Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C30H16O8 |
| Molecular Weight | 504.4432 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C2C3=C(C)C=C(O)C4=C3C5=C6C2=C(C(O)=C1)C(=O)C7=C6C(=C(O)C=C7O)C8=C5C(C4=O)=C(O)C=C8O
InChI
InChIKey=BTXNYTINYBABQR-UHFFFAOYSA-N
InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
| Molecular Formula | C30H16O8 |
| Molecular Weight | 504.4432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Hypericin (4,5,7,4',5',7'-hexahydroxy-2,2'-dimethylnaphtodianthrone) is a naturally occurring chromophore found in some species of the genus Hypericum, especially Hypericum perforatum L. (St. John's wort), and in some basidiomycetes (Dermocybe spp.) or endophytic fungi (Thielavia subthermophila). Among its antidepressant and light-dependent antiviral actions, hypericin is a powerful natural photosensitizer that is applicable in the photodynamic therapy (PDT) of various oncological diseases. Hypericin may act as an inhibitor of enzymes such as MAO (monoaminoxidase), PKC (protein kinase C), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450), has yielded results supporting therapeutic potential. Research of hypericin and its effect on GABA-activated (gamma amino butyric acid) currents and NMDA (N-methyl-D-aspartat) receptors also indicate the therapeutic potential of this substance whereby new insights in stroke research (apoplexy) are expected. Topical SGX301 (synthetic hypericin as a potent photosensitizer in photodynamic therapy) is in phase 3 for the treatment of cutaneous T-cell lymphoma.
CNS Activity
Curator's Comment: St. John's wort (Hypericum perforatum) is a perennial herb that has become a widely used depression therapy. Extracts of hypericum have shown affinity for receptors within multiple neurochemical systems. The primary active substance responsible for the antidepressant effect is not well defined, but most work has concentrated specifically on the hypericin and hyperforin components.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.3 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.2 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1920 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8820 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23090 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
41.4 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
198 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
494 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
24.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
26.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7857509/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
24.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
250 μg single, oral dose: 250 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
43.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
750 μg single, oral dose: 750 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
48.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8878586/ |
1500 μg single, oral dose: 1500 μg route of administration: Oral experiment type: SINGLE co-administered: |
HYPERICIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Endogenous expression of interleukin-8 and interleukin-10 in nasopharyngeal carcinoma cells and the effect of photodynamic therapy. | 2002-07 |
|
| Jasmonic acid-induced hypericin production in cell suspension cultures of Hypericum perforatum L. (St. John's wort). | 2002-06 |
|
| Hypericin induced death receptor-mediated apoptosis in photoactivated tumor cells. | 2002-06 |
|
| St John's wort (Hypericum perforatum) modulates evoked potentials in guinea pig hippocampal slices via AMPA and GABA receptors. | 2002-06 |
|
| [St. John's wort (Hypericum perforatum L.). A plant with relevance for dermatology]. | 2002-05 |
|
| Aqueous ethanolic extract of St. John's wort (Hypericum perforatum L.) induces growth inhibition and apoptosis in human malignant cells in vitro. | 2002-05 |
|
| Hypericin-based fluorescence diagnosis of bladder carcinoma. | 2002-05 |
|
| Hypocrellins and Hypericin induced apoptosis in human tumor cells: a possible role of hydrogen peroxide. | 2002-05 |
|
| Determining hyperforin and hypericin content in eight brands of St. John's wort. | 2002-03-15 |
|
| Long-term effects of St. John's wort and hypericin on monoamine levels in rat hypothalamus and hippocampus. | 2002-03-15 |
|
| Photodynamic therapy with hypericin induces vascular damage and apoptosis in the RIF-1 mouse tumor model. | 2002-03-10 |
|
| The separation of hypericine and pseudohypericine from Hypericum perforatum L. | 2002-03 |
|
| Hypericin in cancer treatment: more light on the way. | 2002-03 |
|
| Molecular aspects of photodynamic therapy: low energy pre-sensitization of hypericin-loaded human endometrial carcinoma cells enhances photo-tolerance, alters gene expression and affects the cell cycle. | 2002-02-13 |
|
| Short term treatment with St. John's wort, hypericin or hyperforin fails to induce CYP450 isoforms in the Swiss Webster mouse. | 2002-02-01 |
|
| Hypericin--a new antiviral and antitumor photosensitizer: mechanism of action and interaction with biological macromolecules. | 2002-02 |
|
| Phototoxic and apoptosis-inducing capacity of pseudohypericin. | 2002-02 |
|
| New aspect of photodynamic diagnosis of bladder tumors: fluorescence cytology. | 2002-02 |
|
| Decreased plasma levels of amitriptyline and its metabolites on comedication with an extract from St. John's wort ( Hypericum perforatum ). | 2002-02 |
|
| Improved procedure for the quality control of Hypericum perforatum L. | 2002-01-17 |
|
| Impact of hypericum (St.-John's-wort) given prenatally on cognition of mice offspring. | 2002-01-17 |
|
| Biodistribution of hypericin in orthotopic transitional cell carcinoma bladder tumors: implication for whole bladder wall photodynamic therapy. | 2002-01-10 |
|
| Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow. | 2002-01-01 |
|
| St. John's wort (Hypericum perforatum)--is it safe during breastfeeding? | 2002-01 |
|
| A pharmacophore for human pregnane X receptor ligands. | 2002-01 |
|
| Transferrin-mediated targeting of hypericin embedded in sterically stabilized PEG-liposomes. | 2002-01 |
|
| Influence of structure of human, rat, and bovine serum albumins on binding properties of photoactive drug hypericin. | 2002 |
|
| Determination of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry. | 2002 |
|
| High performance liquid chromatographic analysis of St. John's wort with photodiode array detection. | 2001-12-05 |
|
| Determination of hyperforin, hypericin, and pseudohypericin in human plasma using high-performance liquid chromatography analysis with fluorescence and ultraviolet detection. | 2001-12-05 |
|
| Hypericin and hypocrellin induced apoptosis in human mucosal carcinoma cells. | 2001-12-01 |
|
| Photodynamic therapy in superficial bladder cancer: past, present and future. | 2001-12 |
|
| Saint John's wort: an in vitro analysis of P-glycoprotein induction due to extended exposure. | 2001-12 |
|
| Development of a simple, rapid and reproducible HPLC assay for the simultaneous determination of hypericins and stabilized hyperforin in commercial St. John's wort preparations. | 2001-12 |
|
| Inhibition of c-erbB-2 expression an activity in human ovarian carcinoma cells by hypericin. | 2001-11-29 |
|
| [Experimental cultivation of Hypericum perforatum L. in Bratislava]. | 2001-11 |
|
| A study of hypericin-induced teratogenicity during organogenesis using a whole rat embryo culture model. | 2001-11 |
|
| Induction of apoptosis by Hypericin through activation of caspase-3 in human carcinoma cells. | 2001-11 |
|
| Catalytic inhibition of human DNA topoisomerase IIalpha by hypericin, a naphthodianthrone from St. John's wort (Hypericum perforatum). | 2001-10-15 |
|
| [Mania during the use of a combination preparation with St. John's wort (Hypericum perforatum)]. | 2001-10-06 |
|
| Severe phototoxic reaction to laser treatment in a patient taking St John's Wort. | 2001-09 |
|
| Photodynamic therapy of murine fibrosarcoma with topical and systemic administration of hypericin. | 2001-09 |
|
| A systematic review and meta-analysis of Hypericum perforatum in depression: a comprehensive clinical review. | 2001-09 |
|
| Tumor-specific and photodependent cytotoxicity of hypericin in the human LNCaP prostate tumor model. | 2001-08 |
|
| Variability in the content of the constituents of Hypericum perforatum L. and some commercial extracts. | 2001-07 |
|
| The effect of quercetin on light-induced cytotoxicity of hypericin. | 2001 |
|
| [Hyperici herba (Hypericum perforatum L]. | 2001 |
|
| Intracellular localisation of hypericin in human glioblastoma and carcinoma cell lines. | 2001 |
|
| Final report on the safety assessment of Hypericum perforatum extract and Hypericum perforatum oil. | 2001 |
|
| [Studies on synthesis and anti-HIV RT activity of hypericin and ethylhypericin]. | 1998 |
Sample Use Guides
Phase 3 study for the treatment of Cutaneous T-Cell Lymphoma: 0.25% SGX301 (synthetic hypericin) in USP Hydrophilic Ointment applied twice per week, covered by opaque bandage for 12-24 hours, then treated with an initial dose of 5 J/cm^2 fluorescent light.
Phase I studies of hypericin as an antiretroviral agent in HIV-infected adults: Intravenous hypericin, 0.25 or 0.5 mg/kg of body weight twice weekly or 0.25 mg/kg three times weekly, or oral hypericin, 0.5 mg/kg daily.
Route of Administration:
Other
Both cisplatin and the hypericin exhibited a dose-dependent cytotoxic effect in the MCF-7 cell line. Although the LD50 of the hypericin was significantly lower when compared to cispaltin (5 vs. 20 μg/ml), it continued to decrease the growth rate of the MCF-7 cells when tested at higher concentration than LD50. In contrast, cisplatine, at higher concentration than LD50, completely inhibited the growth of the MCF-7 in 48 h. Regarding Annexin V/Propidium results, treatment of MCF-7 cells with LD50 concentration of cisplatin and hypericin showed 60 and 52 % apoptosis in 24 h, respectively. ICC analysis for bcl2 and p53 also confirmed our results; in treated samples for the dose of LD50 in 24 and 48 h of cisplatin and hypercin, more cells expressed p53 (guardian of cells in front of tumor formation/progression) and less expressed bcl2 (which has anti apoptotic activity) compared to untreated samples.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:40:34 GMT 2025
by
admin
on
Mon Mar 31 18:40:34 GMT 2025
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| Record UNII |
7V2F1075HD
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| Record Status |
Validated (UNII)
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| Record Version |
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EU-Orphan Drug |
EU/3/15/1515
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FDA ORPHAN DRUG |
835521
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FDA ORPHAN DRUG |
131199
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DSLD |
2501 (Number of products:15)
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FDA ORPHAN DRUG |
131099
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100000156035
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548-04-9
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DTXSID40203270
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C004965
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SUB130124
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208-941-0
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5835
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C37456
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1546455
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SUB14167MIG
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1372719-41-9
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DB13014
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HYPERICIN
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407313
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5281051
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11835
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7V2F1075HD
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HI-192
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
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