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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22N2.ClH.H2O
Molecular Weight 332.868
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TRIPROLIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=CUZMOIXUFHOLLN-UMVVUDSKSA-N
InChI=1S/C19H22N2.ClH.H2O/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;1H;1H2/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
[Myoclonia caused by a combination of triprolidine, pseudoephedrine and paracetamol].
1982 Jun 26
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
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
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
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 Fri Dec 15 15:13:03 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:03 GMT 2023
Record UNII
YAN7R5L890
Record Status Validated (UNII)
Record Version
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Name Type Language
TRIPROLIDINE HYDROCHLORIDE
MART.   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
ACTAHIST COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF ALLERFED
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF CORPHED
Common Name English
Triprolidine hydrochloride monohydrate [WHO-DD]
Common Name English
TRIPROLIDINE HCL
Common Name English
CORPHED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF MYFED
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF ACTAHIST
Common Name English
TRIPROLIDINE HYDROCHLORIDE MONOHYDROCHLORIDE MONOHYDRATE
Common Name English
TRIPROLIDINE HYDROCHLORIDE [VANDF]
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF ACTIFED
Common Name English
TRIPROLIDINE HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
TRIPROLIDINE HYDROCHLORIDE [MART.]
Common Name English
HISTAFED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE MONOHYDRATE
MART.   MI   WHO-DD  
Common Name English
TRIPHED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
TRIPROLIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF HISTAFED
Common Name English
MYFED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF TRIPHED
Common Name English
PYRIDINE, 2-(1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1-PROPENYL)-, MONOHYDROCHLORIDE, MONOHYDRATE, (E)-
Common Name English
TRIPROLIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ALLERFED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
MYIDYL
Brand Name English
NSC-757361
Code English
(E)-2-(3-(1-PYRROLIDINYL)-1-P-TOLYLPROPENYL)PYRIDINE MONOHYDROCHLORIDE MONOHYDRATE
Common Name English
TRIACIN-C COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
TRILITRON COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE [USP-RS]
Common Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF TRILITRON
Common Name English
ACTIDIL
Brand Name English
TRIPROLIDINE HYDROCHLORIDE COMPONENT OF TRIACIN-C
Common Name English
ACTIFED COMPONENT TRIPROLIDINE HYDROCHLORIDE
Common Name English
TRIPROLIDINE HYDROCHLORIDE MONOHYDRATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
CFR 21 CFR 341.12
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
Code System Code Type Description
EVMPD
SUB04984MIG
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID0021410
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
DAILYMED
YAN7R5L890
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL855
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
DRUG BANK
DBSALT000623
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
MERCK INDEX
m11192
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY Merck Index
CAS
6138-79-0
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
PUBCHEM
5282442
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
NSC
757361
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
RS_ITEM_NUM
1696007
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
SMS_ID
100000090473
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
CHEBI
32265
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
RXCUI
71534
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY RxNorm
FDA UNII
YAN7R5L890
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
NCI_THESAURUS
C61993
Created by admin on Fri Dec 15 15:13:03 GMT 2023 , Edited by admin on Fri Dec 15 15:13:03 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY