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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H6O2
Molecular Weight 146.1431
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COUMARIN

SMILES

c1ccc2c(c1)ccc(=O)o2

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 146.1431
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
New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity.
2001 Apr
Coumarin formation in novobiocin biosynthesis: beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI.
2001 Apr
Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk.
2001 Apr
[Hepatotoxicity of medications].
2001 Apr 14
Frequency-domain fluorescence microscopy with the LED as a light source.
2001 Aug
Diels--Alder bioconjugation of diene-modified oligonucleotides.
2001 Aug 10
[Recurrent coumarin necrosis in type II protein S deficiency].
2001 Feb
The in vivo dermal absorption and metabolism of [4-14C] coumarin by rats and by human volunteers under simulated conditions of use in fragrances.
2001 Feb
Rapid high-performance liquid chromatography analysis for the quantitative determination of oleuropein in Olea europaea leaves.
2001 Feb
Genetic polymorphisms of cytochrome P450 2A6 in a case-control study on lung cancer in a French population.
2001 Feb
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.
2001 Feb
Genetic polymorphisms in the cytochrome P450 2A6 (CYP2A6) gene: implications for interindividual differences in nicotine metabolism.
2001 Feb
Coumarin and chromen-4-one analogues as tautomerase inhibitors of macrophage migration inhibitory factor: discovery and X-ray crystallography.
2001 Feb 15
Development of a profitable procedure for the extraction of 2-H-1-benzopyran-2-one (coumarin) from Mikania glomerata.
2001 Jan
Inhibition of concanavalin A-induced mice hepatitis by coumarin derivatives.
2001 Jan
Terpenoids from Guarea rhophalocarpa.
2001 Jan
Antimicrobial activity of new coumarin derivatives.
2001 Jan
Spectral studies on metal-ligand bonding in complexes of 1-acetyl-2-(coumariniminecarboxamide-3-yl)hydrazine.
2001 Jan
[Sensitization and crossreaction of simple coumarins].
2001 Jan
Dietary strategies to counteract the effects of mycotoxins: a review.
2001 Jan
Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans.
2001 Jan
Tissue factor activity in human monocytes is regulated by plasma: implications for the high and low responder phenomenon.
2001 Jan
Characterization of xenobiotic-metabolizing cytochrome P450 (CYP) forms in ringed and grey seals from the Baltic Sea and reference sites.
2001 Jan
Oral anticoagulants: mechanism of action, clinical effectiveness, and optimal therapeutic range.
2001 Jan
In utero exposure to coumarins and cognition at 8 to 14 years old.
2001 Jan
cAMP mediated upregulation of CYP2A5 in mouse hepatocytes.
2001 Jan 26
Chemical constituents of Prangos tschiniganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity.
2001 Jul
On-wafer spectrofluorometric method for determination of relative quantum yields of photoacid generation in chemically amplified resists.
2001 Jul 15
[Conservative therapy of acute pelvic-leg vein thrombosis].
2001 Jun
Ischaemic jejunal stenosis complicating portal and mesenteric vein thrombosis: a report of two cases.
2001 Jun
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs.
2001 Jun
Fine Tuning of physico-chemical parameters to optimise a new series of novobiocin analogues.
2001 Jun 4
Cnidicin, a coumarin, from the root of Angelica koreana, inhibits the degranulation of mast cell and the NO generation in RAW 264.7 cells.
2001 Mar
A comparative molecular field analysis of cytochrome P450 2A5 and 2A6 inhibitors.
2001 Mar
Immunomodulatory principles of Pelargonium sidoides.
2001 Mar
P450 enzyme expression patterns in the NCI human tumor cell line panel.
2001 Mar
In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene.
2001 Mar
Intramolecular fluorescence resonance energy transfer system with coumarin donor included in beta-cyclodextrin.
2001 Mar 1
Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues.
2001 Mar 1
A novel single nucleotide polymorphism altering stability and activity of CYP2a6.
2001 Mar 2
Frequency of CYP2A6 gene deletion and its relation to risk of lung and esophageal cancer in the Chinese population.
2001 Mar 20
Synthesis, physicochemical characterization, and cytotoxic screening of new zirconium complexes with coumarin derivatives.
2001 May
A prenyloxycoumarin from Psiadia dentata.
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
[Psychiatric comorbidity in somatic disorders. Psychophytopharmaceuticals are worth a try].
2001 May 28
Antiproliferative effect of isopentenylated coumarins on several cancer cell lines.
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 Jun 25 22:23:09 UTC 2021
Edited
by admin
on Fri Jun 25 22:23:09 UTC 2021
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
COUMARIN [WHO-DD]
Common Name English
CIS-O-COUMARINIC ACID LACTONE
Common Name English
CUMARIN
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 Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
NCI_THESAURUS C263
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
NCI_THESAURUS C54060
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
EPA PESTICIDE CODE 127301
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
FDA ORPHAN DRUG 84294
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
Code System Code Type Description
DRUG BANK
DB04665
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
CAS
91-64-5
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
MESH
C030123
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
PUBCHEM
323
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
HSDB
1623
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
DRUG CENTRAL
738
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
WIKIPEDIA
COUMARIN
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
RXCUI
2898
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
202-086-7
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL6466
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
MERCK INDEX
M3820
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY Merck Index
FDA UNII
A4VZ22K1WT
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
NCI_THESAURUS
C397
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
EPA CompTox
91-64-5
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
EVMPD
SUB13479MIG
Created by admin on Fri Jun 25 22:23:10 UTC 2021 , Edited by admin on Fri Jun 25 22:23:10 UTC 2021
PRIMARY
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