name English
Isoetarine mesilate [WHO-DD]
Common Name English
ISOETHARINE MESYLATE [ORANGE BOOK]
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((1-METHYLETHYL)AMINO)-BUTYL)-, METHANESULFONATE (SALT)
Common Name English
NSC-759286
Code English
4-(1-HYDROXY-2-(ISOPROPYLAMINO)BUTYL)BENZENE-1,2-DIOL METHANESULFONATE (SALT)
Common Name English
ISOETARINE MESILATE [MART.]
Common Name English
3,4-DIHYDROXY-.ALPHA.-(1-(ISOPROPYLAMINO)PROPYL)BENZYL ALCOHOL METHANESULPHONATE (SALT)
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((1-METHYLETHYL)AMINO)-BUTYL)-, METHANESULPHONATE (SALT)
Common Name English
ISOETHARINE MESYLATE [VANDF]
Common Name English
ISOETHARINE MESILATE
Common Name English
3,4-Dihydroxy-α-[1-(isopropylamino)propyl]benzyl alcohol methanesulfonate (salt)
Common Name English
ISOETARINE MESILATE
MART.   WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65976
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
230-695-8
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045571
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
FDA UNII
DV74WJ5PJB
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
PUBCHEM
76972622
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
EVMPD
SUB02788MIG
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
RXCUI
6024
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201213
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
NSC
759286
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
SMS_ID
100000086437
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
DRUG BANK
DBSALT000886
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
CAS
7279-75-6
Created by admin on Fri Dec 15 16:13:11 GMT 2023 , Edited by admin on Fri Dec 15 16:13:11 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY