Pipecuronium bromide: Difference between revisions

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			{{Short description\|Chemical compound}}
			{{cs1 config\|name-list-style=vanc\|display-authors=6}}
	{{Drugbox		{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
		⚫	\| verifiedrevid = 464207336
	\| Watchedfields = changed
⚫	\| verifiedrevid = ~~400853810~~
	\| IUPAC_name = (2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)androstane dibromide		\| IUPAC_name = (2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)androstane dibromide
	\| image = Pipecuronium bromide.svg		\| image = Pipecuronium bromide.svg
	\| width = 250		\| width = 250
			\| image2 = Pipecuronium bromide ball-and-stick.png

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename = Arduan
	\| Drugs.com = {{drugs.com\|international\|pipecuronium-bromide}}		\| Drugs.com = {{drugs.com\|international\|pipecuronium-bromide}}
	\| pregnancy_category =		\| pregnancy_category =
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	<!--Identifiers-->		<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|changed\|??}}
	\| CAS_number = 52212-02-9		\| CAS_number = 52212-02-9
	\| CAS_supplemental = {{CAS\|68399-58-6}}		\| CAS_supplemental = {{CAS\|68399-58-6}}
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	\| UNII_Ref = {{fdacite\|changed\|FDA}}		\| UNII_Ref = {{fdacite\|changed\|FDA}}
	\| UNII = R6ZTY81RE1		\| UNII = R6ZTY81RE1
	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D00764		\| KEGG = D00764
	\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
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	<!--Chemical data-->		<!--Chemical data-->
	\| C=35 \| H=62 \| Br=2 \| N=4 \| O=4		\| C=35 \| H=62 \| Br=2 \| N=4 \| O=4
	\| molecular_weight = 762.699 g/mol
	\| smiles = ..O=C(O6(N1CC(C)(C)CC1)C56(C)CC35CC4C(OC(=O)C)(N2CC(CC2)(C)C)C34C)C		\| smiles = ..O=C(O6(N1CC(C)(C)CC1)C56(C)CC35CC4C(OC(=O)C)(N2CC(CC2)(C)C)C34C)C
	\| InChI = 1/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1
	\| InChIKey = TXWBOBJCRVVBJF-VGKUAFPFBT
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1		\| StdInChI = 1S/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1
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	}}		}}

			'''Pipecuronium''' ('''Arduan''') is a bisquaternary ] ]<ref>{{cite web\|url=https://www.whocc.no/atc_ddd_index/?code=M03AC06 \| title = Pipecuronium Bromide \| id = M03AC06 \| work = WHOCC - ATC/DDD Index}}</ref> which blocks ]<ref name="drugbank1">{{cite web\|url=https://www.drugbank.ca/drugs/DB01338\|title = Pipecuronium \| work = DrugBank }}</ref><ref>{{cite book \| vauthors = Singh H, Jindal DP, Yadav MR, Kumar M \| chapter = 5 Heterosteroids and drug research. \| title = Progress in Medicinal Chemistry \| date = January 1991 \| volume = 28 \| pages = 233-300 (270) \| doi = 10.1016/S0079-6468(08)70366-7 \| pmid = 1843548 \| isbn = 978-0-444-81275-9 }}</ref> at the ]. It is also an antagonist of ] and ]<ref name="drugbank1"/> and is the most ] ] of the aminosteroid class.{{citation needed\|date=April 2019}}
	'''Pipecuronium''' ('''Arduan''') is a ] which acts as a ] ].

			It is sold under the ] Arduan and Pycuron.<ref>{{cite web\|url=https://www.drugs.com/international/pipecuronium-bromide.html \|title=Pipecuronium - brand name list from \|publisher=Drugs.com \|date= \|accessdate=2022-09-17}}</ref>

			==See also==
			*]

	== References ==		== References ==
	{{~~Reflist\|2~~}}		{{reflist}}


	{{Muscle relaxants}}		{{Muscle relaxants}}
			{{Nicotinic acetylcholine receptor modulators}}
	{{Cholinergics}}



	]		]
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	]		]
	]		]
			]
			]


			{{steroid-stub}}
	{{musculoskeletal-drug-stub}}		{{musculoskeletal-drug-stub}}

	]

Latest revision as of 06:58, 17 July 2024

Chemical compound

Pharmaceutical compound

Pipecuronium bromide
Clinical data


Trade names	Arduan
AHFS/Drugs.com	International Drug Names
ATC code	M03AC06 (WHO)
Identifiers
IUPAC name (2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)androstane dibromide
CAS Number	52212-02-9 68399-58-6
PubChem CID	65332
ChemSpider	58815
UNII	R6ZTY81RE1
KEGG	D00764
ChEMBL	ChEMBL1200722
CompTox Dashboard (EPA)	DTXSID8023478
ECHA InfoCard	100.052.475
Chemical and physical data
Formula	C₃₅H₆₂Br₂N₄O₄
Molar mass	762.713 g·mol
3D model (JSmol)	Interactive image
SMILES ..O=C(O6(N1CC(C)(C)CC1)C56(C)CC35CC4C(OC(=O)C)(N2CC(CC2)(C)C)C34C)C
InChI InChI=1S/C35H62N4O4.2BrH/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36;;/h26-33H,9-23H2,1-8H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1 Key:TXWBOBJCRVVBJF-YTGGZNJNSA-L
(what is this?) (verify)

Pipecuronium (Arduan) is a bisquaternary aminosteroid muscle relaxant which blocks nicotinic acetylcholine receptors at the neuromuscular junction. It is also an antagonist of M2 and M3 muscarinic receptors and is the most potent neuromuscular blocking agent of the aminosteroid class.

It is sold under the trade names Arduan and Pycuron.

References

"Pipecuronium Bromide". WHOCC - ATC/DDD Index. M03AC06.
^ "Pipecuronium". DrugBank.
Singh H, Jindal DP, Yadav MR, Kumar M (January 1991). "5 Heterosteroids and drug research.". Progress in Medicinal Chemistry. Vol. 28. pp. 233-300 (270). doi:10.1016/S0079-6468(08)70366-7. ISBN 978-0-444-81275-9. PMID 1843548.
"Pipecuronium - brand name list from". Drugs.com. Retrieved 2022-09-17.

Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids

4° ammonium agents

ultra-short duration: Gantacurium

short duration: Rapacuronium
Mivacurium
Chandonium

unsorted: Hexafluronium (Hexafluorenium)

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine)

Polyalkylene derivatives: Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Phenprobamate Styramate Tybamate
Benzodiazepines	Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam
Nonbenzodiazepines	Eszopiclone
Thienodiazepines	Etizolam
Quinazolines	Methaqualone
Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine
Other	Arbaclofen placarbil Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Eperisone Fenyramidol Flopropione Gabapentin GHB Inaperisone Lanperisone Mephenesin Mephenoxalone Metaxalone Methocarbamol Phenibut Pregabalin Pridinol Promoxolane Quinine Silperisone Thiocolchicoside Tizanidine Tolperisone Zoxazolamine

Directly acting

Dantrolene

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

Precursors
(and prodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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Categories:

Latest revision as of 06:58, 17 July 2024

See also

References