Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H21NO3 |
| Molecular Weight | 239.3107 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | BRONKOSOL Approved UseTo prevent and treat reversible bronchospasm from chronic bronchitis or emphysema. |
|||
| Palliative | BRONKOSOL Approved UseTo prevent and treat reversible bronchospasm from chronic bronchitis or emphysema. |
Cmax
| 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 |
T1/2
| 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: |
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... |
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
| 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: |
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
| Title | Date | PubMed |
|---|---|---|
| Hypomania related to phenelzine and isoetharine interaction in one patient. | 1987 Apr |
|
| A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma. | 1991 Oct |
|
| Pharmacological treatment of chronic obstructive pulmonary disease. | 2006 |
|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
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SUBSTANCE RECORD
