Compounds > clausenamide

Page last updated: 2024-12-07

clausenamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

clausenamide: Chinese drug isolated from leaves of Clausena lansium (Lour) Skeels; used in treatment of viral hepatitis; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Lansium	genus	[no description available]	Meliaceae	The mahogany plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida.[MeSH]
Clausena	genus	A plant genus of the family RUTACEAE. Members contain anethole and CARBAZOLES.[MeSH]	Rutaceae	A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]
Clausena lansium	species	[no description available]	Rutaceae	A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID Source	ID
PubMed CID	128412
CHEMBL ID	508970
SCHEMBL ID	6369855
MeSH ID	M0150381

Synonyms (16)

Synonym
clausenamide
(+)-clausenamide
(-)-clausenamide
CHEMBL508970
(3r,4s,5s)-3-hydroxy-5-[(r)-hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
(3r,4s,5s)-3-hydroxy-5-((r)-hydroxyphenylmethyl)-1-methyl-4-phenylpyrrolidin-2-one
109905-95-5
103541-15-7
2-pyrrolidinone,3-hydroxy-5-((r)-hydroxyphenylmethyl)-1-methyl-4-phenyl-, (3r,4s,5s)-rel
dl-xylonic acid, 3,4-dideoxy-4-(methylamino)-3-phenyl-5-c-phenyl-, gamma-lactam, (s*)-
neoclausenamide
zetaclausenamide
SCHEMBL6369855
DTXSID10908462
(3r,4s,5s)-3-hydroxy-5-[(r)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-p yrrolidin-2-one

Research Excerpts

Overview

Clausenamide is a chiral compound isolated from leaves of the traditional Chinese herb Clausena lansium (lour) Skeels. It has nootropic effects.

Excerpt	Reference	Relevance
"Clausenamide is a chiral compound isolated from leaves of the traditional Chinese herb Clausena lansium (lour) Skeels. "	( (-)Clausenamide facilitates synaptic transmission at hippocampal Schaffer collateral-CA1 synapses. Chen, NH; Han, N; Hu, JF; Ning, N; Sun, JD; Zhang, JT, 2012)	2.44
"(-)clausenamide is a compound isolated from Clausena lansium (lour) Skeel with nootropic effects. "	( Mechanism of (-)clausenamide induced calcium transient in primary culture of rat cortical neurons. Tang, K; Zhang, JT, 2004)	1.29
"Clausenamide is a compound isolated from Clausena lansium (lour) with the structure similar to piracetam. "	( [Anti-lipidperoxidation and cerebral protective effects of clausenamide]. Liu, Y; Shi, CZ; Zhang, JT, 1991)	1.97

Effects

Clausenamide has been reported to be nootropic and improve learning and memory in amnesia animal models. It has the protective effects against the neurotoxicity induced by okadaic acid and Abeta25-35.

Excerpt	Reference	Relevance
"(-)-Clausenamide has been reported to be nootropic and improve learning and memory in amnesia animal models."	( (-)-Clausenamide alleviated ER stress and apoptosis induced by OGD/R in primary neuron cultures. Chen, J; Cheng, H; Feng, Q; Wu, F; Xue, J; Zhang, R, 2020)	1.6
"(-) Clausenamide has the protective effects against the neurotoxicity induced by okadaic acid and Abeta25-35."	( [Protective effect of (-) clausenamide against neurotoxicity induced by okadaic acid and beta-amyloid peptide25-35]. Cheng, Y; Zhang, J; Zhang, JT, 2007)	1.12

Actions

Excerpt	Reference	Relevance
"Clausenamide can enhance the expression of Bcl-2 protein and inhibit apoptosis remarkably."	( [Effect of clausenamide on the expression of Bcl-2 protein and apoptosis after focal cerebral ischemia/reperfusion in renovascular hypertensive rats]. Bi, GN; Jiang, ZC; Shi, SL, 2005)	1.44

Treatment

Excerpt	Reference	Relevance
"(+) Clausenamide treatment showed no effect on Bmax and KD values."	( [Effects of (-), (+) clausenamide on central N-methyl-D-asparate receptors in rodents]. Duan, WZ; Zhang, JT, 1997)	1.1

Pharmacokinetics

Excerpt	Reference	Relevance
" The pharmacokinetic parameters were calculated by 3P97 software."	( [Pharmacokinetics of (-)-clausenamide and its major metabolite 6-hydroxyl-clausenamide in beagle dogs by HPLC/MS]. Hang, TJ; Qian, W; Song, M; Zhang, ZX, 2005)	0.63

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay ID	Title	Year	Journal	Article
AID353954	Nootropic activity in hippocampus assessed as increase in amplitude of population spikes after 30 mins by long-term potentiation enhancement assay relative to control	2009	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8	Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers.
AID353953	Nootropic activity in hippocampus assessed as increase in amplitude of population spikes after 15 mins by long-term potentiation enhancement assay relative to control	2009	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8	Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers.
AID353955	Nootropic activity in hippocampus assessed as increase in amplitude of population spikes after 60 mins by long-term potentiation enhancement assay relative to control	2009	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8	Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.27)	18.7374
1990's	9 (20.45)	18.2507
2000's	20 (45.45)	29.6817
2010's	12 (27.27)	24.3611
2020's	2 (4.55)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.38

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	27.38 (24.57)
Research Supply Index	3.83 (2.92)
Research Growth Index	5.42 (4.65)
Search Engine Demand Index	31.58 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (27.38)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (4.44%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	43 (95.56%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.04	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
huperzine a huperzine A: RN given refers to 5R-(5alpha,9beta,11E)-isomer; structure given in first source. huperzine A : A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.	3.12	1	quinolone
7-nitroindazole 7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure	7	1
berberine [no description available]	3.12	1	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.11	1	aromatic ether; nitrile; polyether; tertiary amino compound
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.45	2	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.02	1	xanthene
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2	1	indazole
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	1.97	1	dialdehyde	biomarker
3-n-butylphthalide 3-n-butylphthalide: isolated from phenolic part of Ligusticum wallichii Franch; structure given in first source	3.12	1	benzofurans
fluo-3 Fluo-3: fluorescent Ca(2+) indicator; permits continuous monitoring of Ca without interference with use of UV-sensitive caged compounds	2.02	1	xanthene dye	fluorochrome
triptolide [no description available]	3.12	1	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
anisodine anisodine: structure in first source	2.4	2
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.12	1
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	2.02	1	myo-inositol trisphosphate	mouse metabolite
ginsenoside rg1 [no description available]	2.01	1	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	neuroprotective agent; pro-angiogenic agent
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	6.75	44
sesquiterpenes [no description available]	3.12	1
nadp [no description available]	2.01	1
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.01	1
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.11	1	organic cation; xanthene dye	fluorochrome
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.01	1	stilbenoid
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	7	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	1.99	1	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
stepholidine stepholidine: protoberberine alkaloid isolated from opium; dual D1 receptor agonist and D2 receptor antagonist	3.12	1
sb 204990 [no description available]	2.05	1
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	2.02	1
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	7.03	1	ketal
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	3.12	1

Condition	Relationship Strength	Studies
Cerebral Ischemia [description not available]	2.74	3
Injury, Ischemia-Reperfusion [description not available]	2.74	3
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.74	3
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.74	3
Acute Liver Injury, Drug-Induced [description not available]	2.25	1
Acute Hepatic Failure [description not available]	2.25	1
Liver Failure, Acute A form of rapid-onset LIVER FAILURE, also known as fulminant hepatic failure, caused by severe liver injury or massive loss of HEPATOCYTES. It is characterized by sudden development of liver dysfunction and JAUNDICE. Acute liver failure may progress to exhibit cerebral dysfunction even HEPATIC COMA depending on the etiology that includes hepatic ISCHEMIA, drug toxicity, malignant infiltration, and viral hepatitis such as post-transfusion HEPATITIS B and HEPATITIS C.	2.25	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.25	1
Amentia [description not available]	3.04	1
Age-Related Memory Disorders [description not available]	3.39	2
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	8.04	1
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	3.39	2
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.42	2
Anterior Circulation Transient Ischemic Attack [description not available]	2.01	1
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.01	1
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.01	1
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	2.01	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.42	2
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.02	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.02	1
Blood Pressure, High [description not available]	2.02	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.02	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.03	1
Amnesia-Memory Loss [description not available]	2.4	2
Amnesia Pathologic partial or complete loss of the ability to recall past experiences (AMNESIA, RETROGRADE) or to form new memories (AMNESIA, ANTEROGRADE). This condition may be of organic or psychologic origin. Organic forms of amnesia are usually associated with dysfunction of the DIENCEPHALON or HIPPOCAMPUS. (From Adams et al., Principles of Neurology, 6th ed, pp426-7)	2.4	2
Anoxia, Brain [description not available]	1.97	1

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