7-hydroxywarfarin

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

Description

7-hydroxywarfarin: a warfarin metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	54682507
CHEMBL ID	145880
CHEBI ID	180534
SCHEMBL ID	17132373
MeSH ID	M0232543

Synonyms (33)

Synonym
7-hydroxywarfarin
CHEBI:180534
17834-03-6
4,7-dihydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
NCGC00165932-01
CHEMBL145880
2,7-dihydroxy-3-(3-oxo-1-phenyl-butyl)chromen-4-one
A812360
b92sfw09lj ,
unii-b92sfw09lj
4,7-dihydroxy-3-(3-oxo-1-phenylbutyl)-2h-1-benzopyran-2-one
2h-1-benzopyran-2-one, 4,7-dihydroxy-3-(3-oxo-1-phenylbutyl)-
63740-81-8
7-hydroxy warfarin
FT-0637612
coumarin, 3-(.alpha.-acetonylbenzyl)-4,7-dihydroxy-
BQSUFDMOXLLKQK-UHFFFAOYSA-N
3-(.alpha.-acetonylbenzyl)-4,7-dihydroxycoumarin
SCHEMBL17132373
AS-71155
7-hydroxy warfarin
(r)-7-hydroxy warfarin
4,7-dihydroxy-3-(3-oxo-1-phenylbutyl)-2h-chromen-2-one
DTXSID10939074
2,7-dihydroxy-3-(3-oxo-1-phenylbutyl)-4h-1-benzopyran-4-one
Q27274527
3-(alpha-acetonylbenzyl)-4,7-dihydroxycoumarin
AKOS037646845
STARBLD0009682
PD039346
2h-1-benzopyran-2-one, 4,7-dihydroxy-3-[3-oxo-1-(phenyl-d5)butyl]-
2h-1-benzopyran-2-one, 4,7-dihydroxy-3-[(1s)-3-oxo-1-phenylbutyl]-
2,7-dihydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-4-one

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" The mean plasma concentrations and elimination half-life of (R)-warfarin of all the subjects were about 2-fold greater than those of (S)-warfarin."	( The effect of CYP2C19 genotypes on the pharmacokinetics of warfarin enantiomers. Sugawara, K; Sugimoto, K; Tateishi, T; Uno, T, 2008)	0.35
" Pharmacokinetic parameters were analysed using non-compartmental methods."	( Effects of etravirine on the pharmacokinetics and pharmacodynamics of warfarin in rats. Abobo, CV; Hsiao, C; John, J; John, M; Liang, D; Wu, L, 2013)	0.39

Compound-Compound Interactions

Excerpt	Reference	Relevance
" These data suggest that fluconazole can be expected to interact with any drug whose clearance is dominated by P450s 2C9, 3A4, and other as yet undefined isoforms."	( Warfarin-fluconazole. II. A metabolically based drug interaction: in vivo studies. Bauwens, JE; Black, DJ; Evans, JS; Gidal, BE; Kunze, KL; McDonnell, ND; Seaton, TL; Trager, WF; Wienkers, LC, 1996)	0.29

Dosage Studied

Excerpt	Relevance	Reference
" Dosing with St John's wort or ginseng was continued for 7 days after administration of the warfarin dose."	( Effect of St John's wort and ginseng on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects. Ammit, AJ; Day, RO; Duke, CC; Jiang, X; Liauw, WS; McLachlan, AJ; Roufogalis, BD; Williams, KM, 2004)	0.32
"The aim of this study was to determine whether folic acid supplementation increases the dosage requirement of the CYP2C9 substrate warfarin, and the formation clearance of the CYP2C9-mediated product, (S)-7-hydroxywarfarin."	( Effects of folic acid supplementation on the pharmacokinetics and anticoagulant effect of warfarin: an open-label, prospective study of long-term administration in adults. Adar, L; Bialer, O; Blotnick, S; Caraco, Y; Cascorbi, I; Muszkat, M; Ufer, M; Xie, HG, 2010)	0.55
"Patients aged >or=18 years with folic acid deficiency who were receiving long-term treatment with a stable dosage of warfarin were studied prospectively, before and 30 to 60 days after the initiation of supplementation with folic acid."	( Effects of folic acid supplementation on the pharmacokinetics and anticoagulant effect of warfarin: an open-label, prospective study of long-term administration in adults. Adar, L; Bialer, O; Blotnick, S; Caraco, Y; Cascorbi, I; Muszkat, M; Ufer, M; Xie, HG, 2010)	0.36
" Changes in warfarin dosage requirements and INR were nonsignificant."	( Effects of folic acid supplementation on the pharmacokinetics and anticoagulant effect of warfarin: an open-label, prospective study of long-term administration in adults. Adar, L; Bialer, O; Blotnick, S; Caraco, Y; Cascorbi, I; Muszkat, M; Ufer, M; Xie, HG, 2010)	0.36
"The present study results provide, insights on the effect of CYP2C9 genetic polymorphisms on inter-individual variability in warfarin metabolism and emphasizes utility of phenotyping in a setting of genotype-guided dosing of warfarin in South Indian population."	( Influence of CYP2C9 Polymorphisms on Plasma Concentration of Warfarin and 7-Hydroxy Warfarin in South Indian Patients. Adithan, C; Chandran B V, S; Kumar, DK; Shewade, DG; Uppugunduri, CRS, 2021)	0.62

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
hydroxycoumarin	Any coumarin carrying at least one hydroxy substituent.
[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 (7)

Assay ID	Title	Year	Journal	Article
AID16345	Compound incubated with microsomal preparations from phenobarbital treated male rats with the substrate rac 8-D and the amount of deuterium retained was reported after normal workup	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
AID16342	Amount of deuterium retained was reported after reincubation followed by normal workup in phenobarbital treated male rats with rac 8-D	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
AID16340	Amount of deuterium retained was reported after normal workup in rats	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
AID16341	Amount of deuterium retained was reported after reincubation followed by normal workup in phenobarbital treated male rats	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
AID16343	Compound incubated with microsomal preparations from beta-naphthoflavone-treated male rats with the substrate rac 7-D and the amount of deuterium retained was reported after reincubation followed by normal workup	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
AID293981	Inhibition of rat microsomal VKER	2007	Bioorganic & medicinal chemistry, Mar-15, Volume: 15, Issue:6	Synthesis and structure-activity relationships of novel warfarin derivatives.
AID16339	Amount of deuterium retained was reported after normal workup in beta-naphthoflavone-treated male rats with the substrate rac 7-D	1985	Journal of medicinal chemistry, Aug, Volume: 28, Issue:8	Substrate probes for the mechanism of aromatic hydroxylation catalyzed by cytochrome P-450: selectively deuterated analogues of warfarin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (36)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.78)	18.7374
1990's	7 (19.44)	18.2507
2000's	11 (30.56)	29.6817
2010's	15 (41.67)	24.3611
2020's	2 (5.56)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.22

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.

Metric	This Compound (vs All)
Research Demand Index	19.22 (24.57)
Research Supply Index	3.71 (2.92)
Research Growth Index	5.30 (4.65)
Search Engine Demand Index	15.26 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (19.22)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	4 (11.11%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	32 (88.89%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
3-methoxymorphinan 3-methoxymorphinan: dextromethorphan metabolite; RN & N1 from 9th CI Form Index; RN given refers to cpd without isomeric designation; structure in first source	2.01	1	0
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2.08	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.15	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	3.37	1	1	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
hydroxymethyltolbutamide hydroxymethyltolbutamide: tolbutamide metabolite. 4-hydroxytolbutamide : A urea that consists of 1-butylurea having a 4-hydroxymethylbenzenesulfonyl group attached at the 3-position.	2.39	2	0	benzyl alcohols; sulfonamide; ureas	metabolite
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	2.01	1	0	imidazolidine-2,4-dione	anticonvulsant
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.15	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.01	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
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.	2.04	1	0	primary 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
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.39	2	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	7.04	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.05	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	1.99	1	0	dihydrogen
4'-hydroxydiclofenac 4'-hydroxydiclofenac: metabolite of diclofenac; structure in first source. 4'-hydroxydiclofenac : A monocarboxylic acid that is the 4'-hydroxylated metabolite of diclofenac.	2.15	1	0	dichlorobenzene; monocarboxylic acid; phenols; secondary amino compound	allergen; drug metabolite
4-hydroxymephenytoin 4-hydroxymephenytoin: metabolite of mephenytoin; RN given refers to cpd without isomeric designation	2.01	1	0	imidazolidine-2,4-dione
etravirine [no description available]	2.08	1	0	aminopyrimidine; aromatic ether; dinitrile; organobromine compound	antiviral agent; HIV-1 reverse transcriptase inhibitor
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.15	1	0
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	2	1	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	2.46	2	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
xk 469 XK 469: structure in first source	2.05	1	0
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.03	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
acenocoumarol Acenocoumarol: A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233). acenocoumarol : A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group.	2.03	1	0	C-nitro compound; hydroxycoumarin; methyl ketone	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
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.	7.5	35	4	benzenes; hydroxycoumarin; methyl ketone
ferulenol ferulenol: intoxicating component of powdered Ferula communis variety brevifolia; RN given for (E,E)-isomer	2.03	1	0
bromfenacoum [no description available]	2.03	1	0	benzenes; naphthalenes; ring assembly
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.	2.03	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
4'-hydroxywarfarin 4'-hydroxywarfarin: metabolite of warfarin; RN given refers to cpd without isomeric designation; structure given in first source	2.7	3	0	hydroxycoumarin
6-hydroxywarfarin 6-hydroxywarfarin: metabolite of (R)-warfarin; RN given refers to parent cpd	3.71	10	0
10-hydroxywarfarin 10-hydroxywarfarin: structure given in first source	2.75	3	0	hydroxycoumarin
8-hydroxywarfarin 8-hydroxywarfarin: metabolic marker for (S)-mephenytoin hydroxylase (P4502C19); structure in first source	8.42	7	0
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	3.44	1	1	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient

Condition	Relationship Strength	Studies
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.15	1
Blood Clot [description not available]	2.15	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.15	1
Inborn Errors of Metabolism [description not available]	2.11	1
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	2.11	1
Auricular Fibrillation [description not available]	2.05	1
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	2.05	1
Thromboembolism Obstruction of a blood vessel (embolism) by a blood clot (THROMBUS) in the blood stream.	2.02	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.68	3

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