BERGAPTEN

Possibly Marketed Outside US

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

SMILES

COC1=C2C=CC(=O)OC2=CC3=C1C=CO3

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

Molecular Formula	C12H8O4
Molecular Weight	216.1895
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Activator 1,430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43	Primary		Phase III 656	Geralen
Breast cancer 434	Primary		Basic research	Unknown

C_max

Value	Dose	Analyte	Population
82 ng/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
89 ng/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
175 ng/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
108 μg/L	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
322 μg/L	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
1754 ng × h/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
1757 ng × h/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
3282 ng × h/mL	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
276 μg × h/L	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens
942 μg × h/L	1.2 mg/kg single, oral	BERGAPTEN serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1.2 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, ADULT	Other AEs: Vomiting...

Showing 1 to 1 of 1 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Vomiting	4%	1.2 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, ADULT

Showing 1 to 1 of 1 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Plasma and skin concentration of 5-methoxypsoralen in psoriatic patients after oral administration.	2001 Aug	11511320
The psoralens adversely affect reproductive function in male wistar rats.	2001 Mar-Apr	11297873
Analysis of limette and bergamot distilled essential oils by HPLC.	2002 Apr	12073882
Genotoxicity of Brosimum gaudichaudii measured by the Salmonella/microsome assay and chromosomal aberrations in CHO cells.	2002 Jul	12065160
Zabon phytophotodermatitis: first case reports due to Citrus maxima.	2002 May	12004296

Showing 1 to 5 of 33 entries

Previous1 2 3 4 5 6 7Next

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.