From Wikipedia, the free encyclopedia
Chemical compound
Diphenylpyraline (DPP ; sold as Allergen , Arbid , Belfene , Diafen , Hispril , Histyn , Lergobine , Lyssipol , Mepiben , Neargal ) is a
first-generation antihistamine with
anticholinergic effects of the
diphenyl
piperidine class.
[2]
[3]
[4] It is marketed in
Europe for the treatment of
allergies .
[2]
[3]
[5] DPP has also been found to act as a
dopamine reuptake inhibitor and produces
hyperactivity in rodents.
[6] It has been shown to be useful in the treatment of
Parkinsonism .
[7]
Synthesis
Diphenylpyraline synthesis via coupling of 4-hydroxy-1-methylpiperidine with benzhydrylbromide
[8]
[9]
References
^ Graham G, Bolt AG (June 1974). "Half-life of diphenylpyraline in man". Journal of Pharmacokinetics and Biopharmaceutics . 2 (3): 191–5.
doi :
10.1007/BF01059761 .
PMID
4156058 .
S2CID
38955052 .
^
a
b Swiss Pharmaceutical Society (2000).
Index Nominum 2000: International Drug Directory (Book with CD-ROM) . Boca Raton: Medpharm Scientific Publishers.
ISBN
3-88763-075-0 .
^
a
b Puhakka H, Rantanen T, Virolainen E (1977). "Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis". J Int Med Res . 5 (1): 37–41.
doi :
10.1177/030006057700500106 .
PMID
14039 .
S2CID
19330175 .
^ Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987).
"Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay" . Japanese Journal of Pharmacology . 43 (3): 277–82.
doi :
10.1254/jjp.43.277 .
PMID
2884340 .
^ Hruby VJ, Vardanyan R, Vardanyan R (2006).
"Antihistamine Drugs" . Synthesis of Essential Drugs . Amsterdam: Elsevier.
ISBN
0-444-52166-6 .
^ Lapa G, Mathews T, Harp J, Budygin E, Jones S (2005). "Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties". Eur J Pharmacol . 506 (3): 237–40.
doi :
10.1016/j.ejphar.2004.11.017 .
PMID
15627433 .
^ Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I (2001). "Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients". J Neurol Sci . 182 (2): 95–7.
doi :
10.1016/S0022-510X(00)00441-X .
PMID
11137513 .
S2CID
35946097 .
^
US 2479843 , Knox LH, Kapp R, "1-Alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation", issued 23 August 1949, assigned to Nopco Chemical Company.
^
DE 934890 ,
Schuler WA , "Verfahren zur Herstellung von basischen Benzhydryläthern [Process for the production of basic benzhydrylethers]", issued 10 November 1955, assigned to Chemische Fabrik Promonta LLC.
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (
+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g.,
brompheniramine ,
buclizine ,
captodiame ,
chlorphenamine (chlorpheniramine) ,
cinnarizine ,
clemastine ,
cyproheptadine ,
dimenhydrinate ,
dimetindene ,
diphenhydramine ,
doxylamine ,
meclizine ,
mequitazine ,
perlapine ,
phenindamine ,
pheniramine ,
phenyltoloxamine ,
promethazine ,
propiomazine ,
triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g.,
clozapine ,
fluperlapine ,
olanzapine (
+fluoxetine ),
rilapine ,
quetiapine ,
tenilapine ,
zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (
+beclometasone/formoterol ,
+indacaterol ,
+neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (
+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,
femoxetine ,
paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin ,
mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g.,
amitriptyline (
+perphenazine ),
amitriptylinoxide ,
butriptyline ,
cidoxepin ,
clomipramine ,
desipramine ,
desmethyldesipramine ,
dibenzepin ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
lofepramine ,
nitroxazepine ,
northiaden (desmethyldosulepin) ,
nortriptyline ,
protriptyline ,
quinupramine ,
trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
chlorprothixene ,
cyamemazine (cyamepromazine) ,
loxapine ,
mesoridazine ,
thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists (and
PAMs Tooltip positive allosteric modulators )
5-HIAA
6-Chloronicotine
A-84,543
A-366,833
A-582,941
A-867,744
ABT-202
ABT-418
ABT-560
ABT-894
Acetylcholine
Altinicline
Anabasine
Anatabine
Anatoxin-a
AR-R17779
Bephenium hydroxynaphthoate
Butinoline
Butyrylcholine
Carbachol
Choline
Cotinine
Cytisine
Decamethonium
Desformylflustrabromine
Dianicline
Dimethylphenylpiperazinium
Epibatidine
Epiboxidine
Ethanol (alcohol)
Ethoxysebacylcholine
EVP-4473
EVP-6124
Galantamine
GTS-21
Ispronicline
Ivermectin
JNJ-39393406
Levamisole
Lobeline
MEM-63,908 (RG-3487)
Morantel
Nicotine (
tobacco )
NS-1738
PHA-543,613
PHA-709,829
PNU-120,596
PNU-282,987
Pozanicline
Pyrantel
Rivanicline
RJR-2429
Sazetidine A
SB-206553
Sebacylcholine
SIB-1508Y
SIB-1553A
SSR-180,711
Suberyldicholine
Suxamethonium (succinylcholine)
Suxethonium (succinyldicholine)
TC-1698
TC-1734
TC-1827
TC-2216
TC-5214
TC-5619
TC-6683
Tebanicline
Tribendimidine
Tropisetron
UB-165
Varenicline
WAY-317,538
XY-4083
Antagonists (and
NAMs Tooltip negative allosteric modulators )
Precursors (and
prodrugs )
DAT Tooltip Dopamine transporter (
DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (
NRIs Tooltip Norepinephrine reuptake inhibitors )
Others:
Antihistamines (e.g.,
brompheniramine ,
chlorphenamine ,
pheniramine ,
tripelennamine )
Antipsychotics (e.g.,
loxapine ,
ziprasidone )
Arylcyclohexylamines (e.g.,
ketamine ,
phencyclidine )
Dopexamine
Ephenidine
Ginkgo biloba
Indeloxazine
Nefazodone
Opioids (e.g.,
desmetramadol ,
methadone ,
pethidine (meperidine) ,
tapentadol ,
tramadol ,
levorphanol )
SERT Tooltip Serotonin transporter (
SRIs Tooltip Serotonin reuptake inhibitors )
Others:
A-80426
Amoxapine
Antihistamines (e.g.,
brompheniramine ,
chlorphenamine ,
dimenhydrinate ,
diphenhydramine ,
mepyramine (pyrilamine) ,
pheniramine ,
tripelennamine )
Antipsychotics (e.g.,
loxapine ,
ziprasidone )
Arylcyclohexylamines (e.g.,
3-MeO-PCP ,
esketamine ,
ketamine ,
methoxetamine ,
phencyclidine )
Cyclobenzaprine
Delucemine
Dextromethorphan
Dextrorphan
Efavirenz
Hypidone
Medifoxamine
Mesembrine
Mifepristone
MIN-117 (WF-516)
N-Me-5-HT
Opioids (e.g.,
dextropropoxyphene ,
methadone ,
pethidine (meperidine) ,
levorphanol ,
tapentadol ,
tramadol )
Roxindole
VMATs Tooltip Vesicular monoamine transporters Others