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Encyclopedia > Azathioprine
Chemical structure of Azathioprine
Azathioprine
Systematic (IUPAC) name
6-(3-methyl-5-nitro-imidazol-4-yl)sulfanyl-7H-purine
Identifiers
CAS number 446-86-6
ATC code L04AX01
PubChem 2265
DrugBank APRD00811
Chemical data
Formula C9H7N7O2S 
Mol. weight 277.264
Pharmacokinetic data
Bioavailability Well absorbed
Metabolism  ?
Half life Approximately 5 hours for the unchanged drug and its metabolites.
Excretion  ?
Therapeutic considerations
Pregnancy cat.

D Download high resolution version (608x606, 10 KB) Molecule structure of Azathioprine, typeset with PPCHTeX. startchemical chemical[FIVE,B1,+SB24,-SB35,EB14,Z35,SR3,R1,RZ31][N,N,H_3C,NO_2] chemical[ADJ1,SIX,-SB3,Z3,MOV2,+SB4][S] chemical[MOV3,B16,EB135,+SB24,-SB35,Z35,ADJ1,FIVE,ROT3,+SB24,-SB35,EB4... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Overview of the citric acid cycle The citric acid cycle, one of the central metabolic pathways in aerobic organisms. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Approved Drug The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes oral

Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation, autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease such as Crohn's disease. It is a pro-drug, converted in the body to the active metabolites 6-mercaptopurine and 6-thioinosinic acid. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Chemotherapy is the use of chemical substances to treat disease. ... Immunosuppression is the medical suppression of the immune system. ... An organ transplant is the moving of a whole or partial organ from one body to another (or from a donor site on the patients own body), for the purpose of replacing the recipients damaged or failing organ with a working one from the donor site. ... Autoimmune diseases arise from an overactive immune response of the body against substances and tissues normally present in the body. ... Rheumatoid arthritis (RA) is traditionally considered a chronic, inflammatory autoimmune disorder that causes the immune system to attack the joints. ... H&E section of non-caseating granuloma seen in the colon of someone affected by Crohns disease. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Mercaptopurine (also called 6-MP or by its brand name Purinethol®) is an immunosuppressive drug used to treat leukemia. ...


Azathioprine is produced by a number of generic manufacturers and as branded names (Azasan® by Salix in US, and Imuran® by GlaxoSmithKline in Canada and UK). Species About 350, including: Salix alba - White Willow Salix amygdaloides - Peachleaf Willow Salix arbuscula - Mountain Willow Salix aurita - Eared Willow Salix babylonica - Peking Willow Salix caprea- Goat Willow Salix caroliniana - Coastal Plain Willow Salix cinerea - Grey Sallow Salix fragilis - Crack Willow Salix herbacea - Dwarf Willow Salix lanata - Woolly Willow Salix... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ...

Contents

History

Azathioprine was first introduced into clinical practice by Sir Roy Calne, the British pioneer in transplantation. Following the work done by Sir Peter Medawar in discovering the immunological basis of rejection of transplanted tissues and organs, Calne introduced 6-mercaptopurine as an experimental immunosuppressant for kidney transplants. When azathioprine was discovered, he then introduced it as a less toxic replacement for 6-mercaptopurine. For many years, dual therapy with azathioprine and steroids was the standard anti-rejection regime, until cyclosporine was introduced into clinical practice (also by Calne) in 1978. Sir Roy Calne is a fellow of the Royal Society. ... Sir Peter Brian Medawar (February 28, 1915 – October 2, 1987) was a Brazilian-born English scientist best known for his work on how the immune system rejects or accepts organ transplants. ... Transplant rejection occurs when the immune system of the recipient of a transplant attacks the transplanted organ or tissue. ... Ciclosporin (INN), cyclosporine or cyclosporin (former BAN), is an immunosuppressant drug. ...


Mechanism of action

Azathioprine acts to inhibit purine synthesis necessary for the proliferation of cells, especially leukocytes and lymphocytes. It is an effective drug used alone in certain autoimmune diseases, or in combination with other immunosuppressants in organ transplantation. Its most severe side effect is bone marrow suppression, and caution should be exercised when it is used in conjunction with purine analogues such as allopurinol. The enzyme thiopurine S-methyltransferase (TPMT) deactivates 6-mercaptopurine. Genetic polymorphisms of TPMT can lead to excessive drug toxicity, thus assay of serum TPMT may be useful to prevent this complication.[1] White Blood Cells is also the name of a White Stripes album. ... A lymphocyte is a type of white blood cell involved in the human bodys immune system. ... Bone marrow suppression is a serious side effect of chemotherapy and certain drugs affecting the immune system such as azathioprine. ... Allopurinol is a white, powdery drug used to treat gout. ... Thiopurine methyltransferase, drawn from PDB 2BZG. Thiopurine methyltransferase or thiopurine S-methyltransferase (TPMT) is an enzyme (EC 2. ... In biology, polymorphism can be defined as the occurrence in the same habitat of two or more forms of a trait in such frequencies that the rarer cannot be maintained by recurrent mutation alone. ...


Mycophenolate mofetil is increasingly being used in place of azathioprine in organ transplantation as it is associated with less bone marrow suppression, fewer opportunistic infections and a lower incidence of acute rejection.[2] However azathioprine certainly still has a major role. Mycophenolate mofetil (MMF, trade name Cellcept®) is an immunosuppresant drug used to prevent rejection in organ transplantation. ... Bone marrow suppression is a serious side effect of chemotherapy and certain drugs affecting the immune system such as azathioprine. ... Opportunistic infections are infections in immunodeficient patients caused by pathogens which are incapable of causing infection in immunocompetent individuals. ...


Long term side effects

Metabolic pathway for azathioprine
Metabolic pathway for azathioprine

It is listed as a human carcinogen in the 11th Report on Carcinogens of the US Department of Health and Human Sciences, although they note that the International Agency for Research on Cancer (IARC) considered some of the animal studies to be inconclusive because of limitations in the study design and inadequate reporting.[3] The risks involved seem to be related both to the duration and dosage used. People who have previously been treated with an alkylating agent may have an excessive risk of cancers if treated with azathioprine. Epidemiological studies have provided "sufficient" evidence of Azathioprine carcinogenicity in humans,[4] although the methodology of past studies and the possible underlying mechanisms are questioned.[5] The various dieases requiring transplantation, and thus azathioprine, may in themselves increase the risks of non-Hodgkin's lymphoma, squamous cell carcinomas of the skin, hepatobiliary carcinomas and mesenchymal tumours to which azathioprine may add additional risks. Interestingly those receiving azathioprine for rheumatoid arthritis may have a lesser risk than those following transplantation.[6] Image File history File links Download high-resolution version (938x564, 32 KB) Metabolic pathway of azathioprine, showing three steps for conversion of 6-mercaptopurine (6-MP), the active metabolite of azathioprine after non-enzymatic cleavage in the liver. ... Image File history File links Download high-resolution version (938x564, 32 KB) Metabolic pathway of azathioprine, showing three steps for conversion of 6-mercaptopurine (6-MP), the active metabolite of azathioprine after non-enzymatic cleavage in the liver. ... The term carcinogen refers to any form of substance, radionuclide or radiation which is an agent in the promotion or direct involvement in the facilitation of cancer or genomic instability due to the disruption or damage of cellular metabolic changes. ... The International Agency for Research on Cancer (IARC, or CIRC in its French acronym) is an intergovernmental agency forming part of the World Health Organisation of the United Nations. ... Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. ... Non-Hodgkins lymphoma is a type of cancer. ... Biopsy of a highly differentiated squamous cell carcinoma of the mouth. ... // [edit] Introduction Cholangiocarcinoma is an adenocarcinoma of the biliary duct system. ... Mesenchyme (also known as embryonic connective tissue) is the mass of tissue that develops mainly from the mesoderm (the middle layer of the trilaminar germ disc) of an embryo. ...


Azathioprine is not thought to cause fetal malformation (teratogenesis) and any risk to the offspring of treated men is small.[7] A more recent product monograph produced by Glaxo Smith Kline and dated June 2005 does note that IMURAN® can cause fetal harm when given to a pregnant woman. Their document also states that the drug should not be given during pregnancy or in patients of reproductive potential without careful weighing of benefit versus the risks and should be avoided whenever possible in pregnant women. It goes on to say that when used in pregnancy the patient should be apprised of the potential hazard to the fetus. While stating that no adequate and well-controlled studies have taken place in humans, it notes that when given to animals in doses equivalent to human dosages teratogenic was observed. Transplant patients already on this drug should not discontinue on becoming pregnant. This contrasts to the later developed drugs tacrolimus and myophenolate which are contra-indicated by the manufacturers during pregnancy.[7] As for all cytotoxic drugs, it is advised not to breastfeed whilst taking azathioprine. // Teratogenesis is a medical term from the Greek, literally meaning monster-birth, which derives from teratology, the study of the frequency, causation, and development of congenital malformations—misleadingly called birth defects. ... Tacrolimus (also FK-506 or Fujimycin) is a 23-membered macrolide lactone discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. ... Mycophenolate mofetil (MMF, trade name Cellcept®) is an immunosuppresant drug used to prevent rejection in organ transplantation. ...


Under FDA rules, this drug, like many others, excludes eligiblity for blood donation.


References

  1. ^ Konstantopoulou M, Belgi A, Griffiths K, Seale J, Macfarlane A (2005). "Azathioprine-induced pancytopenia in a patient with pompholyx and deficiency of erythrocyte thiopurine methyltransferase.". BMJ 330 (7487): 350-1. PMID 15705694. 
  2. ^ Woodroffe R, Yao G, Meads C, Bayliss S, Ready A, Raftery J, Taylor R (2005). "Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study.". Health Technol Assess 9 (21): 1-194. PMID 15899149. 
  3. ^ National Toxicology Program. "Azathioprine", Substance Profiles, Report on Ccarcinogens, Eleventh Edition, U.S. Department of Health and Human Services. 
  4. ^ International Agency for Research on Cancer (IARC) (1987). Azathioprine - 5. Summary of Data Reported and Evaluation. Summaries & Evaluations VOL.: 26 (1981) (p. 47). World Health Organization.
  5. ^ Gombar V, Enslein K, Blake B, Einstein K (1993). "Carcinogenicity of azathioprine: an S-AR investigation.". Mutat Res 302 (1): 7-12. PMID 7683109. 
  6. ^ International Agency for Research on Cancer (IARC) (1987). Azathioprine - Evidence for carcinogenicity to humans (sufficient). Summaries & Evaluations Supplement 7: (1987) (p. 119). World Health Organization.
  7. ^ a b British National Formulary 45 March 2003

The International Agency for Research on Cancer (IARC, or CIRC in its French acronym) is an intergovernmental agency forming part of the World Health Organisation of the United Nations. ... The World Health Organization (WHO) is a specialized agency of the United Nations that acts as a coordinating authority on international public health, headquartered in Geneva, Switzerland. ... The International Agency for Research on Cancer (IARC, or CIRC in its French acronym) is an intergovernmental agency forming part of the World Health Organisation of the United Nations. ... The World Health Organization (WHO) is a specialized agency of the United Nations that acts as a coordinating authority on international public health, headquartered in Geneva, Switzerland. ... Otherwise known as the doctors prescribing Bible the British National Formulary (BNF) contains a wide spectrum of information on prescribing and pharmacology, among others indications, side effects and costs of the prescription of all medication drugs available on the National Health Service. ...

External links

  • Imuran® (GlaxoSmithKline Patient Information Leaflet)
  • Azasan® (manufacturer's website)
  • Medline Plus advice on Imuran ( A service of the National Institutes of Health)
  • GKS Product Monograph for Imuran
  • Links to external chemical sources


[edit]Immunosuppressants (L04)

Abatacept, Abetimus, Adalimumab, Afelimomab, Anakinra, Alefacept, Antilymphocyte immunoglobulin (horse), Antithymocyte immunoglobulin (rabbit), Aselizumab, Atorolimumab, Azathioprine, Basiliximab, Belimumab, Bertilimumab, Cedelizumab, Ciclosporin, Citilimumab, Clenoliximab, Daclizumab, Dorlimomab aritox, Eculizumab, Efalizumab, Elsilimomab, Enlimomab, Enlimomab pegol, Erlizumab, Etanercept, Everolimus, Faralimomab, Fontolizumab, Galiximab, Gavilimomab, Golimumab, Gomiliximab, Gusperimus, Infliximab, Inolimomab, Ipilimumab, Keliximab, Leflunomide, Lerdelimumab, Lumiliximab, Maslimomab, Mepolizumab, Metelimumab, Methotrexate , Muromonab-CD3, Mycophenolic acid, Natalizumab, Ocrelizumab, Odulimomab, Omalizumab, Pascolizumab, Pexelizumab, Pimecrolimus, Reslizumab, Rovelizumab, Ruplizumab, Siplizumab, Sirolimus, Tacrolimus, Talizumab, Telimomab aritox, Teneliximab, Thalidomide, Ticilimumab, Tilolizumab, Tocilizumab, Toralizumab, Vapaliximab, Vepalimomab, Visilizumab, Zanolimumab, Ziralimumab, Zolimomab aritox For a list of immunosuppressive drugs, see the transplant rejection page. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Abatacept (Orencia) is a first-generation hybrid protein composed of an immunoglobulin and CTLA-4, which is a molecule crucial for T-cell costimulation. ... Adalimumab (Humira®) is the third TNF antagonist (after infliximab and etanercept) to be approved in the US. Like infliximab and etanercept, adalimumab binds to TNFα, preventing it from activating TNF receptors; adalimumab was constructed from a fully human monoclonal antibody, while infliximab is a mouse-human chimeric antibody and etanercept... Afelimomab (also known as Fab 2) is a anti-TNF-α monoclonal antibody. ... // Basic chemical, pharmacological and marketing data Anakinra is an IL-1 receptor antagonist. ... Alefacept is a genetically engineered immunosuppressive drug sold under the brand name Amevive in Canada and the United States. ... Aselizumab is an immunosuppressive drug. ... Atorolimumab is an immunosuppressive drug. ... Basiliximab (Simulect) is a chimeric mouse-human monoclonal antibody to the IL-2Rα receptor of T cells. ... Belimumab (marketed under the trade name LymphoStat-B), is a human monoclonal antibody which its used to inhibit TNFα. Categories: | ... Bertilimumab is a human monoclonal antibody and which its used to treat severe allergic disorders. ... Cedelizumab is an immunosuppressive drug. ... Ciclosporin (INN), cyclosporine or cyclosporin (former BAN), is an immunosuppressant drug. ... Citilimumab is an immunosuppressive drug. ... Clenoliximab is an immunosuppressive drug. ... Daclizumab (Zenapax) is a murine-human chimaerised monoclonal antibody to the IL-2Rα receptor of T cells. ... Dorlimomab aritox is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Eculizumab is a monoclonal antibody directed against the complement protein C5. ... Efalizumab (Raptiva®, Genentech) is a medication used to treat psoriasis. ... Elsilimomab is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... It has been suggested that this article or section be merged into Enlimomab pegol. ... It has been suggested that Enlimomab be merged into this article or section. ... Erlizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Etanercept (Enbrel®, co-marketed by Amgen and Wyeth) is a human recombinant, soluble tumor necrosis factor-alpha (TNFα) receptor. ... Everolimus is a new mTOR inhibitor drug used as an immunosuppressant to prevent rejection of organ transplants. ... Faralimomab is a mouse monoclonal antibody which its an immunosuppressive drug. ... Fontolizumab (marketed under the trade name HuZAFâ„¢) is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Galiximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... Gavilimomab is a mouse monoclonal antibody (also known as ABX-CBL) is an immunosuppresive drug. ... Golimumab is a human monoclonal antibody which its used as an immunosuppressive drug. ... Gomiliximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... // Chemical Designation Common references are: (+-)-15-Deoxyspergualin, 1-Amino-19-guanidino-11-hydroxy-4,9,12-triazanonadecane-10,13-dione, 15-Deoxyspergualin, 15-Deoxyspergualin Hydrochloride, 7-{(Aminoiminomethyl)amino]-N-[2-[[4-[(3-aminopropyl)amino]butyl]amino]-1-hydroxy-2-oxoethyl]heptanamide, Gusperimus (Trihydrochloride), N-[[[4-[(3-Aminopropyl)amino]-butyl]carbamoyl... It has been suggested that Infliximab (Remicade) be merged into this article or section. ... Inolimomab is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Ipilimumab (also known as MDX-010) is a human monoclonal antibody which its used as an immunosuppressive drug. ... Keliximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... // Basic Chemical, Pharmacological, and Marketing Data Leflunomide is a pyrimidine synthesis inhibitor belonging to the DMARD class of drugs, which are chemically and pharmacologically very heterogen. ... Lerdelimumab is a human monoclonal antibody which its used as an immunosuppressive drug. ... Lumiliximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... Maslimomab is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Mepolizumab is a humanized monoclonal antibody and which its used an immunosuppressive drug. ... Metelimumab is a human monoclonal antibody which its used as an immunosuppressive drug. ... Methotrexate (rINN) (IPA: ), abbreviated MTX and formerly known as amethopterin, is an antimetabolite drug used in treatment of cancer and autoimmune diseases. ... Muromonab-CD3 (generic name) is a monoclonal antibody (mAb), also known as Orthoclone OKT3 (Brand name). ... Mycophenolic acid (INN) (IPA: ) or mycophenolate is an immunosuppressant drug used to prevent rejection in organ transplantation. ... Natalizumab is a drug co-marketed by Biogen Idec and Élan as Tysabri. ... Ocrelizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Odulimomab is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Omalizumab (marketed under the name Xolair®) is a monoclonal antibody made by Genentech / Novartis and used mainly in allergy-related asthma therapy, with the purpose of reducing allergic hypersensitivity. ... Pascolizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Pexelizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Pimecrolimus is an immunomodulating agent used in the treatment of atopic dermatitis. ... Reslizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Rovelizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Ruplizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Siplizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Sirolimus is a relatively new immunosuppressant drug used to prevent rejection in organ transplantation, and is especially useful in kidney transplants. ... Tacrolimus (also FK-506 or Fujimycin) is a 23-membered macrolide lactone discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. ... Talizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Telimomab aritox is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Teneliximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... // Thalidomide is a sedative, hypnotic, and anti-inflammatory medication. ... Ticilimumab is a human monoclonal antibody which its used as an immunosuppressive drug. ... Tilolizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Tocilizumab (marketed under the trade name Actemraâ„¢) is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Toralizumab is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Vapaliximab is a chimeric monoclonal antibody which its used as an immunosuppressive drug. ... Vepalimomab is a mouse monoclonal antibody which its used as an immunosuppressive drug. ... Visilizumab (marketed under the trade name Nuvion®) is a humanized monoclonal antibody which its used as an immunosuppressive drug. ... Zanolimumab (marketed under the trade name HuMax-CD4) is a human monoclonal antibody which its used as an immunosuppressive drug. ... Ziralimumab is a human monoclonal antibody which its used as an immunosuppressive drug. ... Zolimomab aritox is a mouse monoclonal antibody which its used as an immunosuppressive drug. ...


  Results from FactBites:
 
Azathioprine - Wikipedia, the free encyclopedia (680 words)
Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation, autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease such as Crohn's disease.
Azathioprine acts to inhibit purine synthesis necessary for the proliferation of cells, especially leukocytes and lymphocytes.
Mycophenolate mofetil is increasingly being used in place of azathioprine in organ transplantation as it is associated with less bone marrow suppression, fewer opportunistic infections and a lower incidence of acute rejection.
Azathioprine (637 words)
Azathioprine is such a medication, though it is important to realize that it can have some of its own adverse side effects in some individuals.
Azathioprine disrupts the synthesis of DNA and RNA.
Azathioprine is typically started once a day and then tapered to every other day use and is almost always started in conjunction with other immune suppressive agents.
  More results at FactBites »

 
 

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