Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H18ClNO |
| Molecular Weight | 227.73 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NCC(O)C1=C(Cl)C=CC=C1
InChI
InChIKey=YREYLAVBNPACJM-UHFFFAOYSA-N
InChI=1S/C12H18ClNO/c1-12(2,3)14-8-11(15)9-6-4-5-7-10(9)13/h4-7,11,14-15H,8H2,1-3H3
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.mylan.co.jp/-/media/MylanJP/documents/epd_products/interview_updated/if_hokunalin.pdf
Curator's Comment: description was created based on several sources, including:
http://www.mylan.co.jp/-/media/MylanJP/documents/epd_products/interview_updated/if_hokunalin.pdf
Tulobuterol is a long-acting beta2-adrenergic receptor agonist. Tulobuterol has almost no effects on blood pressure and heart rate and is highly selective for the tracheal muscle. It is indicated to improve symptoms such as respiratory distress caused by airway obstruction of bronchial asthma, bronchitis, chronic obstructive pulmonary disease (COPD) and emphysema. Serious side effects detected were: tremor, palpitations and serum potassium level decrease.
CNS Activity
Sources: http://www.mylan.co.jp/-/media/MylanJP/documents/epd_products/interview_updated/if_hokunalin.pdf
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Hokunalin Approved UseIt is usually used to improve symptoms such as respiratory distress caused by airway obstruction of bronchial asthma, acute bronchitis, chronic bronchitis, or emphysema. Launch Date1981 |
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| Palliative | Hokunalin Approved UseIt is usually used to improve symptoms such as respiratory distress caused by airway obstruction of bronchial asthma, acute bronchitis, chronic bronchitis, or emphysema. Launch Date1981 |
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| Palliative | Hokunalin Approved UseIt is usually used to improve symptoms such as respiratory distress caused by airway obstruction of bronchial asthma, acute bronchitis, chronic bronchitis, COPD or emphysema. Launch Date1981 |
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| Palliative | Hokunalin Approved UseIt is usually used to improve symptoms such as respiratory distress caused by airway obstruction of bronchial asthma, acute bronchitis, chronic bronchitis, or emphysema. Launch Date1981 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6 ng/mL |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: |
|
4.46 ng/mL |
20 μg/kg bw single, oral dose: 20 μg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL blood | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
0.48 ng/mL |
0.5 mg single, topical dose: 0.5 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.59 ng/mL |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.29 ng/mL |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
400 μg single, respiratory dose: 400 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
600 μg single, respiratory dose: 600 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
800 μg single, respiratory dose: 800 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
4 mg single, topical dose: 4 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
6 mg single, topical dose: 6 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30.5 ng × h/mL |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: |
|
10.75 ng × h/mL |
0.5 mg single, topical dose: 0.5 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
11.09 ng × h/mL |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
27.62 ng × h/mL |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
400 μg single, respiratory dose: 400 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
600 μg single, respiratory dose: 600 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
800 μg single, respiratory dose: 800 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
27.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
53.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
4 mg single, topical dose: 4 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
82.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
6 mg single, topical dose: 6 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
27.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.19 h |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: |
|
3.56 h |
20 μg/kg bw single, oral dose: 20 μg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL blood | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
11.1 h |
0.5 mg single, topical dose: 0.5 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.4 h |
1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
11 h |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
400 μg single, respiratory dose: 400 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
600 μg single, respiratory dose: 600 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
800 μg single, respiratory dose: 800 μg route of administration: Respiratory experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
2 mg single, topical dose: 2 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
4 mg single, topical dose: 4 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
6 mg single, topical dose: 6 mg route of administration: Topical experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8099880/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TULOBUTEROL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
71.86% |
TULOBUTEROL serum | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 mg 2 times / day multiple, oral Recommended Dose: 1 mg, 2 times / day Route: oral Route: multiple Dose: 1 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Serum potassium decreased... AEs leading to discontinuation/dose reduction: Serum potassium decreased Sources: |
2 mg 1 times / day multiple, transdermal Recommended Dose: 2 mg, 1 times / day Route: transdermal Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
400 ug 4 times / day multiple, respiratory Studied dose Dose: 400 ug, 4 times / day Route: respiratory Route: multiple Dose: 400 ug, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
2 mg 1 times / day multiple, transdermal Recommended Dose: 2 mg, 1 times / day Route: transdermal Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Anaphylaxis, Serum potassium decreased... AEs leading to discontinuation/dose reduction: Anaphylaxis Sources: Serum potassium decreased |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Serum potassium decreased | Disc. AE | 1 mg 2 times / day multiple, oral Recommended Dose: 1 mg, 2 times / day Route: oral Route: multiple Dose: 1 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Anaphylaxis | Disc. AE | 2 mg 1 times / day multiple, transdermal Recommended Dose: 2 mg, 1 times / day Route: transdermal Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Serum potassium decreased | Disc. AE | 2 mg 1 times / day multiple, transdermal Recommended Dose: 2 mg, 1 times / day Route: transdermal Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Induction and reduction of muscle tremor upon acute and repeated administration of the beta 2-agonists terbutaline, salbutamol and tulobuterol. | 1987 Dec |
|
| Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis. | 2001 Feb |
|
| [Pharmacological action and clinical aspects of salmeterol]. | 2003 Sep |
|
| [Clinical evaluation of tulobuterol patch in patients with mild or moderate persistent bronchial asthma-effects of long-term treatment on airway inflammation and hypersensitivity]. | 2004 Feb |
|
| Clinical efficacy and safety of transdermal tulobuterol in the treatment of stable COPD: an open-label comparison with inhaled salmeterol. | 2005 |
|
| Alteration of the circadian rhythm in peak expiratory flow of nocturnal asthma following nighttime transdermal beta2-adrenoceptor agonist tulobuterol chronotherapy. | 2005 |
|
| Improvement of pulmonary function and dyspnea by tiotropium in COPD patients using a transdermal beta(2)-agonist. | 2007 |
|
| Transdermal treatment with tulobuterol increases isometric contractile properties of diaphragm muscle in mice. | 2007 Jul |
|
| Adherence to treatment by patients with asthma or COPD: comparison between inhaled drugs and transdermal patch. | 2007 Sep |
|
| Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. | 2010 Apr |
Patents
Sample Use Guides
In general, for adults and children aged 9 or older, apply 2 mg of the tape to the chest, back, or upper arm, once daily. For children aged 6 months to 2 years, apply 0.5 mg of the tape to the chest, back, or upper arm, once daily. For children aged 3 to 8 years, apply 1 mg of the tape to the chest, back, or upper arm, once daily. This preparation contains 2 mg of the active ingredients in a piece of tape.
Route of Administration:
Transdermal
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Common Name | English |
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NCI_THESAURUS |
C319
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NCI_THESAURUS |
C48149
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WHO-VATC |
QR03AC11
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WHO-ATC |
R03CC11
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WHO-VATC |
QR03CC11
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WHO-ATC |
R03AC11
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38967
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5606
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DB12248
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C152783
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758643
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SUB11365MIG
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41570-61-0
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4564
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591I9SU0F7
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DTXSID7048457
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TULOBUTEROL
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m11261
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100000091817
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CHEMBL1159717
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C010809
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2782
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
