氨甲酰基吡嗪
Pyrazinamide
CAS: 98-96-4
Molecular Formula: C5H5N3O
氨甲酰基吡嗪 - Names and Identifiers
| Name | Pyrazinamide |
| Synonyms | mk56 MK 56 Eprazin Farmizina Aldinamid NCI-C01785 Aldinamide Pyrazinamide 2-Carbamylpyrazine Pyrazinecarboxamide |
| CAS | 98-96-4 |
| EINECS | 202-717-6 |
| InChI | InChI=1/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9) |
氨甲酰基吡嗪 - Physico-chemical Properties
| Molecular Formula | C5H5N3O |
| Molar Mass | 123.11 |
| Density | 1.3260 (rough estimate) |
| Melting Point | 189-191 °C (lit.) |
| Boling Point | 229.19°C (rough estimate) |
| Flash Point | >110°(230°F) |
| Water Solubility | 15 mg/mL |
| Solubility | Soluble in water (50 mg/ml), methanol (13.8 mg/ml at 25 °C), ethanol (5.7 mg/ml at 25 |
| Appearance | Transparent to off-white crystalline powder |
| Color | White |
| Merck | 14,7956 |
| BRN | 112306 |
| pKa | 0.5(at 25℃) |
| PH | 7 (H2O) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5900 (estimate) |
| MDL | MFCD00006132 |
| Physical and Chemical Properties | melting point 188-191°C water-soluble 15 mg/mL |
| Use | For anti-tuberculosis drugs |
氨甲酰基吡嗪 - Risk and Safety
| Risk Codes | R11 - Highly Flammable R34 - Causes burns |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
| WGK Germany | 3 |
| RTECS | UQ2275000 |
| TSCA | Yes |
| HS Code | 29339990 |
| Toxicity | LD50 intraperitoneal in mouse: 1680mg/kg |
氨甲酰基吡嗪 - Reference
| Reference Show more | 1. [IF=2.363] Li Xie et al."A sensitive EZMTT method provides microscale, quantitative and high-throughput evaluation of drug efficacy in the treatment of Mycobacterium tuberculosis infectious diseases."J Microbiol Meth. 2021 Feb;181:106136 2. [IF=4.098] Jie Liang et al."Deep learning aided quantitative analysis of anti-tuberculosis fixed-dose combinatorial formulation by terahertz spectroscopy."Spectrochim Acta A. 2022 Mar;269:120746 |
氨甲酰基吡嗪 - Standard
Authoritative Data Verified Data
This product is pyrazine formamide. Calculated as dried product, containing no less than 99.0% of C5H5N30.
Last Update：2024-01-02 23:10:35
氨甲酰基吡嗪 - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder.
- This product is slightly soluble in water, slightly soluble in methanol or ethanol.
melting point
The melting point of this product (General 0612) is 188~192°C.
Last Update：2022-01-01 11:57:04
氨甲酰基吡嗪 - Differential diagnosis
Authoritative Data Verified Data
- take 0.lg of this product, add 10ml of water to dissolve, add 1ml of ferrous sulfate test solution, and the solution shows orange red color; Add sodium hydroxide test solution to make it alkaline and turn it into blue.
- take an appropriate amount of this product, add water to dissolve and dilute to make a solution containing about 50ug per lml, as a test solution (1), according to UV-visible spectrophotometry (General 0401) the maximum absorption was measured at a wavelength of 310Nm. The test solution (1) is diluted with water to make a solution containing about 10ug per 1 ml, which is used as the test solution (2), according to ultraviolet-visible spectrophotometry (General 0401) the maximum absorption was measured at a wavelength of 268nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 191).
Last Update：2022-01-01 11:57:04
氨甲酰基吡嗪 - Exam
Authoritative Data Verified Data
acidity
take this product, add water to dissolve and dilute to make a solution containing about 15mg per lml, according to the law (General 0631) ,pH value should be 5.0~7.0. The color of the solution to take this product 0.10g, add water 10ml after dissolution, the solution should be colorless.
sulfate
take 0.30g of this product and check it according to law (General rule 0802). Compared with the control solution made of 0.033% of standard potassium sulfate solution, it should not be more concentrated ().
Related substances
take about 20mg of this product, add water to dissolve and dilute to make a solution containing about 0.4mg per 1 ml, as a test solution; Take an appropriate amount of precision, A solution containing about 0.8ug per 1 ml was prepared as a control solution by quantitative dilution with water. According to the determination by high performance liquid chromatography (General 0512), silica gel bonded with eighteen alkyl silane is used as filler; Water (adjusted to pH 3.0 with glacial acetic acid)-methanol (92:8) is used as mobile phase; the detection wavelength was 268nm. Take an appropriate amount of pyrazinamide, add water to dissolve and quantitatively dilute to make a solution containing about 0.04mg per lml, take 4ml of the solution and 1 ml of hydrochloric acid, mix well, and heat in a water bath for 5 minutes, pyrazinamide was partially hydrolyzed to pyrazinic acid and allowed to cool as a system suitability test solution. 20u1 is injected into the liquid chromatograph, and the chromatogram is recorded. The number of theoretical plates is not less than 3000 based on pyrazinamide peak, and the separation degree between pyrazine acid peak and pyrazinamide peak, the largest degradation product, should be greater than 3.0. 20ul of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 2 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 (0.2%).
loss on drying
take this product, put the phosphorus pentoxide dryer under reduced pressure to dry to constant weight, the weight loss should 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
take 0.5g of this product, add 2ml of acetate buffer (pH 3.5) and 23ml of water, after heating and dissolving, check according to law (General Principles 0821 first method), heavy metals should not be more than 20 parts per million.
Last Update：2022-01-01 11:57:05
氨甲酰基吡嗪 - Content determination
Authoritative Data Verified Data
take this product about 0.10g, precision weighing, add acetic anhydride 50ml dissolved, according to the potential titration method (General 0701), with perchloric acid titration solution (0.1 mol/L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 12.31mg of C5H5N3O.
Last Update：2022-01-01 11:57:06
氨甲酰基吡嗪 - Category
Authoritative Data Verified Data
anti-tuberculosis drugs.
Last Update：2022-01-01 11:57:06
氨甲酰基吡嗪 - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:57:06
氨甲酰基吡嗪 - Pyrazinamide tablets
Authoritative Data Verified Data
This product contains Pyrazinamide (C5H5N30) should be labeled the amount of 95.0% ~ 105.0%.
trait
This product is white or off-white.
identification
- take an appropriate amount of fine powder of this product (about 0.5g of pyrazinamide), add 10ml of anhydrous ethanol, grind to dissolve, filter, and evaporate the filtrate to dryness in water bath, the residue was taken according to the identification (1) Test under the item of pyrazinamide, and showed the same reaction.
- the sample solution under the content measurement item was taken and measured by ultraviolet-visible spectrophotometry (General rule 0401), and there was a maximum absorption at a wavelength of 268mn.
- The residue under Item (1) of identification was taken, dried at 105°C for 30 minutes, and then determined according to law (General rule 0402); Another pyrazinamide reference product was taken, and the same method was performed, the infrared absorption spectrum of this product should be consistent with that of the reference product.
examination
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 second method), water 900ml as the dissolution medium, the speed of 50 rpm, according to the law, after 45 minutes, take 5ml of the solution, filter, take the appropriate amount of the filtrate, and dilute it quantitatively with water to prepare a solution containing about 10ug of pyrazinamide per lml, which is used as the test solution, UV-Vis spectrophotometry (General rule 0401), at the wavelength of 268nm absorbance; Another pyrazinamide reference, precision weighing, water was added to dissolve and diluted to prepare a solution containing about 10ug per 1 ml. As a reference solution, the absorbance was measured by the same method, and the dissolution amount of each tablet was calculated. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- appropriate amount of fine powder under the content determination item is taken, dissolved and diluted with mobile phase to make a solution containing about 0.4mg of pyrazinamide per 1 ml, filtered, and the continued filtrate is taken as the test solution; an appropriate amount was taken in a precise amount and diluted with the mobile phase to prepare a solution containing about 0.8ug per 1 ml as a control solution. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2% ) , the sum of each impurity peak area shall not be greater than 2.5 times (0.5%) of the main peak area of the control solution.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product, precision weighing, fine grinding, precision weighing a proper amount of fine powder (about 0.25g equivalent to pyrazinamide), put it in a 100ml measuring flask, add an appropriate amount of water, shake to dissolve pyrazinamide, dilute to the scale with water, shake well, filter, accurately take lml of continued filtrate, put it in a 250ml measuring flask, dilute to the scale with water, shake well, as a test solution, according to UV-visible spectrophotometry (General rule 0401), absorbance was measured at the wavelength of 268mn; Another pyrazinamide reference substance, water is added to dissolve and quantitatively dilute to prepare a solution containing about 10ug per lml, which is determined and calculated by the same method.
category
Same as pyrazinamide.
specification
(1)0.25g (2)0.5g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:57:07
氨甲酰基吡嗪 - PyrazinamideCapsules
Authoritative Data Verified Data
This product contains Pyrazinamide (C5H5N30) should be labeled the amount of 95.0% ~ 105.0%.
trait
The content of this product is white or off-white powder.
identification
- take an appropriate amount of the content of this product (about 0.5g equivalent to pyrazinamide), add anhydrous ethanol 10ml, dissolve, filter, filtrate water bath evaporation, take the residue, the same response was shown in the identification (1) Test under pyrazinamide.
- the sample solution under the content measurement item was taken and measured by ultraviolet-visible spectrophotometry (General rule 0401), and there was a maximum absorption at a wavelength of Nm.
- The residue under Item (1) of identification was taken, dried at 105°C for 30 minutes, and then determined according to law (General rule 0402); Another pyrazinamide reference product was taken, and the same method was performed, the infrared absorption spectrum of this product should be consistent with that of the reference product.
examination
- 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, take 5ml of the solution, filter, take the appropriate amount of the filtrate, and dilute it quantitatively with water to prepare a solution containing about 10ug of pyrazinamide per lml, which is used as the test solution, UV-Vis spectrophotometry (General rule 0401), at the wavelength of 268nm absorbance; Another pyrazinamide reference, precision weighing, water was added to dissolve and diluted to prepare a solution containing about 10ug per 1 ml. As a reference solution, the absorbance was measured by the same method, and the dissolution amount of each particle was calculated. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- relevant substances: Take appropriate amount of the contents of this product, add the mobile phase to dissolve and dilute to make a solution containing about 0.4mg of pyrazinamide per 1 ml, filter, and take the continued filtrate as the test solution; an appropriate amount was taken in a precise amount and diluted with the mobile phase to prepare a solution containing about 0.8ug per 1 ml as a control solution. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2% ) , the sum of each impurity peak area shall not be greater than 2.5 times (0.5%) of the main peak area of the control solution.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
take the contents under the difference of loading amount, mix evenly, weigh an appropriate amount (about 0.25g equivalent to pyrazinamide), put it in a 100ml measuring flask, and add an appropriate amount of water, shake to dissolve pyrazinamide, dilute to the scale with water, shake well, filter, accurately take lml of continued filtrate, put it in a 250ml measuring flask, dilute to the scale with water, shake well, as a test solution, according to UV-visible spectrophotometry (General rule 0401), absorbance was measured at the wavelength of 268mn; Another pyrazinamide reference substance, water is added to dissolve and quantitatively dilute to prepare a solution containing about 10ug per lml, which is determined and calculated by the same method.
category
Same as pyrazinamide.
specification
0.25g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:57:08
氨甲酰基吡嗪 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| anti-tuberculosis drugs | Pyrazinamide is a second-line anti-tuberculosis drug, also known as pyrazinecarboxamide, carbamoylpyrazine, isonicotamide, white crystalline powder at room temperature, slightly soluble in water, odorless, slightly bitter taste. Human Mycobacterium tuberculosis has better antibacterial effect, pH value between 5-5.5, the strongest bactericidal effect, in particular, it has the best effect on tuberculosis in phagocytic cells that grow slowly in an acidic environment. Pyrazinamide penetrates into phagocytic cells and enters the bacteria of Mycobacterium tuberculosis. The amidase in the bacteria makes it remove the amide group and convert it into pyrazine acid to play an antibacterial effect. In Vivo inhibitory concentration of 12.5 μg/ml, up to 50 μg/ml can kill Mycobacterium tuberculosis. The inhibitory concentration of Mycobacterium tuberculosis in cells was 10 times lower than that in cells, and there was almost no inhibitory effect in neutral and alkaline environment. The bacteriostatic effect is between streptomycin and sodium p-aminosalicylate, which is toxic and easy to produce drug resistance, and should be combined with other anti-tuberculosis drugs. Pyrazinamide is similar to nicotinamide in chemical structure. It can interfere with dehydrogenase by substituting nicotinamide, prevent dehydrogenation, inhibit the utilization of oxygen by Mycobacterium tuberculosis, and cause the bacteria to be unable to metabolize normally and die. It is easily absorbed by oral administration and widely distributed in tissues and body fluids, including liver, lung, cerebrospinal fluid, kidney and bile. 2 hours later, the drug peak was reached. Cerebrospinal fluid and blood concentration is similar, liver metabolism, hydrolysis into gallic acid, with antibacterial activity of metabolites, and then hydroxylated into inactive metabolites, urine excretion after glomerular filtration. t1/2 is 8 to 10 hours. Can be combined with other anti-tuberculosis drugs, for some complex cases of tuberculosis and tuberculous meningitis patients. |
| drug interaction | 1, in combination with allopurinol, colchicine, probenecid, pyrazinamide can increase the concentration of blood uric acid, thereby reducing the efficacy of these drugs for gout. Therefore, when the above drugs are used in combination with pyrazinamide, the dose should be adjusted to control hyperuricemia and gout. 2, when combined with ethylisocyanamide can enhance adverse reactions. 3, the blood concentration of cyclosporine and pyrazinamide may decrease, so the blood concentration should be monitored and the dose should be adjusted. 4, with isoniazid, rifampicin combination with a synergistic effect, and can delay the emergence of drug resistance. |
| indication | used in combination with other anti-TB drugs (such as streptomycin, isoniazid, rifampicin and ethambutol) ineffective treatment of tuberculosis. This product is only effective against mycobacteria. pyrazinamide has been used as a second-line drug in retreatment patients who have failed other anti-tuberculosis drugs. A large number of clinical studies have shown that: the short-term treatment plan containing this product is suitable for sputum bacteria positive initial treatment cases, and the general application is 2~3 months, this scheme can make the end of treatment, sputum positive rate significantly reduced. This product has been recognized as the composition of triple or quadruple regimen in short-course chemotherapy-. |
| usage and dosage | in combination with other anti-tuberculosis drugs, the usual dosage for adults is 5-8.75mg/kg of body weight every 6 hours, or 6.7-11.7mg/kg body weight every 8 hours, up to 3g daily. treatment of isoniazid-resistant bacterial infections can be increased to 60mg/kg daily. children with caution, must use the reference dosage: daily 20-25mg/kg, divided into 3 times orally, the highest daily 2G, the course of treatment is generally 2~3 months, not more than 6 months. |
| Emergency Treatment | 1. 2. Patients with liver function damage during treatment should be discontinued and given liver protection treatment. 3. The author of gout given probenecid (carbenesulfonamide) 0.25g/Times, 3 times a day oral, can promote the excretion of uric acid. 4. Patients with allergies should be treated with antihistamines and corticosteroids. |
| adverse reactions and side effects | long-term or high-dose use of the product is easy to cause liver damage, increased blood uric acid, it can also cause gastrointestinal irritation and allergic reactions. patients with higher incidence: anorexia, Fever, abnormal Fatigue or weakness, eyes or skin yellow (liver toxicity). The incidence of less: Chills, joint pain (especially big toe, condyle, knee) or lesions of the joint skin tension Fever (acute gout Arthralgia). The application of this product in the treatment of blood uric acid often increased, can cause acute gout attack, serum uric acid determination. The adverse reactions are related to the dose course of treatment. At present, the adverse reactions are rare after the application of conventional dose. liver damage: about 15% of the patients had liver damage, hepatomegaly, tenderness, elevated transaminases and jaundice when taking 3g daily. At present, the use of daily 1.5g, 3 months of treatment, liver toxicity is rare. Arthralgia: the metabolites of PZA can inhibit the excretion of uric acid, causing hyperuricemia and gout-like manifestations, which can be recovered after discontinuation. gastrointestinal reaction: inappetence, Nausea, Vomit. allergic reaction: Fever and rash occasionally, even jaundice. skin reaction: individual was sensitive to light, and the exposed skin was bright red-brown. Long-term users, The skin was bronze, which could be gradually recovered after drug withdrawal. It is difficult to control blood glucose in diabetic patients taking pyrazinamide. |
| Use | Anti-TB drugs |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:12
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View History
氨甲酰基吡嗪
Arsenotrithious acid (9CI)
3-溴-2-乙酰基噻吩
172967-04-3
CHINENSIOSIDE B
2-hexylcyclopent-2-en-1-one
化合物TEPOTINIB HYDROCHLORIDE(1 : X)
S-环戊基乙胺
BLASTICIDIN S, HYDROCHLORIDE, STREPTOMYCES GRISEOCHROMOGENES
5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷
Arsenotrithious acid (9CI)
3-溴-2-乙酰基噻吩
172967-04-3
CHINENSIOSIDE B
2-hexylcyclopent-2-en-1-one
化合物TEPOTINIB HYDROCHLORIDE(1 : X)
S-环戊基乙胺
BLASTICIDIN S, HYDROCHLORIDE, STREPTOMYCES GRISEOCHROMOGENES
5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖糖苷