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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O5
Molecular Weight 260.2426
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KHELLIN

SMILES

Cc1cc(=O)c2c(c3ccoc3c(c2o1)OC)OC

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
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

Sources: DOI: 10.1002/cber.19380710118

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Calcium influx
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Palliative
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Palliative
Ammivin

Approved Use

Khellin is used for Angina pectoris, Asthma, Vitiligo, Ultraviolet irradiation and other conditions.
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
weak [IC50 34.6 uM]
yes [IC50 0.04 uM]
yes [IC50 4.02 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Coronin 7, the mammalian POD-1 homologue, localizes to the Golgi apparatus.
2004 Aug 27
Cytotoxic activity of five compounds isolated from Colombian plants.
2004 Mar
Cholesterol-sensor initiates M. tuberculosis entry into human macrophages.
2004 Mar
Treatment of vitiligo with local khellin and UVA: comparison with systemic PUVA.
2004 Mar
Topical khellin and natural sunlight in the outpatient treatment of recalcitrant palmoplantar pompholyx: report of an open pilot study.
2005
Homotypic dimerization of the actin-binding protein p57/coronin-1 mediated by a leucine zipper motif in the C-terminal region.
2005 Apr 15
Conformational changes in the Arp2/3 complex leading to actin nucleation.
2005 Jan
Coronin proteins as multifunctional regulators of the cytoskeleton and membrane trafficking.
2005 Jun
Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions.
2005 Oct 20
Downregulation of TACO gene transcription restricts mycobacterial entry/survival within human macrophages.
2005 Sep 1
Phosphorylation of coronin 1B by protein kinase C regulates interaction with Arp2/3 and cell motility.
2005 Sep 9
Green tea polyphenol inhibits Mycobacterium tuberculosis survival within human macrophages.
2006
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
Coronins: the return of the crown.
2006 Aug
Effusion and solid lymphomas have distinctive gene and protein expression profiles in an animal model of primary effusion lymphoma.
2006 Aug
Requirement for coronin 1 in T lymphocyte trafficking and cellular homeostasis.
2006 Aug 11
Immunology. When F-actin becomes too much of a good thing.
2006 Aug 11
Transcriptional regulation of artemin is related to neurite outgrowth and actin polymerization in mature DRG neurons.
2006 Aug 14
Localization of CORO1A in the macrophages containing Mycobacterium leprae.
2006 Aug 30
Time-resolved responses to chemoattractant, characteristic of the front and tail of Dictyostelium cells.
2006 Dec 11
The identification of a new actin-binding region in p57.
2006 Jan
The crystal structure of murine coronin-1: a regulator of actin cytoskeletal dynamics in lymphocytes.
2006 Jan
Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process.
2006 Mar
Microtubules regulate disassembly of epithelial apical junctions.
2006 Mar 1
The tumor suppressor protein p53 is required for neurite outgrowth and axon regeneration.
2006 Sep 6
The embryonic muscle transcriptome of Caenorhabditis elegans.
2007
A new steroid glycoside and furochromones from Cyperus rotundus L.
2007 Apr
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
Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents.
2007 Aug
Lipoamide dehydrogenase mediates retention of coronin-1 on BCG vacuoles, leading to arrest in phagosome maturation.
2007 Aug 15
Neuronal morphogenesis is regulated by the interplay between cyclin-dependent kinase 5 and the ubiquitin ligase mind bomb 1.
2007 Aug 29
Mechanism of inducible nitric oxide synthase exclusion from mycobacterial phagosomes.
2007 Dec
Actin-binding proteins coronin-1a and IBA-1 are effective microglial markers for immunohistochemistry.
2007 Jul
Survival of mycobacteria in macrophages is mediated by coronin 1-dependent activation of calcineurin.
2007 Jul 13
TB or not TB: calcium regulation in mycobacterial survival.
2007 Jul 13
Epithelial grafting for vitiligo requires ultraviolet A phototherapy to increase success rate.
2007 Jun
Coronin 1B coordinates Arp2/3 complex and cofilin activities at the leading edge.
2007 Mar 9
Coronin function is required for chemotaxis and phagocytosis in human neutrophils.
2007 May 1
F-actin binding is essential for coronin 1B function in vivo.
2007 May 15
STATc is a key regulator of the transcriptional response to hyperosmotic shock.
2007 May 21
Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.
2007 Nov 7
An actin-based wave generator organizes cell motility.
2007 Sep
Functional analysis of cancer-associated EGFR mutants using a cellular assay with YFP-tagged EGFR intracellular domain.
2007 Sep 18
Competition between targeting signals in hybrid proteins provides information on their relative in vivo affinities for subcellular compartments.
2008 Feb
Coronin-1A stabilizes F-actin by bridging adjacent actin protomers and stapling opposite strands of the actin filament.
2008 Feb 22
The lupus-related Lmb3 locus contains a disease-suppressing Coronin-1A gene mutation.
2008 Jan
Distinct roles for Arp2/3 regulators in actin assembly and endocytosis.
2008 Jan
Coronin-1A epigenomics governs mycobacterial persistence in tuberculosis.
2008 Jan
Expression of coronin-3 (coronin-1C) in diffuse gliomas is related to malignancy.
2008 Mar
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.
Name Type Language
KHELLIN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NSC-37744
Code English
KHELLIN [INN]
Common Name English
KHELLIN [MI]
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
KHELLIN [WHO-DD]
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
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
Code System Code Type Description
MERCK INDEX
M6626
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY Merck Index
EVMPD
SUB08380MIG
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
NCI_THESAURUS
C75957
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
FDA UNII
5G117T0TJZ
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-392-8
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
CAS
82-02-0
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
RXCUI
6147
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY RxNorm
INN
192
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
MESH
D007666
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
PUBCHEM
3828
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
EPA CompTox
82-02-0
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL44746
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
WIKIPEDIA
KHELLIN
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY
DRUG CENTRAL
3313
Created by admin on Sat Jun 26 11:39:11 UTC 2021 , Edited by admin on Sat Jun 26 11:39:11 UTC 2021
PRIMARY