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Caramiphen

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Caramiphen
Clinical data

Trade names	Carafen
ATC code	None
Identifiers
IUPAC name 2-(Diethylamino)ethyl 1-phenylcyclopentanecarboxylate
CAS Number	77-22-5
PubChemCID	6472
ChemSpider	6228
UNII	97J7NP0XJY
ChEMBL	ChEMBL61946
CompTox Dashboard(EPA)	DTXSID0022729
ECHA InfoCard	100.000.922
Chemical and physical data
Formula	C₁₈H₂₇NO₂
Molar mass	289.419 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OCCN(CC)CC)C2(c1ccccc1)CCCC2
InChI InChI=1S/C18H27NO2/c1-3-19(4-2)14-15-21-17(20)18(12-8-9-13-18)16-10-6-5-7-11-16/h5-7,10-11H,3-4,8-9,12-15H2,1-2H3 Key:OFAIGZWCDGNZGT-UHFFFAOYSA-N

Caramiphen is ananticholinergic drug used in the treatment ofParkinson's disease.^[1] In combination withphenylpropanolamine it is used as acough suppressant andnasal decongestant to treat symptoms associated with respiratory illnesses such ascold,allergies,hay fever, andsinusitis.^[2] It was added to theBritish National Formulary in 1963, with a dosage of 10 to 20 mg. Side effects include nausea, dizziness, and drowsiness.^[3]

It binds to thesigma-1 receptor with anIC₅₀ value of 25 nM.^[4]

References

^"Caramiphen". drugs.com. Retrieved26 September 2012.
^"Caramiphen with phenylpropanolamine-oral, Ordrine AT, Rescaps-D, Tuss Vernade, Tusso-Gest". medicine.net. Archived fromthe original on 29 October 2012. Retrieved26 September 2012.
^Beirn SF, Lavelle S (May 1964)."To-day's drugs: Cough suppressants".British Medical Journal.1 (5391):1165–1167.doi:10.1136/bmj.1.5391.1165.PMC 1813498.PMID 14120813.
^Musacchio JM, Klein M (June 1988)."Dextromethorphan binding sites in the guinea pig brain".Cellular and Molecular Neurobiology.8 (2):149–156.doi:10.1007/BF00711241.PMC 11567495.PMID 3044591.S2CID 33844132.

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Cough and cold preparations (R05)

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine^# (+guaifenesin) Dextromethorphan Dihydrocodeine Dimemorfan Ethylmorphine Heroin Hydrocodone (+guaifenesin,+homatropine) Hydromorphone Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon
Other	Alloclamide Benproperine Benzonatate Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Dibunate Dimethoxanate Diphenhydramine Dropropizine Droxypropine Fedrilate Fominoben Gefapixant Glaucine Isoaminile Levodropropizine Meprotixol Moguisteine Morclofone Nepinalone Oxeladin Oxolamine Pentoxyverine Pipazetate Piperidione Prenoxdiazine Tipepidine Zipeprol

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Pharmacodynamics

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Ion channel modulators

VDCCsTooltip Voltage-dependent calcium channels

R-type-selective:SNX-482

L-type-selective:Bay K8644

VGKCsTooltip Voltage-gated potassium channels

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

K_ATPTooltip ATP-sensitive potassium channel-specific:Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

K_ATPTooltip ATP-sensitive potassium channel-specific:Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:ML-297 (VU0456810)

K_CaTooltip Calcium-activated potassium channel

Blockers	BK_Ca-specific:Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific:Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2PsTooltip Tandem pore domain potassium channel

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

VGSCsTooltip Voltage-gated sodium channels

Antianginals:Ranolazine

Aconitine
Atracotoxins (ω-Atracotoxin,Robustoxin,Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaCTooltip Epithelial sodium channel

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICsTooltip Acid-sensing ion channel

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

CaCCsTooltip Calcium-activated chloride channel

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTRTooltip Cystic fibrosis transmembrane conductance regulator

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	Seehere instead.
LGICsTooltip Ligand gated ion channels	Seehere instead.

See also:Receptor/signaling modulators •Transient receptor potential channel modulators

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Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Nicotinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

v t e Sigma receptor modulators
σ₁	Agonists:3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists:3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators:Phenytoin;Positive:Methylphenylpiracetam SOMCL-668 Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists:3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists:AC-927 BD-1008 BD-1067 CM-156 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Zervimesine (CT-1812) Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists:Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists:AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators:SKF-83959 Unknown/unsorted:18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also:Receptor/signaling modulators

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