CARAMIPHEN

First approved in 1949

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H27NO2
Molecular Weight	289.4125
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCOC(=O)C1(CCCC1)C2=CC=CC=C2

InChI

InChIKey=OFAIGZWCDGNZGT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446426 | https://www.ncbi.nlm.nih.gov/pubmed/18110872

Caramiphen is a muscarinic M1 acetylcholine receptor antagonist, which was used for the treatment of Parkinson Disease and cough, but then there using were discontinued. Caramiphen is also used in local anesthesia, and effect could be achieved through the suppression of voltage-gated Na⁺ currents.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
voltage-gated Na⁺ currents 3 Target ID: voltage-gated Na⁺ currents Sources: https://www.ncbi.nlm.nih.gov/pubmed/25446426	Inhibitor 8297		52.1 µM [IC50]
Muscarinic acetylcholine receptor M1 169 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8449241	Antagonist 2778		1.2 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3322860	Primary		Approved 8429	SKF TUSS-ORNADE Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18110872	Primary		Approved 8429	parpanit Approved Use Unknown

Doses

Dose	Population	Adverse events
20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult n = 30 Health Status: healthy Condition: cough Age Group: adult Sex: unknown Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	Other AEs: Nausea, Dizziness... Other AEs: Nausea (3 patients) Dizziness (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/

AEs

AE	Significance	Dose	Population
Dizziness	2 patients	20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult n = 30 Health Status: healthy Condition: cough Age Group: adult Sex: unknown Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/
Nausea	3 patients	20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/	healthy, adult n = 30 Health Status: healthy Condition: cough Age Group: adult Sex: unknown Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/25201353/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY571133	https://www.001chemical.com/chem/77-22-5
Acorn PharmaTech	ACN-057466	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	K02.797.422	http://online.aurorafinechemicals.com/info?ID=K02.797.422
ChemMol	99151441	http://www.chemmol.com/chemmol/99151441.html
Chemspace	CSSS00020619634	https://chem-space.com/CSSS00020619634
Molcore	MC571133	https://www.molcore.com/product/77-22-5
Smolecule	S522623	http://www.smolecule.com/products/s522623
THE BioTek	bt-262712	https://www.thebiotek.com/product/inhibitors/bt-262712
eNovation Chemicals	D671966	https://www.enovationchem.com/ProductDetails.asp?ProductID=D671966
mcule	MCULE-4063768824	https://mcule.com/MCULE-4063768824/

PubMed

Title	Date	PubMed
Anti-nicotinic properties of anticholinergic antiparkinson drugs.	1998 Nov	9877318
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.	2008 Feb	17710542
Efficacy of antidotal treatment against sarin poisoning: the superiority of benactyzine and caramiphen.	2008 Feb 15	18320638
Therapy against organophosphate poisoning: the importance of anticholinergic drugs with antiglutamatergic properties.	2008 Oct 15	18680758
Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test.	2010 Sep 13	20621160
The anticholinergic and antiglutamatergic drug caramiphen reduces seizure duration in soman-exposed rats: synergism with the benzodiazepine diazepam.	2012 Mar 15	22310180

Patents

Sample Use Guides

In Vivo Use Guide

2.5 to 6.0 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

It was investigated the effect of caramiphen (300uM) on voltage-gated sodium channels in differentiated neuronal NG108-15 cells. Caramiphen exhibited a milder state-dependence of block (IC₅₀ of 52.1 and 99.5 µM at holding potentials of -70 and -100 mV, respectively).

Name

Type

Language

CARAMIPHEN

Official Name

English

caramiphen [INN]

Common Name

English

Caramiphen [WHO-DD]

Common Name

English

CARAMIPHEN [MI]

Common Name

English

1-PHENYLCYCLOPENTANECARBOXYLIC ACID 2-(DIETHYLAMINO)ETHYL ESTER

Systematic Name

English

CARAMIPHEN [VANDF]

Common Name

English

DIETHYLAMINOETHYL 1-PHENYLCYCLOPENTANE-1-CARBOXYLATE

Systematic Name

English

2-DIETHYLAMINOETHYL 1-PHENYLCYCLOPENTANE-1-CARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66917