Azathioprine
- CAS No.
- 446-86-6
- Chemical Name:
- Azathioprine
- Synonyms
- IMURAN;muran;Imrel;azamun;azanin;imurek;imurel;Zytrim;Azasan;bw57-322
- CBNumber:
- CB2170327
- Molecular Formula:
- C9H7N7O2S
- Molecular Weight:
- 277.26
- MOL File:
- 446-86-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/21 22:41:43
| Melting point | 243-244°C |
|---|---|
| Boiling point | 521.0±60.0 °C(Predicted) |
| Density | 1.5379 (rough estimate) |
| refractive index | 1.7400 (estimate) |
| storage temp. | 2-8°C |
| solubility | Soluble in Dichloromethane and dimethyl sulfoxide. |
| pka | 8.2(at 25℃) |
| form | Solid |
| color | Pale-yellow crystals from Me2CO (aq) |
| Water Solubility | <0.1 g/100 mL at 23 ºC |
| Merck | 14,902 |
| BCS Class | 4 |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| InChIKey | LMEKQMALGUDUQG-UHFFFAOYSA-N |
| CAS DataBase Reference | 446-86-6(CAS DataBase Reference) |
| IARC | 1 (Vol. 26, Sup 7, 100A) 2012 |
| EPA Substance Registry System | Azathioprine (446-86-6) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H315-H319-H335-H350-H361fd | |||||||||
| Precautionary statements | P202-P261-P301+P312-P302+P352-P305+P351+P338-P308+P313 | |||||||||
| Hazard Codes | Xi,T,Xn | |||||||||
| Risk Statements | 45-22-36/37/38-20/21/22 | |||||||||
| Safety Statements | 53-22-26-36/37-45-36 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UO8925000 | |||||||||
| HazardClass | IRRITANT | |||||||||
| HS Code | 29339900 | |||||||||
| Toxicity | LD50 orl-rat: 535 mg/kg NIIRDN 6,3,82 | |||||||||
| NFPA 704 |
|
Azathioprine price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1282 | Azathioprine Pharmaceutical Secondary Standard; Certified Reference Material | 446-86-6 | 1G | ₹8042.98 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A4638 | Azathioprine ≥98% | 446-86-6 | 1G | ₹10446.13 | 2022-06-14 | Buy |
| TCI Chemicals (India) | A2069 | Azathioprine | 446-86-6 | 5G | ₹10300 | 2022-05-26 | Buy |
| TCI Chemicals (India) | A2069 | Azathioprine | 446-86-6 | 25G | ₹14200 | 2022-05-26 | Buy |
Azathioprine Chemical Properties,Uses,Production
Description
This immunosuppressive and antineoplastic drug is derived from 6-mercaptopurine. It caused occupational dermatitis in a pharmaceutical worker, reconditioner of old tablet packaging machines and in a production mechanic, working in packaging for a pharmaceutical company.
Chemical Properties
Azathioprine is a complex heterocyclic compound which forms pale yellow crystals.
Uses
An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD). Azathioprine is a purine analog with immunosuppressive effects.
Indications
Azathioprine (Imuran) is a cytotoxic agent that preferentially destroys any rapidly dividing cell. Since immunologically competent cells are generally rapidly dividing cells, azathioprine is very effective as an immunosuppressive drug. Unfortunately, any cell that is replicating is a target for this action. This lack of specificity leads to serious side effects. Azathioprine, in combination with corticosteroids, has historically been used more widely than any other drug in immunosuppressive therapy. It is classified as a purine antimetabolite and is a derivative of 6-mercaptopurine.
Definition
ChEBI: A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and a ter organ transplantation and also for treatment of Crohn's didease and MS.
General Description
Pale yellow crystals or yellowish powder. Decomposes at 243-244°C. Used for the treatment of rheumatoid arthritis. A known carcinogen.
Air & Water Reactions
Sensitive to oxidation in the air. Insoluble in water.
Reactivity Profile
Azathioprine may react exothermically with acids. Incompatible with isocyanates, peroxides, phenols, epoxides, anhydrides, and acid halides. Hydrolyzed by strongly basic solutions . May react with strong reducing agents to generate flammable gaseous hydrogen or hydrogen sulfide.
Hazard
Confirmed carcinogen.
Fire Hazard
Flash point data for Azathioprine are not available. Azathioprine is probably combustible.
Contact allergens
This immunosuppressive and antineoplastic drug is derived from 6-mercaptopurine. It caused allergic contact dermatitis in a mother crushing tablets for her leukemic son, and occupational dermatitis in a pharmaceutical reconditioner of old tablet packaging machines, and in a production mechanic working in packaging for a pharmaceutical company.
Mechanism of action
Azathioprine is a phase-specific drug that is toxic to
cells during nucleic acid synthesis. Phase-specific drugs
are toxic during a specific phase of the mitotic cycle,
usually the S-phase, when DNA synthesis is occurring,
as opposed to cycle-specific drugs that kill both cycling
and intermitotic cells.
Azathioprine is converted in vivo to thioinosinic
acid, which competitively inhibits the synthesis of inosinic
acid, the precursor to adenylic acid and guanylic
acid. In this way, azathioprine inhibits DNA synthesis
and therefore suppresses lymphocyte proliferation.This
effectively inhibits both humoral and cell-mediated immune
responses.
Pharmacology
Azathioprine is well absorbed following oral administration, with peak blood levels occurring within 1 to 2 hours. It is rapidly and extensively metabolized to 6- mercaptopurine, which is further converted in the liver and erythrocytes to a variety of metabolites, including 6- thiouric acid. Metabolites are excreted in the urine.The half-life of azathioprine and its metabolites in the blood is about 5 hours.
Clinical Use
Azathioprine is a relatively powerful antiinflammatory
agent. Although its beneficial effect in various conditions
is principally attributable to its direct immunosuppressive
action, the antiinflammatory properties of the
drug play an important role in its overall therapeutic effectiveness.
Azathioprine has been used widely in combination
with corticosteroids to inhibit rejection of organ transplants,
particularly kidney and liver allografts. However,
it is usually reserved for patients who do not respond to
cyclosporine plus corticosteroids alone.
Azathioprine also has applications in certain disorders
with autoimmune components, most commonly
rheumatoid arthritis. It is as effective as cyclophosphamide
in the treatment of Wegener’s granulomatosis.
It has largely been replaced by cyclosporine in immunosuppressive
therapy. Relative to other cytotoxic
agents, the better oral absorption of azathioprine is the
reason for its more widespread clinical use.
Side effects
The therapeutic use of azathioprine has been limited by the number and severity of adverse effects associated with its administration. Bone marrow suppression resulting in leukopenia, thrombocytopenia, or both may occur. GI toxicity may be a problem. It is also mildly hepatotoxic. Because of its immunosuppressive activity, azathioprine therapy can lead to serious infections. It has been shown to be mutagenic in animals and humans and carcinogenic in animals.
Safety Profile
Confirmed human carcinogen producing bladder tumors and leukemia. Poison by subcutaneous, intradermal, and intraperitoneal routes. Moderately toxic by ingestion. Human systemic effects: liver changes, hypermotility, diarrhea, nausea or vomiting, increased body temperature, BP lowering, decreased urine volume or anuria, normocytic anemia, bone marrow changes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NO,xand SOx. An immunosuppressant.
Potential Exposure
Azathioprine is an immunosuppressive agent, generally used in combination with a corticosteroid to prevent rejection following renal homotransplantations. It also is used following transplantation of other organs. Other uses of azathioprine include the treatment of a variety of presumed autoimmune diseases, including rheumatoid arthritis; ankylosing spondylitis; systemic lupus erythematosus; dermatonyositis, periarteritis nodosa, scleroderma, refractory thombocytopenic purpura; autoimmune hemolytic anemia; chronic active liver disease; regional enteritis; ulcerative colitis; various autoimmune diseases of the eye; acute and chronic glomerulonephritis; the nephritic syndrome; Wegener’s granulomatosis; and multiple sclerosis.
Carcinogenicity
Azathioprine is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Incompatibilities
Incompatible with reducing agents, such as hydrides (may cause the release of explosive gases), oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong acids (violent exothermic reaction), strong bases.
Azathioprine Preparation Products And Raw materials
Raw materials
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| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| AARTI INDUSTRIES LIMITED | 912267976666 | New Delhi, India | 172 | 58 | Inquiry |
| Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
| Micro Orgo Chem | +91-91-022-24969510 +91-9082984052 | Mumbai, India | 66 | 58 | Inquiry |
| Flax Laboratories | +91-9867665132 +91-9867665132 | Maharashtra, India | 44 | 58 | Inquiry |
| Aarti Industries Limited (AIL) | +91-84596144931 +91-9920899935 | Maharashtra, India | 235 | 58 | Inquiry |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | +91-26463395 +91-7926462688 | Gujarat, India | 1615 | 58 | Inquiry |
| Zydus Lifesciences Ltd. | +91-0265-2315243 +91-6358895661 | Gujarat, India | 89 | 58 | Inquiry |
| Besil Chem LLP | +91-7760252666 +91-9880731835 | Bangalore, India | 163 | 58 | Inquiry |
| Humble Healthcare Limited | +91-9720093000 +91-8006400378 | Uttar Pradesh, India | 141 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| AARTI INDUSTRIES LIMITED | 58 |
| Jigs Chemical ltd | 58 |
| Micro Orgo Chem | 58 |
| Flax Laboratories | 58 |
| Aarti Industries Limited (AIL) | 58 |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | 58 |
| Zydus Lifesciences Ltd. | 58 |
| Besil Chem LLP | 58 |
| Humble Healthcare Limited | 58 |
| Ralington Pharma | 58 |
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