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446-86-6

446-86-6 structural image
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.

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