Compounds > cyclocumarol
Page last updated: 2024-12-05

cyclocumarol

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

Description

Cyclocumarol is a synthetic anticoagulant that was initially developed as a potential replacement for dicumarol. It acts by inhibiting the synthesis of vitamin K-dependent clotting factors, which are essential for blood coagulation. However, cyclocumarol has a narrow therapeutic index and a high risk of bleeding complications, which has limited its clinical use. Despite its limited use in human medicine, cyclocumarol is still used in veterinary medicine for anticoagulation in animals. It is also used as a research tool to investigate the mechanisms of blood coagulation and the effects of anticoagulants on the body.'

cyclocumarol: anticoagulant similar to, but less potent than warfarin; may cause hemorrhage if used indiscriminately; minor descriptor (76-84); on-line search 4-HYDROXYCOUMARINS (76-84); Index Medicus search 4-HYDROXYCOUMARINS (77-84), COUMARINS (76); RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10606
CHEMBL ID2104144
CHEBI ID135368
SCHEMBL ID38087
MeSH IDM0262618

Synonyms (42)

Synonym
2h,5h-pyrano[3,2-c][1]benzopyran-5-one, 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-
anticoagulans 63
bl 5
cumopyrin
cyclocoumarol
cumopyran
pyranocoumarin
compound 63 link
3,4-dihydro-2-methoxy-2-methyl-4-phenyl-2h,5h-pyrano(3,2-c)(1)benzopyran-5-one
pyranocumarin [german]
2h-pyran-5-carboxylic acid, 3,4-dihydro-6-(o-hydroxyphenyl)-2-methoxy-2-methyl-4-phenyl-, delta-lactone
2h,5h-pyrano(3,2-c)(1)benzopyran-5-one, 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-
2-methyl-2-methoxy-4-phenyl-3,4-dihydro-pyrano-(3,2-c)-cumarin [german]
3,4-dihydro-2-methoxy-2-methyl-4-phenylpyrano(3,2-c)chromen-5-one
methanopyranorin
einecs 208-248-3
cyclocumarol
NCGC00166195-01
CHEBI:135368
2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5-one
cyclocoumarol [inn:ban]
2-methyl-2-methoxy-4-phenyl-3,4-dihydro-pyrano-(3,2-c)-cumarin
518-20-7
725p8aw50m ,
unii-725p8aw50m
pyranocumarin
CHEMBL2104144
SCHEMBL38087
cyclocumarol [mi]
2-methoxy-2-methyl-4-phenyl-3,4-dihydro-2h,5h-pyrano[3,2-c]chromen-5-one #
2h-pyran-5-carboxylic acid, 3,4-dihydro-6-(o-hydroxyphenyl)-2-methoxy-2-methyl-4-phenyl-, .delta.-lactone
3,4-(2'-methyl-2'-methoxy-4'-phenyl)dihydropyranocoumarin
anticoagulant no. 63
ZGFASEKBKWVCGP-UHFFFAOYSA-N
SR-01000883723-1
sr-01000883723
pyranocoumarin, pestanal(r), analytical standard
FT-0708808
DTXSID60862101
2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5(2h)-one
Q27266024
STARBLD0009647
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
coumarins
[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 (1)

Assay IDTitleYearJournalArticle
AID1353254Inhibition of COX-2 in mouse RAW264.7 cells assessed as reduction in PGE2 production at 10 uM preincubated for 2 hrs followed by LPS stimulation measured after 24 hrs by enzyme immunoassay relative to control2018European journal of medicinal chemistry, Feb-25, Volume: 146New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (62.50)18.7374
1990's2 (25.00)18.2507
2000's0 (0.00)29.6817
2010's1 (12.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.99

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.99 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.19 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.99)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
coumarin
2H-chromen-2-one: coumarin derivative		2.6230coumarinsfluorescent dye;
human metabolite;
plant metabolite
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide
N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide: structure given in first source. NS-398 : A C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2.		2.1710aromatic ether;
C-nitro compound;
sulfonamide		antineoplastic agent;
cyclooxygenase 2 inhibitor
sulfaphenazole
Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.		210primary amino compound;
pyrazoles;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antibacterial drug;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor;
P450 inhibitor
7-hydroxycoumarin
7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.		1.9810hydroxycoumarinfluorescent probe;
food component;
plant metabolite
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		3.260benzenes;
hydroxycoumarin;
methyl ketone
phenprocoumon
Phenprocoumon: Coumarin derivative that acts as a long acting oral anticoagulant.. phenprocoumon : A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group.		210hydroxycoumarinanticoagulant;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Cardiovascular Stroke
[description not available]		01.9310
Blood Clot
[description not available]		02.3320
Myocardial Infarction
NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).		01.9310
Thrombosis
Formation and development of a thrombus or blood clot in the blood vessel.		02.3320
Deficiency, Factor II
[description not available]		01.9210