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Details

Stereochemistry ACHIRAL
Molecular Formula C17H23N3O.C4H4O4
Molecular Weight 401.4562
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE MALEATE

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-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phenylephrine/ pyrilamine
Primary
MIDOL PMS
Primary
Phenylephrine/ pyrilamine
PubMed

PubMed

TitleDatePubMed
QSAR study on binding affinity of PATs (rodenticides) to the [3H]-mepyramine-labelled H1 receptor in rat and guinea pig brain.
2001
Role of L-arginine/nitric oxide pathway in the antinociceptive activities of morphine and mepyramine in mice.
2001
Activation of the p38 and p42/p44 mitogen-activated protein kinase families by the histamine H(1) receptor in DDT(1)MF-2 cells.
2001 Aug
Comparative effect of Phoneutria nigriventer spider venom and capsaicin on the rat paw oedema.
2001 Aug 17
Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.
2001 Dec
Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells.
2001 Feb
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.
2001 Jul
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
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
Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells.
2001 Nov
Histamine H(1)-receptor activation of nuclear factor-kappa B: roles for G beta gamma- and G alpha(q/11)-subunits in constitutive and agonist-mediated signaling.
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
Pharmacological characterization of cyclosporine A-induced kaolin intake in rats.
2001 Oct-Nov
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
Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness.
2002 Apr
Contractile response of horse deep dorsal penile vein to histamine.
2002 Apr
Stimulation of protein kinase B and p70 S6 kinase by the histamine H1 receptor in DDT1MF-2 smooth muscle cells.
2002 Apr
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.
2002 Apr
GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND).
2002 Apr 11
The control effect of histamine on body temperature and respiratory function in IgE-dependent systemic anaphylaxis.
2002 Aug
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.
2002 Aug 21
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.
2002 Aug 23
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
Urothelium derived inhibitory factor and cross-talk among receptors in the trigone of the bladder of the pig.
2002 Feb
Orexins activate histaminergic neurons via the orexin 2 receptor.
2002 Feb 1
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation.
2002 Jan 18
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.
2002 Jan-Feb
Suppression of spontaneous scratching in hairless rats by sedatives but not by antipruritics.
2002 Jul-Aug
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.
2002 Jun
Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States.
2002 Mar
Effects of the NMDA antagonist MK-801 on radial maze performance in histidine-deficient rats.
2002 Mar 22
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
Enhancement of neutrophil infiltration in histidine decarboxylase-deficient mice.
2002 Oct
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
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
Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release.
2002 Sep 1
Effects of NMDA antagonist MK-801 on radial maze performance in Zucker rats.
2002 Sep 20
Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways.
2002 Sep 6
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Tue Oct 22 00:39:13 UTC 2019
Edited
by admin
on Tue Oct 22 00:39:13 UTC 2019
Record UNII
R35D29L3ZA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRILAMINE MALEATE
GREEN BOOK   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PYRILAMINE MALEATE [USP]
Common Name English
PYRILAMINE MALEATE [MI]
Common Name English
PARMAL
Brand Name English
N-(4-METHOXYBENZYL)-N',N'-DIMETHYL-N-PYRIDIN-2-YLETHANE-1,2-DIAMINE (2Z)-BUT-2-ENEDIOATE
Systematic Name English
MEPYRAMINE MALEATE [EP]
Common Name English
ANTAMINE
Brand Name English
2-((2-(DIMETHYLAMINO)ETHYL)(P-METHOXYBENZYL)AMINO)PYRIDINE MALEATE (1:1)
Common Name English
MEPYRAMINE MALEATE [MART.]
Common Name English
NEO-ANTERGAN
Brand Name English
1,2-ETHANEDIAMINE, N-((4-METHOXYPHENYL)METHYL)-N',N'-DIMETHYL-N-2-PYRIDINYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
ANTHISAN
Brand Name English
PYRILAMINE MALEATE COMPONENT OF PREFRIN-A
Common Name English
PYRILAMINE MALEATE [VANDF]
Common Name English
HISTALON
Brand Name English
PYRILAMINE MALEATE [USP-RS]
Common Name English
DORANTAMIN
Brand Name English
THYLOGEN
Brand Name English
STAMINE
Brand Name English
PYRILAMINE MALEATE [ORANGE BOOK]
Common Name English
PYRAMAL
Brand Name English
HISTAN
Brand Name English
PARAMINYL
Brand Name English
MEPYRAMINE MALEATE
EP   MART.   WHO-DD  
Common Name English
STANGEN
Brand Name English
PYRILAMINE MALEATE [GREEN BOOK]
Common Name English
MEPYRAMINE MALEATE [WHO-DD]
Common Name English
ENRUMAY
Brand Name English
HISTATEX
Brand Name English
HISTAPYRAN
Brand Name English
NSC-3604
Code English
PREFRIN-A COMPONENT PYRILAMINE MALEATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.2063
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
CFR 21 CFR 341.12
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
NCI_THESAURUS C29578
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
Code System Code Type Description
EPA CompTox
59-33-6
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
MERCK INDEX
M9367
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY Merck Index
RXCUI
82091
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL511
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-422-7
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
EVMPD
SUB14516MIG
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
NCI_THESAURUS
C61915
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
CAS
59-33-6
Created by admin on Tue Oct 22 00:39:13 UTC 2019 , Edited by admin on Tue Oct 22 00:39:13 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY