PHENYLTOLOXAMINE CITRATE

US Previously Marketed

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H21NO.C6H8O7
Molecular Weight	447.4783
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOC1=C(CC2=CC=CC=C2)C=CC=C1

InChI

InChIKey=ZZYHCCDMBJTROG-UHFFFAOYSA-N

InChI=1S/C17H21NO.C6H8O7/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-11H,12-14H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

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

Molecular Formula	C17H21NO
Molecular Weight	255.3547
Charge	0
Count

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

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 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8227466	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Allergy 44 Sources: https://livertox.nih.gov/Phenyltoloxamine.htm https://www.drugs.com/international/phenyltoloxamine.html	Palliative	Approved 8429	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 504	DOLOGESIC Approved Use Unknown
Headache 47 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Palliative	Not Provided 504	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 504	DOLOGESIC Approved Use Unknown
Fever 23 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=738e7767-42de-4076-acf2-9152484c2007	Palliative	Not Provided 504	DOLOGESIC Approved Use Unknown

PubMed

Title	Date	PubMed
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Ligand-based approach to in silico pharmacology: nuclear receptor profiling.	2006 Nov-Dec	17125212
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007 May	17539447
Feasibility study of day case thyroidectomy.	2008 Oct	18959638
Identification of potent chemotypes targeting Leishmania major using a high-throughput, low-stringency, computationally enhanced, small molecule screen.	2009 Nov 3	19888337
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
(2-Methyl-phen-yl)(phen-yl)methanol.	2010 Jul 31	21588424
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.	2010 Oct 6	20925935
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:18:18 GMT 2023` Edited by `admin` on `Fri Dec 15 16:18:18 GMT 2023`
Record UNII	8UE48MJH8M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYLTOLOXAMINE CITRATE

Common Name

English

PHENYLTOLOXAMINE CITRATE [USP MONOGRAPH]

Common Name

English

PHENYLTOLOXAMINE CITRATE [MART.]

Common Name

English

Phenyltoloxamine citrate [WHO-DD]

Common Name

English

NSC-169860

Code

English

N,N-DIMETHYL-2-(.ALPHA.-PHENYL-O-TOLYLOXY)ETHYLAMINE, CITRATE (1:1) SALT

Common Name

English

PHENYLTOLOXAMINE DIHYDROGEN CITRATE

Common Name

English

PHENYLTOLOXAMINE CITRATE [USP-RS]

Common Name

English

2-(2-Dimethylaminoethoxy)diphenylmethane, citrate (1:1) salt

Common Name

English

PHENYLTOLOXAMINE DIHYDROGEN CITRATE [VANDF]

Common Name

English

PHENYLTOLOXAMINE CITRATE [VANDF]

Common Name

English

PHENYLTOLOXAMINE DIHYDROGEN CITRATE [MI]

Common Name

English

N,N-DIMETHYL-(A-PHENYL-O-TOLOXY) ETHYLAMINE DIHYDROGEN CITRATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578