St. John's Wort

Identification

Summary

St. John's Wort is an herbal ingredient used in non-prescription therapeutic products for the short-term treatment of minor skin irritations, insomnia, depression, and anxiety.

Generic Name
St. John's Wort
DrugBank Accession Number
DB01323
Background

Not Available

Type
Biotech
Groups
Approved, Investigational, Nutraceutical
Synonyms
  • Common st johnswort flowering top
  • Common st. john's wort flowering top
  • Common st. john's wort herb
  • Common st. johnswort flowering top
  • Guanyejinsitao
  • Hyperici herba
  • Hypericum nachitschevanicum flowering top
  • Hypericum perforatum flowering top
  • Hypoxis hemerocallidea root extract
  • Klamath weed flowering top
  • Klamathweed flowering top
  • Saint johns wort
  • St john's wort
  • St Johns Wort
  • St. john’s wort
  • St. johns wort
  • St. johnswort flowering top

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAnxiety••• •••••
Treatment ofDepression••• •••••
Symptomatic treatment ofHot flashes••• •••••
Treatment ofInsomnia••• •••••
Symptomatic treatment ofMuscle pain••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be increased when combined with St. John's Wort.
AbametapirThe serum concentration of St. John's Wort can be increased when it is combined with Abametapir.
AbataceptThe metabolism of St. John's Wort can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be decreased when it is combined with St. John's Wort.
AbirateroneThe metabolism of Abiraterone can be increased when combined with St. John's Wort.
Food Interactions
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ethical Herbals ST. John's WortTablet300 mg/1OralAshbury Research CorporationNot applicableNot applicableCanada flag
Ethical Herbals ST. John's WortTablet150 mg/1OralAshbury Research CorporationNot applicableNot applicableCanada flag
Felis Forte Capsules 425mgCapsule425 mg / capOralRhoxalpharma IncNot applicableNot applicableCanada flag
Felis Tablets 250mgTablet250 mg / tabOralRhoxalpharma IncNot applicableNot applicableCanada flag
ST. John's WortCapsule1500 mgOralSisu Inc.1998-02-112007-07-20Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dynamiclear RapidSt. John's Wort (0.5 mg/1mL) + Calendula officinalis flower (0.5 mg/1mL) + Cupric sulfate pentahydrate (40 mg/1mL)LiquidTopicalRX PHARMA-PACK, INC.2019-02-062022-12-31US flag
Dynamiclear RapidSt. John's Wort (0.5 mg/1mL) + Calendula officinalis flower (0.5 mg/1mL) + Cupric sulfate pentahydrate (40 mg/1mL)LiquidTopicalRX PHARMA-PACK, INC.2019-02-062022-12-31US flag
Nite-capsSt. John's Wort (20 mg / cap) + Hops (40 mg / cap) + Valerian (40 mg / cap)CapsuleOralFlora Manufacturing And Distributing Ltd.1991-12-312002-09-10Canada flag
S. R. FormulaSt. John's Wort (200 mg / mL) + Valerian (133.2 mg / mL)LiquidOralMorinda Canada2002-01-142006-07-12Canada flag

Categories

ATC Codes
N06AX25 — Hyperici herba
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
UFH8805FKA
CAS number
84082-80-4

References

Synthesis Reference

Trevor Percival Castor, Theodore Abraham Tyler, Richard Joseph Student, "Methods for making Hypericum fractions and St. John's Wort products." U.S. Patent US6291241, issued December, 1998.

US6291241
General References
  1. Lecrubier Y, Clerc G, Didi R, Kieser M: Efficacy of St. John's wort extract WS 5570 in major depression: a double-blind, placebo-controlled trial. Am J Psychiatry. 2002 Aug;159(8):1361-6. [Article]
  2. Randlov C, Mehlsen J, Thomsen CF, Hedman C, von Fircks H, Winther K: The efficacy of St. John's Wort in patients with minor depressive symptoms or dysthymia--a double-blind placebo-controlled study. Phytomedicine. 2006 Mar;13(4):215-21. Epub 2006 Jan 19. [Article]
  3. Authors unspecified: Effect of Hypericum perforatum (St John's wort) in major depressive disorder: a randomized controlled trial. JAMA. 2002 Apr 10;287(14):1807-14. [Article]
PubChem Substance
46507869
RxNav
1310069
PharmGKB
PA164924486
Drugs.com
Drugs.com Drug Page
Wikipedia
Hypericum_perforatum

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedNot AvailableDrug Drug Interaction (DDI)2somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD)1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentContraception1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentDepression1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Guna Inc.
  • Pekana Naturheilmittel GmbH
  • Weleda Inc.
Dosage Forms
FormRouteStrength
LiquidTopical
TabletOral900 mg / tab
TabletOral150 mg/1
TabletOral300 mg/1
TabletOral300 mg
CapsuleOral425 mg / cap
TabletOral250 mg / tab
TabletOral180 mg / tab
TabletOral300 mg / tab
Tablet, coated
CapsuleOral
TabletOral1500 mg / tab
Tablet, coated300 MG
Tablet, film coated300 MG
LiquidOral
CapsuleOral1050 mg
CapsuleOral1500 mg / cap
CapsuleOral1500 mg
CapsuleOral300 mg / cap
CapsuleOral750 mg / cap
TabletOral500 mg
LiquidOral1000 mg / mL
CapsuleOral1045 mg / cap
CapsuleOral1320 mg / cap
LiquidOral1 g / 1 mL
CapsuleOral300 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Activator
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Wenk M, Todesco L, Krahenbuhl S: Effect of St John's wort on the activities of CYP1A2, CYP3A4, CYP2D6, N-acetyltransferase 2, and xanthine oxidase in healthy males and females. Br J Clin Pharmacol. 2004 Apr;57(4):495-9. [Article]
  2. Hokkanen J, Tolonen A, Mattila S, Turpeinen M: Metabolism of hyperforin, the active constituent of St. John's wort, in human liver microsomes. Eur J Pharm Sci. 2011 Feb 14;42(3):273-84. doi: 10.1016/j.ejps.2010.12.002. Epub 2010 Dec 17. [Article]
  3. Klotz U: Interaction potential of lercanidipine, a new vasoselective dihydropyridine calcium antagonist. Arzneimittelforschung. 2002;52(3):155-61. doi: 10.1055/s-0031-1299873. [Article]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Hokkanen J, Tolonen A, Mattila S, Turpeinen M: Metabolism of hyperforin, the active constituent of St. John's wort, in human liver microsomes. Eur J Pharm Sci. 2011 Feb 14;42(3):273-84. doi: 10.1016/j.ejps.2010.12.002. Epub 2010 Dec 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. Hokkanen J, Tolonen A, Mattila S, Turpeinen M: Metabolism of hyperforin, the active constituent of St. John's wort, in human liver microsomes. Eur J Pharm Sci. 2011 Feb 14;42(3):273-84. doi: 10.1016/j.ejps.2010.12.002. Epub 2010 Dec 17. [Article]
  2. Rahimi R, Abdollahi M: An update on the ability of St. John's wort to affect the metabolism of other drugs. Expert Opin Drug Metab Toxicol. 2012 Jun;8(6):691-708. doi: 10.1517/17425255.2012.680886. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da
References
  1. Durr D, Stieger B, Kullak-Ublick GA, Rentsch KM, Steinert HC, Meier PJ, Fattinger K: St John's Wort induces intestinal P-glycoprotein/MDR1 and intestinal and hepatic CYP3A4. Clin Pharmacol Ther. 2000 Dec;68(6):598-604. [Article]

Drug created at June 30, 2007 17:20 / Updated at October 21, 2024 08:50