BERGAPTEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H8O4
Molecular Weight	216.1895
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C=COC2=CC3=C1C=CC(=O)O3

InChI

InChIKey=BGEBZHIAGXMEMV-UHFFFAOYSA-N

InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

HIDE SMILES / InChI

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00533195 | doi:10.1186/s12943-015-0403-4 retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498523 |

Bergapten, known as 5-methoxypsoralen, a cumarine-derivate compound, presents in many fruits and vegetables. It has shown antitumor effects in a variety of cell types. The key target of bergapten action in breast cancer cells was identified the oncosuppressor gene PTEN (phosphatase tensin homolog deleted from chromosome 10); bergapten by inducing PTEN expression, produces autophagy in breast cancer cells. Besides, bergapten is under investigation in clinical trial phase III for patients with severe generalized atopic dermatitis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphatase tensin homologue deleted from chromosome 10 1 Target ID: Phosphatase tensin homologue deleted from chromosome 10 Sources: doi:10.1186/s12943-015-0403-4 retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498523/	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 64 Sources: https://clinicaltrials.gov/ct2/show/NCT00533195	Primary		Phase III 665	Geralen Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26148846	Primary		Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
175 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
108 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
322 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
1754 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1757 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3282 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1981428/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
276 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
942 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3994922/	1.2 mg/kg single, oral dose: 1.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	BERGAPTEN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
1.2 mg/kg 1 times / day multiple, oral Studied dose Dose: 1.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 1.2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	Other AEs: Vomiting... Other AEs: Vomiting (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/

AEs

AE	Significance	Dose	Population
Vomiting	4%	1.2 mg/kg 1 times / day multiple, oral Studied dose Dose: 1.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 1.2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1344660/

PubMed

Title	Date	PubMed
The psoralens adversely affect reproductive function in male wistar rats.	2001 Mar-Apr	11297873
Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds.	2001 Sep-Dec	11737987
Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri.	2002 Apr	11937170
Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips.	2002 Apr 24	11958623
Constituents of the fruits and leaves of Euodia daniellii.	2002 Dec	12510833
Bullous phytophotodermatitis associated with high natural concentrations of furanocoumarins in limes.	2002 Mar	11887098
Validation of a microdialysis-gas chromatographic-mass spectrometric method to assess 8-methoxypsoralen in psoriatic patient dermis.	2002 Nov 15	12383487
Determination of 5-methoxypsoralen in human serum.	2002 Oct 15	12367684
Tea: not immoral, illegal, or fattening, but is it innocuous?	2002 Sep 14	12243952
In vivo effect of 5- and 8-methoxypsoralens and cimetidine on R,S-warfarin metabolism in rat.	2002 Sep-Oct	12355562
Effect of psoralens on Fenton-like reaction generating reactive oxygen species.	2003	12400092
Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography.	2003 Jul 4	12929969
Antibacterial coumarins from Angelica gigas roots.	2003 Jun	12877552
Effect of 5-methoxypsoralen (5-MOP) on cell apoptosis and cell cycle in human hepatocellular carcinoma cell line.	2003 Jun	12781206
Coumarins from Cnidium monnieri (L.) and their proliferation stimulating activity on osteoblast-like UMR106 cells.	2004 Aug	15378857
Preparative isolation and purification of bergapten and imperatorin from the medicinal plant Cnidium monnieri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.	2004 Dec 17	15633744
Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae).	2004 Jan	14732282
Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase.	2004 Mar	15009205
Citrus aurantium, an ingredient of dietary supplements marketed for weight loss: current status of clinical and basic research.	2004 Sep	15337824
Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams.	2005 Aug	16124408
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.	2005 Jan	15702516
Internet-based search of randomised trials relevant to mental health originating in the Arab world.	2005 Jul 26	16045805
Post-stress metabolism involves umbelliferone production in anthocyanin-producing and nonproducing cells of Glehnia littoralis suspension cultures.	2005 Jun	16008093
Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides.	2005 Nov 1	16140017
Effects of 5-methoxypsoralen (5-MOP) on arylamine N-acetyltransferase activity in the stomach and colon of rats and human stomach and colon tumor cell lines.	2005 Nov-Dec	16277023
Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar.	2006 Apr	16640727
A method for quantitative determination of furanocoumarins in capsules and tablets of phytochemical preparations.	2006 Apr	16595942
[Studies on chemical constituents from roots of Peucedanum praeruptorum II].	2006 Aug	17061553
[Studies on chemical constituents in roots of Heracleum rapula].	2006 Feb	16706022
Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus.	2006 Mar	16572296
Efficacy of 8-methoxypsoralen vs. 5-methoxypsoralen plus ultraviolet A therapy in patients with mycosis fungoides.	2006 Mar	16445785
Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1.	2006 Sep	16762476
Use of the yeast Saccharomyces cerevisiae as a pre-screening approach for assessment of chemical-induced phototoxicity.	2006 Sep	16497474
Inhibition on human liver cytochrome P450 3A4 by constituents of fennel (Foeniculum vulgare): identification and characterization of a mechanism-based inactivator.	2007 Dec 12	17988092
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007 Feb 26	17324258
Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.	2007 Jul	17452418
Quality assessment of Rhizoma et Radix Notopterygii by HPTLC and HPLC fingerprinting and HPLC quantitative analysis.	2007 Jul 27	17512692
Herbal medicine today: clinical and research issues.	2007 Sep	18227931
[Simultaneous determination of 8-methoxypsoralen and 5-methoxypsoralen in cosmetics using LC-MS/MS].	2007 Sep	18161337
[Simultaneous determination of 5 active components in Fructus Cnidii by HPLC].	2007 Sep	18051896
Coumarins from Peucedanum luxurians.	2007 Sep	17582700
Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544.	2008 Feb 15	18048073
Induction of gamma-globin mRNA, erythroid differentiation and apoptosis in UVA-irradiated human erythroid cells in the presence of furocumarin derivatives.	2008 Feb 15	18022602
In vivo methods for the assessment of topical drug bioavailability.	2008 Jan	17985216
Enhancement of bone morphogenetic protein-2 expression and bone formation by coumarin derivatives via p38 and ERK-dependent pathway in osteoblasts.	2008 Jan 28	17980360
Irritant and cytotoxic coumarins from Angelica glauca Edgew roots.	2008 Jan-Feb	18058380
Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors.	2008 Jan-Feb	18052337
Effective biotic elicitation of Ruta graveolens L. shoot cultures by lysates from Pectobacterium atrosepticum and Bacillus sp.	2008 Mar	17968510
In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon.	2008 May	18337075
Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue).	2008 Oct	18211259

Patents

Sample Use Guides

In Vivo Use Guide

1,2 mg/kg 2 hours before UVA irradiation p.o. 3 times weekly for 5 weeks

Route of Administration: Oral

In Vitro Use Guide

Bone marrow stromal cells (BMSCs) were cultured in osteogenic induction medium with the addition of bergapten for 2 weeks. The concentrations of bergapten used were 0.1, 1, and 10 μmol/L in vitro. Bergapten promotes the expression of alkaline phosphatase (ALP) by BMSCs in vitro in a dose-dependent manner, as revealed by ALP staining.

Name

Type

Language

5-METHOXYPSORALEN

Preferred Name

English

BERGAPTEN

Common Name

English

5-METHOXYPSORALEN [IARC]

Common Name

English

4-METHOXY-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE

Systematic Name

English

BERGAPTEN [MI]

Common Name

English

METHOXSALEN RELATED COMPOUND A [USP-RS]

Common Name

English

GERALEN

Common Name

English

METHOXSALEN RELATED COMPOUND A [USP IMPURITY]

Common Name

English

5-METHOXYPSORALEN [MART.]

Common Name

English

BERGAPTENE

Common Name

English

MAJUDIN

Common Name

English

NSC-95437

Code

English

BERGAPTAN

Common Name

English

HERACLIN

Common Name

English

5-methoxypsoralen [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D05BA03