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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyEtorphine
Identification
- Name
- Etorphine
- Accession Number
- DB01497
- Type
- Small Molecule
- Groups
- Illicit, Vet approved
- Description
A narcotic analgesic morphinan used as a sedative in veterinary practice. In Hong Kong, Etorphine is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. It can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. In the US, Etorphine is listed as a Schedule I drug, although Etorphine hydrochloride is classified as Schedule II.
- Structure
Structure for Etorphine (DB01497)
- Synonyms
- Etorphinum
- External IDs
- DEA No. 9056 / M99
- Product Ingredients
Ingredient UNII CAS InChI Key Etorphine Hydrochloride 8CBE01N748 13764-49-3 JNHPUZURWFYYHW-DTUSRQQPSA-N - Categories
- UNII
- 42M2Y6NU9O
- CAS number
- 14521-96-1
- Weight
- Average: 411.5338
Monoisotopic: 411.240958549 - Chemical Formula
- C25H33NO4
- InChI Key
- CAHCBJPUTCKATP-HBDRVVKHSA-N
- InChI
- InChI=1S/C25H33NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3/t17?,18-,21?,22?,23-,24+,25?/m1/s1
- IUPAC Name
- (1R,2R,6S)-19-(2-hydroxypentan-2-yl)-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11,16-tetraen-11-ol
- SMILES
- [H][C@]12CC3=C4C(OC5[C@@]4(CCN1C)[C@]21CC(C(C)(O)CCC)C5(OC)C=C1)=C(O)C=C3
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
Etorphine is a synthetic cousin of morphine and 40,000 times more powerful. It can be produced from thebaine. It is most often used to immobilize elephants and other large mammals. Etorphine is only available legally for veterinary use and is strictly governed by law.
- Mechanism of action
Etorphine is an agonist at mu, delta, and kappa opioid receptors. It also has a weak affinity for the ORL1 nociceptin/orphanin FQ receptor.
Target Actions Organism AMu-type opioid receptor agonistHuman ADelta-type opioid receptor agonistHuman AKappa-type opioid receptor agonistHuman UNociceptin receptor agonistHuman UE3 ubiquitin-protein ligase TRIM13 agonistHuman UPro-opiomelanocortin Not Available Human - 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
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Etorphine. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Etorphine. 3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine may increase the analgesic activities of Etorphine. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Etorphine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Etorphine is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Etorphine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Acepromazine The risk or severity of adverse effects can be increased when Etorphine is combined with Acepromazine. Aceprometazine The risk or severity of adverse effects can be increased when Etorphine is combined with Aceprometazine. Acetazolamide The risk or severity of adverse effects can be increased when Etorphine is combined with Acetazolamide. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Etorphine. - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 214-217 °C PhysProp logP 2.79 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 0.112 mg/mL ALOGPS logP 3.29 ALOGPS logP 2.47 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 7.48 ChemAxon pKa (Strongest Basic) 11.72 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 62.16 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 116.51 m3·mol-1 ChemAxon Polarizability 45.55 Å3 ChemAxon Number of Rings 6 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
Property Value Probability Human Intestinal Absorption + 0.9954 Blood Brain Barrier + 0.9708 Caco-2 permeable + 0.7322 P-glycoprotein substrate Substrate 0.9173 P-glycoprotein inhibitor I Inhibitor 0.7399 P-glycoprotein inhibitor II Non-inhibitor 0.7779 Renal organic cation transporter Non-inhibitor 0.6479 CYP450 2C9 substrate Non-substrate 0.8713 CYP450 2D6 substrate Substrate 0.7349 CYP450 3A4 substrate Substrate 0.7858 CYP450 1A2 substrate Non-inhibitor 0.9392 CYP450 2C9 inhibitor Non-inhibitor 0.8992 CYP450 2D6 inhibitor Non-inhibitor 0.6197 CYP450 2C19 inhibitor Non-inhibitor 0.8553 CYP450 3A4 inhibitor Non-inhibitor 0.8272 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9294 Ames test Non AMES toxic 0.7862 Carcinogenicity Non-carcinogens 0.9372 Biodegradation Not ready biodegradable 0.9973 Rat acute toxicity 3.2955 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8072 hERG inhibition (predictor II) Non-inhibitor 0.7219
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Morphinans
- Sub Class
- Not Available
- Direct Parent
- Morphinans
- Alternative Parents
- Phenanthrenes and derivatives / Tetralins / Azaspirodecane derivatives / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Tertiary alcohols / Trialkylamines show 5 more
- Substituents
- Morphinan / Phenanthrene / Azaspirodecane / Tetralin / Coumaran / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Piperidine / Benzenoid show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Duttaroy A, Yoburn BC: In vivo regulation of mu-opioid receptor density and gene expression in CXBK and outbred Swiss Webster mice. Synapse. 2000 Aug;37(2):118-24. [PubMed:10881033]
- Melone M, Brecha NC, Sternini C, Evans C, Conti F: Etorphine increases the number of mu-opioid receptor-positive cells in the cerebral cortex. Neuroscience. 2000;100(3):439-43. [PubMed:11098106]
- Stafford K, Gomes AB, Shen J, Yoburn BC: mu-Opioid receptor downregulation contributes to opioid tolerance in vivo. Pharmacol Biochem Behav. 2001 May-Jun;69(1-2):233-7. [PubMed:11420091]
- Gomes BA, Shen J, Stafford K, Patel M, Yoburn BC: Mu-opioid receptor down-regulation and tolerance are not equally dependent upon G-protein signaling. Pharmacol Biochem Behav. 2002 May;72(1-2):273-8. [PubMed:11900797]
- Patel MB, Patel CN, Rajashekara V, Yoburn BC: Opioid agonists differentially regulate mu-opioid receptors and trafficking proteins in vivo. Mol Pharmacol. 2002 Dec;62(6):1464-70. [PubMed:12435815]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Li JG, Benovic JL, Liu-Chen LY: Mechanisms of agonist-induced down-regulation of the human kappa-opioid receptor: internalization is required for down-regulation. Mol Pharmacol. 2000 Oct;58(4):795-801. [PubMed:10999950]
- Li JG, Zhang F, Jin XL, Liu-Chen LY: Differential regulation of the human kappa opioid receptor by agonists: etorphine and levorphanol reduced dynorphin A- and U50,488H-induced internalization and phosphorylation. J Pharmacol Exp Ther. 2003 May;305(2):531-40. Epub 2003 Jan 24. [PubMed:12606694]
- Marie N, Lecoq I, Jauzac P, Allouche S: Differential sorting of human delta-opioid receptors after internalization by peptide and alkaloid agonists. J Biol Chem. 2003 Jun 20;278(25):22795-804. Epub 2003 Apr 2. [PubMed:12672796]
- Sumner BE, Douglas AJ, Russell JA: Pregnancy alters the density of opioid binding sites in the supraoptic nucleus and posterior pituitary gland of rats. Neurosci Lett. 1992 Mar 30;137(2):216-20. [PubMed:1316589]
- Tao PL, Tsai CL, Chang LR, Loh HH: Chronic effect of [D-Pen2,D-Pen5]enkephalin on rat brain opioid receptors. Eur J Pharmacol. 1991 Aug 29;201(2-3):209-14. [PubMed:1665782]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Niwa M, al-Essa LY, Ohta S, Kohno K, Nozaki M, Tsurumi K, Iwamura T, Kataoka T: Opioid receptor interaction and adenylyl cyclase inhibition of dihydroetorphine: direct comparison with etorphine. Life Sci. 1995;56(21):PL395-400. [PubMed:7739347]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Niwa M, al-Essa LY, Ohta S, Kohno K, Nozaki M, Tsurumi K, Iwamura T, Kataoka T: Opioid receptor interaction and adenylyl cyclase inhibition of dihydroetorphine: direct comparison with etorphine. Life Sci. 1995;56(21):PL395-400. [PubMed:7739347]
- Wannemacher KM, Yadav PN, Howells RD: A select set of opioid ligands induce up-regulation by promoting the maturation and stability of the rat kappa-opioid receptor in human embryonic kidney 293 cells. J Pharmacol Exp Ther. 2007 Nov;323(2):614-25. Epub 2007 Aug 24. [PubMed:17720886]
- Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. [PubMed:16433932]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Nociceptin receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for the endogenous neuropeptide nociceptin. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-b...
- Gene Name
- OPRL1
- Uniprot ID
- P41146
- Uniprot Name
- Nociceptin receptor
- Molecular Weight
- 40692.775 Da
References
- Hawkinson JE, Acosta-Burruel M, Espitia SA: Opioid activity profiles indicate similarities between the nociceptin/orphanin FQ and opioid receptors. Eur J Pharmacol. 2000 Feb 18;389(2-3):107-14. [PubMed:10688973]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- E3 ubiquitin ligase involved in the retrotranslocation and turnover of membrane and secretory proteins from the ER through a set of processes named ER-associated degradation (ERAD). This process ac...
- Gene Name
- TRIM13
- Uniprot ID
- O60858
- Uniprot Name
- E3 ubiquitin-protein ligase TRIM13
- Molecular Weight
- 46987.08 Da
References
- Maneckjee R, Archer S, Zukin RS: Characterization of a polyclonal antibody to the mu opioid receptor. J Neuroimmunol. 1988 Feb;17(3):199-208. [PubMed:2828423]
- Stojilkovic SS, Dufau ML, Catt KJ: Opiate receptor subtypes in the rat hypothalamus and neurointermediate lobe. Endocrinology. 1987 Jul;121(1):384-94. [PubMed:3036471]
- Pesce G, Lang MA, Russell JT, Rodbard D, Gainer H: Characterization of kappa opioid receptors in neurosecretosomes from bovine posterior pituitary. J Neurochem. 1987 Aug;49(2):421-7. [PubMed:3037028]
- Pfeiffer A, Herz A: Discrimination of three opiate receptor binding sites with the use of a computerized curve-fitting technique. Mol Pharmacol. 1982 Mar;21(2):266-71. [PubMed:6124875]
- Audigier Y, Mazarguil H, Gout R, Cros J: Structure-activity relationships of enkephalin analogs at opiate and enkephalin receptors: correlation with analgesia. Eur J Pharmacol. 1980 Apr 11;63(1):35-46. [PubMed:6247160]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Type 4 melanocortin receptor binding
- Specific Function
- ACTH stimulates the adrenal glands to release cortisol.MSH (melanocyte-stimulating hormone) increases the pigmentation of skin by increasing melanin production in melanocytes.Beta-endorphin and Met...
- Gene Name
- POMC
- Uniprot ID
- P01189
- Uniprot Name
- Pro-opiomelanocortin
- Molecular Weight
- 29423.72 Da
References
- Sanchez-Blazquez P, Garzon J: Further characterization of alpha N-acetyl beta-endorphin-(1-31) regulatory activity, I: Effect on opioid- and alpha 2-mediated supraspinal antinociception in mice. Life Sci. 1992;50(26):2083-97. [PubMed:1318989]
- Xu JY, Fujimoto JM, Tseng LF: Involvement of supraspinal epsilon and mu opioid receptors in inhibition of the tail-flick response induced by etorphine in the mouse. J Pharmacol Exp Ther. 1992 Oct;263(1):246-52. [PubMed:1328609]
- Nicolas P, Li CH: Beta-endorphin-(1-27) is a naturally occurring antagonist to etorphine-induced analgesia. Proc Natl Acad Sci U S A. 1985 May;82(10):3178-81. [PubMed:2987913]
- Dum J, Gramsch C, Herz A: Activation of hypothalamic beta-endorphin pools by reward induced by highly palatable food. Pharmacol Biochem Behav. 1983 Mar;18(3):443-7. [PubMed:6132412]
- Lemaire S, Livett B, Tseng R, Mercier P, Lemaire I: Studies on the inhibitory action of opiate compounds in isolated bovine adrenal chromaffin cells: noninvolvement of stereospecific opiate binding sites. J Neurochem. 1981 Mar;36(3):886-92. [PubMed:6259293]
Drug created on July 31, 2007 07:09 / Updated on August 02, 2018 07:44