(1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide
Tiotropium bromide
CAS: 136310-93-5
Molecular Formula: C19H22BrNO4S2
(1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide - Names and Identifiers
(1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide - Physico-chemical Properties
| Molecular Formula | C19H22BrNO4S2 |
| Molar Mass | 472.42 |
| Melting Point | 218-2200C |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | White solid |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['240nm(lit.)'] |
| Merck | 14,9454 |
| Storage Condition | Inert atmosphere,2-8°C |
(1a,2b,4b,5a,7b)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide - Reference Information
| Bronchodilator | Tiotropium bromide, also known as Teutonium bromide, is a new type of bronchodilator, successfully developed by the Dutch Boehringer Ingelheim Company. It is a long-acting anticholinergic drug, has a selective inhibitory effect on M3 receptors, and has the advantages of long blood concentration maintenance time and small side effects, tiotropium bromide is equivalent to ipratropium bromide in the treatment of chronic obstructive pulmonary disease (COPD), but its advantage is that it only needs to be administered once a day, while the latter needs to be administered 4 times a day. Recent studies have shown that long-acting β2-adrenoceptor agonists (such as formoterol) can also effectively expand the bronchi compared with short-acting ones. Both formoterol and tiotropium bromide can significantly increase the forced expiratory volume in the first second (FEV1), forced vital capacity (FVC) and deep inhalation volume (IC) in the resting state, and the combination of the two can be compared with single The improvement of lung function is more obvious. tiotropium bromide powder inhalation is a bronchodilator, suitable for the maintenance treatment of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema, maintenance treatment of accompanying dyspnea and prevention of acute attack. Tiotropium Bromide Inhaled Powder is contraindicated in patients who have allergic reactions to tiotropium, atropine or its derivatives, such as ipratropium bromide or oxitropium bromide or lactose, the excipient of this product. |
| pharmacological effects | tiotropium bromide is a quaternary ammonium derivative, which is a highly selective anticholinergic drug and has the same affinity for five muscarinic receptors of M1 ~ M5 type. In the human airway, this product has a high affinity with receptors, and is slowly dissociated from muscarinic M1 and M3 receptors, which can block cholinergic nerve-mediated bronchial smooth muscle contraction for a long time. However, this product dissociates from muscarinic M2 receptors quite quickly, thus showing unique kinetic selectivity to M1 and M3 receptors. the dilation effect of tiotropium bromide on bronchi can last for more than 24 hours, and the blood concentration is about 2pg/ml. This product is absorbed rapidly in human body, reaching the blood drug peak value of 6pg/ml 5 minutes after inhalation of 10 μg g, and returning to the steady-state blood drug concentration of 2pg/ml after 1 hour. The final t1/2 is 5~6 days. It is suitable for maintenance treatment of chronic obstructive pulmonary disease (COPD). |
| toxicity | intravenous administration of 5 μg can significantly increase the heart rate of awake dogs. Only when inhaled at extremely high doses can it have a significant effect on the heart. Toxicological studies lasting for 2 years show that the drug is safe. Single-dose and multiple-dose studies of volunteers have shown that tiotropium does not produce drug-related adverse reactions to the pupil, saliva secretion, or electrocardiogram. |
| adverse reactions | the most common adverse reactions are dry mouth and cough, with an incidence of no more than 15%, followed by pharyngitis, upper respiratory tract infection, bitter mouth, transient allergic reaction, headache, nervousness, excitement and dizziness. Rare systemic adverse reactions include urinary retention, prostatitis, constipation, tachycardia, and palpitations. |
| precautions | ① use the spray device correctly and avoid spraying to eyes. ② Patients with dental caries are more likely to cause dry mouth when using this product. ③ Be cautious for patients with angle-closure glaucoma. This product can cause eye pain, blurred vision, hallucinations and conjunctival congestion. ④ Be cautious for patients with benign prostatic hyperplasia. This product can cause urinary retention and bladder discomfort. ⑤ patients with arrhythmia should be used with caution. ⑥ The recommended dose should be used in elderly patients and patients with renal function and liver dysfunction. |
| use | atropine derivatives. Bronchodilators. Muscarinic receptor antagonists. |
| production method | 50.87g di (2-thienyl) glycolate methyl ester (I) and 31.04g scopoletin (ii) are dissolved in 100ml of toluene, 1.65g of metallic sodium is added in batches at 90 ℃, then distilled at 78-90 ℃ and 50kPa for 5h to remove the generated methanol. After treatment, 33.79g of compound (Ⅲ) was obtained. In the mixed solution of dichloromethane and acetonitrile, it reacts with methyl bromide to quaternize to obtain the product. |
Last Update：2024-04-10 22:29:15
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