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624-49-7

624-49-7 | (E)-Dimethyl fumarate

CAS No: 624-49-7 Catalog No: AG003PM2 MDL No:MFCD00064438

Product Description

Catalog Number:
AG003PM2
Chemical Name:
(E)-Dimethyl fumarate
CAS Number:
624-49-7
Molecular Formula:
C6H8O4
Molecular Weight:
144.1253
MDL Number:
MFCD00064438
IUPAC Name:
dimethyl (E)-but-2-enedioate
InChI:
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChI Key:
LDCRTTXIJACKKU-ONEGZZNKSA-N
SMILES:
COC(=O)/C=C/C(=O)OC
EC Number:
210-849-0
UNII:
FO2303MNI2

Properties

Complexity:
141  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
144.042g/mol
Formal Charge:
0
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
144.126g/mol
Monoisotopic Mass:
144.042g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
52.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.7  

Literature

Title Journal
Dimethyl fumarate targets GAPDH and aerobic glycolysis to modulate immunity. Science (New York, N.Y.) 20180427
Metformin, A New Era for an Old Drug in the Treatment of Immune Mediated Disease? Current drug targets 20180101
Dimethyl fumarate influences innate and adaptive immunity in multiple sclerosis. Journal of autoimmunity 20180101
Characterization of the Potent, Selective Nrf2 Activator, 3-(Pyridin-3-Ylsulfonyl)-5-(Trifluoromethyl)-2H-Chromen-2-One, in Cellular and In Vivo Models of Pulmonary Oxidative Stress. The Journal of pharmacology and experimental therapeutics 20171001
Fumarate Mediates a Chronic Proliferative Signal in Fumarate Hydratase-Inactivated Cancer Cells by Increasing Transcription and Translation of Ferritin Genes. Molecular and cellular biology 20170601
Chemical proteomic map of dimethyl fumarate-sensitive cysteines in primary human T cells. Science signaling 20160913
Disease modifying therapies for relapsing multiple sclerosis. BMJ (Clinical research ed.) 20160822
Distinct Nrf2 Signaling Mechanisms of Fumaric Acid Esters and Their Role in Neuroprotection against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine-Induced Experimental Parkinson's-Like Disease. The Journal of neuroscience : the official journal of the Society for Neuroscience 20160608
Dimethyl Fumarate Inhibits the Nuclear Factor κB Pathway in Breast Cancer Cells by Covalent Modification of p65 Protein. The Journal of biological chemistry 20160212
Preventing Allograft Rejection by Targeting Immune Metabolism. Cell reports 20151027
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. Pharmacological research 20131001
Dimethyl fumarate - only an anti-psoriatic medication? Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20121101
Placebo-controlled phase 3 study of oral BG-12 or glatiramer in multiple sclerosis. The New England journal of medicine 20120920
Placebo-controlled phase 3 study of oral BG-12 for relapsing multiple sclerosis. The New England journal of medicine 20120920
The 'poison chair' treatment for multiple sclerosis. The New England journal of medicine 20120920
Validation of the multiple sensor mechanism of the Keap1-Nrf2 system. Free radical biology & medicine 20120815
Dimethyl fumarate inhibits dendritic cell maturation via nuclear factor κB (NF-κB) and extracellular signal-regulated kinase 1 and 2 (ERK1/2) and mitogen stress-activated kinase 1 (MSK1) signaling. The Journal of biological chemistry 20120810
Drugs: An injection of hope. Nature 20120412
Fumarate is cardioprotective via activation of the Nrf2 antioxidant pathway. Cell metabolism 20120307
Effect of BG-12 on contrast-enhanced lesions in patients with relapsing--remitting multiple sclerosis: subgroup analyses from the phase 2b study. Multiple sclerosis (Houndmills, Basingstoke, England) 20120301
Safety profiles come to fore as more drugs approach MS market. Nature biotechnology 20120109
Dimethyl fumarate contact dermatitis of the foot: an increasingly widespread disease. International journal of dermatology 20120101
Effects of dimethyl fumarate on neuroprotection and immunomodulation. Journal of neuroinflammation 20120101
Allergic contact dermatitis from dimethyl fumarate after contact with a Chinese sofa. Journal of cutaneous medicine and surgery 20120101
Dimethylfumarate attenuates renal fibrosis via NF-E2-related factor 2-mediated inhibition of transforming growth factor-β/Smad signaling. PloS one 20120101
Mechanisms of oxidative damage in multiple sclerosis and neurodegenerative diseases: therapeutic modulation via fumaric acid esters. International journal of molecular sciences 20120101
Determination of dimethyl fumarate in desiccant and antimould sachets by reversed-phase liquid chromatography. Biomedical chromatography : BMC 20111201
IκBα glutathionylation and reduced histone H3 phosphorylation inhibit eotaxin and RANTES. The European respiratory journal 20111201
Downregulation of endothelial adhesion molecules by dimethylfumarate, but not monomethylfumarate, and impairment of dynamic lymphocyte-endothelial cell interactions. Experimental dermatology 20111201
Dimethyl fumarate, an immune modulator and inducer of the antioxidant response, suppresses HIV replication and macrophage-mediated neurotoxicity: a novel candidate for HIV neuroprotection. Journal of immunology (Baltimore, Md. : 1950) 20111115
Oral treatment for multiple sclerosis. The Lancet. Neurology 20111101
[New information about fumaric acid esters (Fumaderm): results of a workshop of experts]. Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20110901
Correlation between lesion site and concentration of dimethyl fumarate in different parts of shoes in patients with contact dermatitis caused by dimethyl fumarate in footwear. Contact dermatitis 20110801
A Summary of shoe allergic contact dermatitis caused by dimethyl fumarate in Spain. Contact dermatitis 20110801
Dimethylfumarate inhibits MIF-induced proliferation of keratinocytes by inhibiting MSK1 and RSK1 activation and by inducing nuclear p-c-Jun (S63) and p-p53 (S15) expression. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20110701
Contact dermatitis caused by dimethylfumarate in Argentina. Clinical toxicology (Philadelphia, Pa.) 20110701
Dimethylfumarate inhibits angiogenesis in vitro and in vivo: a possible role for its antipsoriatic effect? The Journal of investigative dermatology 20110601
Suppression of VEGFR2 expression in human endothelial cells by dimethylfumarate treatment: evidence for anti-angiogenic action. The Journal of investigative dermatology 20110601
Mechanisms of drug action: the potential of dimethylfumarate for the treatment of neoplasms. The Journal of investigative dermatology 20110601
Fumarate esters as angiogenesis inhibitors: key to action in psoriasis? The Journal of investigative dermatology 20110601
Trial watch: Phase III success for Biogen's oral multiple sclerosis therapy. Nature reviews. Drug discovery 20110601
Survey of dimethyl fumarate in desiccant products during 2009 in Italy. Bulletin of environmental contamination and toxicology 20110401
BG-12 reduces evolution of new enhancing lesions to T1-hypointense lesions in patients with multiple sclerosis. Journal of neurology 20110301
Fumaric acid esters exert neuroprotective effects in neuroinflammation via activation of the Nrf2 antioxidant pathway. Brain : a journal of neurology 20110301
Treatment of recurrent aphthous stomatitis with fumaric acid esters. Archives of dermatology 20110301
[Current treatment of multiple sclerosis]. Lege artis medicinae : uj magyar orvosi hirmondo 20110201
Oral therapies for multiple sclerosis: a review of agents in phase III development or recently approved. CNS drugs 20110101
Leucoderma after Chinese sofa dermatitis. Contact dermatitis 20110101
Transient alteration of cellular redox buffering before irradiation triggers apoptosis in head and neck carcinoma stem and non-stem cells. PloS one 20110101
Dimethyl fumarate. Dermatitis : contact, atopic, occupational, drug 20110101
Dimethyl fumarate: a human health hazard. Dermatitis : contact, atopic, occupational, drug 20110101
Efficacy of fumaric acid esters in the R6/2 and YAC128 models of Huntington's disease. PloS one 20110101
The anti-inflammatory effects of dimethyl fumarate in astrocytes involve glutathione and haem oxygenase-1. ASN neuro 20110101
Cytokine secretion pattern in treatment of lymphocytes of multiple sclerosis patients with fumaric acid esters. Immunological investigations 20110101
Determination of dimethyl fumarate (DMFu) in silica gel pouches using gas chromatography coupled ion trap mass spectrometry. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20110101
Globalisation and allergy. European journal of dermatology : EJD 20110101
Epidemiological description of an outbreak of dermatitis related to dimethylfumarate, France, 2008. Archives of environmental & occupational health 20110101
Dimethyl fumarate for multiple sclerosis. Expert opinion on investigational drugs 20101201
Sofa dermatitis. Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20101101
Targeting glutathione by dimethylfumarate protects against experimental malaria by enhancing erythrocyte cell membrane scrambling. American journal of physiology. Cell physiology 20101001
Persistent shoe dermatitis caused by dimethyl fumarate. Acta dermato-venereologica 20100901
[Allergic contact dermatitis due to shoes with dimethylfumarate]. Medicina clinica 20100619
[Allergic contact dermatitis due to dimethyl fumarate in boots]. Actas dermo-sifiliograficas 20100501
An outbreak of furniture related dermatitis ('sofa dermatitis') in Finland and the UK: history and clinical cases. Journal of the European Academy of Dermatology and Venereology : JEADV 20100401
Combination of dacarbazine and dimethylfumarate efficiently reduces melanoma lymph node metastasis. The Journal of investigative dermatology 20100401
[Contact dermatitis due to dimethyl fumarate]. Actas dermo-sifiliograficas 20100401
Sofa dermatitis presenting as a chronic treatment resistant dermatitis. Irish medical journal 20100401
Allergic contact dermatitis to shoes induced by dimethylfumarate: A new allergen imported from China. Dermatology online journal 20100315
Treatment of severe, recalcitrant, chronic plaque psoriasis with fumaric acid esters: a prospective study. The British journal of dermatology 20100201
Sensitization to dimethyl fumarate with multiple concurrent patch test reactions. Contact dermatitis 20100201
Allergic contact dermatitis to dimethyl fumarate in footwear. Contact dermatitis 20100201
An epidemic of furniture-related dermatitis: searching for a cause. The British journal of dermatology 20100101
Dimethylfumarate inhibits microglial and astrocytic inflammation by suppressing the synthesis of nitric oxide, IL-1beta, TNF-alpha and IL-6 in an in-vitro model of brain inflammation. Journal of neuroinflammation 20100101
Dimethylfumarate for psoriasis: Pronounced effects on lesional T-cell subsets, epidermal proliferation and differentiation, but not on natural killer T cells in immunohistochemical study. American journal of clinical dermatology 20100101
Effects of fumaric acids on cuprizone induced central nervous system de- and remyelination in the mouse. PloS one 20100101
Multiple sclerosis therapies: molecular mechanisms and future. Results and problems in cell differentiation 20100101
DMF inhibits PDGF-BB induced airway smooth muscle cell proliferation through induction of heme-oxygenase-1. Respiratory research 20100101
Inhibition of NF-κB and AP-1 by dimethylfumarate correlates with down-regulated IL-6 secretion and proliferation in human lung fibroblasts. Swiss medical weekly 20100101
A case of contact dermatitis to dimethylfumarate in shoes identified in Italy. Annali dell'Istituto superiore di sanita 20100101
Shoe contact dermatitis from dimethyl fumarate: clinical manifestations, patch test results, chemical analysis, and source of exposure. Contact dermatitis 20091101
Dimethylfumarate inhibits tumor cell invasion and metastasis by suppressing the expression and activities of matrix metalloproteinases in melanoma cells. Cell biology international 20091001
Gas-chromatography-mass spectrometry analysis of dimethyl fumarate in consumer products. Journal of chromatography. A 20090925
Dimethylfumarate inhibits NF-{kappa}B function at multiple levels to limit airway smooth muscle cell cytokine secretion. American journal of physiology. Lung cellular and molecular physiology 20090801
Determination of dimethyl fumarate and other potential allergens in desiccant and antimould sachets. Analytical and bioanalytical chemistry 20090801
Occupational allergic contact dermatitis associated with dimethyl fumarate in clothing. Contact dermatitis 20090801
Determination of dimethyl fumarate in desiccant and mouldproof agents using ultrasound-assisted extraction gas chromatography with electron-capture detection. Journal of chromatography. A 20090724
Efficacy and safety of fumaric acid esters in the long-term treatment of psoriasis--a retrospective study (FUTURE). Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20090701
Contact dermatitis to dimethylfumarate in armchairs. Allergy 20090501
[Lichenoid dermatitis resulting from sensitization to dimethylfumarate: atypical presentation of 'Chinese sofa dermatitis']. Annales de dermatologie et de venereologie 20090301
[Acute dimethylfumarate-induced eczema on the foot]. Annales de dermatologie et de venereologie 20090301
Molecular mechanisms of Nrf2-mediated antioxidant response. Molecular carcinogenesis 20090201
Computational evaluation of enantioselective Diels-Alder reactions mediated by Corey's cationic oxazaborolidine catalysts. The Journal of organic chemistry 20090116
Detection of metabolites of fumaric acid esters in human urine: implications for their mode of action. The Journal of investigative dermatology 20090101
Phytochemical induction of cell cycle arrest by glutathione oxidation and reversal by N-acetylcysteine in human colon carcinoma cells. Nutrition and cancer 20090101
Treatment of disseminated granuloma annulare with low-dose fumaric acid. Acta dermato-venereologica 20090101
The derivatization of bioplatform molecules by using KF/alumina catalysis. ChemSusChem 20090101
The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. Biochemical and biophysical research communications 20081031
Oral fumarate for relapsing-remitting multiple sclerosis. Lancet (London, England) 20081025
Efficacy and safety of oral fumarate in patients with relapsing-remitting multiple sclerosis: a multicentre, randomised, double-blind, placebo-controlled phase IIb study. Lancet (London, England) 20081025
Beneficial effects of dimethyl fumarate on experimental autoimmune myocarditis. Archives of medical research 20081001
The cause of the Chinese sofa/chair dermatitis epidemic is likely to be contact allergy to dimethylfumarate, a novel potent contact sensitizer. The British journal of dermatology 20080701
Dimethyl fumarate, a small molecule drug for psoriasis, inhibits Nuclear Factor-kappaB and reduces myocardial infarct size in rats. European journal of pharmacology 20080531
Dimethylfumarate reduces leukocyte rolling in vivo through modulation of adhesion molecule expression. The Journal of investigative dermatology 20080201
[Fumaric acid and its esters in the treatment of multiple sclerosis: studies and effects]. Der Nervenarzt 20080201
Fumaric acid esters. Clinics in dermatology 20080101
Experimental and computational evidence for alpha-lactone intermediates in the addition of aqueous bromine to disodium dimethyl-maleate and -fumarate. Organic & biomolecular chemistry 20071221
Macrophage colony stimulating factor expression in human cardiac cells is upregulated by tumor necrosis factor-alpha via an NF-kappaB dependent mechanism. Journal of thrombosis and haemostasis : JTH 20071201
Drug evaluation: BG-12, an immunomodulatory dimethylfumarate. Current opinion in investigational drugs (London, England : 2000) 20071101
[Modulatory effect of fumaric acid esters on superoxide-anion generation in human phagocytes]. Yao xue xue bao = Acta pharmaceutica Sinica 20071101
A salutary case of Fumaderm potentially masking the symptoms of bowel cancer and partial bowel obstruction. The British journal of dermatology 20071001
Dimethylfumarate specifically inhibits the mitogen and stress-activated kinases 1 and 2 (MSK1/2): possible role for its anti-psoriatic effect. The Journal of investigative dermatology 20070901
Treatment of psoriasis with fumaric acid esters (Fumaderm). Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20070801
Dimethylfumarate inhibits nuclear binding of nuclear factor kappaB but not of nuclear factor of activated T cells and CCAAT/enhancer binding protein beta in activated human T cells. The British journal of dermatology 20070501
Novel oral agents for multiple sclerosis. Current neurology and neuroscience reports 20070501
Dimethylfumarate induces immunosuppression via glutathione depletion and subsequent induction of heme oxygenase 1. The Journal of investigative dermatology 20070401
Improvement of noninfectious uveitis with fumaric acid esters: results of a pilot study. Archives of ophthalmology (Chicago, Ill. : 1960) 20070401
Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-L-cysteine--preparation of S-substituted thiosuccinic acid esters. Bioorganic & medicinal chemistry 20070101
Use of fumaric acid esters in psoriasis. Indian journal of dermatology, venereology and leprology 20070101
Dimethylfumarate impairs melanoma growth and metastasis. Cancer research 20061215
Therapeutic potential of selectin antagonists in psoriasis. Expert opinion on investigational drugs 20060801
Treatment of therapy-resistant Alopecia areata with fumaric acid esters. European journal of medical research 20060731
Fumaric acid esters are effective in chronic experimental autoimmune encephalomyelitis and suppress macrophage infiltration. Clinical and experimental immunology 20060701
Oral fumaric acid esters for the treatment of active multiple sclerosis: an open-label, baseline-controlled pilot study. European journal of neurology 20060601
Modest induction of phase 2 enzyme activity in the F-344 rat prostate. BMC cancer 20060101
Chemistry of Ru(eta6-1,3,5-cyclooctatriene)(eta2-dimethyl fumarate)2. Chemical record (New York, N.Y.) 20060101
Evidence of covalent interaction of fumaric acid esters with sulfhydryl groups in peptides. Journal of mass spectrometry : JMS 20051001
Improvement of herpetic stromal keratitis with fumaric acid derivate is associated with systemic induction of T helper 2 cytokines. Clinical and experimental immunology 20051001
Fumaric acid esters in necrobiosis lipoidica: results of a prospective noncontrolled study. The British journal of dermatology 20051001
Enhancement of antibacterial superoxide-anion generation in human monocytes by fumaric acid esters. Archives of dermatological research 20051001
Detoxication enzyme inducers modify cytokine production in rat mixed glial cells. Journal of neuroimmunology 20050901
Fumaric acid esters for severe psoriasis: a retrospective review of 58 cases. The British journal of dermatology 20050901
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats. Chemico-biological interactions 20050815
Inhibition of vesicular monoamine transporter enhances vulnerability of dopaminergic cells: relevance to Parkinson's disease. Neurochemistry international 20050301
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells. Anti-cancer drugs 20050201
Fumaric acid esters therapy: a new treatment modality in pityriasis rubra pilaris? The British journal of dermatology 20050201
Dimethylfumarate for psoriasis: more than a dietary curiosity. Trends in molecular medicine 20050101
Disseminated granuloma annulare--treatment with fumaric acid esters. Dermatology (Basel, Switzerland) 20050101
BG 12: BG 00012, BG 12/Oral Fumarate, FAG-201, second-generation fumarate derivative--Fumapharm/Biogen Idec. Drugs in R&D 20050101
Identification of anti-inflammatory drugs according to their capacity to suppress type-1 and type-2 T cell profiles. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20041201
Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo. British journal of cancer 20041018
Influence of dimethylfumarate on experimental HSV-1 necrotizing keratitis. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20041001
[Successful treatment of skin and lung sarcoidosis with fumaric acid ester]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20040601
Fumaric acid esters, their place in the treatment of psoriasis. The British journal of dermatology 20040401
Fumaric acid esters in the treatment of psoriasis: an Italian experience. The Journal of dermatological treatment 20040101
In vitro pharmacokinetics of anti-psoriatic fumaric acid esters. BMC pharmacology 20040101
Dimethylfumarate is a potent inducer of apoptosis in human T cells. The Journal of investigative dermatology 20031201
Presystemic metabolism and intestinal absorption of antipsoriatic fumaric acid esters. Biopharmaceutics & drug disposition 20030901
Efficacy of fumaric acid ester monotherapy in psoriasis pustulosa palmoplantaris. The British journal of dermatology 20030701
Induction of NAD(P)H quinone: oxidoreductase1 inhibits carcinogen-induced aberrant crypt foci in colons of Sprague-Dawley rats. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20030601
Radiation response of cells during altered protein thiol redox. Radiation research 20030401
[Vision disorders in therapy with fumaric acid esters?]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20030301
Clearance of necrobiosis lipoidica with fumaric acid esters. Dermatology (Basel, Switzerland) 20030101
Dimethylfumarate inhibits TNF-induced nuclear entry of NF-kappa B/p65 in human endothelial cells. Journal of immunology (Baltimore, Md. : 1950) 20020501
Topical calcipotriol plus oral fumaric acid is more effective and faster acting than oral fumaric acid monotherapy in the treatment of severe chronic plaque psoriasis vulgaris. Dermatology (Basel, Switzerland) 20020101
Successful treatment of recalcitrant cutaneous sarcoidosis with fumaric acid esters. BMC dermatology 20020101
Experimental therapies for psoriasis. Archivum immunologiae et therapiae experimentalis 20020101
Dimethylfumarate inhibits tumor-necrosis-factor-induced CD62E expression in an NF-kappa B-dependent manner. The Journal of investigative dermatology 20011201
The antipsoriatic drug dimethylfumarate strongly suppresses chemokine production in human keratinocytes and peripheral blood mononuclear cells. The British journal of dermatology 20010601
Inhibition of Escherichia coli by dimethyl fumarate. International journal of food microbiology 20010411
Preferential expression of antioxidant response element mediated gene expression in astrocytes. Journal of neurochemistry 20010301
[Granuloma annulare disseminatum: successful therapy with fumaric acid ester]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20010301
[Effects of chemical agents on the prevention of fungal contamination during household wheat storage in Cixian county]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20010301
Dimethylfumarate is an inhibitor of cytokine-induced nuclear translocation of NF-kappa B1, but not RelA in normal human dermal fibroblast cells. The Journal of investigative dermatology 20010101
Dithranol and dimethylfumarate suppress the interferon-gamma-induced up-regulation of cytokeratin 17 as a putative psoriasis autoantigen in vitro. Skin pharmacology and applied skin physiology 20010101
Addition of pentoxifylline could reduce the side effects of fumaric acid esters in the treatment of psoriasis. Acta dermato-venereologica 20010101
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds. Journal of medicinal chemistry 19770401

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