TOLAZOLINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H12N2.ClH
Molecular Weight	196.677
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.C(C1=NCCN1)C2=CC=CC=C2

InChI

InChIKey=RHTNTTODYGNRSP-UHFFFAOYSA-N

InChI=1S/C10H12N2.ClH/c1-2-4-9(5-3-1)8-10-11-6-7-12-10;/h1-5H,6-8H2,(H,11,12);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C10H12N2
Molecular Weight	160.2157
Charge	0
Count

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

Description
Sources: https://www.drugs.com/pro/priscoline.html | https://www.ncbi.nlm.nih.gov/pubmed/8487790

Tolazoline, also known as priscoline, was used in treatment of persistent pulmonary hypertension of the newborn. But that prescription was discontinued. Priscoline given intravenously produces vasodilatation, primarily due to a direct effect on vascular smooth muscle, and cardiac stimulation; the blood pressure response depends on the relative contributions of the two effects. Priscoline usually reduces pulmonary arterial pressure and vascular resistance. The mechanisms of its therapeutic effects are not clear, but is known, that tolazoline is a non-selective competitive α-adrenergic receptor antagonist and it possesses histamine agonist activity.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11938943	Antagonist 2778
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8487790	Agonist 2678
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8487790	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Persistent pulmonary hypertension of the newborn 3 Sources: https://www.drugs.com/pro/priscoline.html	Primary		Approved 8429	PRISCOLINE Approved Use Unknown Launch Date -6.8774402E11

C_max

Value	Dose	Co-administered	Analyte	Population
3.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3576663	3.2 mg single, intravenous dose: 3.2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TOLAZOLINE blood	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3576663	3.2 mg single, intravenous dose: 3.2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TOLAZOLINE blood	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	Other AEs: Erythema, Thrombocytopenia... Other AEs: Erythema (60%) Thrombocytopenia (45%) Hyponatremia (40%) Gastric acid increased (36%) Seizures (30%) Hematuria (23%) Hypotension (19%) Oliguria (11%) Abdominal distension (9%) Activity motor exaggerated (6%) Tracheal bleeding (6%) Sources: https://pubmed.ncbi.nlm.nih.gov/6970261

AEs

AE	Significance	Dose	Population
Oliguria	11%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Hypotension	19%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Hematuria	23%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Seizures	30%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Gastric acid increased	36%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Hyponatremia	40%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Thrombocytopenia	45%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Activity motor exaggerated	6%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Tracheal bleeding	6%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Erythema	60%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261
Abdominal distension	9%	2 mg/kg single, intravenous Highest studied dose Dose: 2 mg/kg Route: intravenous Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6970261	unhealthy, 36 weeks n = 47 Health Status: unhealthy Age Group: 36 weeks Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6970261

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Ca2+ channels 57

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ channels 60	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/1983153/	likely

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY562109	https://www.001chemical.com/chem/59-98-3
3B Scientific (Wuhan) Corp	3B2-1620	http://www.3bsc.com/index/pro_info.php?id=55336
AA Blocks	AA00E8O3	http://www.aablocks.com/goods/Goods/detail?id=AA00E8O3
AEchem Scientific Corp., USA	AE026734	http://www.aechemsc.com/info_products/AE026734.php
AHH Chemical co.,ltd	MT-59558	http://www.ahhchemical.com/product/MT-59558.html
AK Scientific, Inc. (AKSCI)	67867	http://www.aksci.com/item_detail.php?cat=67867
Aaron Chemicals	AR00E9FV	http://www.aaronchem.com/59-98-3
Achemica	ACMC-209mh8	http://www.achemica.com/prodinfo/?id=129496
Anward	ANW-33402	http://www.anward.com/pro_result/5475
Ark Pharma Scientific Limited	H-002242	http://www.arkpharmtech.com/product/7297.html
AstaTech, Inc.	FD7203	http://www.astatechinc.com/CPSResult.php?CRNO=37292
Aurora Fine Chemicals LLC	A00.762.267	http://online.aurorafinechemicals.com/info?ID=A00.762.267
BLD Pharm	BD154330	http://www.bldpharm.com/products/59-98-3.html
CSNpharm	CSN12104	https://www.csnpharm.com/products/tolazoline.html
Chem Scene	CS-3181	http://www.chemscene.com/59-98-3.html
ChemMol	49416425	http://www.chemmol.com/chemmol/49416425.html
ChemMol	49416427	http://www.chemmol.com/chemmol/49416427.html
ChemMol	99115266	http://www.chemmol.com/chemmol/99115266.html
Chemspace	CSSB00011215504	https://chem-space.com/CSSB00011215504
DC Chemicals	DC31889	http://www.dcchemicals.com//product_show-Tolazoline.html
Debye Scientific	DB-053506	http://www.debyesci.com/cas_59-98-3.html
Finetech	FT-0603251	http://www.finetechnology-ind.com/prod/detail/pub/59-98-3.html
Glentham Life Sciences	GL5593	http://www.glentham.com/products/product/GL5593/
Hairui	HR140028	http://www.hairuichem.com/en/product/59-98-3.html
Lab Network	LN00246265	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00246265
Matrix Scientific	204596	https://www.matrixscientific.com/204596.html
MedChem Express	HY-A0066	https://www.medchemexpress.com/tolazoline.html
Molcore	MC562109	https://www.molcore.com/product/59-98-3
MuseChem	I004252	https://www.musechem.com/product/I004252.html
OChem	11944	http://www.ocheminc.com/index.php?act=psearch&pid=059T983
Oakwood	336858	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=165581&ExtHyperLink=1
Parchem	30162	http://www.parchem.com/chemical-supplier-distributor/Tolazoline-020162.aspx
Sigma-Aldrich	293490_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/293490?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S545537	http://www.smolecule.com/products/s545537
Smolecule	S772617	https://www.smolecule.com/products/s772617
TCI (Tokyo Chemical Industry)	B3806	http://www.tcichemicals.com/eshop/en/us/commodity/B3806/index.html
THE BioTek	bt-285913	https://www.thebiotek.com/product/inhibitors/bt-285913
Yuhao Chemical	YH09263	http://www.chemyuhao.com/59-98-3.html
abcr GmbH	AB331678	http://www.abcr.com/shop/en/AB331678
eNovation Chemicals	K09775	http://www.enovationchem.com/productDetails.asp?productID=K09775
eNovation Chemicals	Y0978225	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0978225
mcule	MCULE-5694308124	https://mcule.com/MCULE-5694308124/

PubMed

Title	Date	PubMed
DDT-induced myoclonus: serotonin and alpha noradrenergic interaction.	1979 Feb	37558
Hypochloremic metabolic alkalosis following tolazoline-induced gastric hypersecretion.	1980 Feb	7354974
[Tolazoline and dopamine in the treatment of the persistent fetal circulation syndrome].	1983 Oct	6646141
[Renal disorders in the newborn infant].	1984 Jan-Feb	6397726
Bolus and continuous infusion of tolazoline in neonates with hypoxemia.	1986	3486756
Blood flow distribution and brain metabolism during tolazoline-induced hypotension in newborn dogs.	1990 Aug	2395600
Spasms of the hepatic artery following percutaneous transluminal angioplasty and tolazoline administration in a liver transplant patient.	1996 May-Jun	8661646
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.	1998 Apr 1	9605427
Persistent pulmonary hypertension of the newborn: experience in a single institution.	2001 Mar-Apr	11355072
Inhaled nitric oxide applications in paediatric practice.	2002 Jan	22368608
Use of azaperone and zuclopenthixol acetate to facilitate translocation of white-tailed deer (Odocoileus virginianus).	2002 Jun	12398308
[Aggression to the immature kidney].	2002 Mar-Apr	11987507
Re: Nonlocalized lower gastrointestinal bleeding: provocative bleeding studies with intraarterial tPA, heparin, and tolazoline.	2002 May	11997369
Efficacy and safety of tolazoline for treatment of severe hypoxemia in extremely preterm infants.	2002 May	11986446
Anesthesia of polar bears using xylazine-zolazepam-tiletamine or zolazepam-tiletamine.	2003 Jul	14567228
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust.	2003 Jul 14	12761824
Comparison of the vasodilating effect of nitroglycerin, verapamil, and tolazoline in hand angiography.	2003 Jun	12817042
A comparison of two intramuscular doses of xylazine-ketamine combination and tolazoline reversal in llamas.	2004 Apr	15053746
The effects of imidazoline agents on the aggregation of human platelets.	2004 Feb	15005880
Effectiveness of antagonists for tiletamine-zolazepam/xylazine immobilization in female white-tailed deer.	2004 Jul	15465721
Clinically diagnosed nonocclusive mesenteric ischemia after cardiopulmonary bypass: retrospective study.	2004 Mar	15248641
Characterisation of some pharmacological effects of the venom from Vipera lebetina.	2004 Mar 15	15051401
2-(Anilino)imidazolines and 2-(benzyl)imidazoline derivatives as h5-HT1D serotonin receptor ligands.	2004 Sep 20	15324890
Prevention and management of meconium aspiration syndrome--assessment of evidence based practice.	2005 May	15731907
Clinical assessment of epidural analgesia induced by xylazine-lidocaine combination accompanied by xylazine sedation in calves.	2005 Oct 1	21851664
Antagonism of detomidine sedation in the horse using intravenous tolazoline or atipamezole.	2006 May	16706278
A comparison of two combinations of xylazine-ketamine administered intramuscularly to alpacas and of reversal with tolazoline.	2008 May	18282257
Effect of vasoactive agents on the dermatopharmacokinetics and systemic disposition of model compounds, salicylate and FITC-dextran 4 kDa, following intracutaneous injection of the compounds.	2008 May 22	18294788
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions.	2008 Oct	18812576
Evaluation of intramuscular butorphanol, azaperone, and medetomidine and nasal oxygen insufflation for the chemical immobilization of white-tailed deer, Odocoileus virginianus.	2008 Sep	18817017
A novel approach for percutaneous treatment of massive nonocclusive mesenteric ischemia: tolazoline and glycerol trinitrate as effective local vasodilators.	2009 Feb 1	19156878
The clinical outcomes of transcatheter microcoil embolization in patients with active lower gastrointestinal bleeding in the small bowel.	2009 Jul-Aug	19568468
Physiologic effects of nasal oxygen or medical air administered prior to and during carfentanil-xylazine anesthesia in North American elk (Cervus canadensis manitobensis).	2009 Mar	19368239
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Pharmacological characterization of a Bombyx mori alpha-adrenergic-like octopamine receptor stably expressed in a mammalian cell line.	2010 Feb	19918790
Cardiovascular effects of sub-daily levels of ambient fine particles: a systematic review.	2010 Jun 15	20550697
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

An initial dose of 1 to 2 mg/kg, via scalp vein, followed by an infusion of 1 to 2 mg/kg per hour have usually resulted in significant increases in arterial oxygen. There is very little experience with infusions lasting beyond 36 to 48 hours. Response, if it occurs, can be expected within 30 minutes after the initial dose.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:03:33 UTC 2023` Edited by `admin` on `Fri Dec 15 15:03:33 UTC 2023`
Record UNII	E669Z6S1JG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOLAZOLINE HYDROCHLORIDE

Common Name

English

NSC-757353

Code

English

1H-IMIDAZOLE, 4,5-DIHYDRO-2-(PHENYLMETHYL)-, MONOHYDROCHLORIDE

Common Name

English

Tolazoline hydrochloride [WHO-DD]

Common Name

English

TOLAZOLINE HYDROCHLORIDE [MART.]

Common Name

English

TOLAZOLINE HYDROCHLORIDE [USP-RS]

Common Name

English

TOLAZOLINE HYDROCHLORIDE [JAN]

Common Name

English

TOLAZOLINE HCL

Common Name

English

TOLAZOLINE HYDROCHLORIDE [MI]

Common Name

English

PRISCOLINE

Code

English

TOLAZOLINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

TOLAZOLINE HYDROCHLORIDE [VANDF]

Common Name

English

TOLAZOLINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

2-Benzyl-2-imidazoline monohydrochloride

Systematic Name

English

TOLAZOLINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.2474