7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine
diprophylline
CAS: 479-18-5
Molecular Formula: C10H14N4O4
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Names and Identifiers
| Name | diprophylline |
| Synonyms | Airet Dilor circair Circain Emfaseem Dyphylline Neothylline diprophylline Lufyllin-EPG component of Dilor g component of Neothylline-gg 7-(2,3-Dihydroxypropyl)theophylline 7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine 1h-purine-2,6-dione,7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl 7-(2,3-Dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione 1H-Purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl- 7-[(2R)-2,3-dihydroxypropyl]-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione 7-[(2S)-2,3-dihydroxypropyl]-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione |
| CAS | 479-18-5 |
| EINECS | 207-526-1 |
| InChI | InChI=1/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3/t6-/m1/s1 |
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Physico-chemical Properties
| Molecular Formula | C10H14N4O4 |
| Molar Mass | 254.24 |
| Density | 1.3036 (rough estimate) |
| Melting Point | 161-162°C(lit.) |
| Boling Point | 397.46°C (rough estimate) |
| Flash Point | 310.4°C |
| Water Solubility | 33 g/100 mL (25 ºC) |
| Solubility | Freely soluble in water, slightly soluble in ethanol (96 per cent). |
| Vapor Presure | 9.57E-15mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White |
| Merck | 14,3479 |
| BRN | 284563 |
| pKa | 13.74±0.20(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Sensitive | Sensitive to light |
| Refractive Index | 1.6200 (estimate) |
| MDL | MFCD00005759 |
| Physical and Chemical Properties | White crystalline powder. Melting point 158 °c (159-163.5 °c). Soluble in water, 1g of this product can be dissolved in 3 ml of water (25 ° C); In ethanol solubility of 2g/100, in chloroform 1g/100. Odorless and bitter. |
| Use | For the treatment of bronchial asthma |
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36 - Wear suitable protective clothing. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | XH5100000 |
| TSCA | Yes |
| HS Code | 29395900 |
| Toxicity | LD50 in mice (mg/kg): 3400 orally; 1430 s.c. (Al'tshuler) |
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Standard
Authoritative Data Verified Data
This product is 1, 3-dimethyl-7-(2, 3-dihydroxypropyl)-3, 7-dihydro-1h-purin-2, 6-dione. The content of CIflHhN404 shall not be less than 98.0% calculated as dried product.
Last Update：2024-01-02 23:10:35
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Trait
Authoritative Data Verified Data
- This product is white powder or granules; Odorless.
- This product is soluble in water, slightly soluble in ethanol, and slightly soluble in chloroform or ether.
melting point
The melting point of this product (General 0612) is 160~164°C.
absorption coefficient
take this product, precision weighing, adding water to dissolve and quantitative dilution to make a solution containing about 10ug per lml, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 273nm, and the absorption coefficient was 354 to 376.
Last Update：2022-01-01 11:29:55
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Introduction
No odor, bitter taste; easy to deteriorate when exposed to light. Easily soluble in water, slightly soluble in ethanol. The pH of the aqueous solution is 6.5-7.4, and the 10.87% aqueous solution is isotonic. Solubility: 1g/3ml water (25 C), 2g/100ml ethanol and 1g/100ml chloroform.
Last Update：2022-10-16 17:25:22
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Differential diagnosis
Authoritative Data Verified Data
- take about 0.1g of this product, add lml of hydrochloric acid and 0.lg of potassium chlorate, and steam dry on a water bath. The residue will appear purple when exposed to ammonia.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 12).
Last Update：2022-01-01 11:29:56
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Exam
Authoritative Data Verified Data
pH
take 0.50g of this product, Add 10ml of water to dissolve, add 5 drops of bromine grinding vanilla phenol blue finger solution, should be yellow or green; Add sodium hydroxide titration solution (0.02mol/L)0.20, blue.
clarity and color of solution
take this product l. Add 10ml of water and shake to dissolve, the solution should be clear and colorless; If the color is colored, it should not be deeper compared with yellow or yellow-green No. 1 Standard Colorimetric solution (General rule 0901 method 1).
chloride
take 0.25g of this product, add 5ml of water and 1.0ml of sodium hydroxide solution, boil for 30 seconds, cool, check according to law (General rule 0801), and standard sodium chloride solution 7.0ml should not be more concentrated (0.028%) compared with the control solution prepared by the same method.
Related substances
take an appropriate amount of this product, weigh it accurately, add water to dissolve and quantitatively dilute it to make about 1 per lml. 0mg of the solution, as the test solution; Another 10mg of theophylline reference, precision weighing, 100ml flask, dissolved and diluted to the scale, shake, 10ml and 1 ml of the test solution were precisely weighed, placed in a 200ml measuring flask, diluted to the scale with water, and shaken to obtain a control solution. According to the high performance liquid chromatography (General 0512) test, with eighteen alkyl silane bonded silica gel as filler; With potassium dihydrogen phosphate solution (take potassium dihydrogen phosphate l. 0g, dissolved in water and diluted to 1000ml)-methanol (72: 8) as mobile phase; The detection wavelength was 254nm. Take the control solution 10 u1 and inject it into human liquid chromatograph. The number of theoretical plates shall not be less than 2000 according to the peak of dihydroxypropylline, and the separation degree of dihydroxypropylline peak and theophylline peak shall be greater than 3.5. The sample solution and the control solution are respectively 10(J, injected with human liquid chromatograph respectively, and the chromatogram is recorded to 3 times of the retention time of the main component peak. If there is theophylline peak in the chromatogram of the test solution, the peak area shall be calculated according to the external standard method, and shall not exceed 0.5%; The sum of the peak areas of other impurities shall not be greater than the peak area of dihydroxypropionophylline in the control solution (0.5%).
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
not more than 0.15% (General rule 0841).
Heavy metals
take this product l. Add 2ml of acetate buffer solution (pH3.5) and appropriate amount of water to dissolve 25ml, and check according to law (General rule 0821 method 1), containing no more than 20 parts per million of heavy metals.
Last Update：2022-01-01 11:29:57
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Content determination
Authoritative Data Verified Data
take about 0.2g of this product, weigh precisely, add 2ml of anhydrous formic acid to dissolve, slowly add 50ml of acetic anhydride, shake for 3 minutes, add 4-5 drops of Sudan IV indicator solution, with perchloric acid titration solution (0.1 mol/L) titration to the solution is purple, and the result of the titration is corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 25.42mg of C10H14N404.
Last Update：2022-01-01 11:29:57
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Category
Authoritative Data Verified Data
smooth muscle relaxant.
Last Update：2022-01-01 11:29:58
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Storage
Authoritative Data Verified Data
sealed and stored in a dry place.
Last Update：2022-01-01 11:29:58
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Dihydroxypropylline tablets
Authoritative Data Verified Data
This product contains dihydroxypropylline (clflHuN4C)4) should be 93.0% to 107.0% of the label amount.
trait
This product is white tablet.
identification
- take an appropriate amount of fine powder of this product (about 0.5g), add water (5ml), shake to dissolve the dihydroxypropylline, filter; Take 1 ml of filtrate, and put it on a water bath to evaporate, the same reaction was shown in the identification (1) Test under the item of dihydroxypropylline.
- take the solution under the content determination item, according to UV-visible spectrophotometry (General 0401), there is a maximum absorption at the wavelength of 273nm, there is minimal absorption at a wavelength of 246nm.
- take an appropriate amount of this product, add water to dissolve and dilute to prepare a solution containing 0.2mg of dipropionylline per 1 ml, as a test solution; Take an appropriate amount of dipropionylline reference, water was added to dissolve and diluted to prepare a solution containing 0.2mg per 1 ml as a control solution. According to the chromatographic conditions under the item of related substances, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- Related Substances: take an appropriate amount of fine powder of this product (equivalent to 50mg of dipropylline), weigh it accurately, put it in a 50ml measuring flask, add an appropriate amount of water, and sonicate it to dissolve dipropylline, and let it cool, and dilute with water to the scale, shake, filter, take the continued filtrate as a test solution, according to the method under the item of dihydroxypropylline related substances, if there is theophylline peak in the chromatogram of the test solution, the peak area shall be calculated according to the external standard method, and 0.5% of the labeled amount shall not be exceeded; The sum of the peak areas of other impurities shall not be greater than the peak area of dihydroxypropylline in the control solution (0.5%).
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 first method), with water as the dissolution medium, the speed is 100 rpm, according to the law, after 30 minutes, the solution is filtered, and the filtrate is 3ml, and the 25ml measuring flask (0.lg specification) or 50ml measuring bottle (0401G specification), diluted with water to the scale, shake, UV-visible spectrophotometry (general rule), at the wavelength of 273nm absorbance, the elution amount of each tablet was calculated as the absorption coefficient of c1dh14n404 was 365. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 0.15g equivalent to dipropionylline), put it in a 500ml measuring flask, add an appropriate amount of water, fully shake to dissolve dihydroxypropylline, dilute to scale with water, shake well, take 10ml continuous filtrate accurately, put it in 200ml measuring flask, dilute to scale with water, shake well, the absorbance was measured at a wavelength of 273mn by ultraviolet-visible spectrophotometry (General rule 0401), and the absorption coefficient of C10H14N404 was calculated as 365.
category
Same as dihydroxypropylline.
specification
(l)0.lg (2)0.2g
storage
sealed and stored in a dry place.
Last Update：2022-01-01 11:29:59
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Diprophylline Injection
Authoritative Data Verified Data
This product is a sterile aqueous solution of dihydroxypropylline. The content of dihydroxypropylline (C10H14N404) shall be between 90.0% and 110.0% of the labeled amount.
trait
This product is a clear colorless liquid.
identification
- take 1ml of this product, add 2ml of water, shake well, add a few drops of tannic acid solution to generate white precipitate.
- take 1ml of this product and dry it on a water bath, add 1ml of hydrochloric acid and 0.lg of potassium chlorate, continue to dry, and the residue will appear purple when exposed to ammonia. Add several drops of sodium hydroxide test solution, and the purple color will disappear.
- take an appropriate amount of this product and dilute it with water to make a solution containing 0.2mg of dipropionylline per 1 ml as a test solution, water was added to dissolve and diluted to prepare a solution containing 0.2mg per 1 ml as a control solution. According to the chromatographic conditions under the item of related substances, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
The pH value should be 4.0 to 7.0 (General 0631).
Precise measurement of related substances an appropriate amount of this product shall be taken and diluted with water to prepare a solution containing about 1 mg of dipropylline per 1 ml, which shall be used as a test solution for determination according to the method for dipropylline related substances, if there is theophylline peak in the chromatogram of the test solution, the peak area shall be calculated according to the external standard method, and 0.5% of the labeled amount shall not be exceeded; The sum of the peak areas of other impurities shall not be greater than the peak area of dihydroxypropylline in the control solution (0.5%).
Bacterial endotoxin take the goods, according to inspection (General 1143), per 1 mg of dihydroxypropionylline containing endotoxin should be less than 0.30EU.
Others should comply with the relevant provisions under injections (General rule 0102).
Content determination
take an appropriate amount of this product (equivalent to 0.25g of dihydroxypropionylline), put it in a 500ml measuring flask, dilute it with water until it is calibrated, shake well, take 5ml of this product for precision measurement, put it in a 200ml measuring flask, dilute with water to the scale, shake, according to UV-visible spectrophotometry (General 0401), at the wavelength of 273mn absorbance was measured, calculated according to C10H14N4O4 absorption coefficient of 365.
category
Same as dihydroxypropylline.
specification
2ml:0.25g
storage
light shielding, closed storage.
Last Update：2022-01-01 11:30:00
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Commonly used clinical antiasthmatic drugs | Dihydroxypropyltheophylline is also known as asthmatic, and its chemical name is 1,3-dimethyl -7-(2,3 dihydroxypropyl)-3, 7-dihydro-1H-purin-2, 6-dione. It is a commonly used clinical antiasthmatic drug. It is a xanthine derivative of the condensation of theophylline and monochlorodipropanol, the antiasthmatic effect is similar to aminophylline. Its bronchial dilation effect is about 1/10 of aminophylline, and the cardiac excitation effect is only 1/20~1/10 of aminophylline. This product has little pain response after intramuscular injection, and has little irritation to gastrointestinal tract after oral administration. The oral bioavailability is 70% and the half-life is about 2 hours. It is not metabolized in the body, and most of it is excreted in the urine in its original form. It is clinically used for the relief of wheezing symptoms such as bronchial asthma, asthmatic bronchitis, and obstructive emphysema. It can also be used for cardiogenic asthma, especially for asthma patients with tachycardia and cannot tolerate theophylline. Theophylline Theophylline is an alkaloid that exists in tea, coffee and other plants. It is a derivative of methylxanthine. It has more prednisone to relax bronchial smooth muscle, excite the heart and diuresis. Theophylline is widely used in clinical practice, mainly for the treatment of bronchial asthma, cardiogenic asthma and cardiogenic edema. When theophylline is used as a bronchodilator, its effective concentration in plasma (5~20mg/L) should be strictly controlled to avoid side effects due to excessive concentration. Aminophylline Aminophylline is a compound salt of theophylline and ethylenediamine. Its pharmacological effects mainly come from theophylline, and ethylenediamine enhances its water solubility. This product has a direct relaxation effect on respiratory smooth muscle. In addition, theophylline is a purine receptor blocker, which can resist the contractile effect of adenine on the respiratory tract. Theophylline can enhance the contractility of the diaphragm, especially when the diaphragm is weak, so it is beneficial to improve respiratory function. This product can still slightly relax coronary arteries, peripheral blood vessels and bile duct smooth muscle, and slightly increase myocardial contractility and slight diuresis. |
| pharmacological action | the antiasthmatic effect of this product is slightly weaker than theophylline, and the cardiac excitation effect is only 1/20~1/10 of aminophylline, which has little effect on the heart and nervous system, especially suitable for asthma patients with tachycardia. This product has a direct relaxation effect on respiratory smooth muscle, and its mechanism of action is the same as theophylline. In the past, it was believed that by inhibiting phosphodiesterase, the intracellular cAMP content was increased. In recent years, it is believed that the bronchodilation effect of theophylline is partly due to the release of endogenous epinephrine and norepinephrine. In addition, theophylline is a purine receptor blocker, which can resist the contractile effect of adenine on the respiratory tract. Theophylline can enhance the contractility of the diaphragm, especially when the diaphragm is weak, so it helps to improve respiratory function. Fig. 1 is the structural formula of dihydroxypropyltheophylline |
| indication | is used to relieve wheezing symptoms such as bronchial asthma, wheezing bronchitis, obstructive emphysema, etc. It can also be used for cardiogenic asthma, especially for asthma patients with tachycardia and cannot tolerate theophylline. |
| usage and dosage | 1. adult (1) oral administration: 100~200mg once, 3 times a day. The maximum amount at a time is 500mg. (2) intramuscular injection: 250~500mg once, 3~4 times a day. (3) intravenous injection: 250~500mg once, 3~4 times a day. 25% (or 50%) glucose injection should be added into 20~40ml, and slowly injected in 15~20 minutes. (4) intravenous drip: 250~750mg once, 5% (or 10%) glucose injection or normal saline for intravenous drip, the total amount per day is less than 2g. (5) rectal administration: 250~500mg once, 2~3 times a day. For patients with creatinine clearance rate (Ccr) of 50 ml/min, the dosage is 75% of those with normal renal function. For patients with Ccr of 10~50 ml/min, the dosage is 50% of those with normal renal function. For patients with Ccr below 10 ml/min, the dosage is 25% of those with normal renal function. The dose during hemodialysis is 1/3 of the conventional dose. 2. Children: when using this product sodium chloride injection, a 2~4 mg/kg, slow intravenous drip. |
| adverse reactions | 1. cardiovascular system: it can cause palpitations, tachycardia, premature contraction, significant hypotension, facial flushing, ventricular arrhythmia, etc. in severe cases, heart failure may occur. 2. Central nervous system: can cause headache, irritability, irritability, insomnia, excessive excitement, etc., and even lead to clonic, systemic seizures. 3. Metabolism and endocrine system: can lead to hyperglycemia. 4. Genitourinary system: can cause proteinuria, macroscopic or microscopic hematuria and polyuria symptoms. 5. Gastrointestinal tract: can cause dry mouth, nausea, vomiting, upper abdominal pain, hematemesis, diarrhea, loss of appetite, etc. |
| taboo | 1. those who are allergic to this product or other theophyllin drugs. 2. Patients with active peptic ulcer. 3. Patients with uncontrolled convulsive disease. |
| precautions | 1. this product is not the first choice for patients with acute severe asthma attacks. 2. Theophylline drugs can cause arrhythmia and/or worsen the original arrhythmia; if the patient's heart rate is too fast and/or has any abnormal changes in other heart rhythms, close attention should be paid. 3. Patients who are using other xanthine derivatives should use this product with caution. 4. The dosage should be adjusted according to the patient's symptoms and reactions. 5. Intravenous drip too fast can cause transient hypotension and peripheral circulatory failure. 6. The following conditions should be used with caution: ① Patients with severe heart disease (including congestive heart failure, acute myocardial damage, pulmonary heart disease, etc.). ② Patients with hypertension. ③ Patients with severe hypoxemia. ④ Glaucoma patients. ⑤ Hyperthyroidism. ⑥ Patients with persistent fever. ⑦ Those with a history of peptic ulcer. ⑧ Patients with liver diseases. ⑨ Kidney disease patients. ⑩ Alcohol poisoning. (2016-03-18) |
| drug interaction | 1. this product will produce synergistic effect when combined with ephedrine or other sympathomimetic amine bronchodilators. 2. Combined with phenytoin sodium, carbamazepine, cimetidine, caffeine or other xanthine drugs, etc., can increase the effect and toxicity of this product. 3. When combined with clindamycin, lincomycin and certain macrolides and quinolone antibiotics, it can reduce the clearance rate of this product in the liver, increase the blood concentration, and even cause toxic reactions. Adjust the dosage of this product before and after administration. 4. Probenecid can increase the blood concentration of this product, which is dangerous to cause excessive poisoning. It will also compete with this product for renal tubular secretion and prolong the half-life of this product. 5. When combined with propranolol, the bronchodilation effect of this product may be inhibited. 6. Lithium carbonate can accelerate the removal of this product and reduce the curative effect of this product. This product can also increase the renal excretion of lithium and affect the effect of lithium salt. |
| use | has the effect of dilating bronchi and coronary arteries, and has diuretic effect. This product and aminophylline belong to the same xanthine dilator. It is suitable for the treatment of bronchial asthma, asthmatic bronchitis and chronic emphysema. It can also be used to prevent bronchial asthma attacks, and can also be used for angina pectoris and Cardiac edema treatment. Theophylline is a representative variety of xanthine drugs. In order to improve the solubility of theophylline, aminophylline (a compound salt of theophylline and ethylenediamine), cholophylline (a compound salt of theophylline and choline), and dihydroxypropylline (a N-7 derivative of theophylline) were developed. Dihydroxypropylline is more water-soluble than aminophylline, but its effect is weaker than theophylline, and its toxicity is about 1/5 of aminophylline. The oral LD50 of mice is 3400 mg/kg. |
| Production method | It is obtained by condensation of theophylline sodium salt and monochloropropanediol. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:50
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