Melagatran is a peptidomimetic scaffold studied for its interactions with serine-protease active sites. The molecule incorporates noncanonical functional groups enabling tight binding and hydrogen-bond complementarity. Researchers explore its conformational landscape to understand enzyme-ligand complementarity. Applications include mechanistic enzymology, inhibitor-design studies, and structure-activity evaluation.
CAT No: R2611
CAS No:159776-70-2
Synonyms/Alias:Melagatran;159776-70-2;Melagatran [INN];UNII-2A9QP32MD4;Melagatran (INN);2A9QP32MD4;CHEBI:43966;MELAGATRAN [MI];2-[[(1R)-2-[(2S)-2-[(4-carbamimidoylphenyl)methylcarbamoyl]azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino]acetic acid;MELAGATRAN [MART.];MELAGATRAN [WHO-DD];N-((R)-(((2S)-2-((-p-Amidobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycine;Glycine, N-[(1R)-2-[(2S)-2-[[[[4-(aminoiminomethyl)phenyl]methyl]amino]carbonyl]-1-azetidinyl]-1-cyclohexyl-2-oxoethyl]-;DTXSID30166724;H-319/68;159776-70-2 (free base);[((1R)-2-{(2S)-2-[({4-[AMINO(IMINO)METHYL]BENZYL}AMINO)CARBONYL]AZETIDINYL}-1-CYCLOHEXYL-2-OXOETHYL)AMINO]ACETIC ACID;N-[(1R)-2-[(2S)-2-[[[[4-(Aminoiminomethyl)phenyl]methyl]amino]carbonyl]-1-azetidinyl]-1-cyclohexyl-2-oxoethyl]glycine;MELAGATRAN (MART.);2-(((R)-2-((S)-2-((4-Carbamimidoylbenzyl)carbamoyl)azetidin-1-yl)-1-cyclohexyl-2-oxoethyl)amino)acetic acid;Glycine, N-((1R)-2-((2S)-2-((((4-(aminoiminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-1-cyclohexyl-2-oxoethyl)-;Glycine, N-(2-(2-((((4-(aminoiminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-1-cyclohexyl-2-oxoethyl)-, (S-(R*,S*))-;N-[(1R)-2-{(2S)-2-[(4-carbamimidoylbenzyl)carbamoyl]azetidin-1-yl}-1-cyclohexyl-2-oxoethyl]glycine;H-319-68;((R)-2-((S)-2-((4-carbamimidoylbenzyl)carbamoyl)azetidin-1-yl)-1-cyclohexyl-2-oxoethyl)glycine;melagatranum;MELAGATRAN (ASTRA-ZENECA);2-(((1R)-2-((2S)-2-((4-carbamimidoylphenyl)methylcarbamoyl)azetidin-1-yl)-1-cyclohexyl-2-oxoethyl)amino)acetic acid;N-((1R)-2-((2S)-2-((((4-(Aminoiminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-1-cyclohexyl-2-oxoethyl)glycine;N-((1R)-2-((2S)-2-((4-carbamimidoylbenzyl)carbamoyl)azetidin-1-yl)-1-cyclohexyl-2-oxoethyl)glycine;Melagatran AstraZeneca;SCHEMBL27652;CHEMBL266349;GTPL6382;DTXCID1089215;BDBM29388;B01AE04;1k22;EX-A11153;AKOS022181213;DB13616;N-((R)-(((2S)-2-((p-Amidinobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycine;DA-65325;TS-07835;HY-129056;CS-0103405;NS00009077;C21551;D07143;G12919;Q27084209;
Melagatran is a synthetic, small-molecule direct thrombin inhibitor widely recognized for its significance in biochemical and pharmacological research. As a non-peptidic compound, it possesses a distinctive molecular scaffold that enables high-affinity, selective inhibition of thrombin, a central serine protease in the coagulation cascade. Its well-characterized mechanism and structural features make it a valuable reference molecule for scientists investigating hemostatic regulation, protease activity, and anticoagulant strategies. Due to its specificity and reversible binding profile, Melagatran is frequently utilized as a tool compound in studies dissecting enzymatic pathways and the molecular dynamics of blood coagulation.
Enzyme inhibition studies: Melagatran serves as a robust probe in the assessment of thrombin activity and inhibition kinetics. Researchers employ it to characterize the catalytic properties of thrombin, evaluate the efficacy of novel anticoagulant candidates, and elucidate structure-activity relationships for serine protease inhibitors. Its defined binding mode allows for precise determination of inhibition constants and mechanistic insights into active site interactions, supporting both basic enzymology and drug discovery workflows.
Coagulation pathway research: In experimental models of hemostasis, Melagatran is used to selectively modulate thrombin-dependent processes, facilitating the study of fibrin formation, platelet activation, and feedback regulation within the coagulation cascade. By providing a means to finely control thrombin activity, it enables detailed exploration of the molecular interplay among coagulation factors and the identification of critical regulatory nodes in blood clotting.
Structural biology and binding studies: Owing to its well-resolved interactions with thrombin, Melagatran is frequently utilized in structural biology investigations, including X-ray crystallography and molecular docking analyses. These studies help delineate the conformational changes induced upon inhibitor binding and inform rational design of next-generation anticoagulants. Its use as a reference ligand aids in mapping the active site topology and understanding the determinants of selectivity and potency among related protease targets.
Analytical assay development: In the context of in vitro assay systems, Melagatran is employed as a standard or control inhibitor for validating the performance of thrombin activity assays, chromogenic substrate methods, and high-throughput screening platforms. Its predictable inhibitory profile ensures assay reproducibility and accuracy, supporting the development of sensitive analytical tools for quantifying protease activity in complex biological samples.
Comparative pharmacology: As a benchmark direct thrombin inhibitor, Melagatran is integral to comparative studies assessing the selectivity, reversibility, and pharmacodynamic properties of novel anticoagulant agents. Researchers utilize it to establish reference data sets, calibrate bioassay systems, and contextualize the activity of experimental compounds within the broader landscape of anticoagulant research. Its inclusion in such studies enhances the interpretability and translational value of preclinical findings.
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