Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H18ClNO.ClH |
| Molecular Weight | 264.191 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)(C)NCC(O)C1=C(Cl)C=CC=C1
InChI
InChIKey=RSLNRVYIRDVHLY-UHFFFAOYSA-N
InChI=1S/C12H18ClNO.ClH/c1-12(2,3)14-8-11(15)9-6-4-5-7-10(9)13;/h4-7,11,14-15H,8H2,1-3H3;1H
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 |
|||
| 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 |
|||
| 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 |
|||
| 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 |
|---|---|---|
| Effect of porous silica on sustained release behaviors of pH sensitive pluronic F127/poly(acrylic acid) hydrogels containing tulobuterol. | 2010-10-15 |
|
| [Determination of fifteen beta-agonists in animal urine by high performance liquid chromatography-tandem mass spectrometry]. | 2010-08 |
|
| Characterization and release behaviors of porous PCL/Eudragit RS microcapsules containing tulobuterol. | 2010-04-01 |
|
| Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. | 2010-04 |
|
| Simultaneous determination of beta2-agonists in human urine by fast-gas chromatography/mass spectrometry: method validation and clinical application. | 2010-04 |
|
| Additive effects of transdermal tulobuterol to inhaled tiotropium in patients with COPD. | 2010-02 |
|
| Comparative study of skin permeation profiles between brand and generic tulobuterol patches. | 2010 |
|
| Effects of the addition of Beta2-agonist tulobuterol patches to inhaled corticosteroid in patients with asthma. | 2009-12 |
|
| Tulobuterol patch maintains diaphragm muscle contractility for over twenty-four hours in a mouse model of sepsis. | 2009-08 |
|
| Chronic eosinophilic pneumonia: a case report and review of the literature. | 2009-07-02 |
|
| Detection of tulobuterol crystal in transdermal patches using terahertz pulsed spectroscopy and imaging. | 2009-06 |
|
| Comparison of adherence and efficacy between inhaled salmeterol and transdermal tulobuterol patch in elderly patients with chronic obstructive pulmonary disorder. | 2009-05 |
|
| Chemical mapping of tulobuterol in transdermal tapes using microscopic laser Raman spectroscopy. | 2009-03 |
|
| Anti-inflammatory effects and clinical efficacy of theophylline and tulobuterol in mild-to-moderate chronic obstructive pulmonary disease. | 2008-12 |
|
| [Simultaneous determination of nine beta-agonist residues in animal derived foods by ultra performance liquid chromatography-tandem mass spectrometry]. | 2008-11 |
|
| Cough and transdermal long-acting beta2 agonist in Japan. | 2008-10 |
|
| Characterization of monolithic matrix patch system containing tulobuterol. | 2008-08 |
|
| Clinical efficacy of the transdermal tulobuterol patch in patients with chronic obstructive pulmonary disease: a comparison with slow-release theophylline. | 2008 |
|
| Comparison of bronchodilatory properties of transdermal and inhaled long-acting beta 2-agonists. | 2008 |
|
| Adherence to treatment by patients with asthma or COPD: comparison between inhaled drugs and transdermal patch. | 2007-09 |
|
| Bioequivalence of marketed transdermal delivery systems for tulobuterol. | 2007-08 |
|
| [Simultaneous determination of nine beta2-agonists residues in urines by ultra performance liquid chromatography-electrospray tandem mass spectrometry]. | 2007-07 |
|
| Transdermal treatment with tulobuterol increases isometric contractile properties of diaphragm muscle in mice. | 2007-07 |
|
| Addition of transdermal or inhaled long-acting Beta2-agonists in adult asthmatic patients treated with inhaled corticosteroids: switchover study from tulobuterol patch to salmeterol dry powder inhaler. | 2007-03 |
|
| [The efficacy and safety of tulobuterol tape in mild and moderate persistent asthma patients]. | 2007-01 |
|
| Treatment with beta2-adrenoceptor agonist in vivo induces human clock gene, Per1, mRNA expression in peripheral blood. | 2007 |
|
| Improvement of pulmonary function and dyspnea by tiotropium in COPD patients using a transdermal beta(2)-agonist. | 2007 |
|
| Comparison of the effects of tulobuterol patch and salmeterol in moderate to severe asthma. | 2006-11 |
|
| Comparison of the clinical efficacy of salmeterol and sustained-release tulobuterol (patch) on inadequately controlled asthma patients on inhaled corticosteroids. | 2006-09 |
|
| The use of patch formulation of tulobuterol, a long-acting beta2-adrenoreceptor agonist, in the treatment of severe pediatric asthma. | 2006-06 |
|
| Immunology and homeopathy. 3. Experimental studies on animal models. | 2006-06 |
|
| Differential effects of short-acting beta2-agonists on human granulocyte functions. | 2006 |
|
| Determination of beta-agonists in liver and retina by liquid chromatography-tandem mass spectrometry. | 2005-03-12 |
|
| Determination of beta-agonist residues in bovine urine using liquid chromatography-tandem mass spectrometry. | 2005-03-12 |
|
| High-performance liquid chromatography electrospray ionization mass spectrometry determination of tulobuterol in rabbit's plasma. | 2005-02-07 |
|
| 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 |
|
| Evaluation of MISPE for the multi-residue extraction of beta-agonists from calves urine. | 2004-05-05 |
|
| [Patchs: the success of transdermal administration]. | 2004-04 |
|
| [Clinical evaluation of tulobuterol patch in patients with mild or moderate persistent bronchial asthma-effects of long-term treatment on airway inflammation and hypersensitivity]. | 2004-02 |
|
| Clinical evaluation of a transdermal therapeutic system of the beta2-agonist tulobuterol in patients with mild or moderate persistent bronchial asthma. | 2004 |
|
| [Pharmacological action and clinical aspects of salmeterol]. | 2003-09 |
|
| Effects of a nitro compound patch on neuropathy in Churg-Strauss syndrome. | 2003-07 |
|
| Effects of sustained-release tulobuterol on asthma control and beta-adrenoceptor function. | 2002-12 |
|
| [Development of transdermal formulation of tulobuterol for the treatment of bronchial asthma]. | 2002-01 |
|
| [Long-acting beta 2-stimulants]. | 2001-10 |
|
| [Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion]. | 2001-10 |
|
| Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis. | 2001-02 |
|
| Clinical characteristics of asthmatic patients prescribed various beta-agonist metered-dose inhalers at Yamagata University Hospital. | 2001-01 |
|
| Induction and reduction of muscle tremor upon acute and repeated administration of the beta 2-agonists terbutaline, salbutamol and tulobuterol. | 1987-12 |
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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m11261
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CHEMBL1159717
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ACTIVE MOIETY
SUBSTANCE RECORD