Page last updated: 2024-11-05

apocodeine

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

Description

Apocodeine is a synthetic, semi-synthetic, or naturally occurring alkaloid derived from the opium poppy. It is a dopamine D2 receptor agonist and has been investigated for its potential therapeutic uses, including in the treatment of Parkinson's disease and other movement disorders. Apocodeine has shown promise in preclinical studies, but it has not yet been approved for clinical use due to its potential for side effects. One particular research study reported that apocodeine was synthesized by the reaction of apomorphine with formaldehyde and hydrochloric acid. Further research continues to explore the therapeutic potential of apocodeine for neurodegenerative disorders, including Parkinson's disease, as well as its effects on other aspects of human health.'

apocodeine: monomethyl ether of apomorphine; used as expectorant, hypnotic, & cathartic; RN refers to (R)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID12545
CHEMBL ID154709
SCHEMBL ID1349371
MeSH IDM0049238

Synonyms (34)

Synonym
apocodein
brn 0032938
6a-beta-aporphin-11-ol, 10-methoxy-
apocodeine
4h-dibenzo(de,g)quinolin-11-ol, 5,6,6a,7-tetrahydro-10-methoxy-6-methyl-, (r)-
4h-dibenzo(de,g)quinolin-11-ol, 5,6,6a,7-tetrahydro-10-methoxy-6-methyl-, (r)-(ci)
LOPAC0_000425
NCGC00162151-02
641-36-1
CHEMBL154709 ,
apocideine
10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolin-11-ol(apocideine)
bdbm50016019
CCG-204517
5-21-05-00334 (beilstein handbook reference)
unii-obf8x37y5w
obf8x37y5w ,
SCHEMBL1349371
apomorphine hydrochloride hemihydrate impurity a [ep impurity]
(6ar)-10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo(de,g)quinolin-11-ol
(-)-apocodeine
6a.beta.-aporphin-11-ol, 10-methoxy-
4h-dibenzo(de,g)quinolin-11-ol, 5,6,6a,7-tetrahydro-10-methoxy-6-methyl-, (6ar)-
(-)-(r)-apocodeine
apocodeine [mi]
DZUOQMBJJSBONO-CQSZACIVSA-N
DTXSID901016508
SDCCGSBI-0050410.P002
NCGC00162151-04
nsc785152
nsc-785152
Q27285553
(6ar)-10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinolin-11-ol
apocodeine hcl

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" This method was applied to study apomorphine bioavailability in nine patients with Parkinson's disease before and after coadministration of a catechol-O-methyl transferase inhibitor."( Development of a gas chromatographic/mass spectrometric method to quantify R(-)-apomorphine, R(-)-apocodeine and R(-)-norapomorphine in human plasma and urine.
Coudoré, F; Durif, F; Eschalier, A; Libert, F; Richard, D, 2005
)
0.55
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency39.81070.100020.879379.4328AID588456
ATAD5 protein, partialHomo sapiens (human)Potency18.34890.004110.890331.5287AID493107
GLS proteinHomo sapiens (human)Potency3.54810.35487.935539.8107AID624146
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency7.94330.035520.977089.1251AID504332
D(1A) dopamine receptorHomo sapiens (human)Potency5.81800.02245.944922.3872AID488982; AID488983
chromobox protein homolog 1Homo sapiens (human)Potency50.11870.006026.168889.1251AID488953
M-phase phosphoprotein 8Homo sapiens (human)Potency3.76860.177824.735279.4328AID488949
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency1.69440.060110.745337.9330AID485368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DRattus norvegicus (Norway rat)IC50 (µMol)8.56670.00030.50267.7625AID45982; AID45983; AID61181
D(3) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)6.20000.00030.39075.4000AID45982; AID45983
D(1B) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)6.20000.00030.35635.4000AID45982; AID45983
D(4) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)6.20000.00030.38715.4000AID45982; AID45983
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)4.82670.00010.54948.4000AID45982; AID45983; AID64424
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID182828In vitro inhibition of adenylate cyclase stimulation caused by 10 uM dopamine in rat retinal tissue by 10 uM.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Aporphines as antagonists of dopamine D-1 receptors.
AID61181In vitro binding affinity towards rat Dopamine receptor D1 by [3H]SCH-23390 displacement.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Aporphines as antagonists of dopamine D-1 receptors.
AID34462Dopamine sensitive adenylate cyclase activity (stimulation) in homogenates of rat brain striatal tissue was assessed at 50 uM of compound; Not tested1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
AID45983Inhibition of [3H]spiroperidol binding to calf caudate membrane preparation (p4)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
AID45982Inhibition of [3H]apomorphine binding to calf caudate membrane preparation (p4)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
AID191925Ability to stimulate adenylate cyclase in rat retinal tissue over basal levels; NS=no significant stimulation1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Aporphines as antagonists of dopamine D-1 receptors.
AID64424In vitro binding affinity towards rat Dopamine receptor D2 by [3H]spiperone displacement.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Aporphines as antagonists of dopamine D-1 receptors.
AID1150386Central dopaminergic activity in 6-OH-DA-lesioned specific pathogen-free Sprague-Dawley rat assessed as induction of rotational behavior measured as total time at 5 mg/kg, ip1976Journal of medicinal chemistry, Jan, Volume: 19, Issue:1
Aporphines. 14 Dopaminergic and antinociceptive activity of aporphine derivatives. Synthesis of 10-hydroxyaporphines and 10-hydroxy-N-n-propylnoraporphine.
AID1150393Central dopaminergic activity in 6-OH-DA-lesioned specific pathogen-free Sprague-Dawley rat assessed as induction of rotational behavior measured as total time at 1 mg/kg, ip1976Journal of medicinal chemistry, Jan, Volume: 19, Issue:1
Aporphines. 14 Dopaminergic and antinociceptive activity of aporphine derivatives. Synthesis of 10-hydroxyaporphines and 10-hydroxy-N-n-propylnoraporphine.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (16.67)18.7374
1990's2 (11.11)18.2507
2000's3 (16.67)29.6817
2010's5 (27.78)24.3611
2020's5 (27.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.62

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index51.62 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index79.51 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]