Page last updated: 2024-09-22

butamirate

Description

butamirate: RN, N1 & SY refer to citrate salt; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID28891
CHEMBL ID2106133
SCHEMBL ID636120
MeSH IDM0049635
PubMed CID28892
CHEMBL ID1332546
CHEBI ID135310
SCHEMBL ID668881
MeSH IDM0049635

Synonyms (99)

Synonym
2-(2-(diethylamino)ethoxy)ethyl 2-phenylbutyrate citrate (1:1)
butamyrate citrate
hh-197
alpha-ethylbenzeneacetic acid 2-(2-(diethylamino)ethoxy)ethyl ester citrate
phenyl acetic acid diethylaminoethoxyethanol ester citrate
sincodex
einecs 242-006-8
sinecod
abbott 36581
sincodix
butamirate citrate
acodeen
alpha-ethylbenzeneacetic acid, 2-(2-(diethylamino)ethoxy)ethyl ester, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
benzeneacetic acid, alpha-ethyl-2-(2-(diethylamino)ethoxy)ethyl ester, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
butamirate citrate [usan]
2-(2-(diethylamino)ethoxy)-ethyl 2-phenylbutyrate citrate
2-phenylbutyric acid 2-(2-(diethylamino)ethoxy)ethyl ester citrate
diethyl(2-(2-(2-phenylbutyroyloxy)ethoxy)ethyl)ammonium dihydrogencitrate
sincodeen
sincodin
hh 197
butyric acid, 2-phenyl-, 2-(2-(diethylamino)ethoxy)ethyl ester, citrate
18109-81-4
butamirate citrate (usan)
D03184
2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutanoate 2-hydroxypropane-1,2,3-tricarboxylate (salt)
STK069532
FT-0663922
unii-67hp51l98r
67hp51l98r ,
abbott-36581
dtxcid8026270
cas-18109-81-4
dtxsid0046270 ,
tox21_111952
CHEMBL2106133
AKOS005390008
SCHEMBL636120
NCGC00160645-02
tox21_111952_1
2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutyrate citrate (1:1)
butamirate citrate [mi]
butamirate citrate [mart.]
butamirate citrate [who-dd]
benzeneacetic acid, .alpha.-ethyl-2-(2-(diethylamino)ethoxy)ethyl ester, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
J-011560
BCP22355
FT-0663923
butamirate (citrate)
Q27264132
2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutanoate;2-hydroxypropane-1,2,3-tricarboxylic acid
alpha-(ethyl)benzeneacetic acid 2-[2-(diethylamino)ethoxy]ethyl ester
oxeladin impurity d
benzeneacetic acid, alpha-ethyl-, 2-[2-(diethylamino)ethoxy]ethyl ester, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
2-(2-(diethylamino)ethoxy)ethyl 2-phenylbutanoate citrate
butamirate
18109-80-3
butamirate (inn)
codimin (tn)
D07594
MLS001047521
smr000425405
2-phenyl-butyric acid 2-(2-diethylamino-ethoxy)-ethyl ester; compound with 3-carboxy-3-hydroxy-pentanedioic acid
CHEBI:135310
brospamin
butamirato [inn-spanish]
benzeneacetic acid, alpha-ethyl-, 2-(2-(diethylamino)ethoxy)ethyl ester
butamirate [inn:ban]
butamiratum
unii-m75mzg2236
butamirato
ec 242-005-2
m75mzg2236 ,
einecs 242-005-2
butamiratum [inn-latin]
butamyrate
codimin
CHEMBL1332546
AKOS015969721
HMS2784H23
SCHEMBL668881
2-(2-(diethylamino)ethoxy)ethyl 2-phenylbutyrate
butamirate [inn]
benzeneacetic acid, .alpha.-ethyl-2-(2-(diethylamino)ethoxy)ethyl ester
butamirate [who-dd]
butamirate [mi]
DTXSID7048403
benzeneacetic acid, .alpha.-ethyl-, 2-[2-(diethylamino)ethoxy]ethyl ester
2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutyrate
DDVUMDPCZWBYRA-UHFFFAOYSA-N
FT-0696983
butamirat
2-(2- diethylaminoethoxy)ethyl-2-phenylbutyrat
DB13731
2-[2-(diethylamino)ethoxy]ethyl 2-phenylbutanoate
Q2360598
18109-80-3 (free base)
CS-0066328
HY-118545

Drug Classes (1)

ClassDescription
alkylbenzeneA monocyclic arene that is benzene substituted with one or more alkyl groups.
[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 Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency5.95690.000811.382244.6684AID686979
cytochrome P450 2D6Homo sapiens (human)Potency10.96400.00108.379861.1304AID1645840
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency89.12510.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
glp-1 receptor, partialHomo sapiens (human)Potency12.58930.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency29.08100.004110.890331.5287AID504467
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency50.11870.035520.977089.1251AID504332
gemininHomo sapiens (human)Potency33.49830.004611.374133.4983AID624296
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
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.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings 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.
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.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical 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.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The 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.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The 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.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (17.65)18.7374
1990's5 (14.71)18.2507
2000's3 (8.82)29.6817
2010's12 (35.29)24.3611
2020's8 (23.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials6 (23.08%)5.53%
Reviews0 (0.00%)6.00%
Reviews2 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies2 (7.69%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
Other16 (61.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
[The use and safety of butamirate containing drops, syrup and depot tablets in Hungary].
Orvosi hetilap, Mar-27, Volume: 146, Issue: 13
2005
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Combination of large volume sample stacking with polarity switching and cyclodextrin electrokinetic chromatography (LVSS-PS-CDEKC) for the determination of selected preservatives in pharmaceuticals.
Talanta, May-01, Volume: 211
2020
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, Volume: 96, Issue: 5
2019
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
The Journal of biological chemistry, 11-15, Volume: 294, Issue: 46
2019
Relative bioavailability of different butamirate citrate preparations after single dose oral administration to 18 healthy volunteers.
International journal of clinical pharmacology and therapeutics, Volume: 35, Issue: 3
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (4)

ArticleYear
A randomized placebo controlled trial to evaluate the effects of butamirate and dextromethorphan on capsaicin induced cough in healthy volunteers.
British journal of clinical pharmacology, Volume: 78, Issue: 6
2014
[Butamyrate citrate in cough controlling].
Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego, Volume: 35, Issue: 210
2013
Acute cervical dystonia after the first dose of butamirate citrate.
Pediatric emergency care, Volume: 29, Issue: 1
2013
Relative bioavailability of different butamirate citrate preparations after single dose oral administration to 18 healthy volunteers.
International journal of clinical pharmacology and therapeutics, Volume: 35, Issue: 3
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]