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
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+
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16105724
Curator's Comment: Known to be CNS penetrant in bovine. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22629251 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | TRIACIN-C Approved UseTriacin-C is indicated for temporary relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date4.80297615E11 |
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Palliative | TRIACIN-C Approved UseTriacin-C is indicated for temporary relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date4.80297615E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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5.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2355108/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.22 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2355108/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2355108/ |
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 |
PubMed
Title | Date | PubMed |
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A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis. | 1975 Jan |
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Regulation of membrane histamine H1-receptor binding sites by guanine nucleotides, mono- and divalent cations. | 1986 Apr |
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H1-histamine receptors on human astrocytoma cells. | 1986 Feb |
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Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. | 1991 Aug 15 |
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H1-receptor antagonists. Comparative tolerability and safety. | 1994 May |
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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 |
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A novel phenylaminotetralin (PAT) recognizes histamine H1 receptors and stimulates dopamine synthesis in vivo in rat brain. | 2000 Jan 3 |
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Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation. | 2001 Apr 2 |
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Regional differences in functional receptor distribution and calcium mobilization in the intact human lens. | 2001 Sep |
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Activation of histamine H1-receptor enhances neurotrophic factor secretion from cultured astrocytes. | 2004 Jun |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
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Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors. | 2006 Apr |
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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 |
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H1-antihistamines induce vacuolation in astrocytes through macroautophagy. | 2012 Apr 15 |
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 Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16105724
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
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Record UNII |
2L8T9S52QM
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548164
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WHO-VATC |
QR06AX07
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WHO-ATC |
R06AX07
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NCI_THESAURUS |
C29578
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SUB11323MIG
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DB00427
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TRIPROLIDINE
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2763
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DTXSID3023718
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207-627-0
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1228
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CHEMBL855
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84116
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C61992
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100000076950
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2L8T9S52QM
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10849
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D014311
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2L8T9S52QM
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5282443
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486-12-4
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6316
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m11192
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502
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Triprolidine
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |