| Revision as of 02:35, 12 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 01:28, 30 July 2022 edit undoMplanine (talk | contribs)454 editsm added the 3D structure to the chemical infobox |
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{{Short description|Opioid analgesic}} |
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{{drugbox |
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{{Drugbox |
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| verifiedrevid = 438868679 |
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| Verifiedfields = changed |
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| IUPAC_name = N--N-phenyl-propanamide |
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| Watchedfields = changed |
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| image = R-30490_structure.png |
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| verifiedrevid = 439017639 |
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| width = 200px |
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| IUPAC_name = ''N''--''N''-phenylpropanamide |
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| image = R-30490.svg |
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| image2 = R-30490.png |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_category = |
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| legal_CA = Schedule I |
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| legal_UK = Class A |
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| legal_US = ]<ref name=pmid29932611>{{cite journal | title = Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order | journal = Federal Register | volume = 83 | issue = 25 | pages = 5188–92 | date = February 2018 | pmid = 29932611 | last1 = Drug Enforecement Administration | first1 = Department of Justice }}</ref> |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|cas}} |
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| CAS_number = 60618-49-7 |
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| CAS_number = 60618-49-7 |
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| ATC_prefix = |
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| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 609147 |
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| PubChem = 124716 |
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| PubChem = 124716 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| C=24 | H=32 | N=2 | O=2 |
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| ChemSpiderID = 111042 |
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| molecular_weight = 380.522 g/mol |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| smiles = c2ccccc2N(C(=O)CC)C1(COC)CCN(CC1)CCc3ccccc3 |
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| UNII = 03DNV05OD4 |
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| bioavailability = ? |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| protein_bound = ? |
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| metabolism = ? |
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| DrugBank = DB09179 |
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| elimination_half-life = |
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<!--Chemical data--> |
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| excretion = ? |
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| legal_UK = |
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| C=24 | H=32 | N=2 | O=2 |
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| smiles = CCC(=O)N(c1ccccc1)C2(COC)CCN(CC2)CCc3ccccc3 |
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| legal_US = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| routes_of_administration = |
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| StdInChI = 1S/C24H32N2O2/c1-3-23(27)26(22-12-8-5-9-13-22)24(20-28-2)15-18-25(19-16-24)17-14-21-10-6-4-7-11-21/h4-13H,3,14-20H2,1-2H3 |
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| pregnancy_category = ? |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = GARXJOUQUSNOGK-UHFFFAOYSA-N |
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}} |
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}} |
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'''R-30490''' is an ] analgesic drug related to the highly potent animal tranquilizer ], and with only slightly lower potency. It was first synthesised by a team of chemists at ] led by ], who were investigating the ]s of the ] family of drugs. R-30490 was found to be the most selective agonist for the ] out of all the fentanyl analogues tested, but it has never been introduced for medical use in humans, although the closely related drug ] is widely used for analgesia and anesthesia during major surgery.<ref name="pmid1310142">{{cite journal |author=Cometta-Morini C, Maguire PA, Loew GH |title=Molecular determinants of mu receptor recognition for the fentanyl class of compounds |journal=Molecular Pharmacology |volume=41 |issue=1 |pages=185–96 |year=1992 |month=January |pmid=1310142 |doi= |url=}}</ref><ref>{{Cite doi|10.1016/0014-2999(92)90685-W}}</ref><ref>{{Cite doi|10.1007/BF00449683}}</ref><ref>{{Cite doi|10.1021/jm9903702}}</ref> |
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'''R-30490''' (also known as '''4-methoxymethylfentanyl''') is an ] ] related to the highly potent animal tranquilizer ], and with only slightly lower potency. It was first synthesised by a team of chemists at ] led by ], who were investigating the ]s of the ] family of drugs. R-30490 was found to be the most selective agonist for the ] out of all the fentanyl analogues tested, but it has never been introduced for medical use in humans, although the closely related drug ] is widely used for analgesia and anesthesia during major surgery.<ref name="pmid1310142">{{cite journal | vauthors = Cometta-Morini C, Maguire PA, Loew GH | title = Molecular determinants of mu receptor recognition for the fentanyl class of compounds | journal = Molecular Pharmacology | volume = 41 | issue = 1 | pages = 185–96 | date = January 1992 | pmid = 1310142 }}</ref><ref>{{cite journal | vauthors = Maguire P, Tsai N, Kamal J, Cometta-Morini C, Upton C, Loew G | title = Pharmacological profiles of fentanyl analogs at mu, delta and kappa opiate receptors | journal = European Journal of Pharmacology | volume = 213 | issue = 2 | pages = 219–25 | date = March 1992 | pmid = 1355735 | doi = 10.1016/0014-2999(92)90685-W }}</ref><ref>{{cite journal | vauthors = Meert TF | s2cid = 28280435 | title = Pharmacotherapy of opioids: present and future developments | journal = Pharmacy World & Science | volume = 18 | issue = 1 | pages = 1–15 | date = January 1996 | pmid = 8861825 | doi = 10.1007/BF00449683 }}</ref><ref>{{cite journal | vauthors = Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM | title = Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 3 | pages = 381–91 | date = February 2000 | pmid = 10669565 | doi = 10.1021/jm9903702 }}</ref> |
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Side effects of ] 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 = 626–31 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 | url = http://www.ijdp.org/article/S0955-3959%2815%2900097-3/abstract }}</ref> |
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== See also == |
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==References== |
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== References == |
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{{Reflist|2}} |
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<references/> |
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{{Opioid receptor modulators}} |
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