| Revision as of 05:11, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 456680488 of page Alfentanil for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 01:35, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Synthetic opioid analgesic}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Use dmy dates|date=April 2019}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 477317188 |
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| Verifiedfields = changed |
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| IUPAC_name = ''N''-(1-(2-Phenylethyl)-4-piperidinyl)-''N''-phenylbutyramide |
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| verifiedrevid = 456679075 |
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| image = butyrfentanyl.png |
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| IUPAC_name = ''N''-{1--4-(methoxymethyl)piperidin-4-yl}-''N''-phenylpropanamide |
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| image_class = skin-invert-image |
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| image = Alfentanil-2D-skeletal.svg |
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| width = 200px |
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| width = 220px |
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| image2 = Butyrylfentanyl 3D BS.png |
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| image_class2 = bg-transparent |
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| width2 = 220px |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Alfenta |
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| tradename = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| Drugs.com = {{drugs.com|CONS|alfentanil}} |
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| MedlinePlus = a601130 |
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| legal_BR = F1 |
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| legal_CA = Schedule I |
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| legal_DE = Anlage II |
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| legal_UK = Class A |
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| legal_UK = Class A |
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| legal_US = Schedule II |
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| legal_US = Schedule I |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = 100% |
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| protein_bound = 92% |
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| metabolism = ] |
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| elimination_half-life = 90–111 minutes |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number = 1169-70-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 621174 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| DrugBank = DB09173 |
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| CAS_number = 71195-58-9 |
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| ATC_prefix = N01 |
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| KEGG = C22760 |
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| ATC_suffix = AH02 |
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| ATC_prefix = none |
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| PubChem = 51263 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB00802 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 46451 |
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| ChemSpiderID = 539764 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1N74HM2BS7 |
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| UNII = 07V1H7R6ZN |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07122 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 2569 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 634 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=21 | H=32 | N=6 | O=3 |
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| C=23 | H=30 | N=2 | O=1 |
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| smiles = CCCC(=O)N(C2CCN(CCc1ccccc1)CC2)c3ccccc3 |
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| molecular_weight = 416.517 g/mol |
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| StdInChI = 1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3 |
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| smiles = O=C1N(\N=N/N1CC)CCN3CCC(N(c2ccccc2)C(=O)CC)(CC3)COC |
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| StdInChIKey = QQOMYEQLWQJRKK-UHFFFAOYSA-N |
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| InChI = 1/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3 |
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| InChIKey = IDBPHNDTYPBSNI-UHFFFAOYAV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IDBPHNDTYPBSNI-UHFFFAOYSA-N |
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| melting_point = 140.8 |
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}} |
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}} |
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'''Butyrfentanyl''' or '''butyrylfentanyl''' is a potent short-acting synthetic ] ] ]. It is an ] of ] with around one quarter of its potency. One of the first mentions of this drug can be found in document written by The College on Problem of Drug Dependence, where it is mentioned as ''N''-butyramide fentanyl analog.<ref name="The College on Problem of Drug Dependence">{{cite web | url = http://www.cpdd.vcu.edu/DEC_ARCHIVES/DEC/acrobat/DECindices.pdf | title = The College on Problem of Drug Dependence | archive-url = https://web.archive.org/web/20131219015856/http://www.cpdd.vcu.edu/DEC_ARCHIVES/DEC/acrobat/DECindices.pdf | archive-date=2013-12-19 }}, Foreword to the Drug Evaluation Committee (DEC) Analgesic, Stimulant, and Depressant Drug Indices</ref> This document also states that the article describing its clinical effects (analgesic studies, μ-, δ-, κ-opioid receptor binding, and '']'' measures of drug efficacy, antinociceptive, and narcotic properties) was published in 1987. It is an agonist for the ]s.<ref name="Part II">{{cite thesis | vauthors = Alburges ME | degree = Ph.D. | title = Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine | url= http://content.lib.utah.edu/utils/getfile/collection/etd1/id/1285/filename/1341.pdf | archive-url = https://web.archive.org/web/20131219043413/http://content.lib.utah.edu/utils/getfile/collection/etd1/id/1285/filename/1341.pdf | archive-date = 19 December 2013 | publisher = The University of Utah | date = June 1988 }}</ref> |
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Butyrfentanyl has no current legitimate clinical applications; however, it is being sold as a ].<ref>{{cite journal | vauthors = McIntyre IM, Trochta A, Gary RD, Wright J, Mena O | title = An Acute Butyr-Fentanyl Fatality: A Case Report with Postmortem Concentrations | journal = Journal of Analytical Toxicology | volume = 40 | issue = 2 | pages = 162–166 | date = March 2016 | pmid = 26683128 | doi = 10.1093/jat/bkv138 | doi-access = free }}</ref> |
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Side effects of fentanyl analogs are similar to those of fentanyl itself, which include ], ], and potentially serious ] which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.<ref>{{cite journal | vauthors = Mounteney J, Giraudon I, Denissov G, Griffiths P | title = Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe | journal = The International Journal on Drug Policy | volume = 26 | issue = 7 | pages = 626–631 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 }}</ref> |
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==Pharmacokinetics== |
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Butyrfentanyl binds to the opioid receptor. During the studies of ] inhibition of specific fentanyl binding to the opioid receptor, the order of analogues was: (±)-''cis''-3-methylfentanyl > fentanyl = alpha-methylfentanyl > butyrylfentanyl > benzylfentanyl.<ref name="Part II"/> The studies in inhibition studies on binding affinity achieved the same order of analogues. It means that butyrfentantyl is a less potent opioid-agonist than fentanyl. On the other side, during in vitro studies of cross-reactivity with the fentanyl ] between fentanyl and the fentanyl analogs examined, revealed order: fentanyl = butyrylfentanyl > (±)-''cis''-] > benzylfentanyl > alpha-methylfentanyl.<ref name="Part II" /> High cross-reactivity may be the effect of the shape of the molecule — the shape of butyrfentanyl is closest to the original fentanyl molecule, which makes it easy to bind by fentanyl antibodies. |
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The opioid ] of fentanyl and its analogs was determined from their inhibitory potency in a binding assay with fentanyl as the radioligand. The K<sub>i</sub> value for butyrfentanyl was 32 ± 4.1 nM. Comparing to fentanyl's K<sub>i</sub> (1.06 ± 0.15 nM), butyrfentanyl's ability to displace fentanyl is low and it requires high concentrations of the drug.<ref name="Part II" /> |
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Studies on urinary excretion revealed that almost all of the injected butyrfentanyl was excreted or metabolized within the first 3 hours after injection, and only very low concentrations were still detectable after 3 hours.<ref name="Part II" /> Urinary concentrations of butyrylfentanyl from animals injected with 15 μg/kg and 45 μg/kg i.v. were measured by two techniques: radioreceptorassay and gas chromatography/mass spectrometry (]). |
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==Legal status== |
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There was a proposal being discussed by the UN Commission on Narcotic Drugs (CND) to include butyrfentanyl in Schedule 1 of the 1961 Single Convention on Narcotic Drugs which was passed 16 March 2017.<ref>{{cite web | title = Inclusion of butyrfentanyl in Schedule I of the Single Convention on Narcotic Drugs of 1961 as amended by the 1972 Protocol |url=https://www.unodc.org/documents/commissions/CND/CND_Sessions/CND_60/CNDdec_2017/Decision_60_3_60CND.pdf}}</ref> |
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===United Kingdom=== |
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Butyrfentanyl is illegal in the United Kingdom as it is a modification of fentanyl "by replacement of the N-propionyl group by another acyl group". |
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===United States=== |
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As of May 2016, butyrfentanyl is a Schedule I controlled substance in the United States.<ref>{{cite web | url=https://www.gpo.gov/fdsys/pkg/FR-2016-05-12/pdf/2016-11219.pdf | title=Schedules of Controlled Substances: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl into Schedule I | publisher=] | date=12 May 2016}}</ref> |
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===China=== |
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As of October 2015, butyrfentanyl is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref> |
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===Switzerland=== |
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Butyrfentanyl is illegal in Switzerland as of December 2015.<ref>{{cite web | url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html | title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien | trans-title = EDI regulation on the lists of narcotics, psychotropic substances, precursor substances and auxiliary chemicals | language = German | publisher=Der Bundesrat}}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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== Further reading == |
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{{refbegin}} |
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* {{cite journal |vauthors=Higashikawa Y, Suzuki S | title = Studies on 1-(2-phenethyl)-4-(''N''-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues|journal=Forensic Toxicology |date=June 2008 | volume = 26 | issue = 1 | pages = 1–5 | doi = 10.1007/s11419-007-0039-1 | s2cid = 22092512}} |
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* {{cite journal | vauthors = Alburges ME, Hanson GR, Gibb JW, Sakashita CO, Rollins DE | title = Fentanyl receptor assay. II. Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine | journal = Journal of Analytical Toxicology | volume = 16 | issue = 1 | pages = 36–41 | year = 1992 | pmid = 1322477 | doi = 10.1093/jat/16.1.36 }} |
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* {{cite journal | vauthors = Woods J, Medzihradsky F, Smith C, Winger G, Gmerek D | title = Evaluation of new compounds for opioid activity: 1987 annual report | journal = NIDA Research Monograph | volume = 81 | pages = 543–590 | year = 1988 | pmid = 3136388 }} |
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* {{cite journal | vauthors = Aceto M, Bowman E, Harris L, May E | title = Dependence studies of new compounds in the rhesus monkey, rat, and mouse, 1987 | journal = NIDA Research Monograph | volume = 81 | pages = 485–542 | year = 1988 | pmid = 3136386 }} |
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* {{cite journal |vauthors=Brine GA, Boldt KG, Huang PT, Sawyer DK, Carroll FI | title = Carbon-13 nuclear magnetic resonance spectra of fentanyl analogs | year = 2009 | doi = 10.1002/jhet.5570260329 | journal = Journal of Heterocyclic Chemistry | volume = 26 | issue = 3 | pages = 677–686 | doi-access = free }} |
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{{refend}} |
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{{Analgesics}} |
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{{General anesthetics}} |
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{{Opioidergics}} |
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] |
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] |
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] |
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] |
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] |