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 belonging to the class of peptidomimetics, recognized for its specific action on the coagulation cascade. As a reversible and highly selective inhibitor, Melagatran is structurally designed to bind directly to the active site of thrombin, thereby blocking the conversion of fibrinogen to fibrin. Its chemical stability and predictable pharmacological profile make it a valuable compound for scientific investigations into thrombosis and hemostasis. Due to its unique mechanism of action and well-characterized inhibitory properties, Melagatran is widely utilized in research settings focused on understanding coagulation dynamics and developing novel anticoagulant strategies.
Anticoagulation Mechanism Research: Melagatran serves as a powerful tool in elucidating the molecular mechanisms underlying thrombin-mediated coagulation. By selectively inhibiting thrombin, researchers can dissect the specific contributions of this serine protease to various stages of the coagulation cascade. The compound's direct inhibition allows for precise modulation of thrombin activity in in vitro assays, facilitating the study of clot formation, platelet activation, and the interplay between coagulation factors. This targeted approach aids in identifying potential therapeutic targets and advancing the understanding of pathological conditions such as thrombosis and disseminated intravascular coagulation.
Thrombosis Model Development: In experimental models aiming to simulate thrombotic events, Melagatran is frequently employed to modulate thrombin activity and assess the efficacy of antithrombotic interventions. Its rapid and reversible binding characteristics enable researchers to establish controlled thrombotic environments in animal or ex vivo systems, thereby providing valuable insights into the dynamics of clot development and resolution. By incorporating Melagatran into these models, scientists can evaluate the effects of various procoagulant and anticoagulant agents, investigate the molecular basis of thrombus formation, and optimize protocols for the prevention and treatment of thrombotic disorders.
Platelet Function Studies: The use of this direct thrombin inhibitor extends to the analysis of platelet activation and aggregation under physiological and pathological conditions. By blocking thrombin-induced platelet responses, Melagatran allows for the isolation and examination of alternative pathways contributing to platelet function. This capability is particularly valuable in research exploring the crosstalk between coagulation and platelet biology, as well as in the development of novel antiplatelet agents. The compound's selectivity and reversible action facilitate detailed kinetic and mechanistic studies, supporting the identification of new molecular targets for antithrombotic therapies.
Bioanalytical Method Validation: Melagatran is also utilized as a reference compound in the development and validation of bioanalytical methods designed to quantify direct thrombin inhibitors and related molecules. Its well-defined chemical properties and inhibitory profile make it an ideal standard for calibrating assays such as liquid chromatography-tandem mass spectrometry (LC-MS/MS) or functional coagulation assays. By serving as a benchmark, Melagatran contributes to the establishment of robust, reproducible analytical techniques that are essential for pharmacokinetic and pharmacodynamic studies of new anticoagulant candidates.
Structure-Activity Relationship (SAR) Studies: In medicinal chemistry and drug discovery research, Melagatran provides a valuable framework for structure-activity relationship investigations aimed at optimizing direct thrombin inhibitors. Researchers utilize this compound as a reference molecule to explore modifications in chemical structure that enhance potency, selectivity, and pharmacokinetic properties. Comparative studies involving Melagatran and its analogues inform the rational design of next-generation anticoagulants with improved therapeutic profiles. By leveraging its well-characterized inhibitory mechanism, scientists can systematically assess the impact of structural changes on biological activity, guiding the development of innovative agents targeting thrombin and related serine proteases.
1. TMEM16F and dynamins control expansive plasma membrane reservoirs
2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
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