benextramine: RN given refers to parent cpd
ID Source | ID |
---|---|
PubMed CID | 2317 |
CHEMBL ID | 19060 |
SCHEMBL ID | 467278 |
MeSH ID | M0095255 |
Synonym |
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n'-[(2-methoxyphenyl)methyl]-n-[2-[2-[6-[(2-methoxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethyl]hexane-1,6-diamine |
n~1~-(2-methoxybenzyl)-n~6~-(2-((2-((6-((2-methoxybenzyl)amino)hexyl)amino)ethyl)dithio)ethyl)-1,6-hexanediamine |
benextramine |
68535-69-3 |
nsc364369 |
CHEMBL19060 , |
n,n'-bis(o-methoxybenzylaminohexyl)cystamine |
n-(2-methoxy-benzyl)-n''-(2-{2-[6-(2-methoxy-benzylamino)-hexylamino]-ethyldisulfanyl}-ethyl)-hexane-1,6-diamine (bhc, benextramine) |
n1-(2-methoxybenzyl)-n6-(2-(2-(2-(6-(2-methoxybenzylamino)hexylamino)ethyl)disulfanyl)ethyl)hexane-1,6-diamine |
n-(2-methoxy-benzyl)-n''-(2-{2-[6-(2-methoxy-benzylamino)-hexylamino]-ethyldisulfanyl}-ethyl)-hexane-1,6-diamine |
n-(2-methoxy-benzyl)-n''-(2-{2-[6-(2-methoxy-benzylamino)-hexylamino]-ethyldisulfanyl}-ethyl)-hexane-1,6-diamine .4hcl |
bdbm50020168 |
1n-(2-methoxybenzyl)-6n-(2-{2-[6-(2-methoxybenzylamino)hexylamino]ethyldisulfanyl}ethyl)-1,6-hexanediamine |
2ugy4etx3l , |
1,6-hexanediamine, n,n''-(dithiodi-2,1-ethanediyl)bis(n'-((2-methoxyphenyl)methyl)- |
n,n'-bis-(o-methoxybenzylaminohexyl)-cystamine |
n,n'-bmbac |
69790-18-7 |
n,n''-(dithiodi-2,1-ethanediyl)bis(n'-(2-methoxyphenylmethyl)-1,6-hexanediamine) tetrahydrochloride |
unii-2ugy4etx3l |
DTXSID80220082 |
SCHEMBL467278 |
n1,n1'-(dithiodi-2,1-ethanediyl)bis(n6-((2-methoxyphenyl)methyl)-1,6-hexanediamine |
1,6-hexanediamine, n1,n1'-(dithiodi-2,1-ethanediyl)bis(n6-((2-methoxyphenyl)methyl)- |
Benextramine is a tetraamine disulfide mainly known as irreversible α-adrenergic antagonist. It is able to hit additional targets involved in neurodegeneration.
Excerpt | Reference | Relevance |
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"Benextramine is a tetraamine disulfide mainly known as irreversible α-adrenergic antagonist, but able to hit additional targets involved in neurodegeneration." | ( Benextramine and derivatives as novel human monoamine oxidases inhibitors: an integrated approach. Cozza, G; Di Paolo, ML; Milelli, A; Minarini, A; Minniti, E; Rosini, M; Sarno, S; Ursini, F; Zonta, F, 2019) | 2.68 |
"Benextramine is a useful tool to estimate turnover of alpha 2-adrenergic receptors under normal and pathological situations using the approach described in the present paper." | ( Alpha 2-adrenergic receptor turnover in adipose tissue and kidney: irreversible blockade of alpha 2-adrenergic receptors by benextramine. Berlan, M; Lafontan, M; Taouis, M, 1987) | 1.2 |
Benextramine treatment attenuated the inhibitory effects of progesterone on receptivity. The presence of 3 x 10(-10) M Ang II caused a modest leftward shift of the NE dose-response curve.
Excerpt | Reference | Relevance |
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"Benextramine pretreatment followed by membrane washing demonstrated that benextramine inhibited irreversibly both high and low affinity sites." | ( Binding profile of benextramine at neuropeptide Y receptor subtypes in rat brain areas. Bolognesi, ML; Donatini, A; Ferri, S; Melchiorre, C; Romualdi, P, 1994) | 1.34 |
"Benextramine treatment attenuated the inhibitory effects of progesterone on receptivity (lordosis quotients and percent of responding animals) without affecting either proceptive or rejection behaviors." | ( Benextramine, a putative neuropeptide Y receptor antagonist, attenuates the termination of receptivity. Clark, JT, 1992) | 2.45 |
"In benextramine-pretreated vessels, the presence of 3 x 10(-10) M Ang II caused a modest leftward shift of the NE dose-response curve but increased the maximal responses to all NE concentrations by 200% to 800%." | ( Angiotensin II amplification of alpha-adrenergic vasoconstriction: role of receptor reserve. Purdy, RE; Weber, MA, 1988) | 0.79 |
"Benextramine treatment of fat cell, kidney, and brain membranes reduced or completely suppressed, in an irreversible manner, [3H] clonidine and [3H]yohimbine binding without modifying adenosine (A1-receptor) and beta-adrenergic receptor sites." | ( Alpha 2-adrenergic receptor turnover in adipose tissue and kidney: irreversible blockade of alpha 2-adrenergic receptors by benextramine. Berlan, M; Lafontan, M; Taouis, M, 1987) | 1.2 |
"Pretreatment with benextramine greatly diminished the effect of clonidine." | ( Reversible inhibition of neuronal uptake by benextramine, an irreversible presynaptic alpha-adrenoceptor antagonist. Angus, JA; Lew, MJ, 1984) | 0.85 |
Excerpt | Reference | Relevance |
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" Compound 15 was identified as a selective and high affinity NPY5 antagonist with good oral bioavailability in mice (42%) and rats (92%)." | ( Discovery of Lu AA33810: a highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder. Andersen, K; Chandrasena, G; Desai, M; Jubian, V; Lu, Y; Marzabadi, MR; Noble, SA; Packiarajan, M; Walker, MW; Wiborg, O; Wolinsky, TD; Wong, WC; Zhong, H, 2011) | 0.37 |
Benextramine (3, 6 and 12 mg/Kg) displaced the dose-response curve to methoxamine to the right. The dose- response curve to intra-arterial noradrenaline (after beta-adrenoceptor blockade) was shifted rightwards about ten fold by benextamine.
Excerpt | Relevance | Reference |
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" The second approach was a detailed comparison between alpha 2-receptor occupancy by [3H] UK 14304 and the cyclic AMP inhibitory dose-response curve to this agonist in cells incubated also under conditions avoiding cyclic AMP breakdown." | ( Evidence against the "spare" receptor nature of alpha 2-adrenoceptors in hamster white fat cells. Dieudonne, MN; Giudicelli, Y; Pecquery, R, 1990) | 0.28 |
" Benextramine (3, 6 and 12 mg/Kg) displaced the dose-response curve to methoxamine to the right." | ( Benextramine and nifedipine distinguish between sub-classes of alpha 1-adrenoceptors. Tabrizchi, R; Triggle, CR, 1989) | 2.63 |
" In the presence of Ang II, the NE dose-response curve shifted to the left twofold and the maximal response was not changed." | ( Angiotensin II amplification of alpha-adrenergic vasoconstriction: role of receptor reserve. Purdy, RE; Weber, MA, 1988) | 0.27 |
" Isolated aortic rings were mounted in tissue baths for the measurement of isometric contraction and 5-HT dose-response curves were obtained in the presence and absence of receptor antagonists." | ( Receptors for 5-hydroxytryptamine in rabbit blood vessels: activation of alpha adrenoceptors in rabbit thoracic aorta. Murray, DL; Purdy, RE; Stupecky, GL, 1987) | 0.27 |
" The dose-response curve to intra-arterial noradrenaline (after beta-adrenoceptor blockade) was shifted rightwards about ten fold by benextramine (10 mg kg-1) and by phenoxybenzamine (5 mg kg-1)." | ( Lack of involvement of alpha-adrenoceptors in sympathetic neural vasoconstriction in the hindquarters of the rabbit. Hirst, GD; Lew, MJ, 1987) | 0.48 |
" In rabbit isolated saphenous vein, cumulative dose-response curves to various NPY agonists were obtained." | ( Discrimination by benextramine between the NPY-Y1 receptor subtypes present in rabbit isolated vas deferens and saphenous vein. Corsi, M; Palea, S; Rimland, JM; Trist, DG, 1995) | 0.63 |
" Next, we determined norepinephrine dose-response relations before and after prazosin, yohimbine, and benextramine." | ( Effects of maturation on alpha-adrenergic receptor affinity and occupancy in small cerebral arteries. Elliott, SR; Pearce, WJ, 1994) | 0.5 |
" Furthermore, NPY was without effect on the dose-response curve to ATP in resting conditions." | ( Failure of the putative neuropeptide Y antagonists, benextramine and PYX-2, to inhibit Y2 receptors in rat isolated prostatic vas deferens. Corsi, M; Palea, S; Ratti, E; Rimland, JM; Trist, DG, 1995) | 0.54 |
" The competitive alpha1-adrenoceptor antagonists produced dextral shifts of the dose-response curves to NA in longitudinal and circular muscle." | ( Discrimination by SZL49 between contractions evoked by noradrenaline in longitudinal and circular muscle of human vas deferens. Amobi, NI; Guillebaud, J; Kaisary, AV; Smith, IC; Turner, E, 2002) | 0.31 |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
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Cholinesterase | Homo sapiens (human) | IC50 (µMol) | 6.1659 | 0.0000 | 1.5599 | 10.0000 | AID44422; AID44423 |
Alpha-1B adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0002 | 1.8742 | 10.0000 | AID33131 |
Alpha-2B adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0003 | 1.0914 | 7.7625 | AID33131 |
Alpha-2C adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0003 | 1.0914 | 7.7625 | AID33131 |
Acetylcholinesterase | Homo sapiens (human) | IC50 (µMol) | 7.2429 | 0.0000 | 0.9332 | 10.0000 | AID314091; AID31771; AID31775 |
Alpha-2A adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0003 | 1.0691 | 7.7625 | AID33131 |
Alpha-1D adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0002 | 1.2704 | 10.0000 | AID33131 |
Neuropeptide Y receptor type 1 | Homo sapiens (human) | Ki | 1.8000 | 0.0001 | 0.2295 | 2.3150 | AID620857 |
Adenosine receptor A2a | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0012 | 0.4828 | 9.0000 | AID33131 |
Alpha-1A adrenergic receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.0200 | 0.0000 | 1.8194 | 10.0000 | AID33131 |
Neuropeptide Y receptor type 5 | Homo sapiens (human) | Ki | 5.0000 | 0.0015 | 1.6677 | 5.0000 | AID620858 |
Carboxylic ester hydrolase | Rattus norvegicus (Norway rat) | IC50 (µMol) | 6.1659 | 0.0004 | 1.4811 | 9.8700 | AID44422 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID317108 | Reversal of inhibition of mouse neuroblast cell migration from subventricular zone tissue explants in presence of PR21 | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID184230 | Irreversible inhibition against Norepinephrine (NE)-induced response in rat vas deferens with benextramine (BHC) as standard at a concentration of 2 x 10e-5 M | 1987 | Journal of medicinal chemistry, Jul, Volume: 30, Issue:7 | Structure-activity relationships among di- and tetramine disulfides related to benextramine. |
AID317107 | Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants after 24 hrs | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID195547 | Relative potency in displacing 1 nM [3H]NPY from benextramine-sensitive rat brain NPYsites | 1994 | Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14 | Nonpeptide peptidomimetic antagonists of the neuropeptide Y receptor: benextramine analogs with selectivity for the peripheral Y2 receptor. |
AID36775 | Alpha-2 adrenergic receptor blocking activity by antagonism of clonidine induced depression of twitch response of field stimulated prostatic portion of rat vas deferens | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on alpha-adrenoreceptor blocking activity. |
AID44746 | Inhibition of epinephrine induced human blood platelet aggregation | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on alpha-adrenoreceptor blocking activity. |
AID33128 | Antagonistic blocking activity at alpha adrenergic receptor by NE induced contractions of the epididymal portion of isolated rat vas deferens at the dose of 20 uM | 1985 | Journal of medicinal chemistry, Nov, Volume: 28, Issue:11 | Structure-activity relationships among benextramine-related tetraamine disulfides at peripheral alpha-adrenoreceptors. |
AID146047 | Percentage of maximum displacement of of 1.0 nM [3H]NPY from rat brain membranes homogenates using 1.0 uM NPY to determine specific binding | 1994 | Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14 | Nonpeptide peptidomimetic antagonists of the neuropeptide Y receptor: benextramine analogs with selectivity for the peripheral Y2 receptor. |
AID219105 | Relative potency of compound at alpha-adrenoceptor to that of benextramine was measured by ability to antagonize the effect of epinephrine on the contractions of the electrically stimulated rat vas deferens | 1993 | Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2 | Benextramine-neuropeptide Y receptor interactions: contribution of the benzylic moieties to [3H]neuropeptide Y displacement activity. |
AID142248 | Antagonistic potency of compound towards Muscarinic acetylcholine receptor M2 in guinea pig left atrium. | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID31637 | Selectivity towards acetylcholinesterase over butyrylcholinesterase | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID44745 | Inhibition of ADP induced human blood platelet aggregation | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on alpha-adrenoreceptor blocking activity. |
AID79859 | Ability to reverse the D-tubocurarine-induced neuromuscular blockade in guinea pig left atrium. | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID33131 | Inhibitory activity against alpha adrenergic receptor in rat | 1985 | Journal of medicinal chemistry, Nov, Volume: 28, Issue:11 | Structure-activity relationships among benextramine-related tetraamine disulfides at peripheral alpha-adrenoreceptors. |
AID233592 | Ratio of IC50 towards alpha1 to alpha-2 receptors of rat vas deferens | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on alpha-adrenoreceptor blocking activity. |
AID142126 | Antagonistic potency against Muscarinic acetylcholine receptor M2 (1 uM) receptor; nd= Not determined | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease. |
AID317090 | Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants at 34 uM after 48 hrs relative to control | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID197105 | Alpha-1-adrenoceptor blocking activity by antagonism of (-)-norepinephrine induced contractions of epididymal portion of rat vas deferens | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on alpha-adrenoreceptor blocking activity. |
AID317106 | Inhibition of PR21-stimulated mouse neuroblast cell migration from subventricular zone tissue explants after 24 hrs | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID620857 | Binding affinity to NPY1 receptor | 2011 | Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18 | Discovery of Lu AA33810: a highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder. |
AID31771 | Inhibitory concentration against acetylcholinesterase from human erythrocytes | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID186992 | Antimuscarinic activity against carbachol induced response in rat jejunum | 1985 | Journal of medicinal chemistry, Nov, Volume: 28, Issue:11 | Structure-activity relationships among benextramine-related tetraamine disulfides at peripheral alpha-adrenoreceptors. |
AID146048 | Concentration producing half maximal displacement of [3H]NPY specific binding from benextramine sensitive NPY binding sites in rat brain membranes | 1994 | Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14 | Nonpeptide peptidomimetic antagonists of the neuropeptide Y receptor: benextramine analogs with selectivity for the peripheral Y2 receptor. |
AID141204 | Antagonistic potency against Muscarinic acetylcholine receptor M3 (10 uM); nd= Not determined | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease. |
AID317089 | Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants at 68 uM after 48 hrs relative to control | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID620858 | Binding affinity to NPY5 receptor | 2011 | Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18 | Discovery of Lu AA33810: a highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder. |
AID31775 | Inhibition of acetylcholinesterase (AChE) of human erythrocytes | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease. |
AID44422 | Inhibitory concentration against butyrylcholinesterase from human serum | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID314091 | Inhibition of human AchE | 2008 | Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3 | Multi-target-directed ligands to combat neurodegenerative diseases. |
AID146051 | Displacement of [3H]NPY from rat brain NPY receptor compared to benextramine | 1993 | Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2 | Benextramine-neuropeptide Y receptor interactions: contribution of the benzylic moieties to [3H]neuropeptide Y displacement activity. |
AID44423 | Inhibition of Butyrylcholinesterase (BChE) of human erythrocytes [-log IC50 (uM)] | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease. |
AID146050 | Binding affinity against rat NPY receptor by using [3H]NPY as radioligand | 1993 | Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2 | Benextramine-neuropeptide Y receptor interactions: contribution of the benzylic moieties to [3H]neuropeptide Y displacement activity. |
AID25333 | Apparent dissociation constant of compound was evaluated; n.d. indicates not determined | 2003 | Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6 | Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine. |
AID140901 | Antagonistic potency against Muscarinic acetylcholine receptor M1; nd= Not determined | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease. |
AID317091 | Inhibition of mouse neuroblast cell migration from subventricular zone tissue explants at 6.8 uM after 48 hrs relative to control | 2008 | Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1 | Discovery of new small molecules that influence neuroblast cell migration from the subventricular zone. |
AID184232 | Irreversible inhibition against Norepinephrine (NE)-induced response in rat vas deferens with benextramine (BHC) as standard at a concentration of 6 x 10e-6 M | 1987 | Journal of medicinal chemistry, Jul, Volume: 30, Issue:7 | Structure-activity relationships among di- and tetramine disulfides related to benextramine. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 35 (42.17) | 18.7374 |
1990's | 34 (40.96) | 18.2507 |
2000's | 10 (12.05) | 29.6817 |
2010's | 4 (4.82) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (19.02) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 3 (3.57%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 81 (96.43%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |