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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.

CNS Activity

Originator

Vogel, A.
1
Sources: DOI: 10.1002/andp.18200640205

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
 6.2 µM [IC50]
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Preventing
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Approved
8583
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

2012
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.029 mg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/598421
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/598421
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
1.81 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1036930
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1036930
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1036930
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
1.018 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/598421
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/598421
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
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:
https://pubmed.ncbi.nlm.nih.gov/9929524
unhealthy, 33 - 84
Health Status: unhealthy
Age Group: 33 - 84
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9929524
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (6.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9929524
7 g 1 times / day multiple, oral
Highest studied dose
Dose: 7 g, 1 times / day
Route: oral
Route: multiple
Dose: 7 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8132703
unhealthy, 52.8
Health Status: unhealthy
Age Group: 52.8
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8132703
DLT: Nausea...
Dose limiting toxicities:
Nausea (57%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8132703
1600 mg 1 times / day multiple, oral
Studied dose
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2591993
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2591993
DLT: Function liver abnormal...
Dose limiting toxicities:
Function liver abnormal (0.37%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2591993
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:
https://pubmed.ncbi.nlm.nih.gov/9929524
unhealthy, 33 - 84
Health Status: unhealthy
Age Group: 33 - 84
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9929524
Nausea 57%
DLT, Disc. AE
7 g 1 times / day multiple, oral
Highest studied dose
Dose: 7 g, 1 times / day
Route: oral
Route: multiple
Dose: 7 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8132703
unhealthy, 52.8
Health Status: unhealthy
Age Group: 52.8
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8132703
Function liver abnormal 0.37%
DLT, Disc. AE
1600 mg 1 times / day multiple, oral
Studied dose
Dose: 1600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2591993
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2591993
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
626
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
626
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:28794
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28794
ChemicalBook
CB3112168
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3112168
eMolecules
494397
https://www.emolecules.com/cgi-bin/more?vid=494397
MolPort
MolPort-000-881-054
https://www.molport.com/shop/molecule-link/MolPort-000-881-054
Selleck Chemicals
coumarin
http://www.selleckchem.com/products/coumarin.html
ZINC
ZINC000000074709
http://zinc15.docking.org/substances/ZINC000000074709
PubMed

PubMed

TitleDatePubMed
Role of induction of specific hepatic cytochrome P450 isoforms in epoxidation of 4-vinylcyclohexene.
2001-09
Depentylation of the rat esophageal carcinogen, methyl-n-pentylnitrosamine, by microsomes from various human and rat tissues and by cytochrome P450 2A3.
2001-09
Antiproliferative effect of isopentenylated coumarins on several cancer cell lines.
2001-08-11
Diels--Alder bioconjugation of diene-modified oligonucleotides.
2001-08-10
Frequency-domain fluorescence microscopy with the LED as a light source.
2001-08
Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate.
2001-08
Quassinoids from Eurycoma harmandiana.
2001-08
Lack of effect of coumarin on the formation of micronuclei in an in vivo mouse micronucleus assay.
2001-08
Acetoxy-4-methylcoumarins confer differential protection from aflatoxin B(1)-induced micronuclei and apoptosis in lung and bone marrow cells.
2001-07-25
On-wafer spectrofluorometric method for determination of relative quantum yields of photoacid generation in chemically amplified resists.
2001-07-15
A fluorescent receptor assay for benzodiazepines using coumarin-labeled desethylflumazenil as ligand.
2001-07-01
Chemical constituents of Prangos tschiniganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity.
2001-07
Fenofibrate and warfarin interaction.
2001-07
Screening of organosulfur compounds as inhibitors of human CYP2A6.
2001-07
Neurological outcome in school-age children after in utero exposure to coumarins.
2001-07
[An uncommon cause of severe soft tissue bleeding during phenprocoumon treatment].
2001-06-22
Determination of coumarin in fragrance products by capillary gas chromatography with electron capture detection.
2001-06-22
Identification of a single nucleotide polymorphism in the TATA box of the CYP2A6 gene: impairment of its promoter activity.
2001-06-08
Fine Tuning of physico-chemical parameters to optimise a new series of novobiocin analogues.
2001-06-04
Coumarin derivatives as protease-sensitive prodrugs.
2001-06
[Conservative therapy of acute pelvic-leg vein thrombosis].
2001-06
Cytotoxic constituents of Psoralea corylifolia.
2001-06
Ischaemic jejunal stenosis complicating portal and mesenteric vein thrombosis: a report of two cases.
2001-06
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.
2001-06
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs.
2001-06
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells.
2001-06
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.
2001-06
Consumption of watercress fails to alter coumarin metabolism in humans.
2001-06
Extreme warfarin sensitivity in siblings associated with multiple cytochrome P450 polymorphisms.
2001-06
[Psychiatric comorbidity in somatic disorders. Psychophytopharmaceuticals are worth a try].
2001-05-28
Effects of scopoletin and aflatoxin B1 on bovine hepatic mitochondrial respiratory complexes, 2: a-ketoglutarate cytochrome c and succinate cytochrome c reductases.
2001-05-24
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.
2001-05-16
Coumarin substrates for cytochrome P450 2D6 fluorescence assays.
2001-05-15
Human cytochrome P450 isozymes in metabolism and health effects of gasoline ethers.
2001-05
Synthesis, physicochemical characterization, and cytotoxic screening of new zirconium complexes with coumarin derivatives.
2001-05
Self-management of oral anticoagulation in children with congenital heart disease.
2001-05
A prenyloxycoumarin from Psiadia dentata.
2001-05
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.
2001-05
Expression of CYP2A6 in tumor cells augments cellular sensitivity to tegafur.
2001-05
Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships.
2001-05
Prospective study on the usefulness of lung scan in patients with deep vein thrombosis of the lower limbs.
2001-05
Optimization of an exogenous metabolic activation system for FETAX. I. Post-isolation rat liver microsome mixtures.
2001-05
Does the location of thrombosis determine the risk of disease recurrence in patients with proximal deep vein thrombosis?
2001-05
[Phenprocoumon-induced necrotizing hepatitis].
2001-04-20
[Hepatotoxicity of medications].
2001-04-14
New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity.
2001-04
Determination of coumarin metabolism in Turkish population.
2001-04
Interaction of coumarin derivatives with human serum albumin: investigation by fluorescence spectroscopic technique and modeling studies.
2001-04
Prothrombin time ratio is reduced by magnesium contamination in evacuated blood collection tubes.
2001-04
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
Patents

Patents

JP1051688A
1
JP2000016988A
1
JP2000218940A
1
JP2000256487A
1
JP2000302661A
1
JP2000319154A
18
JP2000328039A
1
JP2002370963A
2
JP2002506806A
4
JP2003212865A
1
JP2003518246A
1
JP2004075709A
1
JP2004123674A
11
JP2004123675A
11
JP2004244407A
1
JP2005247976A
1
JP2005500055A
1
JP2006121111A
1
JP2009171931A
3
JP2010090242A
1
JP2011046736A
1
JP2011514532A
1
JP2011528275A
456
JP2012500780A
10
JPH00859463A
2
JPH01295165A
2
JPH02149501A
2
JPH02169586A
1
JPH03206006A
1
JPH0348674A
1
JPH04124184A
1
JPH04182337A
1
JPH04294148A
1
JPH04308510A
1
JPH05117262A
1
JPH05186454A
1
JPH05331161A
2
JPH06128109A
1
JPH06298758A
1
JPH069892A
1
JPH07207178A
1
JPH07258566A
1
JPH07278132A
1
JPH0776583A
1
JPH0874196A
1
JPH09279081A
1
JPH093054A
1
JPH0952891A
2
JPH10267931A
1
JPH10306110A
1
JPH1038878A
1

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 Mon Mar 31 17:53:07 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:07 GMT 2025
Record UNII
A4VZ22K1WT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COUMARIN
HSDB   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
COUMARINUM
HPUS  
Preferred 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
NCI-C07103
Common Name English
COUMARIN (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
COUMARIN [MART.]
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 Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
NCI_THESAURUS C263
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
NCI_THESAURUS C54060
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
EPA PESTICIDE CODE 127301
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
FDA ORPHAN DRUG 84294
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
Code System Code Type Description
NSC
8774
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
DRUG BANK
DB04665
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
CAS
91-64-5
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
MESH
C030123
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
PUBCHEM
323
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
HSDB
1623
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
DRUG CENTRAL
738
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
DAILYMED
A4VZ22K1WT
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
WIKIPEDIA
COUMARIN
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
RXCUI
2898
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
202-086-7
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
ChEMBL
CHEMBL6466
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
MERCK INDEX
m3820
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY Merck Index
FDA UNII
A4VZ22K1WT
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
NCI_THESAURUS
C397
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
SMS_ID
100000079833
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID7020348
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
CHEBI
28794
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
EVMPD
SUB13479MIG
Created by admin on Mon Mar 31 17:53:07 GMT 2025 , Edited by admin on Mon Mar 31 17:53:07 GMT 2025
PRIMARY
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ACTIVE MOIETY
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