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Azathioprine

Application in Particular Diseases
Azathioprine
Azathioprine structure
CAS No.
446-86-6
Chemical Name:
Azathioprine
Synonyms
muran;Imrel;azamun;azanin;imurek;imurel;IMURAN;Zytrim;Azasan;bw57-322
CBNumber:
CB2170327
Molecular Formula:
C9H7N7O2S
Formula Weight:
277.27
MOL File:
446-86-6.mol

Azathioprine Properties

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. 
Freezer
solubility 
Soluble in Dichloromethane and dimethyl sulfoxide.
pka
8.2(at 25℃)
form 
neat
color 
Pale-yellow crystals from Me2CO (aq)
Water Solubility 
<0.1 g/100 mL at 23 ºC
Merck 
14,902
Stability:
Stable. Incompatible with strong oxidizing agents, strong bases.
InChIKey
LMEKQMALGUDUQG-UHFFFAOYSA-N
CAS DataBase Reference
446-86-6(CAS DataBase Reference)
FDA UNII
MRK240IY2L
IARC
1 (Vol. 26, Sup 7, 100A) 2012
Proposition 65 List
Azathioprine
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
Precautionary statements  P501a-P202-P264-P270-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P405-P501-P201-P280-P301+P312+P330-P305+P351+P338-P308+P313-P261
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
Hazard Note  Irritant
HazardClass  IRRITANT
HS Code  29339900
Toxicity LD50 orl-rat: 535 mg/kg NIIRDN 6,3,82

Azathioprine price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A4638 Azathioprine ≥98% 446-86-6 1g $95.8 2020-08-18 Buy
Sigma-Aldrich 1046001 Azathioprine United States Pharmacopeia (USP) Reference Standard 446-86-6 200mg $366 2020-08-18 Buy
TCI Chemical A2069 Azathioprine >98.0%(HPLC)(T) 446-86-6 5g $145 2020-06-24 Buy
TCI Chemical A2069 Azathioprine >98.0%(HPLC)(T) 446-86-6 25g $496 2020-06-24 Buy
Alfa Aesar J62314 Azathioprine 446-86-6 1g $88.5 2020-06-24 Buy

Azathioprine Chemical Properties,Uses,Production

Application in Particular Diseases

In Rheumatic Arthritis:
Azathioprine is a purine analog that is converted to 6-mercaptopurine and is thought to interfere with DNA and RNA synthesis. Antirheumatic effects may be seen in 3 to 4 weeks. It should be discontinued if no response is observed after 12 weeks at maximal doses. Its major adverse effects are bone marrow suppression (leukopenia, macrocytic anemia, thrombocytopenia, pancytopenia), stomatitis, GI intolerance, infections, drug fever, hepatotoxicity, and oncogenic potential.

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

Yellow Solid

Chemical Properties

Azathioprine is a complex heterocyclic compound which forms pale yellow crystals.

Originator

Imuran,Wellcome,UK,1964

Uses

immunosuppressant, antineoplastic, antirheumatic

Uses

An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD). Azathioprine is a purine analog with immunosuppressive effects.

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.

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.

Manufacturing Process

N,N'-Dimethyloxaldiamide is reacted with PCl5, to give 4-chloro-1-methyl imidazole. This is nitrated with HNO3 to give 5-nitro-1-methyl-4- chloroimidazole. Then, a mixture of 4.6 grams of anhydrous 6- mercaptopurine, 5 grams of 1-methyl-4-chloro-5-nitroimidazole and 2.5 grams of anhydrous sodium acetate in 100 ml of dry dimethyl sulfoxide was heated at 100°C for 7 hours.
After standing overnight at room temperature, the mixture was poured into 200 ml of cold water and the yellow precipitate of 6-(1'-methyl-4'-nitro-5'- imidazolyl)mercaptopurine (7.0 grams) collected. After recrystallization from 50% aqueous acetone, the product melted at 243-244°C, dec., and had an UV spectrum with λ maximum = 280 nm at pH 1 and λ max. = 285 nm at pH 11.

brand name

Imuran (Promethus).

Therapeutic Function

Immunosuppressive

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.

Veterinary Drugs and Treatments

In veterinary medicine, azathioprine is used primarily as an immunosuppressive agent in the treatment of immune-mediated diseases in dogs. See Doses below for more information. For autoagglutinizing immune mediated hemolytic anemia, azathioprine is generally recommended to start at the time of diagnosis. When used in combination with cyclosporine, azathioprine has been used to prevent rejection of MHC-matched renal allografts in dogs.
Although the drug can be very toxic to bone marrow in cats, it is sometimes used to treat feline autoimmune skin diseases.

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

Preparation Products


Azathioprine Suppliers

Global( 248)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
PI & PI BIOTECH INC.
18371201331
020-81716319 Sales@pipitech.com CHINA 3048 55
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 19929 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21841 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22624 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30039 58
Yunbio Tech Co.,Ltd.
010-60605551
010-60605551 yunbiochem@126.com CHINA 258 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6371 58
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 linda@hubeijusheng.com CHINA 23041 58
BOC Sciences
1-631-619-7922 1-631-619-7922
1-631-614-7828 inquiry@bocsci.com United States 20039 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 35434 58

View Lastest Price from Azathioprine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-01 Azathioprine
446-86-6
US $100.00 / KG 1KG 99% Customized career henan chemical co

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