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Details

Stereochemistry RACEMIC
Molecular Formula C13H21NO3.ClH
Molecular Weight 275.772
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOETHARINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=MUFDLGGSOCHQOC-HTKOBJQYSA-N
InChI=1S/C13H21NO3.ClH/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;1H/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 ClH
Molecular Weight 36.461
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
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 16:33:35 GMT 2023
Edited
by admin
on Fri Dec 15 16:33:35 GMT 2023
Record UNII
51V8U784H3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOETHARINE HYDROCHLORIDE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
ISOETHARINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ASTHMALITAN
Brand Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((1-METHYLETHYL)AMINO)BUTYL)-, HYDROCHLORIDE
Systematic Name English
ISOETHARINE HYDROCHLORIDE [MI]
Common Name English
NUMOTAC
Brand Name English
ISOETHARINE HYDROCHLORIDE [VANDF]
Common Name English
BETA-2
Brand Name English
3,4-Dihydroxy-α-[1-(isopropylamino)propyl]benzyl alcohol hydrochloride
Systematic Name English
ISOETHARINE HYDROCHLORIDE [USP-RS]
Common Name English
ISOETARINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
ISOETHARINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
1,2-BENZENEDIOL, 4-((1R,2S)-1-HYDROXY-2-((1-METHYLETHYL)AMINO)BUTYL)-, HYDROCHLORIDE (1:1), REL-
Systematic Name English
ISOETHARINE HCL
Common Name English
BRONKOSOL
Brand Name English
Isoetarine hydrochloride [WHO-DD]
Common Name English
DL-ISOETHARINE HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
Code System Code Type Description
MERCK INDEX
m6485
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1201213
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
DRUG BANK
DBSALT000349
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
RXCUI
102397
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID00101890
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
SMS_ID
100000086456
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
PUBCHEM
71465
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
EVMPD
SUB02787MIG
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
CAS
50-96-4
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C65975
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
CAS
2576-92-3
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
FDA UNII
51V8U784H3
Created by admin on Fri Dec 15 16:33:35 GMT 2023 , Edited by admin on Fri Dec 15 16:33:35 GMT 2023
PRIMARY
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