Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Propiram: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 14:36, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 451726862 of page Propiram for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 11:34, 12 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,609 edits Added s2cid. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. 
Line 1: Line 1:
{{Short description|Opioid analgesic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 447990520 | verifiedrevid = 464216831
| IUPAC_name = ''N''-(1-methyl-2-piperidin-1-ylethyl)-''N''-pyridin-2-ylpropanamide | IUPAC_name = ''N''-(1-Methyl-2-piperidin-1-ylethyl)-''N''-pyridin-2-ylpropanamide
| image = Propiram.svg | image = Propiram2DCSD.svg
| width = 180 | width = 180


Line 9: Line 11:
| tradename = | tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S8
| legal_CA = | legal_BR = A2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-03 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_UK = | legal_UK =
| legal_US = Schedule I | legal_US = Schedule I
| legal_status = | legal_DE = Anlage II
| routes_of_administration = oral, injected | routes_of_administration = ], injected


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
Line 22: Line 25:
| protein_bound = | protein_bound =
| elimination_half-life = 5.2 hours | elimination_half-life = 5.2 hours
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 15686-91-6 --> | CAS_number = 15686-91-6
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
Line 38: Line 42:
<!--Chemical data--> <!--Chemical data-->
| C=16 | H=25 | N=3 | O=1 | C=16 | H=25 | N=3 | O=1
| molecular_weight = 275.39 g/mol
| smiles = O=C(N(c1ncccc1)C(CN2CCCCC2)C)CC | smiles = O=C(N(c1ncccc1)C(CN2CCCCC2)C)CC
| InChI = 1/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3
| InChIKey = ZBAFFZBKCMWUHM-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3 | StdInChI = 1S/C16H25N3O/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3
Line 48: Line 49:
| synonyms = | synonyms =
}} }}

'''Propiram''' ('''Algeril''', '''Dirame''', '''Bay 4503''')<ref>US3163654A Pyridine derivatives and their preparation (n-tertiary aminoalkyl-n-acyl)-amino pyridines</ref> is a partial ] agonist and weak μ antagonist ] from the ampromide family of drugs related to other drugs such as ] and ]. It was invented in 1963 in the United Kingdom by Bayer<ref>{{US Patent|3163654}}</ref> but was not widely marketed, although it saw some limited clinical use, especially in dentistry. Propiram reached ]s in the United States and Canada.<ref>{{cite book | title = Drug Facts & Comparisons | edition = 56th | date = 2002}}</ref>

==Pharmacology==
Propiram exhibits weak opioid antagonist activity on the μ receptor—quite a bit weaker than its agonist effects—and the effect on ] and ], ], or the ] system are not well understood. Other drugs of the partial μ-opioid agonist/antagonist type include ], ], ], ], ], ], ] and its relatives.

With about 10% of the analgesic potency of ], 50&nbsp;mg of propiram is equivalent to about 60&nbsp;mg of codeine or 50&nbsp;mg of pentazocine. In many patients, propiram is an effective analgesic comparable to other drugs such as these as well as ], with a normal dose of around 50–100&nbsp;mg and a duration of action of 3 to 6 hours.<ref>{{cite journal | vauthors = Wilson RS, Landers JH | title = Use of a new oral analgesic, propiram fumarate, in treating postoperative ocular pain | journal = Annals of Ophthalmology | volume = 14 | issue = 12 | pages = 1172–4 | date = December 1982 | pmid = 7165237 }}</ref> It is more potent and effective than codeine,<ref>{{cite journal | vauthors = Desjardins PJ, Cooper SA, Gallegos TL, Allwein JB, Reynolds DC, Kruger GO, Beaver WT | title = The relative analgesic efficacy of propiram fumarate, codeine, aspirin, and placebo in post-impaction dental pain | journal = Journal of Clinical Pharmacology | volume = 24 | issue = 1 | pages = 35–42 | date = January 1984 | pmid = 6368614 | doi = 10.1002/j.1552-4604.1984.tb01811.x | s2cid = 11070740 }}</ref> and longer-lasting and with a faster onset of action compared to pethidine.<ref>{{cite journal | vauthors = Korduba CA, Veals J, Radwanski E, Symchowicz S, Chung M | title = Bioavailability of orally administered propiram fumarate in humans | journal = Journal of Pharmaceutical Sciences | volume = 70 | issue = 5 | pages = 521–3 | date = May 1981 | pmid = 7241356 | doi = 10.1002/jps.2600700515 }}</ref> Side effects include ], ], ] and ].<ref>{{cite journal | vauthors = Goa KL, Brogden RN | title = Propiram. A review of its pharmacodynamic and pharmacokinetic properties, and clinical use as an analgesic | journal = Drugs | volume = 46 | issue = 3 | pages = 428–445 | date = September 1993 | pmid = 7693433 | doi = 10.2165/00003495-199346030-00008 | s2cid = 195691876 }}</ref> Propiram has been available in oral, rectal, and injectable formulations, with bioavailability above 97% after oral administration.

==Derivatives==
Many related compounds are known, although only propiram was ever commercialized.<ref>{{cite journal | vauthors = Hiltmann R, Hoffmeister F, Niemers E, Schlichting U, Wollweber H | title = | journal = Arzneimittel-Forschung | volume = 24 | issue = 4 | pages = 584–600 | date = April 1974 | pmid = 4406861 }}</ref> The addition of a 4-phenyl group on the piperidine increases potency by a factor of 133x compared to the parent compound. Addition of a 3,3-dimethyl moiety to the piperidine ring increases potency by 45x compared to the title compound <ref>Wollweber H. Stereochemische Untersuchungen über Arzneimittel. ''European Journal of Medicinal Chemistry'' 1982; 17: 125–133.</ref> and 3D overlay using CHARMM shows that this class overlays the fentanyl scaffold in the positioning of aryl groups, basic nitrogen and amide moieties perfectly.
]{{clear-left}}

==Regulation==
Propiram is currently a Schedule I/Narcotic controlled substance in the United States with an ACSCN of 9649 and a zero annual aggregate manufacturing quota as of 2014. It has been almost exclusively ] as the ] ].

== References ==
{{Reflist|2}}

{{Opioidergics}}

]
]
]
]