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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22N2
Molecular Weight 278.3914
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRIPROLIDINE

SMILES

CC1=CC=C(C=C1)C(=C/CN2CCCC2)\C3=CC=CC=N3

InChI

InChIKey=CBEQULMOCCWAQT-WOJGMQOQSA-N
InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+

HIDE SMILES / InChI

Molecular Formula C19H22N2
Molecular Weight 278.3914
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Triprolidine is a first generation histamine H1 antagonist, which in combination with codeine phosphate and pseudoephedrine hydrochloride is sold under brand name TRIACIN-C. TRIACIN-C is indicated for temporary relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold.

CNS Activity

Curator's Comment: Known to be CNS penetrant in bovine. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
TRIACIN-C

Approved Use

Triacin-C is indicated for temporary relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold.

Launch Date

1985
Palliative
TRIACIN-C

Approved Use

Triacin-C is indicated for temporary relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold.

Launch Date

1985
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.6 ng/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIPROLIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
31.22 ng × h/mL
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIPROLIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIPROLIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 130.6 uM]
PubMed

PubMed

TitleDatePubMed
A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis.
1975 Jan
Clinical and therapeutic aspects of sinusitis in children with bronchial asthma.
1981 Dec
[Myoclonia caused by a combination of triprolidine, pseudoephedrine and paracetamol].
1982 Jun 26
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.
1991 Aug 15
The histamine H1-receptor antagonist binding site. A stereoselective pharmacophoric model based upon (semi-)rigid H1-antagonists and including a known interaction site on the receptor.
1995 Aug 18
Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation.
2001 Apr 2
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors.
2006 Apr
H1-antihistamines induce vacuolation in astrocytes through macroautophagy.
2012 Apr 15
Patents

Patents

Sample Use Guides

Adults and children 12 years and older: 2 teaspoonfuls (10 mL) every 4 to 6 hours, not to exceed 8 teaspoonfuls (40 mL) in 24 hours. Children 6 to under 12 years: 1 teaspoonful (5 mL) every 4 to 6 hours, not to exceed 4 teaspoonfuls (20 mL) in 24 hours. Children 2 to under 6 years: ½ teaspoonful (2.5 mL) every 4 to 6 hours, not to exceed 2 teaspoonfuls.
Route of Administration: Oral
In vitro experiments were conducted using Sweetana-Grass (Navicyte) vertical diffusion cells to evaluate the effect of directionality, donor concentration and pH on the permeation of hydroxyzine and triprolidine across excised bovine olfactory mucosa. These studies demonstrated that the Jm-s (mucosal-submucosal flux) and Js-m (submucosal-mucosal flux) of hydroxyzine and triprolidine across the olfactory mucosa were linearly dependent upon the donor concentration without any evidence of saturable transport. Hydroxyzine inhibited the efflux of P-gp substrates like etoposide and chlorpheniramine across the olfactory mucosa. Both hydroxyzine and triprolidine reduced the net flux (Js-m-Jm-s) of etoposide with IC50 values of 39.2 and 130.6 microM, respectively. The lipophilicty of these compounds, coupled with their ability to inhibit P-gp, enable them to freely permeate across the olfactory mucosa. Despite the presence of a number of protective barriers such as efflux transporters and metabolizing enzymes in the olfactory system, lipophilic compounds such as hydroxyzine and triprolidine can access the CNS primarily by passive diffusion when administered via the nasal cavity.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:58 GMT 2023
Record UNII
2L8T9S52QM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIPROLIDINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TRIPROLIDINE [MI]
Common Name English
Triprolidine [WHO-DD]
Common Name English
TRIPROLIDINE [VANDF]
Common Name English
TRIPROLIDINE [HSDB]
Common Name English
triprolidine [INN]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548164
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
WHO-VATC QR06AX07
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
WHO-ATC R06AX07
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
Code System Code Type Description
EVMPD
SUB11323MIG
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PRIMARY
DRUG BANK
DB00427
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
WIKIPEDIA
TRIPROLIDINE
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
DRUG CENTRAL
2763
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PRIMARY
EPA CompTox
DTXSID3023718
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PRIMARY
ECHA (EC/EINECS)
207-627-0
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PRIMARY
IUPHAR
1228
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ChEMBL
CHEMBL855
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PRIMARY
CHEBI
84116
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PRIMARY
NCI_THESAURUS
C61992
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PRIMARY
SMS_ID
100000076950
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PRIMARY
FDA UNII
2L8T9S52QM
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
RXCUI
10849
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PRIMARY RxNorm
MESH
D014311
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PRIMARY
DAILYMED
2L8T9S52QM
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
PUBCHEM
5282443
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PRIMARY
CAS
486-12-4
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PRIMARY
HSDB
6316
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PRIMARY
MERCK INDEX
m11192
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PRIMARY Merck Index
INN
502
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
LACTMED
Triprolidine
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY