446-86-6
Product Name:
Azathioprine
Formula:
C9H7N7O2S
Synonyms:
6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine;6-[(1-Methyl-4-nitro-1H imidazol-5yl) sulfanyl]-7H-purine
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CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Azathioprine appears as pale yellow crystals or yellowish powder. Decomposes at 243-244 °C. Used for the treatment of rheumatoid arthritis. A known carcinogen. |
|---|---|
| Color/Form | Pale yellow crystals from 50% aq acetone |
| Melting Point | 469 to 471 °F (decomposes) (NTP, 1992) |
| Solubility | >41.6 [ug/mL] (The mean of the results at pH 7.4) |
| LogP | 0.1 |
| Stability/Shelf Life | Azathioprine... is stated to be stable in neutral or acid solns but is hydrolyzed to mercaptopurine in alkaline solns, expecially on warming. Max stability occurs at pH 5.5-6.5. Hydrolysis to mercaptopurine also occurs in the presence of sulfhydryl compounds such as cysteine. /Azathioprine sodium/ |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitric oxides & sulfur oxides/. |
| Dissociation Constants | 7.87 (at 25 °C) |
| Collision Cross Section | 155.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] |
| Other Experimental Properties | Soly in water: 10 mg/ml /Sodium salt/ |
| Chemical Classes | Other Uses -> Pharmaceuticals |
SAFETY INFORMATION
| Signal word | Danger |
|---|---|
| Pictogram(s) |
 Exclamation Mark Irritant GHS07  Health Hazard GHS08 |
| GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H350:Carcinogenicity |
| Precautionary Statement Codes |
P202:Do not handle until all safety precautions have been read and understood. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P308+P313:IF exposed or concerned: Get medical advice/attention. |
COMPUTED DESCRIPTORS
| Molecular Weight | 277.27 g/mol |
|---|---|
| XLogP3 | 0.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Exact Mass | 277.03819367 g/mol |
| Monoisotopic Mass | 277.03819367 g/mol |
| Topological Polar Surface Area | 143 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 354 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
Azathioprine appears as pale yellow crystals or yellowish powder. It is used for the treatment of rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, and systemic lupus erythematosus; and in kidney transplants to prevent rejection. It is listed by the International Agency for Research on Cancer as a group 1 human carcinogen.