COUMARIN

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

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

Description

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	Inhibitor 8,504
Cytochrome P450 2A13 3	Inhibitor 8,504	6.2 µM [IC50]
Vitamin k epoxide reductase complex subunit 1 isoform 1 22	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Lymphedema 4	Primary	Phase II 1,147	Unknown
Post-thrombotic syndrome 2	Primary	Phase II 1,147	Unknown
Acute myocardial infarction 37	Preventing	Phase II 1,147	Unknown
Allergy 44	Primary	Approved 8,583	HOMEOPATHIC COUMARIN

AUC

Value	Dose	Co-administered	Analyte	Population
0.029 mg × h/mL	0.857 mg/kg single, oral		COUMARIN blood	Homo sapiens
0.191 mg × h/mL	0.25 mg/kg single, intravenous		COUMARIN blood	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.81 h	0.125 mg/kg single, oral	COUMARIN blood	Homo sapiens
1.45 h	0.2 mg/kg single, oral	COUMARIN blood	Homo sapiens
1.49 h	0.25 mg/kg single, oral	COUMARIN blood	Homo sapiens
1.018 h	0.857 mg/kg single, oral	COUMARIN blood	Homo sapiens
0.769 h	0.25 mg/kg single, intravenous	COUMARIN blood	Homo sapiens

Doses

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Dose	Population	Adverse events
200 mg 2 times / day multiple, oral Studied dose	unhealthy, 33 - 84	Disc. AE: Hepatotoxicity...
7 g 1 times / day multiple, oral Highest studied dose	unhealthy, 52.8	DLT: Nausea...
1600 mg 1 times / day multiple, oral Studied dose	unhealthy	DLT: Function liver abnormal...

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AEs

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AE	Significance	Dose	Population
Hepatotoxicity	6.5% Disc. AE	200 mg 2 times / day multiple, oral Studied dose	unhealthy, 33 - 84
Nausea	57% DLT, Disc. AE	7 g 1 times / day multiple, oral Highest studied dose	unhealthy, 52.8
Function liver abnormal	0.37% DLT, Disc. AE	1600 mg 1 times / day multiple, oral Studied dose	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 626

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2A6 626	substrate 4,014	yes

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Sourcing

Sourcing

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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

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PubMed

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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
Long-term clinical course of proximal deep venous thrombosis and detection of recurrent thrombosis.	2001	11288949
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
Lack of effect of coumarin on the formation of micronuclei in an in vivo mouse micronucleus assay.	2001 Aug	11434991