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Identification
- Generic Name
- Bioallethrin
- DrugBank Accession Number
- DB13746
- Background
Bioallethrin refers to a mixture of two of the allethrin isomers (1R,trans;1R and 1R,trans;1S) in an approximate ratio of 1:1, where both isomers are active ingredients. A mixture of the two same stereoisomers, but in an approximate ratio of R:S in 1:3, is called esbiothrin. A mixture containing only S-forms of allethrin is referred to as esbioallethrin or S-bioallethrin. Bioallethrin is a synthetic pyrethroid used as a pesticide against household pest insects such as mosquitoes, houseflies and cockroaches. It is claimed to have low mammalian toxicity.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Bioallethrin (DB13746)
- Weight
- Average: 302.414
Monoisotopic: 302.188194697 - Chemical Formula
- C19H26O3
- Synonyms
- Depalléthrine
Pharmacology
- Indication
Bioallethrin was used for lice and scabies infestation. Other pyrethroids are now used in place of bioallethrin.
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Bioallethrin causes respiratory paralysis in lice and scabies parasites resulting in death 1.
- Mechanism of action
Bioallethrin, like other pyrethroids, binds to voltage gated sodium channels in their closed state and modifies the gating kinetics 1. Channel opening appears to increase affinity of the channel for pyrethroids like bioallethrin. Once bound pyrethroids slow both the opening and closing of the sodium channel resulting in a need for stronger excitatory potentials to produce an action potential and a delay in repolarization. The these changes make the neuron more susceptible to large action potentials and repeated firing by both increasing the initial threshold and reducing the input needed for after-potentials. When repeated firing does occur, the nerve terminal will release more neurotransmitter which can produce muscle paralysis through tetanus. This paralysis stops the breathing of lice and scabies parasites resulting in death.
Some pyrethroids act on calcium channels to increase intracelllular calcium 2. Bioallethrin produces a very small increase in intracellular calcium in mouse neocortical neurons by acting on N-type calcium channels but the effect returns to baseline within 2 min. In contrast bioallethrin has been found to block L T, and P/Q-types of voltage gated calcium channels in human embryonic kidney cell cultures 6. Bioallethrin has been found to inhibit both sodium-calcium dependent and magnesium-calcium ATP hydrolysis in insects although it, along with other type I pyrethroids, has a greater effect on sodium-calcium dependent hydrolysis 3. Bioallethrin may stimulate phosphoinositol breakdown in synaptoneuromes as other type I pyrethroids have been observed to do so 4. Other type I pyrethoids have also been found to bind to kainate receptors 5.
Target Actions Organism ASodium channel protein modulatorPediculus humanus UVoltage-gated sodium channel alpha subunit modulatorHumans UVoltage-dependent calcium channel agonistHumans UVoltage-dependent T-type calcium channel blockerHumans UVoltage-dependent P/Q-type calcium channel blockerHumans UVoltage-dependent L-type calcium channel blockerHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Metabolism of bioallethrin in both rats and humans is considered to be virtually 100% oxidative 7,8. This is because bioallethrin is very resistant to hydrolysis of its ester group although a negligible amount of hydrolysis may occur.
In humans bioallethrin is metabolized primarily by CYP2C19 with some metabolism by CYP2C8, CYP3A4, and CYP2C9*2 7. The metabolites produced include primary alcohols via allylic oxidation near the cyclopropane group and subsequent oxidation to carboxylic acid, formation of a primary alcohol via oxidation of a methyl group to located on the cyclopropane portion of the molecule, formation of a primary alcohol via allylic oxidation near the 5-membered ring or formation of an epoxide at this location and subsequent hydrolysis to a diol.
In rats bioallethrin has been found to be metabolized mainly by CYP2C6, CYP2C11, and CYP3A1 with some contribution from CYP1A1, CYP2A1 and CYP3A2 7. Rats appear to metabolize bioallethrin at about 15 times the rate of humans.
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- Route of elimination
Pyrethroids are excreted in both the feces and urine but values specific to bioallethrin are not available 8.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Bioallethrin can produce hypersensitivity reactions in patients sensitive to ragweed or chrysanthemum 10. Ingestion of bioallethrin can produce life-threatening convulsions or coma. Less serious toxic effects include sore throat, nausea, vomiting, abdominal pain, mouth ulceration, increased secretions and/or dysphagia. Systemic effects include dizziness, headache and fatigue are common, and palpitations, chest tightness and blurred vision and occur 4-48 h after exposure.
Bioallethrin is not carcinogenic or mutagenic 9. In rats doses over 58.7 mg/kg/day produce reproductive effects and doses over 125 mg/kg/day are embryotoxic.
Observed LD50 for various routes in animal studies 9:
Rat
- Male Oral - 709 mg/kg
- Female Oral - 1040 mg/kg
- Inhalation - 2.51 mg/L
Rabbit
- Dermal - >3000 mg/kg
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Bioallethrin can be increased when it is combined with Abametapir. Acebutolol Acebutolol may increase the arrhythmogenic activities of Bioallethrin. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Bioallethrin. Adenosine Adenosine may increase the arrhythmogenic activities of Bioallethrin. Ajmaline Ajmaline may increase the arrhythmogenic activities of Bioallethrin. - Food Interactions
- Not Available
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Para Special Shampoo for Lice & Nits Bioallethrin (1.1 %) + Piperonyl butoxide (4.4 %) Shampoo Topical Medican Technologies Inc. 1989-12-31 2005-09-15 Canada 
Scabene Bioallethrin (0.63 %) + Piperonyl butoxide (5.04 %) Aerosol Topical Medican Technologies Inc. 1997-06-10 2005-09-15 Canada Scabene Aerosol Bioallethrin (.63 %) + Piperonyl butoxide (5.04 %) Aerosol Topical Stiefel Laboratories, Inc. 1991-12-31 1997-11-19 Canada
Categories
- ATC Codes
- P03AC52 — Bioallethrin, combinations
- P03AC — Pyrethrines, incl. synthetic compounds
- P03A — ECTOPARASITICIDES, INCL. SCABICIDES
- P03 — ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Agents causing hyperkalemia
- Agrochemicals
- Antiarrhythmic agents
- Antiparasitic Products, Insecticides and Repellents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Compounds used in a research, industrial, or household setting
- Cyclopentane Monoterpenes
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Ectoparasiticides, Incl. Scabicides
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Insecticides
- Monoterpenes
- Pesticides
- Pyrethrines, Incl. Synthetic Compounds
- Pyrethrins
- Stereoisomerism
- Terpenes
- Toxic Actions
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0X03II877M
- CAS number
- 584-79-2
- InChI Key
- ZCVAOQKBXKSDMS-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
- IUPAC Name
- 2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
- SMILES
- CC(C)=CC1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C
References
- General References
- Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. [Article]
- Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. doi: 10.1124/jpet.110.171850. Epub 2010 Sep 29. [Article]
- Clark JM, Matsumura F: The action of two classes of pyrethroids on the inhibition of brain Na-Ca and Ca + Mg ATP hydrolyzing activities of the American cockroach. Comp Biochem Physiol C. 1987;86(1):135-45. [Article]
- Gusovsky F, Hollingsworth EB, Daly JW: Regulation of phosphatidylinositol turnover in brain synaptoneurosomes: stimulatory effects of agents that enhance influx of sodium ions. Proc Natl Acad Sci U S A. 1986 May;83(9):3003-7. [Article]
- Staatz CG, Bloom AS, Lech JJ: Effect of pyrethroids on [3H]kainic acid binding to mouse forebrain membranes. Toxicol Appl Pharmacol. 1982 Jul;64(3):566-9. [Article]
- Hildebrand ME, McRory JE, Snutch TP, Stea A: Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin. J Pharmacol Exp Ther. 2004 Mar;308(3):805-13. doi: 10.1124/jpet.103.058792. Epub 2003 Nov 21. [Article]
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Miyamoto J: Degradation, metabolism and toxicity of synthetic pyrethroids. Environ Health Perspect. 1976 Apr;14:15-28. [Article]
- WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES: Bioallethrin [Link]
- HSDB: Allethrins [Link]
- External Links
- Human Metabolome Database
- HMDB0243551
- KEGG Compound
- C14337
- PubChem Compound
- 15558638
- PubChem Substance
- 347829312
- ChemSpider
- 10958
- 19338
- ChEBI
- 34572
- ChEMBL
- CHEMBL1872535
- Wikipedia
- Bioallethrin
- MSDS
- Download (273 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Shampoo Topical Aerosol Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 165-170 WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES : BIOALLETHRIN water solubility 4.6 mg/L WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES : BIOALLETHRIN logP 4.7 WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES : BIOALLETHRIN - Predicted Properties
Property Value Source logP 4.06 Chemaxon pKa (Strongest Acidic) 19.47 Chemaxon pKa (Strongest Basic) -5.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.37 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 88.71 m3·mol-1 Chemaxon Polarizability 34.56 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0zms-1393000000-482a81f1fe840ab4d09b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0902000000-9c36361042f74559a8b9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pc9-1911000000-4473b474383296ebbe2c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1911000000-d1b75e355b5756b82c20 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-6930000000-ab6df40b1be91ec96c82 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-057m-5940000000-61ec58b0b318d1182ff9 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 171.67348 predictedDeepCCS 1.0 (2019) [M+H]+ 174.03148 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.48013 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Pediculus humanus
- Pharmacological action
- Yes
- Actions
- Modulator
- Curator comments
- Bioallethrin slows the opening and closing of the channel.
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
- Specific Function
- calcium ion binding
- Gene Name
- Not Available
- Uniprot ID
- Q86DI9
- Uniprot Name
- Sodium channel protein
- Molecular Weight
- 233296.52 Da
References
- Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- Curator comments
- Bioallethrin slows the opening and closing of the channel.
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:14672992). Plays a key role in brain, probably by regulating the moment when neurotransmitters are released in neurons. Involved in sensory perception of mechanical pain: activation in somatosensory neurons induces pain without neurogenic inflammation and produces hypersensitivity to mechanical, but not thermal stimuli
- Specific Function
- voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential
Components:
References
- Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. [Article]
- McCavera SJ, Soderlund DM: Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin. Neurotoxicology. 2012 Jun;33(3):384-90. doi: 10.1016/j.neuro.2012.03.007. Epub 2012 Mar 28. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- Curator comments
- Seems to be a weak agonist at N-type but blocker at L, T, and P/Q-type.
- General Function
- Regulatory subunit of the voltage-gated calcium channel that gives rise to L-type calcium currents in skeletal muscle. Regulates channel inactivation kinetics
- Specific Function
- calcium channel regulator activity
Components:
References
- Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. doi: 10.1124/jpet.110.171850. Epub 2010 Sep 29. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1G gives rise to T-type calcium currents. T-type calcium channels belong to the 'low-voltage activated (LVA)' group and are strongly blocked by mibefradil. A particularity of this type of channel is an opening at quite negative potentials and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes.
- Specific Function
- high voltage-gated calcium channel activity
Components:
References
- Hildebrand ME, McRory JE, Snutch TP, Stea A: Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin. J Pharmacol Exp Ther. 2004 Mar;308(3):805-13. doi: 10.1124/jpet.103.058792. Epub 2003 Nov 21. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1A gives rise to P and/or Q-type calcium currents. P/Q-type calcium channels belong to the 'high-voltage activated' (HVA) group and are specifically blocked by the spider omega-agatoxin-IVA (AC P54282) (By similarity). They are however insensitive to dihydropyridines (DHP)
- Specific Function
- amyloid-beta binding
Components:
References
- Hildebrand ME, McRory JE, Snutch TP, Stea A: Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin. J Pharmacol Exp Ther. 2004 Mar;308(3):805-13. doi: 10.1124/jpet.103.058792. Epub 2003 Nov 21. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Pore-forming, alpha-1C subunit of the voltage-gated calcium channel that gives rise to L-type calcium currents (PubMed:11741969, PubMed:12176756, PubMed:12181424, PubMed:15454078, PubMed:15863612, PubMed:16299511, PubMed:17071743, PubMed:17224476, PubMed:20953164, PubMed:23677916, PubMed:24728418, PubMed:26253506, PubMed:27218670, PubMed:29078335, PubMed:29742403, PubMed:30023270, PubMed:30172029, PubMed:34163037, PubMed:7737988, PubMed:8099908, PubMed:8392192, PubMed:9013606, PubMed:9087614, PubMed:9607315). Mediates influx of calcium ions into the cytoplasm, and thereby triggers calcium release from the sarcoplasm (By similarity). Plays an important role in excitation-contraction coupling in the heart. Required for normal heart development and normal regulation of heart rhythm (PubMed:15454078, PubMed:15863612, PubMed:17224476, PubMed:24728418, PubMed:26253506). Required for normal contraction of smooth muscle cells in blood vessels and in the intestine. Essential for normal blood pressure regulation via its role in the contraction of arterial smooth muscle cells (PubMed:28119464). Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group (Probable)
- Specific Function
- alpha-actinin binding
Components:
References
- Hildebrand ME, McRory JE, Snutch TP, Stea A: Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin. J Pharmacol Exp Ther. 2004 Mar;308(3):805-13. doi: 10.1124/jpet.103.058792. Epub 2003 Nov 21. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). 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:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- Curator comments
- Only metabolized by the CYP2C9*2 variant.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). 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:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- 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
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- 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
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Highly active in the 7-alpha-hydroxylation of testosterone, progesterone and androstenedione.
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- Cyp2a1
- Uniprot ID
- P11711
- Uniprot Name
- Cytochrome P450 2A1
- Molecular Weight
- 55994.635 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins. 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 (CPR; NADPH-ferrihemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. 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 C15alpha and C16alpha positions (By similarity). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (By similarity). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system. Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (By similarity). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (By similarity). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (By similarity).
- Specific Function
- arachidonic acid monooxygenase activity
- Gene Name
- Cyp1a1
- Uniprot ID
- P00185
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 59392.695 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Specific Function
- arachidonic acid 11,12-epoxygenase activity
- Gene Name
- Cyp2c6
- Uniprot ID
- P05178
- Uniprot Name
- Cytochrome P450 2C6
- Molecular Weight
- 56002.315 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and fatty acids. Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes testosterone to 2alpha- and 16alpha-hydroxytestosterone (PubMed:2434473). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFAs) (PubMed:10491410, PubMed:15766564). Converts arachidonic acid (ARA, C20:4(n-6)) primarily to epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, with both R,S and S,R stereochemistry (PubMed:10491410). Preferentially produces 11R,12S-EET enantiomer. To a lesser extent, catalyzes the hydroxylation of arachidonic acid producing hydroxyeicosatetraenoates (HETEs) (PubMed:10491410). Metabolizes eicosapentaenoic acid (EPA, C20:5(n-3)) to epoxyeicosatetraenoic acid (EETeTr) regioisomers, 8,9-, 11,12-, 14,15-, and 17,18-EETeTr, preferentially producing 17R,18S-EETeTr enantiomer (PubMed:15766564). 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:15766564, PubMed:2434473).
- Specific Function
- arachidonic acid 11,12-epoxygenase activity
- Gene Name
- Cyp2c11
- Uniprot ID
- P08683
- Uniprot Name
- Cytochrome P450 2C11
- Molecular Weight
- 57180.595 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Specific Function
- aromatase activity
- Gene Name
- Cyp3a1
- Uniprot ID
- P04800
- Uniprot Name
- Cytochrome P450 3A1
- Molecular Weight
- 57917.375 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Specific Function
- 1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activity
- Gene Name
- Cyp3a2
- Uniprot ID
- P05183
- Uniprot Name
- Cytochrome P450 3A2
- Molecular Weight
- 57731.215 Da
References
- Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF: In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab Dispos. 2009 Jan;37(1):221-8. doi: 10.1124/dmd.108.022343. Epub 2008 Oct 23. [Article]
Drug created at June 23, 2017 20:47 / Updated at December 01, 2022 11:28