U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H6O2
Molecular Weight 146.1427
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COUMARIN

SMILES

O=C1OC2=C(C=CC=C2)C=C1

InChI

InChIKey=ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H

HIDE SMILES / InChI

Molecular Formula C9H6O2
Molecular Weight 146.1427
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Sources: DOI: 10.4172/2157-7544.1000130
Curator's Comment: description was created based on several sources, including: http://www.inchem.org/documents/jecfa/jecmono/v16je10.htm | https://www.ncbi.nlm.nih.gov/pubmed/20024932

Coumarin itself was first isolated from the tonka bean Coumarouna odorata. Coumarin and its derivatives are alpha-benzopyrones. Coumarin is metabolized in humans to 7-hydroxycoumarin. Coumarin is a secondary phytochemical with hepatotoxic and carcinogenic properties. For the carcinogenic effect, a genotoxic mechanism was considered possible. Coumarins have a significant effect on physiological, bacteriostatic and anti-tumor activity. Coumarins have potent edema protective function and thus involved in the treatment of lymphedema, elephantiasis and other high protein edema conditions. Coumarin has appetite-suppressing properties.

Originator

Sources: DOI: 10.1002/andp.18200640205

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
HOMEOPATHIC COUMARIN

Approved Use

For temporary relief of allergies caused by dairy products, foods, tobacco, wheat, bowel disorders including celiac disease, colitis, poor digestion, back and neck pain and asthma.

Launch Date

1.34066877E12
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.029 mg × h/mL
0.857 mg/kg single, oral
dose: 0.857 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.191 mg × h/mL
0.25 mg/kg single, intravenous
dose: 0.25 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.018 h
0.857 mg/kg single, oral
dose: 0.857 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.769 h
0.25 mg/kg single, intravenous
dose: 0.25 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.81 h
0.125 mg/kg single, oral
dose: 0.125 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.45 h
0.2 mg/kg single, oral
dose: 0.2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.49 h
0.25 mg/kg single, oral
dose: 0.25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
COUMARIN blood
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg 2 times / day multiple, oral
Studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources: Page: p.349
unhealthy, 33 - 84
n = 139
Health Status: unhealthy
Condition: Lymphedema
Age Group: 33 - 84
Sex: F
Population Size: 139
Sources: Page: p.349
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (6.5%)
Sources: Page: p.349
7 g 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 7 g, 1 times / day
Route: oral
Route: multiple
Dose: 7 g, 1 times / day
Co-administed with::
cimetidine, p.o(300 mg; 4/day)
Sources: Page: S 40
unhealthy, 52.8
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 52.8
Sex: M+F
Population Size: 7
Sources: Page: S 40
DLT: Nausea...
Dose limiting toxicities:
Nausea (57%)
Sources: Page: S 40
1600 mg 1 times / day multiple, oral (max)
Studied dose
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Sources: Page: p.502
unhealthy
n = 2173
Health Status: unhealthy
Condition: Cancer|Infections
Sex: M+F
Population Size: 2173
Sources: Page: p.502
DLT: Function liver abnormal...
Dose limiting toxicities:
Function liver abnormal (0.37%)
Sources: Page: p.502
AEs

AEs

AESignificanceDosePopulation
Hepatotoxicity 6.5%
Disc. AE
200 mg 2 times / day multiple, oral
Studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources: Page: p.349
unhealthy, 33 - 84
n = 139
Health Status: unhealthy
Condition: Lymphedema
Age Group: 33 - 84
Sex: F
Population Size: 139
Sources: Page: p.349
Nausea 57%
DLT, Disc. AE
7 g 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 7 g, 1 times / day
Route: oral
Route: multiple
Dose: 7 g, 1 times / day
Co-administed with::
cimetidine, p.o(300 mg; 4/day)
Sources: Page: S 40
unhealthy, 52.8
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 52.8
Sex: M+F
Population Size: 7
Sources: Page: S 40
Function liver abnormal 0.37%
DLT, Disc. AE
1600 mg 1 times / day multiple, oral (max)
Studied dose
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Sources: Page: p.502
unhealthy
n = 2173
Health Status: unhealthy
Condition: Cancer|Infections
Sex: M+F
Population Size: 2173
Sources: Page: p.502
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
High-throughput cytochrome P450 (CYP) inhibition screening via a cassette probe-dosing strategy. VI. Simultaneous evaluation of inhibition potential of drugs on human hepatic isozymes CYP2A6, 3A4, 2C9, 2D6 and 2E1.
2001
Drug interaction: omeprazole and phenprocoumon.
2001
Long-term clinical course of proximal deep venous thrombosis and detection of recurrent thrombosis.
2001
New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity.
2001 Apr
Determination of coumarin metabolism in Turkish population.
2001 Apr
Prothrombin time ratio is reduced by magnesium contamination in evacuated blood collection tubes.
2001 Apr
[Hepatotoxicity of medications].
2001 Apr 14
The Cap'n'Collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes.
2001 Apr 15
[Phenprocoumon-induced necrotizing hepatitis].
2001 Apr 20
Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful beta-glucosidase inhibitors.
2001 Apr 23
Frequency-domain fluorescence microscopy with the LED as a light source.
2001 Aug
Quassinoids from Eurycoma harmandiana.
2001 Aug
[Recurrent coumarin necrosis in type II protein S deficiency].
2001 Feb
Caffeine metabolism before and after liver transplantation.
2001 Feb
Micronucleus formation in human lymphocytes and in the metabolically competent human hepatoma cell line Hep-G2: results with 15 naturally occurring substances.
2001 Jan-Feb
Chemical constituents of Prangos tschiniganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity.
2001 Jul
Screening of organosulfur compounds as inhibitors of human CYP2A6.
2001 Jul
Neurological outcome in school-age children after in utero exposure to coumarins.
2001 Jul
A fluorescent receptor assay for benzodiazepines using coumarin-labeled desethylflumazenil as ligand.
2001 Jul 1
Coumarin derivatives as protease-sensitive prodrugs.
2001 Jun
Cytotoxic constituents of Psoralea corylifolia.
2001 Jun
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs.
2001 Jun
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells.
2001 Jun
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.
2001 Jun
Consumption of watercress fails to alter coumarin metabolism in humans.
2001 Jun
[An uncommon cause of severe soft tissue bleeding during phenprocoumon treatment].
2001 Jun 22
Identification of a single nucleotide polymorphism in the TATA box of the CYP2A6 gene: impairment of its promoter activity.
2001 Jun 8
Clinical management of protein C deficiency.
2001 Mar
[Dyspnea caused by spontaneous hematoma of the oropharynx and larynx during marcumar therapy].
2001 Mar
Coagulation factor IX propeptide mutations causing coumarin hypersensitivity: identification of female alanine-10 valine heterozygotes.
2001 Mar
Genetic predisposition to bleeding during oral anticoagulant therapy: evidence for common founder mutations (FIXVal-10 and FIXThr-10) and an independent CpG hotspot mutation (FIXThr-10).
2001 Mar
Coumarins from the aerial part of Halocnemum strobilaceum.
2001 Mar
A comparative molecular field analysis of cytochrome P450 2A5 and 2A6 inhibitors.
2001 Mar
Immunomodulatory principles of Pelargonium sidoides.
2001 Mar
Intramolecular fluorescence resonance energy transfer system with coumarin donor included in beta-cyclodextrin.
2001 Mar 1
In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents.
2001 Mar 21
Induction of apoptosis by esculetin in human leukemia cells.
2001 Mar 23
Effects of scopoletin and aflatoxin B1 on bovine hepatic mitochondrial respiratory complexes, 2: a-ketoglutarate cytochrome c and succinate cytochrome c reductases.
2001 Mar-Apr
Self-management of oral anticoagulation in children with congenital heart disease.
2001 May
Mechanism of biochemical action of substituted benzopyran-2-ones. Part 8: Acetoxycoumarin: protein transacetylase specificity for aromatic nuclear acetoxy groups in proximity to the oxygen heteroatom.
2001 May
Expression of CYP2A6 in tumor cells augments cellular sensitivity to tegafur.
2001 May
Prospective study on the usefulness of lung scan in patients with deep vein thrombosis of the lower limbs.
2001 May
Optimization of an exogenous metabolic activation system for FETAX. I. Post-isolation rat liver microsome mixtures.
2001 May
Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s.
2001 May
Coumarin substrates for cytochrome P450 2D6 fluorescence assays.
2001 May 15
A comparison of aroclor 1254-induced and uninduced rat liver microsomes to human liver microsomes in phenytoin O-deethylation, coumarin 7-hydroxylation, tolbutamide 4-hydroxylation, S-mephenytoin 4'-hydroxylation, chloroxazone 6-hydroxylation and testosterone 6beta-hydroxylation.
2001 May 16
CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity.
2001 May 25
Antiproliferative effect of isopentenylated coumarins on several cancer cell lines.
2001 May-Jun
Determination of coumarin in fragrance products by capillary gas chromatography with electron capture detection.
2001 May-Jun
Role of induction of specific hepatic cytochrome P450 isoforms in epoxidation of 4-vinylcyclohexene.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The therapeutic dose of coumarin for the treatment of lymphedema.
6 mg/kg/day
Route of Administration: Oral
In Vitro Use Guide
Coumarin at concentrations of 100- 500 ug/ml inhibits the incorporation of [3H]thymidine into ACHN cells in a dose-dependent fashion.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:40 UTC 2023
Edited
by admin
on Fri Dec 15 15:17:40 UTC 2023
Record UNII
A4VZ22K1WT
Record Status Validated (UNII)
Record Version
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Name Type Language
COUMARIN
HSDB   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
COUMARIN (PROHIBITED) [FHFI]
Common Name English
COUMARIN (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
COUMARIN [IARC]
Common Name English
CIS-O-COUMARINIC ACID LACTONE
Common Name English
CUMARIN
Common Name English
Coumarin [WHO-DD]
Common Name English
COUMARIN [MI]
Common Name English
COUMARINIC ANHYDRIDE
Systematic Name English
COUMARINUM
HPUS  
Common Name English
NCI-C07103
Common Name English
COUMARIN (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
COUMARIN [MART.]
Common Name English
COUMARIN [INCI]
Common Name English
COUMARINIC LACTONE
Common Name English
2-PROPENOIC ACID, 3-(2-HYDROXYPHENYL)-, .DELTA.-LACTONE
Common Name English
TONKA BEAN CAMPHOR
Common Name English
2H-1-BENZOPYRAN-2-ONE
Systematic Name English
2H-BENZO(B)PYRAN-2-ONE
Systematic Name English
NSC-8774
Code English
COUMARINUM [HPUS]
Common Name English
1,2-BENZOPYRONE
Common Name English
COUMARIN [HSDB]
Common Name English
O-HYDROXYCINNAMIC ACID LACTONE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 189.130
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
NCI_THESAURUS C263
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
NCI_THESAURUS C54060
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
EPA PESTICIDE CODE 127301
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
FDA ORPHAN DRUG 84294
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
Code System Code Type Description
NSC
8774
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
DRUG BANK
DB04665
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
CAS
91-64-5
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
MESH
C030123
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
PUBCHEM
323
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
HSDB
1623
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
DRUG CENTRAL
738
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
DAILYMED
A4VZ22K1WT
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
WIKIPEDIA
COUMARIN
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
RXCUI
2898
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
202-086-7
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL6466
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
MERCK INDEX
m3820
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY Merck Index
FDA UNII
A4VZ22K1WT
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
NCI_THESAURUS
C397
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
SMS_ID
100000079833
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID7020348
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
CHEBI
28794
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
EVMPD
SUB13479MIG
Created by admin on Fri Dec 15 15:17:40 UTC 2023 , Edited by admin on Fri Dec 15 15:17:40 UTC 2023
PRIMARY
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