PENTOLINIUM TARTRATE

US Previously Marketed

First approved in 1954

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H32N2.2C4H5O6
Molecular Weight	538.5858
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C([O-])=O)C(O)=O.O[C@H]([C@@H](O)C([O-])=O)C(O)=O.C[N+]2(CCCCC[N+]1(C)CCCC1)CCCC2

InChI

InChIKey=HSMKTIKKPMTUQH-WBPXWQEISA-L

InChI=1S/C15H32N2.2C4H6O6/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17;2*5-1(3(7)8)2(6)4(9)10/h3-15H2,1-2H3;2*1-2,5-6H,(H,7,8)(H,9,10)/q+2;;/p-2/t;2*1-,2-/m.11/s1

HIDE SMILES / InChI

Molecular Formula	C15H32N2
Molecular Weight	240.428
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13316673 | https://www.ncbi.nlm.nih.gov/pubmed/7761270

Pentolinium (brand name Ansolysen) is a ganglionic cholinergic antagonist, acting on alpha 3 beta 4 neuronal nicotinic acetylcholine receptors (nAChRs). It was used as an antihypertensive drug during surgery or to control hypertensive crises, but Ansolysen was discontinued. Pentolinium inhibits release of adrenaline and noradrenaline from adrenergic nerves.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7761270	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13316673	Primary		Approved 8429	ANSOLYSEN Approved Use Unknown

Doses

Dose	Population	Adverse events
80 mg 3 times / day multiple, intravenous Dose: 80 mg, 3 times / day Route: intravenous Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	Other AEs: Dizziness, Constipation... Other AEs: Dizziness Constipation Vomiting Paralytic ileus (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/13688462

AEs

AE	Significance	Dose	Population
Constipation		80 mg 3 times / day multiple, intravenous Dose: 80 mg, 3 times / day Route: intravenous Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13688462
Dizziness		80 mg 3 times / day multiple, intravenous Dose: 80 mg, 3 times / day Route: intravenous Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13688462
Vomiting		80 mg 3 times / day multiple, intravenous Dose: 80 mg, 3 times / day Route: intravenous Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13688462
Paralytic ileus	grade 5	80 mg 3 times / day multiple, intravenous Dose: 80 mg, 3 times / day Route: intravenous Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13688462	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: hypertension Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13688462

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1B4870
ABI Chem	AC1L1L9T
ABI Chem	AC1Q28R1
Acros Organics	38802
BOC Sciences	52-62-0
ChemTik	CTK8D7628
Enamine	EN300-754676
Frontier Scientific Services	500054405
Kingston Chemistry	KST-1B3415
Lab Network	LN01349207
Molnova	M14862
MuseChem	M071777
NovoSeek	5850
Ryan Scientific	Clorgyline_HCl
Sigma Aldrich	R278084
Sigma Aldrich	R278084\|ALDRICH
TargetMol	T1236
Tetrahedron	TS83657
TimTec	ST50411507
ZINC	ZINC000002041380	http://zinc15.docking.org/substances/ZINC000002041380
eMolecules	713499
mcule	MCULE-6392147155	https://mcule.com/MCULE-6392147155/

PubMed

Title	Date	PubMed
Noradrenaline and the kidney: friends or foes?	2001 Dec	11737909
Central orexin-A augments sympathoadrenal outflow in conscious rabbits.	2001 Jun	11408381
Central human cocaine- and amphetamine-regulated transcript peptide 55-102 increases arterial pressure in conscious rabbits.	2001 Nov	11711504
Short exposure of maturing, bone marrow-derived dendritic cells to norepinephrine: impact on kinetics of cytokine production and Th development.	2002 Aug	12161026
Sympathetic blockade significantly improves cardiovascular alterations immediately after spinal cord injury in rats.	2002 Feb 15	11825679
Altered balance of main vasopressor and vasodepressor systems in rats with genetic hypertension and hypertriglyceridaemia.	2002 Mar	11869167
Chronic central infusion of orexin-A increases arterial pressure in rats.	2002 Mar 15	11927364
The altered balance between sympathetic nervous system and nitric oxide in salt hypertensive Dahl rats: ontogenetic and F2 hybrid studies.	2002 May	12011656
In vivo effects of fenoldopam on autonomic nervous system after inhibition or activation of ganglionic transmission.	2002 May 31	12063080
Human coagulation factor XII-related "new pressor protein": role of PACAP in its cardiovascular and sympathoadrenal effects.	2002 Oct	12420044
Sympathetic activation by fenfluramine depletes brown adipose tissue norepinephrine content in rats.	2002 Oct	12151039
Release of acetylcholine by Die-Huang-Wan to enhance insulin secretion for lowering plasma glucose in Wistar rats.	2002 Sep 30	12422956
Gender-specific genetic determinants of blood pressure and organ weight: pharmacogenetic approach.	2003	14640890
Catecholamine and oxytocin cells respond to hypovolaemia as well as hypotension.	2003 Aug 6	12960771
Resolving the composite trait of hypertension into its pharmacogenetic determinants by acute pharmacological modulation of blood pressure regulatory systems.	2003 Jan	12545249
Central cardiovascular action of urotensin II in conscious rats.	2003 Jan	12544448
The role of renal sympathetic nervous system in the pathogenesis of ischemic acute renal failure.	2003 Nov 28	14642792
Fenfluramine-induced hypothermia is associated with cutaneous dilation in conscious rats.	2004 Feb	14751464
Vasoactive systems in L-NAME hypertension: the role of inducible nitric oxide synthase.	2004 Jan	15106808
Role of bradykinin B2-receptor in the sympathoadrenal effects of 'new pressor protein' related to human blood coagulation factor XII fragment.	2004 Jun	15167453
Ghrelin acts at the nucleus of the solitary tract to decrease arterial pressure in rats.	2004 May	14993197
Peptide YY administration into the posterior hypothalamic nucleus of the rat evokes cardiovascular changes by non-adrenergic, non-cholinergic mechanisms.	2005 Apr	15757505
Cardiovascular effects of noradrenaline microinjected into the dorsal periaqueductal gray area of unanaesthetized rats.	2005 Dec	16367785
Pressor and tachycardic responses evoked by microinjections of L-glutamate into the medial prefrontal cortex of unanaesthetized rats.	2005 May	15932608
Release of acetylcholine by Hon-Chi to raise insulin secretion in Wistar rats.	2006 Aug 14	16762503
Release of acetylcholine to raise insulin secretion in Wistar rats by oleanolic acid, one of the active principles contained in Cornus officinalis.	2006 Aug 14	16759806
Antihypertensive mechanisms of chronic captopril or N-acetylcysteine treatment in L-NAME hypertensive rats.	2006 Dec	17378375
Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats.	2006 Jan-Feb	16445695
Baroreceptor reflex stimulation does not induce cytomegalovirus promoter-driven transgene expression in the ventrolateral medulla in vivo.	2006 Jun 30	16624635
Effects of chronic treatment with 7-nitroindazole in hyperthyroid rats.	2006 Nov	16778061
Pressor effects of noradrenaline injected into the lateral septal area of unanesthetized rats.	2006 Nov 29	17011526
Cardiovascular effects of carbachol microinjected into the bed nucleus of the stria terminalis of the rat brain.	2007 Apr 27	17306779
Vasorelaxant activity of some oxime derivatives.	2007 Dec 1	17706962
Total peripheral resistance responsiveness during the development of secondary renal hypertension in dogs.	2007 Mar	17278982
The participation of brain NO synthase in blood pressure control of adult spontaneously hypertensive rats.	2007 Mar	17009099
Cardiovascular effects of L-glutamate microinjection in the supraoptic nucleus of unanaesthetized rats.	2007 May	17367824
Cardiovascular effects of noradrenaline microinjection in the bed nucleus of the stria terminalis of the rat brain.	2007 May 15	17330275
Angiotensin II-based hypertension and the sympathetic nervous system: the role of dose and increased dietary salt in rabbits.	2007 Sep	17468201
Levels of renal and extrarenal sympathetic drive in angiotensin II-induced hypertension.	2008 Apr	18268138
Cardiovascular responses to noradrenaline microinjection in the ventrolateral periaqueductal gray of unanesthetized rats.	2008 Feb 15	17893924
Release of acetylcholine by syringin, an active principle of Eleutherococcus senticosus, to raise insulin secretion in Wistar rats.	2008 Mar 28	18304730
Neuronal source of plasma dopamine.	2008 Nov	18801936
Angiotensin converting enzyme-regulated, noncholinergic sympathoadrenal catecholamine release mediates the cardiovascular actions of human 'new pressor protein' related to coagulation beta-factor XIIa.	2009 Apr	19340353
Mechanisms involved in the pressor response to noradrenaline microinjection into the supraoptic nucleus of unanesthetized rats.	2009 Jan 28	19059010
Role of N-methyl-D-aspartate and non-N-methyl-D-aspartate receptors in the cardiovascular effects of L-glutamate microinjection into the hypothalamic paraventricular nucleus of unanesthetized rats.	2009 Jul	19229989
The role of nitric oxide in the development of neurogenic pulmonary edema in spinal cord-injured rats: the effect of preventive interventions.	2009 Oct	19675280
Role of the sympathetic nervous system in Schlager genetically hypertensive mice.	2009 Oct	19667247
Enhanced responses to ganglion blockade do not reflect sympathetic nervous system contribution to angiotensin II-induced hypertension.	2009 Sep	19512943
Cardiovascular effects of noradrenaline microinjection into the medial part of the superior colliculus of unanesthetized rats.	2009 Sep 22	19615348
Role of sympathetic tone in BSO-induced hypertension in mice.	2010 Aug	20431527

Patents

Sample Use Guides

In Vivo Use Guide

intramuscularly: 1 to 2 0.25-mg ampoules Ansolysen must be used with caution. The initial dose is from 20-40 mg., taken 15 to 20 minutes before each meal and at bedtime, to ensure an even digestive absorption. Each dose is increased by 20-40 mg. four times a day at intervals of five to seven days until the desired hvpotensive effect is obtained. The maintenance dose varies generally between 160 and 800 mg. a day.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:32 UTC 2023` Edited by `admin` on `Fri Dec 15 15:09:32 UTC 2023`
Record UNII	953357GACY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PENTOLINIUM TARTRATE

Common Name

English

ANSOLYSEN

Brand Name

English

PENTOLINIUM TARTRATE [MI]

Common Name

English

PENTOLONIUM TARTRATE [MART.]

Common Name

English

Pentolonium tartrate [WHO-DD]

Common Name

English

pentolonium tartrate [INN]

Common Name

English

NSC-759890

Code

English

PENTOLONIUM TARTRATE

Official Name

English

PYRROLIDINIUM 1,1'-(1,5-PENTANEDIYL)BIS-(1-METHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE

Common Name

English

PENTOLINIUM TARTRATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270