COUMARIN

US Previously Marketed

First marketed in 1921

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 Search

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2A6 16 Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18064444 \| https://www.ncbi.nlm.nih.gov/pubmed/10781881	Inhibitor 8504
Cytochrome P450 2A13 3 Target ID: CHEMBL3542436 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16988941	Inhibitor 8504	6.2 µM [IC50]
Vitamin k epoxide reductase complex subunit 1 isoform 1 22 Target ID: CHEMBL1930 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17635701 \| DOI: 10.1160/TH05-04-0290	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Lymphedema 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16000056	Primary	Phase II 1147	Unknown Approved Use Unknown
Post-thrombotic syndrome 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18639417	Primary	Phase II 1147	Unknown Approved Use Unknown
Acute myocardial infarction 37 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12163424	Preventing	Phase II 1147	Unknown Approved Use Unknown
Allergy 44 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=02d05771-f46d-405d-a7d7-b6e05a7572a7	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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 626

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2A6 626	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7369699/	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
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	11344532
Coumarin formation in novobiocin biosynthesis: beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI.	2001 Apr	11325587
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	11309284
Quassinoids from Eurycoma harmandiana.	2001 Aug	11454344
Lack of effect of coumarin on the formation of micronuclei in an in vivo mouse micronucleus assay.	2001 Aug	11434991
[Recurrent coumarin necrosis in type II protein S deficiency].	2001 Feb	11284095
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.	2001 Feb	11159803
Coumarin and chromen-4-one analogues as tautomerase inhibitors of macrophage migration inhibitory factor: discovery and X-ray crystallography.	2001 Feb 15	11170644
Spectral studies on metal-ligand bonding in complexes of 1-acetyl-2-(coumariniminecarboxamide-3-yl)hydrazine.	2001 Jan	11209866
Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans.	2001 Jan	11180041
Tissue factor activity in human monocytes is regulated by plasma: implications for the high and low responder phenomenon.	2001 Jan	11167790
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	11299780
Acetoxy-4-methylcoumarins confer differential protection from aflatoxin B(1)-induced micronuclei and apoptosis in lung and bone marrow cells.	2001 Jul 25	11423343
Coumarin derivatives as protease-sensitive prodrugs.	2001 Jun	11475911
Cytotoxic constituents of Psoralea corylifolia.	2001 Jun	11440079
[An uncommon cause of severe soft tissue bleeding during phenprocoumon treatment].	2001 Jun 22	11455667
Fine Tuning of physico-chemical parameters to optimise a new series of novobiocin analogues.	2001 Jun 4	11378377
Identification of a single nucleotide polymorphism in the TATA box of the CYP2A6 gene: impairment of its promoter activity.	2001 Jun 8	11394901
Coagulation factor IX propeptide mutations causing coumarin hypersensitivity: identification of female alanine-10 valine heterozygotes.	2001 Mar	11307837
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	11301870
Coumarins from the aerial part of Halocnemum strobilaceum.	2001 Mar	11295318
A comparative molecular field analysis of cytochrome P450 2A5 and 2A6 inhibitors.	2001 Mar	11289074
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	11181487
Role of dipole moment of solvents in formation and stabilization of the TICT states in Coumarin 445 under nitrogen laser excitation.	2001 Mar 1	11300560
In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents.	2001 Mar 21	11292319
Self-management of oral anticoagulation in children with congenital heart disease.	2001 May	11388620
Does the location of thrombosis determine the risk of disease recurrence in patients with proximal deep vein thrombosis?	2001 May	11343664
Coumarin substrates for cytochrome P450 2D6 fluorescence assays.	2001 May 15	11355862
CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity.	2001 May 25	11278503
[Psychiatric comorbidity in somatic disorders. Psychophytopharmaceuticals are worth a try].	2001 May 28	11434262
Determination of coumarin in fragrance products by capillary gas chromatography with electron capture detection.	2001 May-Jun	11417632

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

COUMARIN

Official Name

English

COUMARINUM

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