KHELLIN

US Previously Marketed

First approved in 1950

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O5
Molecular Weight	260.2421
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2OC=CC2=C(OC)C3=C1OC(C)=CC3=O

InChI

InChIKey=HSMPDPBYAYSOBC-UHFFFAOYSA-N

InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C14H12O5
Molecular Weight	260.2421
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/npp/khella.html | Krutmann, J. et al. (2008) Dermatological Phototherapy and Photodiagnostic Methods, page 168, retrieved from: https://books.google.ru/books?id=Z35aWU5TAWoC | https://www.ncbi.nlm.nih.gov/pubmed/14888509

Khellin is a crystalline extract of a crude drug, which has long been used in Egypt for the treatment of ureteral colic. It is used in the management of bronchial asthma and angina pectoris. Interest in khellin as an adjunct to ultraviolet (UV) light therapy in the treatment of vitiligo is based on the structural similarity between khellin and the psoralens. Success has been reported using oral and topical khellin in clinical studies but it is not likely that khellin will be approved for the treatment of vitiligo. Unwanted side effects of khellin include dizziness, reversible cholestatic jaundice, pseudoallergic reaction, and elevated levels of liver enzymes (transaminases and gamma-glutamyltransferase).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24069365	Inhibitor 8504
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24069365	Activator 1447
Calcium influx 1 Target ID: Calcium influx Sources: https://www.ncbi.nlm.nih.gov/pubmed/2568462	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Vitiligo 9 Sources: https://www.drugs.com/npp/khella.html http://emjreviews.com/blog/khellin-vitiligo-treatment/	Primary	Phase II 1147	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Angina pectoris 110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6421255 http://en.pharmacodia.com/web/drug/1_22584.html https://www.drugs.com/npp/khella.html	Palliative	Approved 8583	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Asthma 244 Sources: https://www.drugs.com/npp/khella.html https://www.ncbi.nlm.nih.gov/pubmed/14868371	Palliative	Approved 8583	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1B1 32 CYP1A2 2153 CYP2C19 2057 OATP1B1 1079 OATP1B3 961		CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDQ3NDYifX0%3D	no [IC50 >10 uM]
CYP1B1 93	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31458985/, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	weak [IC50 34.6 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	yes [IC50 0.04 uM]
CYP1A1 272	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31458985/, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	yes [IC50 4.02 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	yes [Inhibition 10 uM]
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/24069365/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6133	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6133
ChemicalBook	CB5269554	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5269554
eMolecules	524621	https://www.emolecules.com/cgi-bin/more?vid=524621
MolPort	MolPort-000-724-273	https://www.molport.com/shop/molecule-link/MolPort-000-724-273
ZINC	ZINC000000056654	http://zinc15.docking.org/substances/ZINC000000056654

PubMed

Title	Date	PubMed
Expression of coronin-3 (coronin-1C) in diffuse gliomas is related to malignancy.	2008-03	18189330
Coronin-1A stabilizes F-actin by bridging adjacent actin protomers and stapling opposite strands of the actin filament.	2008-02-22	18177666
Competition between targeting signals in hybrid proteins provides information on their relative in vivo affinities for subcellular compartments.	2008-02	18054409
The lupus-related Lmb3 locus contains a disease-suppressing Coronin-1A gene mutation.	2008-01	18199416
Distinct roles for Arp2/3 regulators in actin assembly and endocytosis.	2008-01	18177206
Coronin-1A epigenomics governs mycobacterial persistence in tuberculosis.	2008-01	18031535
Mechanism of inducible nitric oxide synthase exclusion from mycobacterial phagosomes.	2007-12	18069890
Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.	2007-11-07	17988377
Functional analysis of cancer-associated EGFR mutants using a cellular assay with YFP-tagged EGFR intracellular domain.	2007-09-18	17877814
An actin-based wave generator organizes cell motility.	2007-09	17696648
Neuronal morphogenesis is regulated by the interplay between cyclin-dependent kinase 5 and the ubiquitin ligase mind bomb 1.	2007-08-29	17728463
Lipoamide dehydrogenase mediates retention of coronin-1 on BCG vacuoles, leading to arrest in phagosome maturation.	2007-08-15	17652161
Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents.	2007-08	17346862
Survival of mycobacteria in macrophages is mediated by coronin 1-dependent activation of calcineurin.	2007-07-13	17632055
TB or not TB: calcium regulation in mycobacterial survival.	2007-07-13	17632049
Actin-binding proteins coronin-1a and IBA-1 are effective microglial markers for immunohistochemistry.	2007-07	17341475
Epithelial grafting for vitiligo requires ultraviolet A phototherapy to increase success rate.	2007-06	17524129
STATc is a key regulator of the transcriptional response to hyperosmotic shock.	2007-05-21	17517120
F-actin binding is essential for coronin 1B function in vivo.	2007-05-15	17456547
Coronin function is required for chemotaxis and phagocytosis in human neutrophils.	2007-05-01	17442961
Global gene expression analysis and regulation of the principal genes expressed in bovine placenta in relation to the transcription factor AP-2 family.	2007-04-27	17462098
A new steroid glycoside and furochromones from Cyperus rotundus L.	2007-04	17479423
Coronin 3 involvement in F-actin-dependent processes at the cell cortex.	2007-03-10	17274980
Coronin 1B coordinates Arp2/3 complex and cofilin activities at the leading edge.	2007-03-09	17350576
The embryonic muscle transcriptome of Caenorhabditis elegans.	2007	17848203
Time-resolved responses to chemoattractant, characteristic of the front and tail of Dictyostelium cells.	2006-12-11	17126332
The tumor suppressor protein p53 is required for neurite outgrowth and axon regeneration.	2006-09-06	16946709
Localization of CORO1A in the macrophages containing Mycobacterium leprae.	2006-08-30	17327897
Transcriptional regulation of artemin is related to neurite outgrowth and actin polymerization in mature DRG neurons.	2006-08-14	16781061
Requirement for coronin 1 in T lymphocyte trafficking and cellular homeostasis.	2006-08-11	16902139
Immunology. When F-actin becomes too much of a good thing.	2006-08-11	16902113
Coronins: the return of the crown.	2006-08	16806932
Effusion and solid lymphomas have distinctive gene and protein expression profiles in an animal model of primary effusion lymphoma.	2006-08	16741895
Application of 1D BIRD or X-filtered DEPT long-range C-C relay for detection of proton and carbon via four bonds and measuring long-range 13C-13C coupling constants.	2006-04	16395733
Microtubules regulate disassembly of epithelial apical junctions.	2006-03-01	16509970
Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process.	2006-03	16520866
The identification of a new actin-binding region in p57.	2006-01	16467882
The crystal structure of murine coronin-1: a regulator of actin cytoskeletal dynamics in lymphocytes.	2006-01	16407068
Green tea polyphenol inhibits Mycobacterium tuberculosis survival within human macrophages.	2006	16352457
Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions.	2005-10-20	16833259
A novel homologue of coronin colocalizes with actin in filament-like structures in Leishmania.	2005-10	16024104
A single-nucleotide polymorphism in the gene encoding lymphoid protein tyrosine phosphatase (PTPN22) confers susceptibility to generalised vitiligo.	2005-10	16015369
Phosphorylation of coronin 1B by protein kinase C regulates interaction with Arp2/3 and cell motility.	2005-09-09	16027158
Downregulation of TACO gene transcription restricts mycobacterial entry/survival within human macrophages.	2005-09-01	16040207
Proteomic identification of less oxidized brain proteins in aged senescence-accelerated mice following administration of antisense oligonucleotide directed at the Abeta region of amyloid precursor protein.	2005-07-29	15932783
Dynamic properties of Legionella-containing phagosomes in Dictyostelium amoebae.	2005-07	15953031
Coronin proteins as multifunctional regulators of the cytoskeleton and membrane trafficking.	2005-06	15892111
Measurement of daphnoretin in plasma of freely moving rat by liquid chromatography.	2005-05-06	15909531
Topical khellin and natural sunlight in the outpatient treatment of recalcitrant palmoplantar pompholyx: report of an open pilot study.	2005	16286756
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 200 mg/day Topical: as a 2% preparation

Route of Administration: Other

In Vitro Use Guide

In neutral O2-saturated aqueous solution, the photosensitized His degradation quantum yield is about 8x10(-5) for khellin. In O2-saturated aqueous solution, khellin photosensitized the oxidation of Trp with a quantum yield of 1.5x10(-4), which is quite low.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:41 GMT 2025`
Record UNII	5G117T0TJZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KHELLIN

Official Name

English

CORONIN

Preferred Name

English

NSC-37744

Code

English

khellin [INN]

Common Name

English

KHELLIN [MI]

Common Name

English

Khellin [WHO-DD]

Common Name

English

4,9-DIMETHOXY-7-METHYL-5H-FURO(3,2-G)(1)BENZOPYRAN-5-ONE

Systematic Name

English

VISCARDAN

Brand Name

English

KHELLIN [MART.]

Common Name

English

NSC-25509

Code

English

4,9-DIMETHOXY-7-METHYL-5-OXOFURO(3,2-G)-1,2-CHROMENE

Common Name

English

AMMIVIN

Brand Name

English

KHELLOYD

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45597