Chemical Formula: C19H27NO3
Chemical Formula C19H27NO3
Found 40 metabolite its formula value is C19H27NO3
Nateglinide
Nateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naive to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83\\%) and feces (10\\%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound. C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C98079 - Meglitinide Antidiabetic Agent A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins D007004 - Hypoglycemic Agents
Tetrabenazine
A drug formerly used as an antipsychotic but now used primarily in the treatment of various movement disorders including tardive dyskinesia. Tetrabenazine blocks uptake into adrenergic storage vesicles and has been used as a high affinity label for the vesicle transport system. [PubChem] D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators N - Nervous system Same as: D08575
Protoemetine
Protoemetine has been reported in Alangium salviifolium and Carapichea ipecacuanha. Protoemetine (原吐根碱) is a monoterpenoid-derived tetrahydroisoquinoline alkaloid with significant biological functions, primarily observed in its role as a precursor to pharmacologically active compounds and its direct interactions in biological systems. Below is a detailed description of its biological functions based on available evidence: ### 1. **Precursor Role in Biosynthesis of Medicinal Alkaloids** Protoemetine serves as a critical intermediate in the biosynthesis of emetine and cephaeline, two major ipecac alkaloids with established therapeutic applications. These downstream alkaloids are widely recognized for their antiparasitic (e.g., against *Entamoeba histolytica*) and emetic properties. The non-enzymatic Pictet-Spengler reaction initiates protoemetine formation by condensing dopamine with monoterpenoid precursors (secologanin or secologanic acid). ### 2. **Antiviral Activity** While direct evidence for protoemetine's antiviral activity is limited, its structural analogs (e.g., emetine) exhibit potent inhibition against RNA viruses such as dengue virus (DENV). Emetine, derived from protoemetine, reduces viral RNA synthesis and protein translation at concentrations as low as 0.5 μM. This suggests protoemetine’s biosynthetic pathway may indirectly contribute to antiviral defense mechanisms in plants. ### 3. **Antiparasitic Effects** Protoemetine-related alkaloids, particularly emetine, are clinically used to treat parasitic infections like amoebic dysentery. Emetine disrupts protein synthesis in *Entamoeba histolytica* trophozoites by inhibiting ribosomal function. Although protoemetine itself is not directly administered, its metabolic conversion to emetine underscores its biological relevance in antiparasitic therapy. ### 4. **Cytotoxic and Anticancer Potential** Emetine, synthesized from protoemetine, demonstrates cytotoxic effects in cancer cells by inducing apoptosis via modulation of Bcl-2 family proteins (e.g., reducing Bcl-XL/Bcl-XS ratios). Protoemetine’s role in this pathway highlights its indirect contribution to anticancer mechanisms, though further studies are needed to confirm direct activity. ### 5. **Regulation of Plant Defense Mechanisms** In plants such as *Psychotria ipecacuanha* and *Alangium salviifolium*, protoemetine accumulation correlates with tissue-specific defense strategies. Its biosynthesis is spatially regulated (e.g., higher levels in roots and young leaves), suggesting a role in deterring herbivores or pathogens through alkaloid-mediated toxicity. ### Summary of Key Functions: • **Biosynthetic hub**: Central to producing emetine and cephaeline, compounds with antiparasitic and antitussive properties. • **Structural basis for drug activity**: Protoemetine’s tetrahydroisoquinoline scaffold enables interactions with biological targets (e.g., ribosomal machinery, viral polymerases). • **Ecological defense**: Contributes to plant chemical defense systems against pathogens and herbivores. For detailed mechanisms, refer to studies on ipecac alkaloid biosynthesis, emetine’s pharmacological actions, and evolutionary parallels in alkaloid production.
2-(4-Morpholino)ethyl-1-phenylcyclohexane-1-carboxylate
Ac-(E)-6-[2-(1-Hydroxybutyl)-4-methylphenyl]-5-hexenamide
(2E,4E)-N-[(4-hydroxy-3-methoxyphenyl)ethyl]-2,4-decadienamide
A natural product found in Piper boehmeriaefolium.
Nateglinide
C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C98079 - Meglitinide Antidiabetic Agent A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins D007004 - Hypoglycemic Agents CONFIDENCE standard compound; EAWAG_UCHEM_ID 3289
4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid
(4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid
(3R,11bR)-3-(2-methylpropyl)-9,10-bis(trideuteriomethoxy)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
N - Nervous system
2-(4-Morpholino)ethyl-1-phenylcyclohexane-1-carboxylate
(3S,11bS)-tetrabenazine
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators C471 - Enzyme Inhibitor
2-{[4-(Methylethyl)cyclohexyl]carbonylamino}-3-phenylpropanoic acid
1-(Phenylmethyl)cyclopentyl[(1S)-1-formylpentyl]carbamate
TETRABENAZINE
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators N - Nervous system Same as: D08575
