Azathioprine

Purine analog; anti-inflammatory and immunosuppressant CAS# 446-86-6

Azathioprine

Catalog No. BCC4762----Order now to get a substantial discount!

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Quality Control of Azathioprine

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Chemical structure

Azathioprine

3D structure

Chemical Properties of Azathioprine

Cas No. 446-86-6 SDF Download SDF
PubChem ID 2265 Appearance Powder
Formula C9H7N7O2S M.Wt 277.26
Type of Compound N/A Storage Desiccate at -20°C
Synonyms BW 57-322
Solubility DMSO : 50 mg/mL (180.34 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
SMILES CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
Standard InChIKey LMEKQMALGUDUQG-UHFFFAOYSA-N
Standard InChI InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Azathioprine

DescriptionPurine analog. Blocks DNA replication and the de novo pathway of purine synthesis. Immunosuppressive and anti-inflammatory drug; induces apoptosis in human T-lymphocytes. Prodrug of 6-mercaptopurine.

Azathioprine Dilution Calculator

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Azathioprine Molarity Calculator

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Preparing Stock Solutions of Azathioprine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6067 mL 18.0336 mL 36.0672 mL 72.1345 mL 90.1681 mL
5 mM 0.7213 mL 3.6067 mL 7.2134 mL 14.4269 mL 18.0336 mL
10 mM 0.3607 mL 1.8034 mL 3.6067 mL 7.2134 mL 9.0168 mL
50 mM 0.0721 mL 0.3607 mL 0.7213 mL 1.4427 mL 1.8034 mL
100 mM 0.0361 mL 0.1803 mL 0.3607 mL 0.7213 mL 0.9017 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Organizitions Citing Our Products recently

 
 
 

Calcutta University

University of Minnesota

University of Maryland School of Medicine

University of Illinois at Chicago

The Ohio State University

University of Zurich

Harvard University

Colorado State University

Auburn University

Yale University

Worcester Polytechnic Institute

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Stanford University

University of Leipzig

Universidade da Beira Interior

The Institute of Cancer Research

Heidelberg University

University of Amsterdam

University of Auckland
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Background on Azathioprine

Azathioprine(Azasan, Imuran) is a drug that suppresses the immune system and is used in organ transplantation and autoimmune disease.

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References on Azathioprine

Effect of Sequential Intravenous Pulse Cyclophosphamide-Azathioprine in Systemic Sclerosis-Interstitial Lung Disease: An Open-Label Study.[Pubmed:28368564]

Indian J Chest Dis Allied Sci. 2016 Jan-Mar;58(1):7-10.

BACKGROUND: Systemic sclerosis (SSc) is a rare connective tissue disorder of unknown aetiology. Pulmonary involvement contributes substantially to its morbidity and mortality. Treatment of pulmonary disease due to SSc remains unsatisfactory. We examined the effect of sequential six-month intravenous pulse therapy with cyclophosphamide (CYC) followed by Azathioprine and low-dose corticosteroids on SSc associated interstitial lung disease (SSc-ILD). METHODS: In a single-centre, prospective, observational, open-labelled study; nine patients (eight females, one male) with SSc-ILD were treated with intravenous pulse CYC (600mg/m(2) body surface area) at monthly interval for six cycles with oral prednisolone 10mg daily. Subsequently, Azathioprine (2-3mg/Kg) was administered while continuing with the same dose of prednisolone. Primary end-points were forced vital capacity (FVC) and high resolution computed tomography (HRCT) scan of thorax score. Secondary end-points were quality of life measured by health assessment questionnaire-disability index (HAQ-DI) and six-minute walk distance (6WMD) test. RESULTS: After one year of observation, the FVC showed significant improvement (p=0.003). The 6WMD also improved significantly (p=0.0028). However, change in HRCT scan scoring and HAQ-DI score was not significant. CONCLUSIONS: Intravenous, pulse CYC followed by Azathioprine along with low-dose corticosteroids produces significant improvement in FVC and 6WMD at 12-month follow-up without significant change in radiological manifestations and health status.

AZALEP a randomized controlled trial of azathioprine to treat leprosy nerve damage and Type 1 reactions in India: Main findings.[Pubmed:28358815]

PLoS Negl Trop Dis. 2017 Mar 30;11(3):e0005348.

BACKGROUND: Leprosy Type 1 reactions are difficult to treat and only 70% of patients respond to steroid treatment. Azathioprine has been used as an immune-suppressant and we tested its efficacy in treating leprosy T1R. METHODOLOGY: Randomised controlled trial adding Azathioprine to steroid treatment for leprosy reactions. This trial was conducted in four leprosy hospitals in India. Patients with a new leprosy Type 1 reaction affecting either skin or nerve were recruited. They were given a 20 week course of oral prednisolone either with placebo or Azathioprine 50mg for 24, 36 or 48 weeks. Outcomes were measured using a verified combined clinical reaction severity score (CCS) and the score difference between baseline and end of study calculated. An intention to treat analysis was done on the 279 patients who had an outcome. PRINCIPAL FINDINGS: 345 patients were recruited, 145 were lost due to adverse events, loss to follow up or death. 36% needed extra steroids due to a recurrence of their skin and/or nerve reaction. 76% of patients had improvements in their CCS the end of the study, 22% had no change and 1.1% deteriorated. Adding Azathioprine to steroid treatment did not improve CCS. So the improvements were attributable to treatment with steroids. We analysed the skin, sensory and motor scores separately and found that skin improvement contributed most with 78.9% of patients having skin improvement, Azathioprine treatment for 48 weeks improved sensory scores it also improved motor scores but so did treatment with prednisolone alone. We identified significant adverse effects attributable to steroid treatment. When Azathioprine and Dapsone were given together significant numbers of patients developed significant anaemia. CONCLUSIONS: Azathioprine is not recommended for the treatment of leprosy reactions and does not improve steroid treatment. Recurrent reactions are a major challenge. We have also identified that 65% of patients with sensory and 50% with motor nerve damage do not improve. Future studies should test giving Azathioprine in the treatment of nerve damage and giving a higher dose for 48 weeks to patients. These findings highlight the difficulty in switching off leprosy inflammation and the need for better treatments for reactions and nerve damage. There is also a research need to identify patients who have recurrences and optimize treatments for them. Patients with recurrences may benefit from combined treatment with steroids and Azathioprine. We have also shown that significant numbers of patients treated with steroids develop adverse effects and this needs to be highlighted in leprosy programmes. Research is needed to identify patients who do not respond to steroid treatment and develop alternative treatments for them. TRIAL REGISTRATION: ClinicalTrials.gov This trial was registered with the Indian Council of Medical research clinical Trial register as a clinical trial Number-REFCTRI/2016/12/007558.

Multicentric Case-Control Study on Azathioprine Dose and Pharmacokinetics in Early-onset Pediatric Inflammatory Bowel Disease.[Pubmed:28296824]

Inflamm Bowel Dis. 2017 Apr;23(4):628-634.

BACKGROUND: Early-onset inflammatory bowel disease (IBD) is generally aggressive, with a high probability of complications and need of surgery. Despite the introduction of highly effective biological drugs, treatment with Azathioprine continues to be important even for early-onset IBD; however, in these patients Azathioprine response seems to be reduced. This study evaluated Azathioprine doses, metabolite concentrations, and their associations with patients' age in children with IBD treated at 6 tertiary pediatric referral centers. METHODS: Azathioprine doses, metabolites, and clinical effects were assessed after at least 3 months of therapy in 17 early-onset (age < 6 yr, cases) and 51 nonearly-onset (aged > 12 and <18 yrs, controls) patients with IBD. Azathioprine dose was titrated on therapeutic efficacy (response and adverse effects). Azathioprine metabolites and thiopurine methyltransferase activity were determined by high-performance liquid chromatography with ultra violet-vis detection (HPLC-UV) methods. RESULTS: Frequency of patients in remission was similar among early-onset and control groups, respectively (82% and 84%, P value = 0.72). Early-onset patients required higher doses of Azathioprine (median 2.7 versus 2.0 mg.kg.d, P value = 1.1 x 10). Different doses resulted in comparable Azathioprine active thioguanine nucleotide metabolite concentrations (median 263 versus 366 pmol/8 x 10 erythrocytes, P value = 0.41) and methylmercaptopurine nucleotide concentrations (median 1455 versus 1532 pmol/8 x 10 erythrocytes, P value = 0.60). Lower ratios between thioguanine nucleotide metabolites and Azathioprine doses were found in early-onset patients (median 98 versus 184 pmol/8 x 10 erythrocytes.mg.kg.d, P value = 0.017). Interestingly, early-onset patients presented also higher thiopurine methyltransferase activity (median 476 versus 350 nmol methylmercaptopurine/mg hemoglobin/h, P-value = 0.046). CONCLUSIONS: This study demonstrated that patients with early-onset IBD present increased inactivating Azathioprine metabolism, likely because of elevated activity of the enzyme thiopurine methyltransferase.

Description

Azathioprine(Azasan, Imuran; BW 57-322) is a drug that suppresses the immune system and is used in organ transplantation and autoimmune disease.

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