Piminodine: Difference between revisions

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			{{Short description\|Opioid analgesic drug}}
	{{Drugbox		{{Drugbox
			\| Verifiedfields = changed
	\| verifiedrevid = ~~447990189~~		\| verifiedrevid = 400852912
	\| IUPAC_name = ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate		\| IUPAC_name = ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
	\| image = Piminodine.svg		\| image = Piminodine.svg
	\| width = 160		\| width = 160

	<!--Clinical data-->		<!--Clinical data-->\| tradename =
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| tradename =
	\| ~~pregnancy_AU~~ = <!-- A / B1 / B2 / B3 / C / D / X -->		\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
⚫	\| ~~pregnancy_US~~ = <!-- A / B / C / D / X -->
		⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫	\| pregnancy_category =
			\| legal_BR = A1
⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
			\| 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=2023-08-16 \|publisher=] \|language=pt-BR \|publication-date=2023-04-04}}</ref>
⚫	\| ~~legal_CA~~ = <!-- Schedule I -->
	\| ~~legal_UK~~ = <!-- ~~Class~~ A -->		\| legal_CA = <!-- Schedule I -->
			\| legal_UK = <!-- Class A -->
	\| legal_US = Schedule II
		⚫	\| legal_US = <!-- Schedule II -->
	\| legal_status =		\| legal_status =
	\| routes_of_administration =		\| routes_of_administration = <!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion = <!--Identifiers-->
		⚫	\| CAS_number = 13495-09-5
		⚫	\| ATC_prefix = none
		⚫	\| ATC_suffix =
		⚫	\| PubChem = 21950
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank =
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 20628
		⚫	\| UNII_Ref = {{fdacite\|changed\|FDA}}
		⚫	\| UNII = 3IIX447HWS
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = D12683

	<!--~~Pharmacokinetic~~ data-->		<!--Chemical data-->\| C = 23
			\| H = 30
⚫	\| bioavailability =
			\| N = 2
⚫	\| protein_bound =
			\| O = 2
⚫	\| metabolism =
		⚫	\| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCCNc2ccccc2)CC3
⚫	\| elimination_half-life =
		⚫	\| StdInChI2 = 1/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
	\| excretion =
		⚫	\| StdInChIKey2 = PXXKIYPSXYFATG-UHFFFAOYAI

		⚫	\| StdInChIKey2_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	<!--Identifiers-->
		⚫	\| StdInChI = 1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
⚫	\| CAS_number = 13495-09-5
		⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| ATC_prefix = none
		⚫	\| StdInChIKey = PXXKIYPSXYFATG-UHFFFAOYSA-N
⚫	\| ATC_suffix =
		⚫	\| synonyms =
⚫	\| PubChem = 21950
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank =
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| ChemSpiderID = 20628
⚫	\| UNII_Ref = {{fdacite\|~~correct~~\|FDA}}
⚫	\| UNII = 3IIX447HWS

	<!--Chemical data-->
	\| C=23 \| H=30 \| N=2 \| O=2
	\| molecular_weight = 366.497 g/mol
⚫	\| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCCNc2ccccc2)CC3
⚫	\| ~~InChI~~ = 1/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
⚫	\| ~~InChIKey~~ = PXXKIYPSXYFATG-UHFFFAOYAI
⚫	\| ~~StdInChI_Ref~~ = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChI = 1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3
⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChIKey = PXXKIYPSXYFATG-UHFFFAOYSA-N
⚫	\| synonyms =
	}}		}}

	'''Piminodine''' ('''Alvodine''') is an ] ] that is an ] of ] (meperidine).<ref>Sim E, Dimoglo A, Shvets N, Ahsen V. Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics. ''Current Medicinal Chemistry~~''.~~ ~~2002~~ ~~Aug;~~9(16~~):1537-45~~.</ref> It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with ] to intensify the effects. The duration of action is ~~2 to 4~~ hours ~~and~~ 7.~~5 to 10~~ mg via the subcutaneous route is the most common starting dose, being equal to ~~80 to 100~~ mg of pethidine, ~~40 to 60~~ mg of ] and 10 mg of ]. Oral formulations were also available.		'''Piminodine''' ('''Alvodine''') is an ] ] that is an ] of ] (meperidine).<ref name="pmid12171562">{{cite journal \| vauthors = Sim E, Dimoglo A, Shvets N, Ahsen V \| title = Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics \| journal = Current Medicinal Chemistry \| volume = 9 \| issue = 16 \| pages = 1537–45 \| date = August 2002 \| pmid = 12171562 \| doi = 10.2174/0929867023369510 }}</ref> It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with ] to intensify the effects. The duration of action is 2–4 hours; 7.5–10 mg via the subcutaneous route is the most common starting dose, being equal to 80–100 mg of pethidine, 40–60 mg of ] and 10 mg of ]. Oral formulations were also available.

	Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include ], ] and potentially serious ] which can be life-threatening.<ref>Dekornfeld TJ, Lasagna L. The analgesic potency of piminodine (alvodine). ''Journal of Chronic Diseases~~''.~~ ~~1960~~ ~~Aug;~~12~~:252-7~~.</ref><ref>Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH. A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine. ''Toxicology and Applied Pharmacology~~''.~~ ~~1961~~ ~~May;~~3~~:358~~-79.</ref>		Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include ], ] and potentially serious ] which can be life-threatening.<ref name="pmid13815493">{{cite journal \| vauthors = Dekornfeld TJ, Lasagna L \| title = The analgesic potency of piminodine (alvodine) \| journal = Journal of Chronic Diseases \| volume = 12 \| issue = 2\| pages = 252–7 \| date = August 1960 \| pmid = 13815493 \| doi = 10.1016/0021-9681(60)90102-8 }}</ref><ref name="pmid">{{cite journal \| vauthors = Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH \| title = A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine \| journal = Toxicology and Applied Pharmacology\| volume = 3 \| pages = 358–79 \| date = May 1961 \| pmid = 13786579\| doi = 10.1016/0041-008x(61)90072-2 \| hdl = 2027.42/32367 \| hdl-access = free }}</ref>

	== References ==		== References ==
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	{{opioids}}		{{opioids}}
⚫	{{~~pharm~~-stub}}

	]		]
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	]		]
	]		]
	]		]


		⚫	{{analgesic-stub}}
	]

Latest revision as of 04:14, 2 March 2024

Opioid analgesic drug Pharmaceutical compound

Piminodine
Clinical data

ATC code	none
Legal status
Legal status	BR: Class A1 (Narcotic drugs)
Identifiers
IUPAC name ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
CAS Number	13495-09-5
PubChem CID	21950
ChemSpider	20628
UNII	3IIX447HWS
KEGG	D12683
CompTox Dashboard (EPA)	DTXSID60159149
ECHA InfoCard	100.033.455
Chemical and physical data
Formula	C₂₃H₃₀N₂O₂
Molar mass	366.505 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OCC)C3(c1ccccc1)CCN(CCCNc2ccccc2)CC3
InChI InChI=1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3 Key:PXXKIYPSXYFATG-UHFFFAOYSA-N InChI=1/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3 Key:PXXKIYPSXYFATG-UHFFFAOYAI
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Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine). It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2–4 hours; 7.5–10 mg via the subcutaneous route is the most common starting dose, being equal to 80–100 mg of pethidine, 40–60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.

Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.

References

Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
Sim E, Dimoglo A, Shvets N, Ahsen V (August 2002). "Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics". Current Medicinal Chemistry. 9 (16): 1537–45. doi:10.2174/0929867023369510. PMID 12171562.
Dekornfeld TJ, Lasagna L (August 1960). "The analgesic potency of piminodine (alvodine)". Journal of Chronic Diseases. 12 (2): 252–7. doi:10.1016/0021-9681(60)90102-8. PMID 13815493.
Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH (May 1961). "A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine". Toxicology and Applied Pharmacology. 3: 358–79. doi:10.1016/0041-008x(61)90072-2. hdl:2027.42/32367. PMID 13786579.