Myrrh
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Identification
- Generic Name
- Myrrh
- DrugBank Accession Number
- DB11605
- Background
Extractives and their physically modified derivatives such as tinctures, concretes, absolutes, essential oils, oleoresins, terpenes, terpene-free fractions, distillates, residues, obtained from Commiphora abyssinica, Burseraceae.
- Type
- Small Molecule
- Groups
- Approved
- Synonyms
- Bola resin
- Commiphora molmol resin
- Commiphora myrrha gum resin
- Commiphora myrrha resin
- Commiphora myrrha resin extract
- Common myrrh
- Hirabol myrrh
- Mo yao
- Moyao (commiphora molmol)
- Moyao (commiphora myrrha)
- Myhrra
- Myrrh
- Myrrh (commiphora molmol)
- Myrrh (commiphora myrrha)
- Myrrha
- Myrrha (commiphora molmol)
- Myrrha (commiphora myrrha)
- External IDs
- Fema no. 2765
Pharmacology
- Indication
FDA approved only for use in food. Historically used for indigestion, ulcers, colds, cough, asthma, bronchial congestion, arthritic pain, cancer, leprosy, and syphilis. It is also used orally as a stimulant, antispasmodic, and to increase menstrual flow. Topically, myrrh is used for mild inflammation of the oral and pharyngeal mucosa, aphthous ulcers, gingivitis, chapped lips, hemorrhoids, bedsores, wounds, abrasions, furunculosis, bad breath, and loose teeth. In foods and beverages, myrrh is used as a flavoring component. In manufacturing, myrrh is used as a fragrance and fixative in cosmetics. It is also used in embalming and as incense.
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- Pharmacodynamics
Myrrh reduces the production of cytokines and reduces the effects of inflammation 2,3,4,14. It is also suggested to produce an analgesic effect 5,17. Myrrh produces cell damage and death in various cancer cell types 1,6,7. Myrrh has been observed to exert anantibacterial, antiparasitic, and antifungal activities 8,10. Myrrh reduces liver injury in response to carbon tetrachloride insult, suggesting hepoprotective action 9. It also displays antioxidant properties 10. Myrrh reduces low density lipoprotein levels 11. Myrrh appears to be cardioprotective, producing a decrease in heart rate and restoring blood pressure in response to isoproteronol challenge 13. Myrrh lowers plasma glucose and insulin levels in type 2 diabetes mellitus models suggesting an improvement in insulin sensitivity 14,15. Myrrh has been observed to protect against both substance and stress induced gastric lesions 16.
- Mechanism of action
Anti-inflammatory: Myrrh is thought to mediate its anti-inflammatory activity through inducing haem oxygenase activity 2. Haem oxygenase then appears to prevent the degradation of IKBalpha in response to inflammatory receptor activation. This prevents translocation of nuclear factor kappaB (NFkappaB) to the nucleus and inhibits the expression of genes under its control like cyclooxygenase-2 and the inducible form of nitric oxide synthase. The suppression of the NFkappaB pathway likely also reduces the expression of inflammatory cytokines. Myrhh also inhibits the mitogen activated protein kinase (MAPK) pathway, specifically producing inhibition of p38 and c-jun N-terminal kinase (JNK) 3. This is associated with a reduction in c-jun and c-fos expression which would likely result in a reduction in activator protein-1 and and inhibition of its associated inflammatory gene expression. Myrrh exibits inhibitory activity against 5-lipoxygenase helping to suppress the production of leukotrienes, another class of inflammatory cytokine 4. In addition to its effects on the NFkappaB system, myrrh also inhibits the signal transducer and activator of transcription (STAT) -1 and -3 resulting in a decrease in cytokine production by the janus kinase/STAT pathway 14. Myrrh also reduces the downregulation of suppresor of cytokine synthesis (SOCS) in response to interleukin-1beta and interferon-gamma. SOCS serves as an autoregulator of the JAK/STAT pathway under transcriptional control of STATs and inhibits activation of the pathway.
Analgesic: Myrrh appears to produce an analgesic effect associated with its suppression of prostaglandin production 5. Myrrh is also suggested to block inward sodium currents 17.
Anticancer: Myrrh displays an pro-apoptotic effect on cancer cells 1. This seems to involve members of the Bcl family of proteins 6. Myrrh induces the expression of the pro-apoptotic protein Bax while decreasing the expression of Bcl-2 and Bcl-xl, the anti-apoptotic members of the Bcl family. At low doses Myrrh seems to activate the MAPK pathway in cancer cells, promoting the phosphorylation of p38 and JNK 7. The JNK activation in particular appears to mediate an apoptotic influence. Additionally, myrrh appears to induce reactive oxygen species generation in cancer cells further promoting apoptosis.
Antibacterial/Antiparasitic/Antifungal: The precise antibacterial, antiparasitic, and antifungal mechanisms of myrrh are unknown 8,10.
Hepatoprotective: Myrrh has been shown to reduce liver injury and upregulation of superoxide dismutase, glutathione peroxidase and catalase in response to carbon tetrachloride insult. This is thought to be due to anti-oxidant properties of myrrh 9.
Antioxidant: The precise mechanism of myrrh's antioxidant property is unknown.
Lipid lowering: Compounds in myrrh bind to and inhibit the farnesoid X receptor resulting in a reduction in low density lipoprotein 11. This effect is likely to due the attenuation of the suppression of bile synthesis and a reduction in ileal bile acid binding protein in response to farnesoid X receptor stimulation 4. Together these would ensure processing of cholesterol into bile and subsequent loss of that bile by reducing reuptake.
Cardioprotective: The exact mechanism of myrrh's cardioprotective effect is unknown.
Antidiabetic: Much of myrrh's antidiabetic action is attrbutable to it's anti-inflammatory action which protects islet beta cells from inflammatory damage during hyperglycemia 14. The antioxidant properties of myrrh also likely contribute to this effect.
Antiulcer: The antiulcer activity of myrrh is suggested to be due to inhibition of gastric acid secretion, increasing gastric mucus secretion, and myrrh's antioxidant properties 16.
Target Actions Organism UBile acid receptor antagonistHumans UNuclear receptor subfamily 1 group I member 2 partial agonistHumans UPeroxisome proliferator-activated receptor alpha agonistHumans - 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
Oral LD50 for myrrh oil in rats is 1650mg/kg MSDS. The Commiphora erlangeriana species is poisonous to humans and other mammals 1.
- 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.Not Available
- Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Teinture De Myrrhe Liquid 20 g / 100 mL Dental; Topical Lab Valmo EnregistrÉ, Division Of Technilab Inc. 1982-12-31 2000-08-24 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Chase Coldsorex Myrrh (5 %) + Benzoin resin (12.46 %) + Camphor (3 %) + Levomenthol (0.62 %) Liquid Topical Stella Pharmaceutical Canada Inc. 1997-09-04 2003-11-20 Canada CHI. JOA (Anti-inflammatory effect, antibacterial effect, stomatitis improvement, plaque removal) Myrrh (1 g/100g) + Cinnamon (1 g/100g) + Levomenthol (1 g/100g) + Menthol (1 g/100g) + Pear (1 g/100g) + Peppermint (1 g/100g) + Sea salt (47 g/100g) + Silicon dioxide (1 g/100g) + Sorbitol (1 g/100g) + Xylitol (1 g/100g) Powder Topical BIOHERB Co., Ltd. 2023-07-11 2024-07-10 US Cold Sore Lotion Myrrh (3.84 g / 100 mL) + Benzocaine (2 g / 100 mL) + Benzoin resin (2.505 g / 100 mL) + Camphor (10 g / 100 mL) + Levomenthol (200 mg / 100 mL) Lotion Topical D.C. Labs Limited 1966-12-31 2003-07-11 Canada LA FEMME V Feminine Cleanser Myrrh (8.0 mg/800mg) + Nicotinamide (16.0 mg/800mg) + Olea europaea leaf (8.0 mg/800mg) Tablet Vaginal Nature Factory Co., Ltd. 2018-12-01 Not applicable US Lotion Pour Feux Sauvages Myrrh (25 %) + Benzoin resin (25 %) + Camphor (4 %) + Levomenthol (1.2 %) Liquid Topical Sabex Inc 1990-12-31 2001-08-02 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CHI. JOA (Anti-inflammatory effect, antibacterial effect, stomatitis improvement, plaque removal) Myrrh (1 g/100g) + Cinnamon (1 g/100g) + Levomenthol (1 g/100g) + Menthol (1 g/100g) + Pear (1 g/100g) + Peppermint (1 g/100g) + Sea salt (47 g/100g) + Silicon dioxide (1 g/100g) + Sorbitol (1 g/100g) + Xylitol (1 g/100g) Powder Topical BIOHERB Co., Ltd. 2023-07-11 2024-07-10 US LA FEMME V Feminine Cleanser Myrrh (8.0 mg/800mg) + Nicotinamide (16.0 mg/800mg) + Olea europaea leaf (8.0 mg/800mg) Tablet Vaginal Nature Factory Co., Ltd. 2018-12-01 Not applicable US
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- JC71GJ1F3L
- CAS number
- 9000-45-7
- InChI Key
- Not Available
- InChI
- Not Available
- IUPAC Name
- Not Available
- SMILES
- Not Available
References
- General References
- Shen T, Li GH, Wang XN, Lou HX: The genus Commiphora: a review of its traditional uses, phytochemistry and pharmacology. J Ethnopharmacol. 2012 Jul 13;142(2):319-30. doi: 10.1016/j.jep.2012.05.025. Epub 2012 May 21. [Article]
- Cheng YW, Cheah KP, Lin CW, Li JS, Yu WY, Chang ML, Yeh GC, Chen SH, Choy CS, Hu CM: Myrrh mediates haem oxygenase-1 expression to suppress the lipopolysaccharide-induced inflammatory response in RAW264.7 macrophages. J Pharm Pharmacol. 2011 Sep;63(9):1211-8. doi: 10.1111/j.2042-7158.2011.01329.x. Epub 2011 Jul 15. [Article]
- Manjula N, Gayathri B, Vinaykumar KS, Shankernarayanan NP, Vishwakarma RA, Balakrishnan A: Inhibition of MAP kinases by crude extract and pure compound isolated from Commiphora mukul leads to down regulation of TNF-alpha, IL-1beta and IL-2. Int Immunopharmacol. 2006 Feb;6(2):122-32. Epub 2005 Jul 20. [Article]
- Paraskeva MP, van Vuuren SF, van Zyl RL, Davids H, Viljoen AM: The in vitro biological activity of selected South African Commiphora species. J Ethnopharmacol. 2008 Oct 28;119(3):673-9. doi: 10.1016/j.jep.2008.06.029. Epub 2008 Jul 2. [Article]
- Su S, Wang T, Duan JA, Zhou W, Hua YQ, Tang YP, Yu L, Qian DW: Anti-inflammatory and analgesic activity of different extracts of Commiphora myrrha. J Ethnopharmacol. 2011 Mar 24;134(2):251-8. doi: 10.1016/j.jep.2010.12.003. Epub 2010 Dec 15. [Article]
- Singh SV, Zeng Y, Xiao D, Vogel VG, Nelson JB, Dhir R, Tripathi YB: Caspase-dependent apoptosis induction by guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, in PC-3 human prostate cancer cells is mediated by Bax and Bak. Mol Cancer Ther. 2005 Nov;4(11):1747-54. [Article]
- Singh SV, Choi S, Zeng Y, Hahm ER, Xiao D: Guggulsterone-induced apoptosis in human prostate cancer cells is caused by reactive oxygen intermediate dependent activation of c-Jun NH2-terminal kinase. Cancer Res. 2007 Aug 1;67(15):7439-49. [Article]
- Abdul-Ghani RA, Loutfy N, Hassan A: Myrrh and trematodoses in Egypt: an overview of safety, efficacy and effectiveness profiles. Parasitol Int. 2009 Sep;58(3):210-4. doi: 10.1016/j.parint.2009.04.006. Epub 2009 May 13. [Article]
- Gowri Shankar NL, Manavalan R, Venkappayya D, David Raj C: Hepatoprotective and antioxidant effects of Commiphora berryi (Arn) Engl bark extract against CCl(4)-induced oxidative damage in rats. Food Chem Toxicol. 2008 Sep;46(9):3182-5. doi: 10.1016/j.fct.2008.07.010. Epub 2008 Jul 22. [Article]
- Fraternale D, Sosa S, Ricci D, Genovese S, Messina F, Tomasini S, Montanari F, Marcotullio MC: Anti-inflammatory, antioxidant and antifungal furanosesquiterpenoids isolated from Commiphora erythraea (Ehrenb.) Engl. resin. Fitoterapia. 2011 Jun;82(4):654-61. doi: 10.1016/j.fitote.2011.02.002. Epub 2011 Feb 21. [Article]
- Urizar NL, Liverman AB, Dodds DT, Silva FV, Ordentlich P, Yan Y, Gonzalez FJ, Heyman RA, Mangelsdorf DJ, Moore DD: A natural product that lowers cholesterol as an antagonist ligand for FXR. Science. 2002 May 31;296(5573):1703-6. Epub 2002 May 2. [Article]
- Chawla A, Repa JJ, Evans RM, Mangelsdorf DJ: Nuclear receptors and lipid physiology: opening the X-files. Science. 2001 Nov 30;294(5548):1866-70. [Article]
- Ojha SK, Nandave M, Arora S, Mehra RD, Joshi S, Narang R, Arya DS: Effect of Commiphora mukul extract on cardiac dysfunction and ventricular function in isoproterenol-induced myocardial infarction. Indian J Exp Biol. 2008 Sep;46(9):646-52. [Article]
- Lv N, Song MY, Kim EK, Park JW, Kwon KB, Park BH: Guggulsterone, a plant sterol, inhibits NF-kappaB activation and protects pancreatic beta cells from cytokine toxicity. Mol Cell Endocrinol. 2008 Jul 16;289(1-2):49-59. doi: 10.1016/j.mce.2008.02.001. Epub 2008 Feb 9. [Article]
- Sharma B, Salunke R, Srivastava S, Majumder C, Roy P: Effects of guggulsterone isolated from Commiphora mukul in high fat diet induced diabetic rats. Food Chem Toxicol. 2009 Oct;47(10):2631-9. doi: 10.1016/j.fct.2009.07.021. Epub 2009 Jul 25. [Article]
- Al-Howiriny T, Al-Sohaibani M, Al-Said M, Al-Yahya M, El-Tahir K, Rafatullah S: Effect of Commiphora opobalsamum (L.) Engl. (Balessan) on experimental gastric ulcers and secretion in rats. J Ethnopharmacol. 2005 Apr 26;98(3):287-94. [Article]
- Dolara P, Corte B, Ghelardini C, Pugliese AM, Cerbai E, Menichetti S, Lo Nostro A: Local anaesthetic, antibacterial and antifungal properties of sesquiterpenes from myrrh. Planta Med. 2000 May;66(4):356-8. [Article]
- Myrrh Monograph Natural Medicines Database [Link]
- External Links
- MSDS
- Download (47.1 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Gingivitis / Plaque, Dental 1 somestatus stop reason just information to hide 3 Completed Treatment Schistosoma Hematobium Infection / Schistosomiasis Mansoni 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder Topical Lotion Topical Tablet Vaginal Liquid Topical Patch Topical Liquid Dental; Topical 20 g / 100 mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
- Not Available
- Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-activated transcription factor. Receptor for bile acids (BAs) such as chenodeoxycholic acid (CDCA), lithocholic acid, deoxycholic acid (DCA) and allocholic acid (ACA). Plays a essential role in BA homeostasis through the regulation of genes involved in BA synthesis, conjugation and enterohepatic circulation. Also regulates lipid and glucose homeostasis and is involved innate immune response (PubMed:10334992, PubMed:10334993, PubMed:21383957, PubMed:22820415). The FXR-RXR heterodimer binds predominantly to farnesoid X receptor response elements (FXREs) containing two inverted repeats of the consensus sequence 5'-AGGTCA-3' in which the monomers are spaced by 1 nucleotide (IR-1) but also to tandem repeat DR1 sites with lower affinity, and can be activated by either FXR or RXR-specific ligands. It is proposed that monomeric nuclear receptors such as NR5A2/LRH-1 bound to coregulatory nuclear responsive element (NRE) halfsites located in close proximity to FXREs modulate transcriptional activity (By similarity). In the liver activates transcription of the corepressor NR0B2 thereby indirectly inhibiting CYP7A1 and CYP8B1 (involved in BA synthesis) implicating at least in part histone demethylase KDM1A resulting in epigenomic repression, and SLC10A1/NTCP (involved in hepatic uptake of conjugated BAs). Activates transcription of the repressor MAFG (involved in regulation of BA synthesis) (By similarity). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine) (PubMed:12754200, PubMed:15471871, PubMed:17895379). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine) (PubMed:10514450, PubMed:15239098, PubMed:16269519). In the intestine activates FGF19 expression and secretion leading to hepatic CYP7A1 repression (PubMed:12815072, PubMed:19085950). The function also involves the coordinated induction of hepatic KLB/beta-klotho expression (By similarity). Regulates transcription of liver UGT2B4 and SULT2A1 involved in BA detoxification; binding to the UGT2B4 promoter seems to imply a monomeric transactivation independent of RXRA (PubMed:12806625, PubMed:16946559). Modulates lipid homeostasis by activating liver NR0B2/SHP-mediated repression of SREBF1 (involved in de novo lipogenesis), expression of PLTP (involved in HDL formation), SCARB1 (involved in HDL hepatic uptake), APOE, APOC1, APOC4, PPARA (involved in beta-oxidation of fatty acids), VLDLR and SDC1 (involved in the hepatic uptake of LDL and IDL remnants), and inhibiting expression of MTTP (involved in VLDL assembly (PubMed:12554753, PubMed:12660231, PubMed:15337761). Increases expression of APOC2 (promoting lipoprotein lipase activity implicated in triglyceride clearance) (PubMed:11579204). Transrepresses APOA1 involving a monomeric competition with NR2A1 for binding to a DR1 element (PubMed:11927623, PubMed:21804189). Also reduces triglyceride clearance by inhibiting expression of ANGPTL3 and APOC3 (both involved in inhibition of lipoprotein lipase) (PubMed:12891557). Involved in glucose homeostasis by modulating hepatic gluconeogenesis through activation of NR0B2/SHP-mediated repression of respective genes. Modulates glycogen synthesis (inducing phosphorylation of glycogen synthase kinase-3) (By similarity). Modulates glucose-stimulated insulin secretion and is involved in insulin resistance (PubMed:20447400). Involved in intestinal innate immunity. Plays a role in protecting the distal small intestine against bacterial overgrowth and preservation of the epithelial barrier (By similarity). Down-regulates inflammatory cytokine expression in several types of immune cells including macrophages and mononuclear cells (PubMed:21242261). Mediates trans-repression of TLR4-induced cytokine expression; the function seems to require its sumoylation and prevents N-CoR nuclear receptor corepressor clearance from target genes such as IL1B and NOS2 (PubMed:19864602). Involved in the TLR9-mediated protective mechanism in intestinal inflammation. Plays an anti-inflammatory role in liver inflammation; proposed to inhibit pro-inflammatory (but not antiapoptotic) NF-kappa-B signaling) (By similarity)
- Specific Function
- bile acid binding
- Gene Name
- NR1H4
- Uniprot ID
- Q96RI1
- Uniprot Name
- Bile acid receptor
- Molecular Weight
- 55913.915 Da
References
- Urizar NL, Liverman AB, Dodds DT, Silva FV, Ordentlich P, Yan Y, Gonzalez FJ, Heyman RA, Mangelsdorf DJ, Moore DD: A natural product that lowers cholesterol as an antagonist ligand for FXR. Science. 2002 May 31;296(5573):1703-6. Epub 2002 May 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Urizar NL, Liverman AB, Dodds DT, Silva FV, Ordentlich P, Yan Y, Gonzalez FJ, Heyman RA, Mangelsdorf DJ, Moore DD: A natural product that lowers cholesterol as an antagonist ligand for FXR. Science. 2002 May 31;296(5573):1703-6. Epub 2002 May 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as a transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2
- Specific Function
- DNA binding
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- Urizar NL, Liverman AB, Dodds DT, Silva FV, Ordentlich P, Yan Y, Gonzalez FJ, Heyman RA, Mangelsdorf DJ, Moore DD: A natural product that lowers cholesterol as an antagonist ligand for FXR. Science. 2002 May 31;296(5573):1703-6. Epub 2002 May 2. [Article]
Enzymes
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
Components:
Name | UniProt ID |
---|---|
Cytochrome P450 3A4 | P08684 |
Cytochrome P450 3A43 | Q9HB55 |
Cytochrome P450 3A5 | P20815 |
Cytochrome P450 3A7 | P24462 |
References
- Meijerman I, Beijnen JH, Schellens JH: Herb-drug interactions in oncology: focus on mechanisms of induction. Oncologist. 2006 Jul-Aug;11(7):742-52. [Article]
Drug created at June 01, 2016 21:04 / Updated at February 03, 2022 06:26