Home Carboxes 65002-17-7
65002-17-7,MFCD00867570
Catalog No.:AA00EACU

65002-17-7 | (2R)-2-(2-methyl-2-sulfanylpropanamido)-3-sulfanylpropanoic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
25mg
95%
in stock  
$45.00   $32.00
- +
100mg
95%
in stock  
$142.00   $99.00
- +
250mg
95%
in stock  
$291.00   $204.00
- +
1g
95%
in stock  
$724.00   $507.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00EACU
Chemical Name:
(2R)-2-(2-methyl-2-sulfanylpropanamido)-3-sulfanylpropanoic acid
CAS Number:
65002-17-7
Molecular Formula:
C7H13NO3S2
Molecular Weight:
223.3130
MDL Number:
MFCD00867570
SMILES:
CC(C)(C(=O)NC(CS)C(=O)O)S
Properties
Properties
 
Form:
Solid  
MP:
119-123°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
218  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
0.4  

Downstream Synthesis Route

[1]Oya;Matsumoto;Takashina;Watanabe;Iwao[ChemicalandPharmaceuticalBulletin,1981,vol.29,#4,p.940-947]

[1]Mori,Yuji;Fujiwara,Shigeru;Miyachi,Toshiko;Kitanishi,Hiroyuki;Oya,Masayuki;etal.[Chemicalandpharmaceuticalbulletin,1983,vol.31,#5,p.1505-1517]

[1]Oya;Matsumoto;Takashina;Watanabe;Iwao[ChemicalandPharmaceuticalBulletin,1981,vol.29,#4,p.940-947]

[1]Mori,Yuji;Fujiwara,Shigeru;Miyachi,Toshiko;Kitanishi,Hiroyuki;Oya,Masayuki;etal.[Chemicalandpharmaceuticalbulletin,1983,vol.31,#5,p.1505-1517]

[1]CurrentPatentAssignee:SANTENPHARMACEUTICALCOLTD-US5292926,1994,A

Literature

Title: Bucillamine inhibits CD40-mediated Akt activation and antibody production in mouse B-cell lymphoma.

Journal: International immunopharmacology 20120901

Title: Safety and effectiveness responses to etanercept for rheumatoid arthritis in Japan: a sub-analysis of a post-marketing surveillance study focusing on the duration of rheumatoid arthritis.

Journal: Rheumatology international 20120601

Title: Effect of etanercept and entecavil in a patient with rheumatoid arthritis who is a hepatitis B carrier: a review of the literature.

Journal: Rheumatology international 20120401

Title: Etanercept in combination with conventional disease-modifying antirheumatic drugs (DMARDs) in the treatment of rheumatoid arthritis patients intolerant to methotrexate.

Journal: Modern rheumatology 20120201

Title: Single-center, retrospective analysis of efficacy and safety of tacrolimus as a second-line DMARD in combination therapy and the risk factors contributing to adverse events in 115 patients with rheumatoid arthritis.

Journal: Clinical rheumatology 20120201

Title: [ Bone and cartilage destruction in RA and its intervention. Disease-modifying antirheumatic drugs].

Journal: Clinical calcium 20120201

Title: Risk of orthopedic surgical site infections in patients with rheumatoid arthritis treated with antitumor necrosis factor alfa therapy.

Journal: International journal of rheumatology 20120101

Title: The observation of humoral responses after influenza vaccination in patients with rheumatoid arthritis treated with Japanese oriental (kampo) medicine: an observational study.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Studies of the efficacy and safety of methotrexate at dosages over 8 mg/week using the IORRA cohort database.

Journal: Modern rheumatology 20111201

Title: Proximal tubules and podocytes are toxicity targets of bucillamine in a mouse model of drug-induced kidney injury.

Journal: European journal of pharmacology 20111116

Title: Free-radical degradation of high-molecular-weight hyaluronan induced by ascorbate plus cupric ions. Testing of bucillamine and its SA981-metabolite as antioxidants.

Journal: Journal of pharmaceutical and biomedical analysis 20111101

Title: [Treatment of rheumatic diseases: current status and future prospective. Topics: II. Immunosuppressant/antirheumatic drugs; 6. Bucillamine and gold (gold sodium thiomalate and auranofin)].

Journal: Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20111010

Title: Efficacy and safety of additional use of tacrolimus in patients with early rheumatoid arthritis with inadequate response to DMARDs--a multicenter, double-blind, parallel-group trial.

Journal: Modern rheumatology 20111001

Title: Postmarketing surveillance of safety and effectiveness of etanercept in Japanese patients with rheumatoid arthritis.

Journal: Modern rheumatology 20110801

Title: A multicentre trial of bucillamine in the treatment of early rheumatoid arthritis (SNOW study).

Journal: Modern rheumatology 20110601

Title: Aberrant splicing of the hRasGRP4 transcript and decreased levels of this signaling protein in the peripheral blood mononuclear cells in a subset of patients with rheumatoid arthritis.

Journal: Arthritis research & therapy 20110101

Title: Chemerin activates fibroblast-like synoviocytes in patients with rheumatoid arthritis.

Journal: Arthritis research & therapy 20110101

Title: Organizing pneumonia in a patient with rheumatoid arthritis treated with etanercept.

Journal: Modern rheumatology 20101201

Title: Attenuation of warm ischemia-reperfusion injury in the liver by bucillamine through decreased neutrophil activation and Bax/Bcl-2 modulation.

Journal: Journal of gastroenterology and hepatology 20101201

Title: Combined effects of bucillamine and etanercept on a rat type II collagen-induced arthritis model.

Journal: Modern rheumatology 20100801

Title: N-(tert)-butyloxycarbonyl)-beta,beta-cyclopentyl-cysteine (acetamidomethyl)-methyl ester for synthesis of novel peptidomimetic derivatives.

Journal: Protein and peptide letters 20100701

Title: Clinical efficacy of tocilizumab in patients with active rheumatoid arthritis in real clinical practice.

Journal: Rheumatology international 20100601

Title: Multiple vertebral involvement of rheumatoid arthritis in thoracolumbar spine: a case report.

Journal: Journal of Korean medical science 20100301

Title: Description of the efficacy and safety of three new biologics in the treatment of rheumatoid arthritis.

Journal: The Korean journal of internal medicine 20100301

Title: Chlorobenzene induces oxidative stress in human lung epithelial cells in vitro.

Journal: Toxicology and applied pharmacology 20100101

Title: A comprehensive molecular interaction map for rheumatoid arthritis.

Journal: PloS one 20100101

Title: MicroRNA-146a expresses in interleukin-17 producing T cells in rheumatoid arthritis patients.

Journal: BMC musculoskeletal disorders 20100101

Title: A case of rheumatoid arthritis with bucillamine-induced yellow nail syndrome initially manifesting as pulmonary disease.

Journal: Clinical medicine insights. Case reports 20100101

Title: The investigation of synovial genomic targets of bucillamine with microarray technique.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20090901

Title: Japan College of Rheumatology 2009 guidelines for the use of tocilizumab, a humanized anti-interleukin-6 receptor monoclonal antibody, in rheumatoid arthritis.

Journal: Modern rheumatology 20090801

Title: Development and validation of a reversed-phase fluorescence HPLC method for determination of bucillamine in human plasma using pre-column derivatization with monobromobimane.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090715

Title: Multinational evidence-based recommendations for the use of methotrexate in rheumatic disorders with a focus on rheumatoid arthritis: integrating systematic literature research and expert opinion of a broad international panel of rheumatologists in the 3E Initiative.

Journal: Annals of the rheumatic diseases 20090701

Title: Efficacy and toxicity of methotrexate (MTX) monotherapy versus MTX combination therapy with non-biological disease-modifying antirheumatic drugs in rheumatoid arthritis: a systematic review and meta-analysis.

Journal: Annals of the rheumatic diseases 20090701

Title: Long-term safety of methotrexate monotherapy in patients with rheumatoid arthritis: a systematic literature research.

Journal: Annals of the rheumatic diseases 20090701

Title: Efficacy of mizoribine pulse therapy in patients with rheumatoid arthritis who show a reduced or insufficient response to infliximab.

Journal: Modern rheumatology 20090601

Title: Laboratory and febrile features after joint surgery in patients with rheumatoid arthritis treated with tocilizumab.

Journal: Annals of the rheumatic diseases 20090501

Title: Bucillamine improves hepatic microcirculation and reduces hepatocellular injury after liver warm ischaemia-reperfusion injury.

Journal: HPB : the official journal of the International Hepato Pancreato Biliary Association 20090501

Title: [Effect of disease modifying anti-rheumatic drugs on radiographic progression in rheumatoid arthritis].

Journal: Clinical calcium 20090301

Title: [Two cases with ankylosing spondylitis using infliximab (case report)].

Journal: Nihon Rinsho Men'eki Gakkai kaishi = Japanese journal of clinical immunology 20090201

Title: Etanercept improved primary biliary cirrhosis associated with rheumatoid arthritis.

Journal: Joint, bone, spine : revue du rhumatisme 20090101

Title: Differential influences of bucillamine and methotrexate on the generation of fibroblast-like cells from bone marrow CD34+ cells of rheumatoid arthritis patients.

Journal: International immunopharmacology 20090101

Title: A comparative study of the effects of bucillamine and salazosulfapyridine in the treatment of rheumatoid arthritis.

Journal: Modern rheumatology 20090101

Title: Co-existence of acute myeloid leukemia with multilineage dysplasia and Epstein-Barr virus-associated T-cell lymphoproliferative disorder in a patient with rheumatoid arthritis: a case report.

Journal: Journal of hematology & oncology 20090101

Title: Radiographic repair in three Japanese patients with rheumatoid arthritis treated with bucillamine.

Journal: Modern rheumatology 20090101

Title: Nuclear phosphatidylcholine and sphingomyelin metabolism of thyroid cells changes during stratospheric balloon flight.

Journal: Journal of biomedicine & biotechnology 20090101

Title: [Antirheumatic agents for treatment of rheumatoid arthritis].

Journal: Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20081010

Title: Prolonged administration of a dithiol antioxidant protects against ventricular remodeling due to ischemia-reperfusion in mice.

Journal: American journal of physiology. Heart and circulatory physiology 20080901

Title: [False-positive reaction of urinary ketone bodies caused by bucillamine].

Journal: Rinsho byori. The Japanese journal of clinical pathology 20080701

Title: Clinical investigation in highly disease-affected rheumatoid arthritis patients in Japan with adalimumab applying standard and general evaluation: the CHANGE study.

Journal: Modern rheumatology 20080601

Title: [A patient with Mycobacterium avium lung disease presenting with rapid, progressive and multiple cavity formation, who had been treated rheumatoid arthritis with disease modifying anti-rheumatic drugs (DMARDs)].

Journal: Nihon Kokyuki Gakkai zasshi = the journal of the Japanese Respiratory Society 20080301

Title: Photoprotective effects of bucillamine against UV-induced damage in an SKH-1 hairless mouse model.

Journal: Photochemistry and photobiology 20080101

Title: Eosinophilic pneumonia (EP) associated with rheumatoid arthritis in which drug-induced eosinophilic pneumonia could be ruled out.

Journal: Internal medicine (Tokyo, Japan) 20080101

Title: A case with life-threatening interstitial pneumonia associated with bucillamine treatment.

Journal: Modern rheumatology 20080101

Title: The efficacy and safety of bucillamine as a second-line DMARD in the treatment of rheumatoid arthritis: a retrospective cohort study.

Journal: Modern rheumatology 20080101

Title: Bucillamine mechanism inhibiting IL-1beta-induced VEGF production from fibroblast-like synoviocytes.

Journal: International immunopharmacology 20071205

Title: Spontaneous multiple insufficiency fractures after pelvic abscess and sepsis in a rheumatoid arthritis patient treated with high-load corticosteroid therapy: a case report.

Journal: Clinical rheumatology 20071101

Title: [Adverse effects of conventional DMARDs and biologic DMARDs].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20071028

Title: [Drug-induced nephrotic syndrome].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20071028

Title: [Effective combination therapy of TNF antagonists with DMARDs].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20070701

Title: Acute exacerbation of preexisting interstitial lung disease after administration of etanercept for rheumatoid arthritis.

Journal: The Journal of rheumatology 20070501

Title: Yellow nails under bucillamine therapy for rheumatoid arthritis: a report of two cases.

Journal: Rheumatology international 20070401

Title: Scientific basis for the efficacy of combined use of antirheumatic drugs against bone destruction in rheumatoid arthritis.

Journal: Modern rheumatology 20070101

Title: Ten years results of bucillamine in the treatment of rheumatoid arthritis.

Journal: Modern rheumatology 20070101

Title: Pemphigus foliaceus induced by bucillamine.

Journal: European journal of dermatology : EJD 20070101

Title: No correlation exists between disease activity and the expression of killer-cell immunoglobulin-like receptors in patients with rheumatoid arthritis.

Journal: Mediators of inflammation 20070101

Title: NF-kappaB inhibitor dehydroxymethylepoxyquinomicin suppresses osteoclastogenesis and expression of NFATc1 in mouse arthritis without affecting expression of RANKL, osteoprotegerin or macrophage colony-stimulating factor.

Journal: Arthritis research & therapy 20070101

Title: A case of bucillamine-induced interstitial pneumonia with positive lymphocyte stimulation test for bucillamine using bronchoalveolar lavage lymphocytes.

Journal: Internal medicine (Tokyo, Japan) 20070101

Title: Hemophagocytic syndrome associated with rheumatoid arthritis.

Journal: Internal medicine (Tokyo, Japan) 20070101

Title: [Therapeutic management of systemic sclerosis].

Journal: Presse medicale (Paris, France : 1983) 20061201

Title: Antioxidant properties of bucillamine: possible mode of action.

Journal: Biochemical and biophysical research communications 20061027

Title: Bucillamine induces glutathione biosynthesis via activation of the transcription factor Nrf2.

Journal: Biochemical pharmacology 20060814

Title: Radiographic appearance of bronchiolitis obliterans organizing pneumonia (BOOP) developing during Bucillamine treatment for rheumatoid arthritis.

Journal: The American journal of the medical sciences 20060701

Title: Bucillamine-induced pemphigus vulgaris in a patient with rheumatoid arthritis and polymyositis overlap syndrome.

Journal: Journal of Korean medical science 20060601

Title: Guidelines for the proper use of etanercept in Japan.

Journal: Modern rheumatology 20060401

Title: Anti-oxidant and pro-oxidant behaviour of bucillamine.

Journal: Luminescence : the journal of biological and chemical luminescence 20060101

Title: A case of interstitial pneumonia caused by bucillamine: a study using serological markers.

Journal: Modern rheumatology 20060101

Title: Efficacy and safety of bucillamine, a D-penicillamine analogue, in patients with active rheumatoid arthritis.

Journal: Modern rheumatology 20060101

Title: Outcome and treatment of bucillamine-induced nephropathy.

Journal: Nephron. Clinical practice 20060101

Title: Treatment continuation rate in relation to efficacy and toxicity in long-term therapy with low-dose methotrexate, sulfasalazine, and bucillamine in 1,358 Japanese patients with rheumatoid arthritis.

Journal: Clinical and experimental rheumatology 20060101

Title: Inhibitory effect of bucillamine on the increased leukocyte entrapment in the retinal microcirculation of diabetic rats.

Journal: Japanese journal of ophthalmology 20060101

Title: The role of thiols in liver ischemia-reperfusion injury.

Journal: Current pharmaceutical design 20060101

Title: Efficacy profile of bucillamine in rheumatoid arthritis patients in a large observational cohort study, IORRA.

Journal: Modern rheumatology 20060101

Title: The inhibitory effect of disease-modifying anti-rheumatic drugs and steroids on gliostatin/platelet-derived endothelial cell growth factor production in human fibroblast-like synoviocytes.

Journal: Rheumatology international 20051001

Title: Rheumatoid factor is a marker of disease severity in Korean rheumatoid arthritis.

Journal: Yonsei medical journal 20050831

Title: Quantitative analysis of bucillamine and its pharmaceutical formulation using FT-IR spectroscopy.

Journal: Farmaco (Societa chimica italiana : 1989) 20050801

Title: Bucillamine-induced toxic epidermal necrolysis and fixed drug eruption.

Journal: The Journal of dermatology 20050501

Title: [Examination of the escape phenomenon in disease modifying antirheumatic drugs].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20050301

Title: Clinical analysis of 21 patients with psoriasis arthropathy.

Journal: The Journal of dermatology 20050201

Title: [Bucillamine-induced dermatomyositis-like clinical features in a patient with rheumatoid arthritis].

Journal: Rinsho shinkeigaku = Clinical neurology 20050101

Title: The ability of disease modifying antirheumatic drugs to induce and maintain improvement in patients with rheumatoid arthritis. epidemiology of DMARDs treatment in Japan.

Journal: Clinical and experimental rheumatology 20050101

Title: [Disease modifying anti-rheumatic drugs (DMARDs): an overview].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20050101

Title: The role of the T cell in autoimmune inflammation.

Journal: Arthritis research & therapy 20050101

Title: Therapeutic effects of the combination of methotrexate and bucillamine in early rheumatoid arthritis: a multicenter, double-blind, randomized controlled study.

Journal: Modern rheumatology 20050101

Title: Asymptomatic interstitial pneumonitis induced by bucillamine in a patient with rheumatoid arthritis.

Journal: Modern rheumatology 20050101

Title: Quantitative analysis of bucillamine in blood using high-performance liquid chromatography-mass spectrometry technique.

Journal: Biomedical chromatography : BMC 20041201

Title: [Drug induced nephrotic syndrome].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20041001

Title: Patients with rheumatoid arthritis (RA) and proteinuria.

Journal: Clinical and experimental nephrology 20040901

Title: Bucillamine induces the synthesis of vascular endothelial growth factor dose-dependently in systemic sclerosis fibroblasts via nuclear factor-kappaB and simian virus 40 promoter factor 1 pathways.

Journal: Molecular pharmacology 20040201

Title: Adult-onset Still's disease with disseminated intravascular coagulation and multiple organ dysfunctions dramatically treated with cyclosporine A.

Journal: Journal of Korean medical science 20040201

Title: Inhibitory effects of bucillamine on the expression of vascular cell adhesion molecule-1 in human umbilical vein endothelial cells.

Journal: International immunopharmacology 20040101

Title: Triptolide, an active compound identified in a traditional Chinese herb, induces apoptosis of rheumatoid synovial fibroblasts.

Journal: BMC pharmacology 20040101

Title: Treatment of retinopathy of prematurity with topical ketorolac tromethamine: a preliminary study.

Journal: BMC pediatrics 20040101

Title: Clinical course of bucillamine-induced nephropathy in patients with rheumatoid arthritis.

Journal: Clinical and experimental nephrology 20031201

Title: Simultaneous, clonally identical T cell expansion in tonsil and synovium in a patient with rheumatoid arthritis and chronic tonsillitis.

Journal: Arthritis and rheumatism 20030901

Title: [Pharmacokinetics of salazosulfapyridine in a hemodialysis patient].

Journal: Ryumachi. [Rheumatism] 20030601

Title: [A case of sarcoidosis overlapping with rheumatoid arthritis].

Journal: Nihon Jinzo Gakkai shi 20030101

Title: Bucillamine: a potent thiol donor with multiple clinical applications.

Journal: Cardiovascular drug reviews 20030101

Title: Subconjunctival administration of bucillamine suppresses choroidal neovascularization in rat.

Journal: Investigative ophthalmology & visual science 20021101

Title: Inhibitory mechanism of vascular endothelial growth factor (VEGF) by bucillamine.

Journal: British journal of pharmacology 20021101

Title: Gigantomastia induced by bucillamine.

Journal: Annals of plastic surgery 20020801

Title: Inhibitory effects of bucillamine on increased blood-retinal barrier permeability in streptozotocin-induced diabetic rats.

Journal: Current eye research 20020701

Title: Bucillamine induces membranous glomerulonephritis.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation 20020401

Title: [A case of pulmonary infiltration with eosinophilia (PIE) syndrome induced by bucillamine treatment of rheumatoid arthritis].

Journal: Nihon Kokyuki Gakkai zasshi = the journal of the Japanese Respiratory Society 20020401

Title: Thiol antioxidants inhibit the adjuvant effects of aerosolized diesel exhaust particles in a murine model for ovalbumin sensitization.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20020301

Title: [A case of rheumatoid arthritis complicated with a pneumonitis during concomitant treatment with methotrexate and bucillamine].

Journal: Ryumachi. [Rheumatism] 20020201

Title: Angiogenesis in rheumatoid arthritis.

Journal: Arthritis research 20020101

Title: VEGF and imaging of vessels in rheumatoid arthritis.

Journal: Arthritis research 20020101

Title: Inhibitory effect of bucillamine on laser-induced choroidal neovascularization in rats.

Journal: Current eye research 20020101

Title: Two injections of interferon-alpha could trigger the development of rheumatoid arthritis.

Journal: Clinical and experimental rheumatology 20020101

Title: Oxygen-sensing mechanisms and the regulation of redox-responsive transcription factors in development and pathophysiology.

Journal: Respiratory research 20020101

Title: KE-758, an active metabolite of the new anti-rheumatic drug KE-298, suppresses production of tumor necrosis factor-alpha and interleukin-1 beta in THP-1, a human monocyte cell line.

Journal: Drugs under experimental and clinical research 20020101

Title: Bucillamine prevents myocardial reperfusion injury.

Journal: Journal of cardiovascular pharmacology 20011201

Title: Methotrexate inhibits rheumatoid synovitis by inducing apoptosis.

Journal: The Journal of rheumatology 20010801

Title: Effects of KE-758; an active metabolite of the new anti-rheumatic drug KE-298, D-penicillamine, bucillamine and auranofin on the proliferation of murine lymphocytes, and the production of nitric oxide by murine macrophages.

Journal: International immunopharmacology 20010501

Title: A case of BOOP developed during bucillamine treatment for rheumatoid.

Journal: The Korean journal of internal medicine 20010301

Title: Drug-induced pemphigus foliaceus with features of pemphigus vulgaris.

Journal: The British journal of dermatology 20010201

Title: Novel therapy in the treatment of scleroderma.

Journal: Expert opinion on investigational drugs 20010101

Title: Subcorneal pustular dermatosis-type IgA pemphigus induced by thiol drugs.

Journal: European journal of dermatology : EJD 20010101

Title: [A case of drug-induced interstitial pneumonitis in rheumatoid arthritis treated with bucillamine].

Journal: Nihon Kokyuki Gakkai zasshi = the journal of the Japanese Respiratory Society 20010101

Title: Cutaneous drug reaction case reports: from the world literature.

Journal: American journal of clinical dermatology 20010101

Title: [Clinicopathological study of nephropathy in patients with rheumatoid arthritis].

Journal: Ryumachi. [Rheumatism] 19910201

Title: Serum oxidation activities and rheumatoid arthritis.

Journal: International journal of tissue reactions 19870101

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:65002-17-7 Molecular Formula|65002-17-7 MDL|65002-17-7 SMILES|65002-17-7 (2R)-2-(2-methyl-2-sulfanylpropanamido)-3-sulfanylpropanoic acid