Docarpamine is a naturally occurring alkaloid isolated from the bark of the South American tree *D. cava*. It has shown promising activity as a potential therapeutic agent for various conditions, including depression, anxiety, and Alzheimer's disease. Docarpamine's effects are attributed to its ability to modulate neurotransmitter systems, particularly dopamine and serotonin, which play crucial roles in regulating mood, cognition, and behavior. Research into docarpamine's synthesis, effects, and potential therapeutic applications is ongoing. The compound's unique chemical structure and its ability to target multiple neurotransmitter pathways make it a promising candidate for developing novel treatments for neuropsychiatric disorders.'
docarpamine: a dopamine prodrug; RN given refers to (S)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 71137 |
| CHEMBL ID | 2106351 |
| CHEBI ID | 31513 |
| SCHEMBL ID | 219671 |
| SCHEMBL ID | 23356827 |
| MeSH ID | M0148128 |
| Synonym |
|---|
| tanadopa |
| ta-8704 |
| docarpamine |
| ta-870 |
| docarpamina [inn-spanish] |
| carbonic acid, 4-(2-((2-(acetylamino)-4-(methylthio)-1-oxobutyl)amino)ethyl)-1,2-phenylene diethyl ester, (s)- |
| docarpaminum [inn-latin] |
| (-)-(s)-2-acetamido-n-(3,4-dihydroxyphenethyl)-4-(methylthio)butyramide bis(ethyl carbonate) (ester) |
| docarpamine [inn] |
| n-(n-acetyl-l-methionyl)-o,o-bis(ethoxycarbonyl)dopamine |
| D01903 |
| docarpamine (jan/inn) |
| 74639-40-0 |
| tanadopa (tn) |
| [4-[2-[[(2s)-2-acetamido-4-methylsulfanylbutanoyl]amino]ethyl]-2-ethoxycarbonyloxyphenyl] ethyl carbonate |
| docarpaminum |
| docarpamina |
| unii-rpq57d8s72 |
| rpq57d8s72 , |
| CHEMBL2106351 |
| docarpamine [mi] |
| docarpamine [mart.] |
| docarpamine [who-dd] |
| docarpamine [jan] |
| SCHEMBL219671 |
| cas-74639-40-0 |
| dtxcid8031609 |
| tox21_113707 |
| NCGC00249931-01 |
| dtxsid1057820 , |
| CHEBI:31513 |
| (s)-4-(2-(2-acetamido-4-(methylthio)butanamido)ethyl)-1,2-phenylene diethyl dicarbonate |
| SCHEMBL23356827 |
| Q27288234 |
Docarpamine is a dopamine prodrug which has been selected from a large number of dopamine derivatives in order to develop an orally effective dopamine.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Docarpamine is a dopamine prodrug which has been selected from a large number of dopamine derivatives in order to develop an orally effective dopamine. " | ( Metabolism of dopamine prodrug, docarpamine. Nishiyama, S; Takaiti, O; Yoshikawa, M, 1995) | 2.02 |
| "Docarpamine (DOC) is a dopamine prodrug which can be orally administered. " | ( Oral administration of the dopamine prodrug docarpamine shortens need for drip infusion of dopamine in patients with low cardiac output syndrome after cardiac surgery. Matsubayashi, K; Matsuyama, K; Nomoto, T; Ogino, H; Sakakibara, Y; Sugita, T; Ueda, Y, 1999) | 2.01 |
| "Docarpamine is a dopamine prodrug which has been selected from a large number of dopamine derivatives in order to develop an orally effective dopamine. " | ( Effects of docarpamine on hemodynamics after open heart surgery in children. Hirokawa, R; Imura, M; Katsuyama, K; Mori, A; Nakajima, Y; Shiraishi, S; Sugita, T; Watarida, S; Yamamoto, R; Yamamoto, Y, 2000) | 2.14 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Docarpamine was found to metabolize in cirrhotic patients as well as in normal subjects and may be an effective treatment for refractory ascites." | ( Effects of a new orally active dopamine prodrug, docarpamine, on refractory ascites: a pilot study. Funasaki, T; Itoh, T; Kawahara, H; Shimanaka, K; Takase, S; Tsuchishima, M; Tsutsumi, M; Ueshima, Y; Urashima, S, 1999) | 2 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The bioavailability and pharmacokinetics of an oral dopamine prodrug, N-(N-acetyl-L-methionyl)O,O-bis(ethoxycarbonyl)dopamine (1), were examined in dogs, and the mechanism of its absorption and bioactivation was discussed." | ( Bioavailability and pharmacokinetics of an oral dopamine prodrug in dogs. Kohno, K; Murata, K; Noda, K; Samejima, M, 1989) | 0.28 |
| " These results demonstrate that TA-870 was well absorbed from the digestive tract, extensively metabolized to dopamine, and proved to be an orally usable dopamine prodrug." | ( Comparative study on the disposition of a new orally active dopamine prodrug, N-(N-acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine (TA-870) and dopamine hydrochloride in rats and dogs. Endo, H; Harigaya, S; Otsuka, M; Yamaguchi, I; Yoshikawa, M, ) | 0.13 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " In an intravenous cumulative dose-response study of TA-870, the plasma-free-dopamine concentration was elevated depending on the dose of TA-870." | ( A novel orally active dopamine prodrug TA-870. III. Positive inotropic effect and cardiorenal selectivity in anesthetized dogs. Akimoto, Y; Nakajima, H; Nishiyama, S; Yamaguchi, I; Yoshikawa, M, 1990) | 0.28 |
| " dosing of TA-870 (30 mg/kg) were DA greater than homovanillic acid (HVA) greater than 3,4-dihydroxyphenylacetic acid (DOPAC) greater than 3-hydroxyphenylacetic acid (3-HPAC)." | ( Metabolism of a new orally active dopamine prodrug, N-(N-acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine (TA-870) and dopamine after oral administration to rats and dogs. Endo, H; Komatsu, K; Sugawara, Y; Takaiti, O; Yoshikawa, M, 1990) | 0.28 |
| Class | Description |
|---|---|
| organic molecular entity | Any molecular entity that contains carbon. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 14.9601 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 15.0594 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224893 |
| G | Vesicular stomatitis virus | Potency | 24.5454 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 43.8442 | 0.0391 | 47.5451 | 146.8240 | AID1224845 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 17.7787 | 0.0006 | 27.2152 | 1,122.0200 | AID743219 |
| Interferon beta | Homo sapiens (human) | Potency | 24.5454 | 0.0033 | 9.1582 | 39.8107 | AID1645842 |
| HLA class I histocompatibility antigen, B alpha chain | Homo sapiens (human) | Potency | 24.5454 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| Inositol hexakisphosphate kinase 1 | Homo sapiens (human) | Potency | 24.5454 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| cytochrome P450 2C9, partial | Homo sapiens (human) | Potency | 24.5454 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1347094 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347095 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347089 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1347082 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID1347102 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347091 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347100 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347424 | RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 2019 | The Journal of biological chemistry, 11-15, Volume: 294, Issue:46 | Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens. |
| AID1347107 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347105 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347103 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347092 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347108 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1508630 | Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 2021 | Cell reports, 04-27, Volume: 35, Issue:4 | A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. |
| AID1347083 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID1347099 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347097 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347106 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347090 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347154 | Primary screen GU AMC qHTS for Zika virus inhibitors | 2020 | Proceedings 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. |
| AID1347098 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID1347104 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347425 | Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 2019 | The Journal of biological chemistry, 11-15, Volume: 294, Issue:46 | Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens. |
| AID1347101 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347096 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347086 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID1347093 | qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells | 2018 | Oncotarget, Jan-12, Volume: 9, Issue:4 | Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing. |
| AID1347407 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection | 2020 | ACS 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. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 6 (20.00) | 18.7374 |
| 1990's | 12 (40.00) | 18.2507 |
| 2000's | 4 (13.33) | 29.6817 |
| 2010's | 2 (6.67) | 24.3611 |
| 2020's | 6 (20.00) | 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 (20.64) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 5 (15.15%) | 5.53% |
| Reviews | 2 (6.06%) | 6.00% |
| Case Studies | 1 (3.03%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 25 (75.76%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||