Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H23N3O.C4H4O4 |
| Molecular Weight | 401.4562 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1
InChI
InChIKey=JXYWFNAQESKDNC-BTJKTKAUSA-N
InChI=1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| 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 |
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 |
|---|---|---|---|---|
Page: 3.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The major role of peripheral release of histamine and 5-hydroxytryptamine in formalin-induced nociception. | 2001 |
|
| Effect of clobenpropit on regional cerebral blood flow in rat hippocampus. | 2001 Apr |
|
| Comparison of cedar pollen-induced allergic rhinitis in passively and actively sensitized guinea pigs. | 2001 Apr |
|
| Modulation of the immediate allergic wheal reaction in the skin by drugs inhibiting the effects of leukotriene C4 and prostaglandin D2. | 2001 Apr |
|
| Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve. | 2001 Apr |
|
| Beta(3)-adrenoceptor agonist-induced increases in lipolysis, metabolic rate, facial flushing, and reflex tachycardia in anesthetized rhesus monkeys. | 2001 Apr |
|
| The effects of histamine and its antagonists on the cochlear microphonic and the compound action potential of the guinea pig. | 2001 Aug |
|
| Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers. | 2001 Dec |
|
| Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells. | 2001 Feb |
|
| H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways. | 2001 Feb |
|
| Histamine alters gene expression in cultured human nasal epithelial cells. | 2001 Feb |
|
| Regulation of parasympathetic neurons by mast cells and histamine in the guinea pig heart. | 2001 Feb 20 |
|
| Role of mast cells in zymosan-induced peritoneal inflammation in Balb/c and mast cell-deficient WBB6F1 mice. | 2001 Jan |
|
| 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 |
|
| Tachykinin-induced bronchoconstriction in sheep is NK-1 receptor mediated and exhibits tachyphylaxis. | 2001 Jun |
|
| Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon. | 2001 Jun |
|
| Pharmacologic properties of brewery dust extracts in vitro. | 2001 Jun |
|
| The H3 receptor is involved in cholecystokinin inhibition of food intake in rats. | 2001 Jun 15 |
|
| Mechanisms of histamine-induced intracellular Ca2+ release and extracellular Ca2+ entry in MG63 human osteosarcoma cells. | 2001 Jun 15 |
|
| Dopaminergic effects of histamine administration in the nucleus accumbens and the impact of H1-receptor blockade. | 2001 Mar |
|
| VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities. | 2001 May |
|
| Activation of histamine H3 receptors inhibits renal noradrenergic neurotransmission in anesthetized dogs. | 2001 May |
|
| Standard treatment: the role of antihistamines. | 2001 Nov |
|
| The role of central histaminergic neuron system as an anticonvulsive mechanism in developing brain. | 2001 Nov |
|
| The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture. | 2001 Nov |
|
| Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001 Oct |
|
| Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells. | 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 |
|
| Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine. | 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 |
|
| Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats. | 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 |
|
| Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice. | 2002 Aug 15 |
|
| Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor. | 2002 Aug 9 |
|
| 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 |
|
| A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors. | 2002 Jul |
|
| Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf. | 2002 Jul |
|
| Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system. | 2002 Jun |
|
| 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 |
|
| 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 Nov 1 |
|
| Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique. | 2002 Oct |
|
| Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa. | 2002 Sep |
|
| Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release. | 2002 Sep 1 |
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
Fri Dec 15 15:06:58 GMT 2023
by
admin
on
Fri Dec 15 15:06:58 GMT 2023
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| Record UNII |
R35D29L3ZA
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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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CFR |
21 CFR 522.2063
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CFR |
21 CFR 341.12
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NCI_THESAURUS |
C29578
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DBSALT001405
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3604
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DTXSID4021216
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R35D29L3ZA
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5284451
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m9367
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82091
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CHEMBL511
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R35D29L3ZA
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200-422-7
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1588004
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100000091887
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SUB14516MIG
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C61915
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59-33-6
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |