Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H23N3O |
Molecular Weight | 285.384 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1
InChI
InChIKey=YECBIJXISLIIDS-UHFFFAOYSA-N
InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
Molecular Formula | C17H23N3O |
Molecular Weight | 285.384 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Pyrilamine (also known as Mepyramine) is a first generation antihistamine, targeting the H1 receptor. However, it rapidly permeates the brain and so often causes drowsiness as a side effect. It is used in over-the-counter combination products for colds and menstrual symptoms. Mepyramine is a histamine H1 receptor inverse agonist. It binds to a G protein-coupled form of the receptor and promotes a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling. Mepyramine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of Mepyramine occur at the subcortical level of the CNS. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22918191 |
0.8 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Phenylephrine/ pyrilamine Approved UseUses
Temporarily relieves
nasal congestion due to hay fever (allergic rhinitis)
runny nose
sneezing, itching of nose or throat and itchy, watery eyes due to hay fever
or upper respiratory allergies Launch Date4.04697612E11 |
|||
Primary | Phenylephrine/ pyrilamine Approved UseUses
Temporarily relieves
nasal congestion due to hay fever (allergic rhinitis)
runny nose
sneezing, itching of nose or throat and itchy, watery eyes due to hay fever
or upper respiratory allergies Launch Date4.04697612E11 |
|||
Primary | MIDOL PMS Approved UseUses: For the temporary relief of these symptoms associated with menstrual periods:
bloating
water-weight gain
cramps
breast tenderness
headache
backache Launch Date4.04697612E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/ |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PYRILAMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/ |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PYRILAMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/ |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PYRILAMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg single, oral |
healthy, 32-38 years n = 3 Health Status: healthy Age Group: 32-38 years Sex: M Population Size: 3 Sources: |
|
0.3 % 1 times / day steady, ophthalmic Recommended Dose: 0.3 %, 1 times / day Route: ophthalmic Route: steady Dose: 0.3 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: Allergic conjunctivitis Age Group: adult Sex: unknown Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 0.034 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16278312/ Page: 3.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Comparison of cedar pollen-induced allergic rhinitis in passively and actively sensitized guinea pigs. | 2001 Apr |
|
Effects of two newly synthesized analogues of lidocaine on rat arterial blood pressure and heart rate. | 2001 Apr |
|
Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells. | 2001 Feb |
|
Histamine alters gene expression in cultured human nasal epithelial cells. | 2001 Feb |
|
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats. | 2001 Jul |
|
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat. | 2001 Jul |
|
Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats. | 2001 Jul 6 |
|
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex. | 2001 Jul-Aug |
|
Pharmacologic properties of brewery dust extracts in vitro. | 2001 Jun |
|
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities. | 2001 May |
|
Standard treatment: the role of antihistamines. | 2001 Nov |
|
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture. | 2001 Nov |
|
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells. | 2001 Oct |
|
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons. | 2001 Oct |
|
Histamine H(3)-receptor antagonism improves memory retention and reverses the cognitive deficit induced by scopolamine in a two-trial place recognition task. | 2001 Oct 15 |
|
Role of adenosine in ischemic preconditioning in rats depends critically on the duration of the stimulus and involves both A(1) and A(3) receptors. | 2001 Sep |
|
Antiallergic anti-inflammatory effects of H1-antihistamines in humans. | 2002 |
|
Topically applied aspirin decreases histamine-induced wheal and flare reactions in normal and SLS-inflamed skin, but does not decrease itch. A randomized, double-blind and placebo-controlled human study. | 2002 |
|
Antihistamine antinociception is mediated by Gi-protein activation. | 2002 |
|
Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness. | 2002 Apr |
|
Mouse mammary epithelial cells bear histamine receptors. | 2002 Apr |
|
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate). | 2002 Apr |
|
GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND). | 2002 Apr 11 |
|
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery. | 2002 Aug |
|
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine. | 2002 Aug 23 |
|
Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction. | 2002 Feb |
|
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation. | 2002 Jan 18 |
|
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding. | 2002 Jun |
|
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro. | 2002 Mar 8 |
|
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats. | 2002 Oct 4 |
|
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa. | 2002 Sep |
|
Cosensitivity of vagal mucosal afferents to histamine and 5-HT in the rat jejunum. | 2002 Sep |
Sample Use Guides
Usual Adult Dose for Allergic Rhinitis
phenylephrine-pyrilamine 25 mg-60 mg oral tablet:
1 or 2 tablets orally every 12 hours as needed.
phenylephrine-pyrilamine 20 mg-16 mg oral tablet, chewable, extended release:
1 or 2 tablets orally every 12 hours as needed.
phenylephrine-pyrilamine 5 mg-16 mg/5 mL oral suspension, extended release:
5 to 10 mL orally every 12 hours as needed.
phenylephrine-pyrilamine 9 mg-12 mg/5 mL oral suspension, extended release:
5 to 10 mL orally every 12 hours as needed, not to exceed 20 mL in 24 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16627364
Pretreatment with the histamine H1 receptor antagonist pyrilamine (1 uM) could reduce the beta-lactoglobulin-induced response in the in vitro guinea pig mesenteric preparation
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:53:54 UTC 2022
by
admin
on
Fri Dec 16 16:53:54 UTC 2022
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Record UNII |
HPE317O9TL
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
D04AA02
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WHO-ATC |
R06AC01
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QD04AA02
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WHO-VATC |
QR06AC01
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NCI_THESAURUS |
C29578
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M9367
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CHEMBL511
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1227
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D011738
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SUB08762MIG
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9009
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5187
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202-102-2
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106
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Pyrilamine
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C76676
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HPE317O9TL
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HPE317O9TL
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DB06691
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MEPYRAMINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |