Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H23N3O.H2O4S |
| Molecular Weight | 383.463 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1
InChI
InChIKey=CMFMDPKITFHAPR-UHFFFAOYSA-N
InChI=1S/C17H23N3O.H2O4S/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;1-5(2,3)4/h4-11H,12-14H2,1-3H3;(H2,1,2,3,4)
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 Date1982 |
|||
| 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 Date1982 |
|||
| 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 Date1982 |
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 |
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 |
|---|---|---|---|---|
Page: 3.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| LPS-induced platelet response and rapid shock in mice: contribution of O-antigen region of LPS and involvement of the lectin pathway of the complement system. | 2002-11-01 |
|
| Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats. | 2002-10-04 |
|
| Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique. | 2002-10 |
|
| Enhancement of neutrophil infiltration in histidine decarboxylase-deficient mice. | 2002-10 |
|
| Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells. | 2002-10 |
|
| Effects of NMDA antagonist MK-801 on radial maze performance in Zucker rats. | 2002-09-20 |
|
| Suppression of spontaneous scratching in hairless rats by sedatives but not by antipruritics. | 2002-09-10 |
|
| Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways. | 2002-09-06 |
|
| Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release. | 2002-09-01 |
|
| Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa. | 2002-09 |
|
| Cosensitivity of vagal mucosal afferents to histamine and 5-HT in the rat jejunum. | 2002-09 |
|
| Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine. | 2002-08-23 |
|
| Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat. | 2002-08-21 |
|
| Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice. | 2002-08-15 |
|
| Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor. | 2002-08-09 |
|
| The control effect of histamine on body temperature and respiratory function in IgE-dependent systemic anaphylaxis. | 2002-08 |
|
| Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery. | 2002-08 |
|
| Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery. | 2002-08 |
|
| A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors. | 2002-07 |
|
| Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf. | 2002-07 |
|
| The antianaphylactic effects of Crinum glaucum aqueous extract. | 2002-07 |
|
| Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system. | 2002-06 |
|
| Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding. | 2002-06 |
|
| Effects of histamine on phosphoinositide metabolism in chick cerebral cortex. | 2002-05-07 |
|
| GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND). | 2002-04-11 |
|
| The initial inositol 1,4,5-trisphosphate response induced by histamine is strongly amplified by Ca(2+) release from internal stores in smooth muscle. | 2002-04 |
|
| Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness. | 2002-04 |
|
| Mouse mammary epithelial cells bear histamine receptors. | 2002-04 |
|
| Insulin-induced up-regulation of histamine H1-receptors. | 2002-04 |
|
| Contractile response of horse deep dorsal penile vein to histamine. | 2002-04 |
|
| Stimulation of protein kinase B and p70 S6 kinase by the histamine H1 receptor in DDT1MF-2 smooth muscle cells. | 2002-04 |
|
| Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats. | 2002-04 |
|
| 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). | 2002-04 |
|
| Effects of the NMDA antagonist MK-801 on radial maze performance in histidine-deficient rats. | 2002-03-22 |
|
| Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro. | 2002-03-08 |
|
| Role of Rho-associated protein kinase and histamine in lysophosphatidic acid-induced airway hyperresponsiveness in guinea pigs. | 2002-03 |
|
| Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States. | 2002-03 |
|
| The recovery of the neurally evoked secretory response of rat colonic mucosa after irradiation is independent of mast cells. | 2002-03 |
|
| Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction. | 2002-02 |
|
| Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes. | 2002-01 |
|
| Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats. | 2002-01 |
|
| Antiallergic anti-inflammatory effects of H1-antihistamines in humans. | 2002 |
|
| Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine. | 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 |
|
| Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones. | 2002 |
|
| Antihistamine antinociception is mediated by Gi-protein activation. | 2002 |
|
| Impact of soil movement on carbon sequestration in agricultural ecosystems. | 2002 |
|
| Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers. | 2001-12 |
|
| Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells. | 2001-11 |
|
| Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001-10 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 19:10:38 GMT 2025
by
admin
on
Wed Apr 02 19:10:38 GMT 2025
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| Record UNII |
TMU3984PH3
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| Record Status |
Validated (UNII)
|
| Record Version |
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Download
| Name | Type | Language | ||
|---|---|---|---|---|
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Common Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
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TMU3984PH3
Created by
admin on Wed Apr 02 19:10:38 GMT 2025 , Edited by admin on Wed Apr 02 19:10:38 GMT 2025
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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