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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 of PHENYLTOLOXAMINE CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOC1=CC=CC=C1CC2=CC=CC=C2

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

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

1952
114
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Primary
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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

PubMed

TitleDatePubMed
[Antimycobacterial antihistaminics].
1989 Aug
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

US3173835
3

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 Mon Mar 31 18:24:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:33 GMT 2025
Record UNII
8UE48MJH8M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLTOLOXAMINE DIHYDROGEN CITRATE
MI   VANDF  
Preferred Name English
PHENYLTOLOXAMINE CITRATE
MART.   USP   USP-RS   VANDF   WHO-DD  
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 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
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
CFR 21 CFR 310.201
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
Code System Code Type Description
FDA UNII
8UE48MJH8M
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
PUBCHEM
14440
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
SMS_ID
100000085281
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1534402
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
214-644-7
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
CAS
1176-08-5
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
DRUG BANK
DBSALT001531
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
NSC
169860
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID5047790
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
DAILYMED
8UE48MJH8M
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
RXCUI
221141
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY RxNorm
EVMPD
SUB03784MIG
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
NCI_THESAURUS
C82275
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
MERCK INDEX
m8695
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL186720
Created by admin on Mon Mar 31 18:24:33 GMT 2025 , Edited by admin on Mon Mar 31 18:24:33 GMT 2025
PRIMARY
Related Record Type Details
Structure of Anhydrous citric acid
PARENT -> SALT/SOLVATE
Structure of PHENYLTOLOXAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of N-nitroso-desmethyl-phenyltoloxamine
IMPURITY -> PARENT
Related Record Type Details
Structure of PHENYLTOLOXAMINE
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