Azathiopurine
azathioprine usp
CAS: 446-86-6
Molecular Formula: C9H7N7O2S
Azathiopurine - Names and Identifiers
| Name | azathioprine usp |
| Synonyms | azathioprine Azathiopurine azathioprine usp Azathioprine (200 mg) azathioprine crystalline 6-(1-methyl-4-nitroimidazol-5-ylthio)purin 6-(methyl-p-nitro-5-imidazolyl)-thiopurine 6-(1-methyl-4-nitroimidazol-5-ylthio)purine 6-(1-methyl-p-nitro-5-imidazolyl)-thiopurine 6-((1-methyl-4-nitroimidazol-5-yl)thio)-purin 6-((1-methyl-4-nitroimidazol-5-yl)thio)purine 6-(1-Methyl-4-nitro-5-imidazolythio)-9H-pur-ine 6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin 6-[(1-methyl-4-nitro-1h-imidazol-5-yl)thio]-1h-purine 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-5H-purine |
| CAS | 446-86-6 |
| EINECS | 207-175-4 |
| InChI | InChI=1/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-5H,1H3 |
| InChIKey | LMEKQMALGUDUQG-UHFFFAOYSA-N |
Azathiopurine - Physico-chemical Properties
| Molecular Formula | C9H7N7O2S |
| Molar Mass | 277.26 |
| Density | 1.5379 (rough estimate) |
| Melting Point | 243-244°C |
| Boling Point | 521.0±60.0 °C(Predicted) |
| Flash Point | 290°C |
| Water Solubility | <0.1 g/100 mL at 23 ºC |
| Solubility | 1 M NH4OH: 20 mg/mL. Very slightly soluble in ethanol, almost insoluble in water; soluble in dilute ammonia solution. |
| Vapor Presure | 7.98E-12mmHg at 25°C |
| Appearance | Pale yellow crystalline powder |
| Color | Pale-yellow crystals from Me2CO (aq) |
| Merck | 14,902 |
| pKa | 8.2(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Sensitive | Sensitive to heat and light |
| Refractive Index | 1.7400 (estimate) |
| MDL | MFCD00069203 |
| Physical and Chemical Properties | Melting point 243-244°C water-soluble <0.1g/100 mL at 23°C |
| Use | Immunosuppressant |
| In vitro study | In primary human CD4 T lymphocytes, Azathioprine inhibits Rac1 target genes such as activation of NF-κB in Cytokinin-activated protein kinase kinase (MEK), and bcl-X(L), the mitochondrial pathway that leads to apoptosis. Azathioprine converts a costimulatory signal into an apoptotic signal by modulating the activity of Rac1. Azathioprine generates-6-thioggtp, thereby preventing the development of an effective immune response via Vav activity on Rac proteins. Azathioprine(1 mM) restored ATP levels and prevented cell damage, while incubation in glucose-enriched medium enhanced ATP levels and could ameliorate cell death. Azathioprine reduced viability by 5-34% on Day 1 and 42-92% on Day 4. In primary cultured rat hepatocytes, Azathioprine reduces hepatocyte viability and induces the following events: intracellular reduction of glutathione (GSH) depletion, reduction of metabolic activity, and release of lactate dehydrogenase. Effect of Azathioprine on hepatocytes and swelling and increased oxygen consumption in intact isolated rat liver mitochondria. |
| In vivo study | In mouse-rat intracerebral grafts, the combination of Azathioprine and cyclosporin A or prednisolone resulted in survival of 14/15 grafts (93%) compared to 11/14(79%) in the control group. |
Azathiopurine - Risk and Safety
| Risk Codes | R45 - May cause cancer R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UO8925000 |
| HS Code | 29339900 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 orl-rat: 535 mg/kg NIIRDN 6,3,82 |
Azathiopurine - Nature
Open Data Verified Data
- This product is light yellow powder or crystalline powder; Odorless; Slightly bitter taste. Very slightly soluble in ethanol, almost insoluble in water; Soluble in dilute ammonia solution.
- This product is purine antimetabolites, is a derivative of mercaptopurine. In the body quickly break down into mercaptopurine and play an anti-metabolic role. Mercaptopurine is converted in the body to thioinosinic acid, which competitively inhibits the conversion of inosinic acid to adenylate and uridylic acid, interferes with purine metabolism, blocks DNA synthesis, and thereby inhibits lymphocyte proliferation, prevents the transformation of antigen-sensitive lymphocytes into immunoblasts. The inhibitory effect on cellular immunity was stronger than that on humoral immunity, and the inhibitory effect on T cells was stronger than that on B cells. This product can significantly inhibit the delayed type allergic reaction and host anti graft reaction, can also inhibit antibody production, but the effect of inhibiting IgG production is stronger than that of inhibiting IgM production. The effect on the primary immune response was significant, and the response to the secondary immune response could not be completely inhibited even at a very large dose. The main role of the drug in the induction of immune response, generally in the antigen stimulation at the same time or within the following 2 days of medication, antigen stimulation before the drug ineffective. Its anti-inflammatory effect is stronger than cyclophosphamide.
Last Update：2024-01-02 23:10:35
Azathiopurine - Use
Open Data Verified Data
- immunosuppressive drug. Mainly for the treatment of autoimmune diseases, such as autoimmune hemolytic anemia, erythema nodosum, nephrotic syndrome, lupus erythematosus, thrombocytopenia after splenectomy and for kidney transplantation. Can also be used for acute and chronic leukemia.
- usage and dose of oral, 1~5mg per kilogram of body weight per day.
- formulation tablet specifications:(1) 500mg; (2)lOOmg. This product is a light yellow tablet containing azathioprine.
Last Update：2022-01-01 11:12:28
Azathiopurine - Safety
Open Data Verified Data
- The hemogram should be strictly checked during medication; It is contraindicated in patients with hepatic insufficiency. The incidence of side effects is not high, manifested as Nausea, Vomit, Diarrhea, anorexia, oral injury, rash, drug heat, hair loss, acute pancreatitis and Arthralgia, a few people may have cholestatic jaundice, SGPT increased. After drug withdrawal or dose reduction, the above symptoms can be recovered. The myelosuppressive effect of this drug is weaker than the sintering agent, mainly for agranulocytosis, occasionally anemia and thrombocytopenia. Occasionally, renal damage was noted, and teratogenic fetus was noted. When combined with corticosteroids, patients are susceptible to viral infections such as herpes zoster, herpes simplex, and chickenpox. Contraindicated in pregnant women.
- under shading, sealed and preserved.
Last Update：2022-01-01 11:12:29
Azathiopurine - Reference Information
| (IARC) carcinogen classification | 1 (vol. 26, sup 7, 100a) 2012 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | Azathioprine (Azathioprine), an imidazole derivative of mercaptopurine, is decomposed into mercaptopurine in the body and works. Its immune mechanism is the same as that of mercaptopurine, that is, it has purine antagonism. Since immunologically active cells need purine substances in the proliferation period after antigen stimulation, purine antagonism can inhibit DNA, RNA and protein synthesis at this time. Thereby inhibiting the proliferation of lymphocytes, that is, preventing antigen-sensitive lymphocytes from transforming into immunoblasts and producing immune effects. |
| biological activity | Azathioprine is a drug that inhibits the immune system, inhibits the synthesis of purines and the activation of GTP-binding protein Rac1, and is used for organ transplantation and autoimmune diseases. |
| Target | Value |
| use | immunosuppressive drugs. It is a derivative of mercaptopurine, which is decomposed into mercaptopurine in the body and works. It is mainly used to suppress immune rejection during allogeneic transplantation, and is mostly used in combination with corticosteroids. It is also widely used in rheumatoid arthritis, systemic lupus erythematosus, autoimmune hemolytic anemia, thrombocytopenic purpura, active chronic hepatitis, ulcerative colitis, myasthenia gravis, scleroderma and other autoimmune diseases. Blood should be strictly checked during medication; liver insufficiency is prohibited. When combined with corticosteroids, the mouth is susceptible to viral infections such as herpes zoster, herpes simplex and chickenpox. Pregnant women are banned. Used as immunosuppressive drugs, anti-tumor drugs. is immunosuppressant |
| production method | using diethyl oxalate as raw material, it is obtained by amination, cyclization, chlorination, nitrification and condensation. 1. Amination Diethyl oxalate and methanol are put into the reaction pot, cooled to below 20 ℃, dried methylamine gas is introduced to saturation and then cooled to below 10 ℃, crystallization is precipitated, filtered and dried to obtain ethylenedimethylamine with a melting point of 210-212 ℃ and a 95.8% yield. 2. Cyclization and chlorination Put excess ethylene dimethylamine and phosphorus pentachloride into the reaction pot in batches, keep the temperature at 70-80 ℃ for 2 hours, leave it overnight, evaporate phosphorus oxychloride under reduced pressure, cool at a temperature not exceeding 100 ℃, add ice water, stir, adjust the pH to 9-10 with 30-40% alkali solution, and let stand. The oil is separated, the mother liquor is cooled, inorganic salts are precipitated and filtered, washed with chloroform, and the mother liquor is extracted with chloroform. Merge oil layer and chloroform layer, recover chloroform, distillation under reduced pressure, collect boiling point 110-115 ℃(4.0kPa) fraction, 1-methyl -5-chlorimidazole. The yield was 52%. 3. Nitration 1-methyl -5-chlorimidazole is added to the glass-lined reaction pot, and then nitric acid is added under cooling. Continue to add sulfuric acid dropwise under cooling, after adding, react at 100 ℃ for 2h, then cool, add ice water to precipitate the product, and filter and dry to obtain -5 chloro -1-methyl -4-nitroimidazole. The yield was 86%. 4. Condensation The 6-mercaptopurine, sodium hydroxide, water and 5-chloro-1-methyl-4-nitroimidazole are boiled together for 4 hours, and the reaction product is adjusted to pH with acetic acid to precipitate azathioprine. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 535 mg/kg; Oral-mouse LD50: 1389 mg/kg |
| flammability risk characteristics | can burn to produce toxic nitrogen and sulfur oxide smoke; Side effects after patient use: liver function changes, excessive gastrointestinal movement, nausea, vomiting, diarrhea, body temperature rise, low blood pressure, low urine output, no urine |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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