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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22N2
Molecular Weight 278.3921
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRIPROLIDINE

SMILES

Cc1ccc(cc1)/C(=C(/[H])\CN2CCCC2)/c3ccccn3

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 278.3921
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

4.80297615E11
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

4.80297615E11
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
Specific binding of [3H]mepyramine to histamine H1-receptors in vascular smooth muscle membranes.
1983 Apr
Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines).
1985 Nov-Dec
Regulation of membrane histamine H1-receptor binding sites by guanine nucleotides, mono- and divalent cations.
1986 Apr
H1-histamine receptors on human astrocytoma cells.
1986 Feb
Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers.
1987 Jul
Nonsedating histamine H1-receptor antagonists.
1989 May
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.
1991 Aug 15
A role for endogenous histamine in interleukin-8-induced neutrophil infiltration into mouse air-pouch: investigation of the modulatory action of systemic and local dexamethasone.
1994 Jul
H1-receptor antagonists. Comparative tolerability and safety.
1994 May
Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene.
1994 Sep 1
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
A novel phenylaminotetralin (PAT) recognizes histamine H1 receptors and stimulates dopamine synthesis in vivo in rat brain.
2000 Jan 3
Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation.
2001 Apr 2
Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation.
2001 Aug
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.
2002 Jul
Histamine inhibits atrial myocytic ANP release via H2 receptor-cAMP-protein kinase signaling.
2003 Aug
Molecular characterization of specific H1-receptor agonists histaprodifen and its Nalpha-substituted analogues on bovine aortic H1-receptors.
2003 May
Activation of histamine H1-receptor enhances neurotrophic factor secretion from cultured astrocytes.
2004 Jun
Regulation of cytokine production in carcinoembryonic antigen stimulated Kupffer cells by beta-2 adrenergic receptors: implications for hepatic metastasis.
2004 Jun 25
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 histamine receptor antagonists induce genotoxic and caspase-2-dependent apoptosis in human melanoma cells.
2006 Sep
Disruption of the C5a receptor gene increases resistance to acute Gram-negative bacteremia and endotoxic shock: opposing roles of C3a and C5a.
2008 Apr
Involvement of histaminergic receptor mechanisms in the stimulation of NT-3 synthesis in astrocytes.
2011 Jun
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 Sat Jun 26 15:12:27 UTC 2021
Edited
by admin
on Sat Jun 26 15:12:27 UTC 2021
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 [WHO-DD]
Common Name English
TRIPROLIDINE [MI]
Common Name English
TRIPROLIDINE [VANDF]
Common Name English
TRIPROLIDINE [HSDB]
Common Name English
TRIPROLIDINE [INN]
Common Name English
Classification Tree Code System Code
LIVERTOX 1005
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
WHO-VATC QR06AX07
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
WHO-ATC R06AX07
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
Code System Code Type Description
EVMPD
SUB11323MIG
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
DRUG BANK
DB00427
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
WIKIPEDIA
TRIPROLIDINE
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
DRUG CENTRAL
2763
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
EPA CompTox
486-12-4
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-627-0
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
IUPHAR
1228
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL855
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
NCI_THESAURUS
C61992
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
FDA UNII
2L8T9S52QM
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
RXCUI
10849
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY RxNorm
MESH
D014311
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
PUBCHEM
5282443
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
CAS
486-12-4
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
HSDB
6316
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
MERCK INDEX
M11192
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY Merck Index
INN
502
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
LACTMED
Triprolidine
Created by admin on Sat Jun 26 15:12:27 UTC 2021 , Edited by admin on Sat Jun 26 15:12:27 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY