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(C)=CC(=O)C2=C(OC)C3=C1OC=C3

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 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24069365	Inhibitor 8297
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24069365	Activator 1430
Calcium influx 1 Target ID: Calcium influx Sources: https://www.ncbi.nlm.nih.gov/pubmed/2568462	Inhibitor 8297

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 1132	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Angina pectoris 106 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 8429	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Asthma 241 Sources: https://www.drugs.com/npp/khella.html https://www.ncbi.nlm.nih.gov/pubmed/14868371	Palliative	Approved 8429	Ammivin Approved Use Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110 CYP1B1 19 CYP1A2 1524 CYP2C19 1478 OATP1B1 788 OATP1B3 706		CYP1A1 108

Drug as perpetrator

Target	Modality	Activity
CYP2C19 1553	inhibitor 3277 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 1819	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	no [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 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 67	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31458985/, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	weak [IC50 34.6 uM]
CYP1A2 1692	inhibitor 3277 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 218	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31458985/, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6083783/	yes [IC50 4.02 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0NzQ2In19	yes [Inhibition 10 uM]
CYP1A1 218	inducer 1573 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
MolPort	MolPort-000-724-273	https://www.molport.com/shop/molecule-link/MolPort-000-724-273
ZINC	ZINC000000056654	http://zinc15.docking.org/substances/ZINC000000056654
eMolecules	524621	https://www.emolecules.com/cgi-bin/more?vid=524621

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Topical khellin and natural sunlight in the outpatient treatment of recalcitrant palmoplantar pompholyx: report of an open pilot study.	2005	16286756
Dynamic properties of Legionella-containing phagosomes in Dictyostelium amoebae.	2005 Jul	15953031
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 Jul 29	15932783
Coronin proteins as multifunctional regulators of the cytoskeleton and membrane trafficking.	2005 Jun	15892111
Measurement of daphnoretin in plasma of freely moving rat by liquid chromatography.	2005 May 6	15909531
A novel homologue of coronin colocalizes with actin in filament-like structures in Leishmania.	2005 Oct	16024104
A single-nucleotide polymorphism in the gene encoding lymphoid protein tyrosine phosphatase (PTPN22) confers susceptibility to generalised vitiligo.	2005 Oct	16015369
Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions.	2005 Oct 20	16833259
Downregulation of TACO gene transcription restricts mycobacterial entry/survival within human macrophages.	2005 Sep 1	16040207
Phosphorylation of coronin 1B by protein kinase C regulates interaction with Arp2/3 and cell motility.	2005 Sep 9	16027158
Green tea polyphenol inhibits Mycobacterium tuberculosis survival within human macrophages.	2006	16352457
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 Apr	16395733
Coronins: the return of the crown.	2006 Aug	16806932
Effusion and solid lymphomas have distinctive gene and protein expression profiles in an animal model of primary effusion lymphoma.	2006 Aug	16741895
Requirement for coronin 1 in T lymphocyte trafficking and cellular homeostasis.	2006 Aug 11	16902139
Immunology. When F-actin becomes too much of a good thing.	2006 Aug 11	16902113
Transcriptional regulation of artemin is related to neurite outgrowth and actin polymerization in mature DRG neurons.	2006 Aug 14	16781061
Localization of CORO1A in the macrophages containing Mycobacterium leprae.	2006 Aug 30	17327897
Time-resolved responses to chemoattractant, characteristic of the front and tail of Dictyostelium cells.	2006 Dec 11	17126332
The identification of a new actin-binding region in p57.	2006 Jan	16467882
The crystal structure of murine coronin-1: a regulator of actin cytoskeletal dynamics in lymphocytes.	2006 Jan	16407068
Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process.	2006 Mar	16520866
Microtubules regulate disassembly of epithelial apical junctions.	2006 Mar 1	16509970
The tumor suppressor protein p53 is required for neurite outgrowth and axon regeneration.	2006 Sep 6	16946709
The embryonic muscle transcriptome of Caenorhabditis elegans.	2007	17848203
A new steroid glycoside and furochromones from Cyperus rotundus L.	2007 Apr	17479423
Global gene expression analysis and regulation of the principal genes expressed in bovine placenta in relation to the transcription factor AP-2 family.	2007 Apr 27	17462098
Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents.	2007 Aug	17346862
Lipoamide dehydrogenase mediates retention of coronin-1 on BCG vacuoles, leading to arrest in phagosome maturation.	2007 Aug 15	17652161
Neuronal morphogenesis is regulated by the interplay between cyclin-dependent kinase 5 and the ubiquitin ligase mind bomb 1.	2007 Aug 29	17728463
Mechanism of inducible nitric oxide synthase exclusion from mycobacterial phagosomes.	2007 Dec	18069890
Actin-binding proteins coronin-1a and IBA-1 are effective microglial markers for immunohistochemistry.	2007 Jul	17341475
Survival of mycobacteria in macrophages is mediated by coronin 1-dependent activation of calcineurin.	2007 Jul 13	17632055
TB or not TB: calcium regulation in mycobacterial survival.	2007 Jul 13	17632049
Epithelial grafting for vitiligo requires ultraviolet A phototherapy to increase success rate.	2007 Jun	17524129
Coronin 3 involvement in F-actin-dependent processes at the cell cortex.	2007 Mar 10	17274980
Coronin 1B coordinates Arp2/3 complex and cofilin activities at the leading edge.	2007 Mar 9	17350576
Coronin function is required for chemotaxis and phagocytosis in human neutrophils.	2007 May 1	17442961
F-actin binding is essential for coronin 1B function in vivo.	2007 May 15	17456547
STATc is a key regulator of the transcriptional response to hyperosmotic shock.	2007 May 21	17517120
Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.	2007 Nov 7	17988377
An actin-based wave generator organizes cell motility.	2007 Sep	17696648
Functional analysis of cancer-associated EGFR mutants using a cellular assay with YFP-tagged EGFR intracellular domain.	2007 Sep 18	17877814
Competition between targeting signals in hybrid proteins provides information on their relative in vivo affinities for subcellular compartments.	2008 Feb	18054409
Coronin-1A stabilizes F-actin by bridging adjacent actin protomers and stapling opposite strands of the actin filament.	2008 Feb 22	18177666
The lupus-related Lmb3 locus contains a disease-suppressing Coronin-1A gene mutation.	2008 Jan	18199416
Distinct roles for Arp2/3 regulators in actin assembly and endocytosis.	2008 Jan	18177206
Coronin-1A epigenomics governs mycobacterial persistence in tuberculosis.	2008 Jan	18031535
Expression of coronin-3 (coronin-1C) in diffuse gliomas is related to malignancy.	2008 Mar	18189330

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 `Fri Dec 15 15:29:07 UTC 2023` Edited by `admin` on `Fri Dec 15 15:29:07 UTC 2023`
Record UNII	5G117T0TJZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KHELLIN

Official 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

CORONIN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45597