Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H21N3.ClH |
Molecular Weight | 291.819 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CCN(CC1=CC=CC=C1)C2=CC=CC=N2
InChI
InChIKey=FSSICIQKZGUEAE-UHFFFAOYSA-N
InChI=1S/C16H21N3.ClH/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15;/h3-11H,12-14H2,1-2H3;1H
DescriptionSources: https://www.drugs.com/mtm/tripelennamine.html
Sources: https://www.drugs.com/mtm/tripelennamine.html
Tripelennamine (sold as Pyribenzamine by Novartis) is a drug that is used as an antipruritic and first-generation antihistamine. Histamine acting on H1-receptors produces vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine can be used in the treatment of asthma, hay fever, rhinitis, and urticaria, but is now less common as newer antihistamines have replaced it.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7513381 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugs.com/mtm/tripelennamine.html |
Palliative | PBZ Approved UseUnknown Launch Date1948 |
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Sources: https://www.drugs.com/mtm/tripelennamine.html |
Palliative | PBZ Approved UseUnknown Launch Date1948 |
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Palliative | PBZ Approved UseUnknown Launch Date1948 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
199 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
398 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
804 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032 |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
TRIPELENNAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
Other AEs: Weakness, Common cold... Other AEs: Weakness Sources: Common cold (grade 1) Cough Rhinorrhea Vomiting Sleepiness |
25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
Other AEs: Coma, Common cold... Other AEs: Coma Sources: Common cold Nausea Diarrhoea Back pain Headache (grade 3) Appetite lost Dry cough Pyrexia Abdominal pain (grade 3) Vomiting Disorientation |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
Other AEs: Sedation, Sedation... Other AEs: Sedation (grade 1, 8.9%) Sources: Sedation (grade 2, 6.7%) Dizziness (5.5%) Nausea (4.4%) Nose dryness (2.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cough | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
|
Rhinorrhea | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
|
Sleepiness | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
|
Vomiting | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
|
Weakness | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
|
Common cold | grade 1 | 100 mg 1 times / day single, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: single Dose: 100 mg, 1 times / day Sources: |
healthy, 2 years n = 1 Health Status: healthy Age Group: 2 years Sex: F Population Size: 1 Sources: |
Appetite lost | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Back pain | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Coma | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Common cold | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Diarrhoea | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Disorientation | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Dry cough | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Nausea | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Pyrexia | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Vomiting | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
|
Abdominal pain | grade 3 | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
Headache | grade 3 | 25 mg 3 times / day multiple, oral Studied dose Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Co-administed with:: antistin(50 mg; 11 days) Sources: |
unhealthy, 49 years n = 1 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: 49 years Sex: F Population Size: 1 Sources: |
Nose dryness | 2.2% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
Nausea | 4.4% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
Dizziness | 5.5% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
Sedation | grade 1, 8.9% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
Sedation | grade 2, 6.7% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age 36 years n = 90 Health Status: unhealthy Condition: chronic allergic rhinitis Age Group: median age 36 years Sex: M+F Population Size: 90 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
An unusual case of antihistamine intoxication. | 1967 Oct |
|
Pulmonary angiothrombosis caused by "blue velvet" addiction. | 1970 Nov |
|
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. | 1975 Feb |
|
Central nervous system complications of addiction to "T's and Blues". | 1982 Jun |
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Pentazocine/tripelennamine (T's and blues) abuse: a five year survey of St. Louis, Missouri. | 1982 Oct-Nov |
|
Fatal intracranial hemorrhage associated with phenylpropanolamine, pentazocine, and tripelennamine overdose. | 1985 |
|
Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice. | 1986 Dec |
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Behavioral and developmental effects of prenatal exposure to pentazocine and tripelennamine combinations. | 1986 Nov-Dec |
|
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice. | 1987 |
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Antihistaminic-opioid combination: effect on locomotor activity in mice. | 1988 Sep-Oct |
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Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
|
Nitric oxide, superoxide radicals and mast cells in pathogenesis of indomethacin-induced small intestinal lesions in rats. | 1999 Mar |
|
Antinociceptive and antiedematogenic properties and acute toxicity of Tabebuia avellanedae Lor. ex Griseb. inner bark aqueous extract. | 2001 |
|
Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment. | 2001 Feb |
|
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol. | 2001 Nov-Dec |
|
H1-receptor antagonist, tripelennamine, does not affect arterial hypoxemia in exercising Thoroughbreds. | 2002 Apr |
|
Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. | 2002 Feb |
|
Does the neurotransmitter transporter underlie adaptation at a histaminergic photoreceptor synapse? | 2002 May-Jun |
|
Managing patients with local anesthetic complications using alternative methods. | 2002 May-Jun |
|
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists. | 2003 Dec 18 |
|
Prostaglandin E2 aggravates gastric mucosal injury induced by histamine in rats through EP1 receptors. | 2003 Dec 19 |
|
Management of rhinitis and asthma in pregnancy. | 2003 Jun |
|
On the mechanisms underlying histamine induction of gastric mucosal lesions in rats with partial gastric vascular occlusion. | 2003 Jun |
|
Mast cell--pituitary interaction: modulation by serine phospholipids. | 2004 Dec |
|
Treatment of allergic rhinitis during pregnancy. | 2004 Jan-Feb |
|
Medicinal plants in Suriname: hypotensive effect of Gossypium barbadense. | 2004 Mar |
|
Role of N-methyl-D-aspartate receptors in gastric mucosal blood flow induced by histamine. | 2004 Sep 1 |
|
Involvement of histamine H1 and H2 receptors in the regulation of STAT-1 phosphorylation: inverse agonism exhibited by the receptor antagonists. | 2005 Jul |
|
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography. | 2006 Feb 13 |
|
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. | 2007 Apr 20 |
|
Amoxicillin-Induced Eosinophilic Pneumonia with Granulomatous Reaction: Discrepancy between Drug-Induced Lymphocyte Stimulation Test Findings and the Provocation Drug Test. | 2007 Jun 15 |
|
Medullary pain facilitating neurons mediate allodynia in headache-related pain. | 2009 Feb |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
The use of in vitro technologies coupled with high resolution accurate mass LC-MS for studying drug metabolism in equine drug surveillance. | 2010 Jan |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15428185
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 522.2615
Created by
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NCI_THESAURUS |
C29578
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SUB04981MIG
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FWV8GJ56ZN
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91063
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409943
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CHEMBL1241
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154-69-8
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9066
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1695004
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100000084668
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FWV8GJ56ZN
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C47774
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205-833-5
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m11180
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PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD