Page last updated: 2024-11-05

apronalide

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

Description

Apronalide is a synthetic anti-inflammatory drug that has been studied for its potential therapeutic effects in a variety of conditions, including inflammatory bowel disease, rheumatoid arthritis, and cancer. It is a potent inhibitor of cyclooxygenase (COX), an enzyme that plays a key role in the production of prostaglandins, which are involved in inflammation and pain. Apronalide has been shown to reduce inflammation and pain in animal models of these diseases. However, it has been withdrawn from clinical trials due to safety concerns. The mechanism of action of apronalide is believed to be related to its ability to inhibit the production of prostaglandins. Apronalide has been shown to bind to the active site of COX, preventing the enzyme from converting arachidonic acid into prostaglandins. It has also been suggested that apronalide may have other effects, such as inhibiting the production of other inflammatory mediators. '

apronalide: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10715
CHEMBL ID509282
CHEBI ID134827
SCHEMBL ID662209
MeSH IDM0047412

Synonyms (54)

Synonym
4-pentenamide, n-(aminocarbonyl)-2-(1-methylethyl)-
urea, (2-isopropyl-4-pentenoyl)-
allylisopropylacetylurea
D03975
apronal
apronalide
528-92-7
(2-isopropylpent-4-enoyl)urea
n-(aminocarbonyl)-2-(1-methylethyl)-4-pentenamide
isodormid
brn 1775529
sedormid
allylisopropylacetylcarbamide
(2-isopropyl-4-pentenoyl)urea
isopropylallylazetylkarbamid [german]
einecs 208-443-3
CHEBI:134827
n-carbamoyl-2-propan-2-ylpent-4-enamide
CHEMBL509282
inchi=1/c9h16n2o2/c1-4-5-7(6(2)3)8(12)11-9(10)13/h4,6-7h,1,5h2,2-3h3,(h3,10,11,12,13)
ksuumawcgdnlfk-uhfffaoysa-
AKOS006272745
n-carbamoyl-2-isopropylpent-4-enamide
unii-v18j24e25e
isopropylallylazetylkarbamid
v18j24e25e ,
S6450
SCHEMBL662209
(+/-)-apronalide
apronalide [mi]
apronalide, (+/-)-
apronal [who-dd]
(allylisopropylacetyl)urea
(allylisopropylacetyl)carbamide
n-(2-isopropyl-4-pentenoyl)urea #
KSUUMAWCGDNLFK-UHFFFAOYSA-N
CS-7723
allylisoprorylacetylurea
n-carbamoyl-2-isopropyl-4-pentenamide
allyl isopropyl acetylurea
n-(2-isopropyl-4-pentenoyl)urea
AS-58738
apronalide 1.0 mg/ml in methanol
2-isopropyl-4-pentenoyl-harnstoff
HY-B2177
n-(aminocarbonyl)-2-isopropylpent-4-enamide
[2-(propan-2-yl)pent-4-enoyl]urea
DTXSID00862125
DB13221
mfcd00210239
Q1095009
allylisopropylacetylurea;apronalide
D88535
EN300-8092389

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The present study aimed to survey the components of OTC drug package inserts for analgesic and antipyretic drugs and to evaluate the adverse event profiles using the Japanese Adverse Drug Event Report database (JADER)."( Adverse Event Trends Associated with OTC Analgesic and Antipyretic Drug: Data Mining of the Japanese Adverse Drug Event Report Database.
Abe, J; Fukuda, A; Hasegawa, S; Hatahira, H; Iguchi, K; Kato, Y; Motooka, Y; Naganuma, M; Nakamura, M; Nakao, S; Ohmori, T; Sasaoka, S; Shimauchi, A, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylureaA member of the class of ureas that has the general formula R-CO-NH-CO-NH2 or R-CO-NH-CO-NH-CO-R', formally derived by the acylation of one or both of the nitrogens of a urea moiety.
[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]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID409949Inhibition of human liver MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (54)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (79.63)18.7374
1990's3 (5.56)18.2507
2000's6 (11.11)29.6817
2010's1 (1.85)24.3611
2020's1 (1.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.40

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.

MetricThis Compound (vs All)
Research Demand Index27.40 (24.57)
Research Supply Index4.13 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.28%)6.00%
Case Studies9 (14.75%)4.05%
Observational0 (0.00%)0.25%
Other50 (81.97%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]