PHENYLTOLOXAMINE HYDROCHLORIDE

US Previously Marketed

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H21NO.ClH
Molecular Weight	291.816
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PHENYLTOLOXAMINE HYDROCHLORIDE

Structure Search

SMILES

Cl.CN(C)CCOC1=C(CC2=CC=CC=C2)C=CC=C1

InChI

InChIKey=HMBOWANDONYIBI-UHFFFAOYSA-N

InChI=1S/C17H21NO.ClH/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15;/h3-11H,12-14H2,1-2H3;1H

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007

Phenyltoloxamine is an ethanolamine derivative with antihistaminic property, which is used in combination with some analgesics for the temporary relief of minor aches and pains associated with headache; backache; muscular aches; temporarily reduces fever and some others disorders. Phenyltoloxamine blocks H1 histamine receptor, thereby inhibiting phospholipase A2 and production of endothelium-derived relaxing factor, nitric oxide. Subsequent lack of activation of guanylyl cyclase through nitric oxide results in decreased cyclic GMP levels, thereby inhibiting smooth muscle constriction of various tissues, decreasing capillary permeability and decreasing other histamine-activated allergic reactions.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8227466	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Allergy 44 Sources: https://livertox.nih.gov/Phenyltoloxamine.htm https://www.drugs.com/international/phenyltoloxamine.html	Palliative	Approved 8583	Bristalin Approved Use Phenyltoloxamine is a first generation antihistamine that is used for symptoms of the common cold and as a short acting sedative. Launch Date 1951
Minor aches 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Primary	Not Provided 511	DOLOGESIC Approved Use Unknown
Headache 47 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Palliative	Not Provided 511	DOLOGESIC Approved Use Unknown
Premenstrual and menstrual cramps 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Palliative	Not Provided 511	DOLOGESIC Approved Use Unknown
Fever 23 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Palliative	Not Provided 511	DOLOGESIC Approved Use Unknown

Doses

Dose	Population	Adverse events
60 mg single, oral Recommended Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2569485/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2569485/	Sources: https://pubmed.ncbi.nlm.nih.gov/2569485/

PubMed

Title	Date	PubMed
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007 May	17539447
Identification of potent chemotypes targeting Leishmania major using a high-throughput, low-stringency, computationally enhanced, small molecule screen.	2009 Nov 3	19888337
(2-Methyl-phen-yl)(phen-yl)methanol.	2010 Jul 31	21588424
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

adults and children 12 years of age and older: take 1 or 2 tablespoons of DOLOGESIC (acetaminophen, phenyltoloxamine citrate, alcohol liquid); every 4 to 6 hours. children under 12 years of age: Consult a physician; do not give this product to children under 12 years of age. This product will provide more than the recommended dose (overdose) of non-aspirin and could cause serious health problems

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

2-(2-DIMETHYLAMINOETHOXY)DIPHENYLMETHANE, HYDROCHLORIDE

Preferred Name

English

PHENYLTOLOXAMINE HYDROCHLORIDE

Common Name

English

N,N-DIMETHYL-2-(.ALPHA.-PHENYL-O-TOLYLOXY)ETHYLAMINE, HYDROCHLORIDE

Systematic Name

English

PHENYLTOLOXAMINE HYDROCHLORIDE [MI]

Common Name

English

N,N-DIMETHYL-2-(2-(PHENYLMETHYL)PHENOXY)ETHANAMINE, HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578