ProM
proglumide
CAS: 6620-60-6
Molecular Formula: C18H26N2O4
ProM - Names and Identifiers
| Name | proglumide |
| Synonyms | ProM proglumide PROGLUMIDE LABOTEST-BB LT00772215 N-Benzoyl-N′,N′-dipropyl-DL-isoglutamine N~2~-benzoyl-N,N-dipropyl-alpha-glutamine N(2)-benzoyl-N,N-dipropyl-alpha-glutamine 4-benzamido-N,N-dipropyl-DL-glutaramic acid 4-BenzaMido-5-(dipropylaMino)-5-oxopentanoic acid 4-(BenzoylaMino)-5-(dipropylaMino)-5-oxo-pentanoic Acid |
| CAS | 6620-60-6 |
| EINECS | 229-567-4 |
| InChI | InChI=1/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22) |
ProM - Physico-chemical Properties
| Molecular Formula | C18H26N2O4 |
| Molar Mass | 334.41 |
| Density | 1.1944 (rough estimate) |
| Melting Point | 148-150°C |
| Boling Point | 471.21°C (rough estimate) |
| Flash Point | 310.5°C |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 9.33E-15mmHg at 25°C |
| Appearance | Solid |
| Color | Crystals |
| pKa | 4.51±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.5700 (estimate) |
| Physical and Chemical Properties | Colorless crystals or crystalline powders. Melting point 142-145 ℃, soluble in ethanol, methanol, chloroform, insoluble in acetone, water, benzene, almost insoluble in carbon tetrachloride. Odorless and bitter. |
| Use | Gastrin receptor antagonist for gastric and duodenal ulcer disease |
ProM - Risk and Safety
| Toxicity | LD50 in mice (mg/kg): 2211-2649 i.v.; 7350-8861 orally (Rovati) |
ProM - Standard
Authoritative Data Verified Data
This product is (±)-4-benzamido-n, N-dipropylpentanamic acid. Calculated as dried product, the content of C18H26N204 shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
ProM - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Odorless.
- This product is soluble in ethanol or chloroform, very slightly soluble in water; Dissolved in sodium hydroxide solution.
melting point
The melting point of this product (General 0612) is 148.5~152°C.
Last Update：2022-01-01 11:34:52
ProM - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.99 ml | 14.952 ml | 29.903 ml |
| 5 mM | 0.598 ml | 2.99 ml | 5.981 ml |
| 10 mM | 0.299 ml | 1.495 ml | 2.99 ml |
| 5 mM | 0.06 ml | 0.299 ml | 0.598 ml |
Last Update：2024-01-02 23:10:35
ProM - Differential diagnosis
Authoritative Data Verified Data
The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 67).
Last Update：2022-01-01 11:34:52
ProM - Exam
Authoritative Data Verified Data
chloride
take 2.0g of this product, add 1 ml of nitric acid, dilute to 50ml with water, shake, filter, take 25ml of filtrate, check according to law (General rule 0801), not more concentrated (0.005%) than the control solution made from of standard sodium chloride solution.
Related substances
take this product, add mobile phase to dissolve and dilute to make a solution containing about 1 mg per 1ml as a test solution; Take 1ml for precision measurement and put it in a 200ml measuring flask, dilute to the scale with the mobile phase, shake, and serve as a control solution. According to the determination of HPLC (General 0512), silica gel bonded with eighteen alkyl silane was used as filler; Methanol-acetonitrile -2% ammonium acetate solution (30:10:60) was used as mobile phase; the detection wavelength was 240mn. The number of theoretical plates shall not be less than 3000 based on the calculation of proglumide peak. 20 u1 of each of the control solution and the test solution were injected into the liquid chromatograph respectively, and the chromatogram was recorded to 4 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of 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
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:34:53
ProM - Content determination
Authoritative Data Verified Data
take this product about 0.3g, precision weighing, add neutral ethanol (phenolphthalein indicator solution neutral) 30ml dissolved, add phenolphthalein indicator solution 2 drops, with sodium hydroxide titration solution (0.lmol/L) titration. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 33.44mg of C18H26N204.
Last Update：2022-01-01 11:34:53
ProM - Category
Authoritative Data Verified Data
acid inhibitor.
Last Update：2022-01-01 11:34:54
ProM - Storage
Authoritative Data Verified Data
sealed storage.
Last Update：2022-01-01 11:34:54
ProM - Proglumide Tablets
Authoritative Data Verified Data
This product containing proglumide should be labeled amount of 95.0% ~ 105.0%.
trait
This product is white tablet.
identification
- take an appropriate amount of fine powder of this product (about 0.2g equivalent to proglumide), add 20ml of ethanol, make it fully dissolved, filter, and evaporate the filtrate in water bath to dry it at 105°C for 1 hour, determination according to law. The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 67).
- in the chromatogram recorded under the content determination item, 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
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931 second method), and the dissolution medium was 7.2 phosphate buffer (pH 100), and the rotation speed was rpm, operate in accordance with the law, after 30 minutes, take 10ml of the solution to filter, take 3ml of the filtrate, put it in a 50ml measuring flask, dilute it to the scale with phosphate buffer solution (pH 7.2), shake it well, as a test solution; In addition, an appropriate amount of proglumide reference substance was accurately weighed, and phosphate buffer solution (pH 7.2) was added to dissolve and quantitatively dilute to a solution containing about 13.3ug proglumide per 1 ml, as a reference solution. The absorbance was measured at a wavelength of 0401 nm by ultraviolet-visible spectrophotometry (general), and the elution amount of each tablet was calculated. The limit is 70% 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
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica as filler; Methanol-acetonitrile-2% ammonium acetate solution (30:10: 60) as mobile phase; the detection wavelength was 223nmD, and the number of theoretical plates was not less than 3000 according to the calculation of proglumide peak.
- determination of 20 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 50tng equivalent to proglumide), put in a 100ml measuring flask, add an appropriate amount of mobile phase, ultrasonic dissolution of proglumide, cool, dilute to scale with mobile phase, shake, and filter. Precisely take 5ml of continuous filtrate, put it in 50ml measuring flask, dilute it to scale with mobile phase, shake it, use it as sample solution, precisely take 20u1 and inject it into human liquid chromatograph, record chromatogram; in addition, an appropriate amount of proglumide reference substance was carefully weighed, dissolved and quantitatively diluted with mobile phase to prepare a solution containing about 0.05mg proglumide per 1 ml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as proglumide.
specification
0.2g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:34:55
ProM - Proglumide capsules
Authoritative Data Verified Data
This product contains Proglumide (C18H26N204) should be 95.0% ~ 105.0% of the label.
identification
- take an appropriate amount of the content of this product (about 0.2g equivalent to proglumide), grind it finely, add 20ml of ethanol, fully dissolve it, filter it, and evaporate the filtrate to dryness by water bath to obtain crystallization, it was dried at 105°C for 1 hour and measured according to law. The infrared absorption spectrum of this product should be consistent with the spectrum of the control (Spectrum set 67 Figure).
- in the chromatogram recorded under the content determination item, 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
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931 second method), and the dissolution medium was 7.2 phosphate buffer (pH), and the rotation speed was 75 revolutions per minute, operate in accordance with the law, after 45 minutes, take 10ml of the solution to be filtered, take 5ml of the filtrate, put it in a 25ml measuring flask, dilute it to the scale with phosphate buffer solution (pH 7.2), shake it well, as a test solution; In addition, an appropriate amount of proglumide reference substance was accurately weighed, and phosphate buffer solution (pH 7.2) was added to dissolve and quantitatively dilute to a solution containing about 50ug of proglumide per 1 ml, as a reference solution. Accurately measure 20 u1 of each of the reference solution and the test solution, and calculate the dissolution amount of each particle according to the method under the content determination item. The limit is 70% of the labeled amount, which shall meet the requirements D .
- others should comply with the relevant provisions under the capsule (General 0103).
inclusion assay
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica as filler; Methanol-acetonitrile-2% ammonium acetate solution (30:10:60) as mobile phase; the detection wavelength was 223nm. The number of theoretical plates shall not be less than 3000 based on the calculation of proglumide peak.
- determine the contents under the item of difference in loading amount, accurately weigh an appropriate amount (about 50mg equivalent to proglumide), put it in a 100ml measuring flask, add an appropriate amount of mobile phase, and sonicate the proglumide to dissolve, cool, dilute to scale with mobile phase, shake, and filter. 5ml of continuous filtrate was accurately measured, placed in a 50ml measuring flask, diluted to the scale with mobile phase, and then shaken to be used as a sample solution. 20u1 was accurately measured and injected into the liquid chromatograph, and the chromatogram was recorded; in addition, an appropriate amount of proglumide reference substance was accurately weighed, dissolved and quantitatively diluted with mobile phase to prepare a solution containing about 0.05 mg proglumide per 1 ml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as proglumide.
specification
0.2g
storage
sealed storage.
Last Update：2022-01-01 11:34:56
ProM - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | proglumide is the first discovered gastrin antagonist, and both progluric acid and benzotript are derivatives. proglumide, also a racemic compound named (±)-5-dipropylamino-4-benzoylamino-5-oxo-pentanoic acid, recorded in the Chinese Pharmacopoeia 2000 edition, Part Two, page 96, for the gastrin receptor antagonist, chemical structure and gastrin (G-17) and cholecystokinin (CCK) the terminal chemical structures of the two kinds of intestinal kinins are similar. Its functional group, Amide group, competes specifically with gastrin for gastrin receptors on parietal cells, thus it can significantly inhibit the secretion of gastric acid and pepsin caused by gastrin, but has no obvious effect on the secretion of gastric acid caused by histamine and vagus nerve stimulation. |
| indications | for gastric and duodenal ulcer, gastritis (such as Chronic superficial gastritis) and duodenal inflammation. |
| pharmacological action | This product is cholecystokinin receptor and gastrin receptor antagonist, its molecular structure and gastrin (G-17) and cholecystokinin (CCK) two kinds of intestinal kinin terminal molecular structure is similar, so the functional group amide group can be specific and G-17 competing with the Wall cell G-17 receptor, it can obviously inhibit the secretion of gastric acid and pepsin caused by G-17, increase the content of amino hexose in gastric mucosa, promote the synthesis of glycoprotein, protect gastric mucosa, so as to improve the symptoms of peptic ulcer and promote the healing of ulcer. The inhibitory effect of this product on gastric acid secretion caused by histamine and vagus nerve stimulation is not obvious, and the rebound phenomenon of gastric acid secretion does not occur in the treatment of peptic ulcer and gastritis, gastric acid secretion can still be at a normal level for half a year after termination of treatment. Because this product inhibits the role of gastric acid secretion than H2 receptor antagonists weak, clinical is no longer used alone for the treatment of ulcer disease, but recently its choleretic effect more attention. |
| drug interaction | 1. In combination with other anti-ulcer drugs (such as H2 receptor antagonists), it can enhance the effect of inhibiting gastric acid secretion and accelerate the healing of ulcer. 2. Combined with morphine, can enhance the analgesic effect of morphine and prolong the duration of its action. 3. This product can antagonize the effect of haloperidol to make the movement disorder worse, so the treatment of Huntington's Chorea can not be combined. |
| preparation | 1) preparation of N-benzoic acid glutamic acid a 1000 mL three-necked flask was charged with 50 g sodium gallate chlorate, 400 of water and appropriate amount of NaOH. Dissolve with stirring, adjust pH 7-8, add 37.2 mL of benzoyl chloride and 40% NaOH Dropwise below 2 ℃, control reaction temperature below 5 ℃, pH 8. Reaction at 5 deg C for 1 h, with 30% HCI adjusted to pH 1.5, cooling, crystallization, filtration, drying, N-benzoyl glutamic acid crude 71.8g,mp 134~140 deg C. 2) preparation of proglumide 60g(10.24 mot) of crude N-benzoylglutamic acid and 30g(0.22 mol) of acetic anhydride were taken. Add 75 mL of toluene to 500 mL three-mouth bottle, react at 85 ℃ for 30min, steam under normal pressure until no liquid drops out (toluene recovery and application), add 300 mL of ice water. Dipropylamine, 80mL, to be dissolved. React at 0 °c for 1 h, add acetic acid to adjust pH 4.5, stir, crystallize, dilute. The filter cake was added directly without drying. Distilled water, sodium carbonate and activated carbon were decolorized at 80 ℃ for 30min, filtered while hot, the filtrate was adjusted to pH 4.5, cooled, crystallized, filtered and dried to obtain 39 g of fine product, mp l48 ~ 151 ℃, the overall yield was 53.79%. |
| Use | This product is a gastrin receptor antagonist, which has the function of protecting gastric mucosa and promoting ulcer healing. Suitable for gastric and duodenal ulcer, gastritis, Stress ulcer, etc., the effective rate of 81-96%, the application of this product does not occur acid rebound increase, and the recurrence rate is low. gastrin receptor antagonist for gastric and duodenal ulcer disease |
| production method | N-benzoyl glutamic acid was obtained from glutamic acid and benzoyl chloride, then acetic anhydride is reacted to obtain N-benzoyl glutamic anhydride, and then aminated with dipropylamine to obtain proglumide. Based on glutamic acid, the overall yield was 26-30%. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | intraperitoneal-rat LD50: 1420 mg/kg; Oral-mouse LD50: 8070 mg/kg |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
Last Update：2024-04-10 22:29:15
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