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
Molecular Formula | C16H21N3 |
Molecular Weight | 255.358 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
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 |
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 |
---|---|---|---|---|
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 |
---|---|---|
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 |
|
Fatal intracranial hemorrhage associated with phenylpropanolamine, pentazocine, and tripelennamine overdose. | 1985 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Myasthenia gravis-like syndrome in a Hereford heifer. | 2008 Jan-Feb |
|
Medullary pain facilitating neurons mediate allodynia in headache-related pain. | 2009 Feb |
|
Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology. | 2009 Feb 11 |
|
Anomalous photophysics of H1 antihistamines in aqueous solution. | 2009 May 14 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
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
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:02:17 GMT 2023
by
admin
on
Fri Dec 15 15:02:17 GMT 2023
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Record UNII |
FWV8GJ56ZN
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 522.2615
Created by
admin on Fri Dec 15 15:02:17 GMT 2023 , Edited by admin on Fri Dec 15 15:02:17 GMT 2023
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NCI_THESAURUS |
C29578
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SUB04981MIG
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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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100000084668
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FWV8GJ56ZN
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C47774
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205-833-5
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DBSALT000689
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DTXSID6026248
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m11180
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |