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Details

Stereochemistry ACHIRAL
Molecular Formula 2C18H27NO2.C2H6O6S2
Molecular Weight 769.02
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARAMIPHEN EDISYLATE

SMILES

OS(=O)(=O)CCS(O)(=O)=O.CCN(CC)CCOC(=O)C1(CCCC1)C2=CC=CC=C2.CCN(CC)CCOC(=O)C3(CCCC3)C4=CC=CC=C4

InChI

InChIKey=BANIDACEBXZGNK-UHFFFAOYSA-N
InChI=1S/2C18H27NO2.C2H6O6S2/c2*1-3-19(4-2)14-15-21-17(20)18(12-8-9-13-18)16-10-6-5-7-11-16;3-9(4,5)1-2-10(6,7)8/h2*5-7,10-11H,3-4,8-9,12-15H2,1-2H3;1-2H2,(H,3,4,5)(H,6,7,8)

HIDE SMILES / InChI
Molecular Formula C2H6O6S2
Molecular Weight 190.195
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C18H27NO2
Molecular Weight 289.4125
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

1949
70
Targets

Targets

Primary TargetPharmacologyConditionPotency
voltage-gated Na⁺ currents
3
Target ID: voltage-gated Na⁺ currents
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)
Antagonist
2778
 1.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
SKF TUSS-ORNADE

Approved Use

Unknown
Primary
Approved
8429
parpanit

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
Anticholinergic and antiglutamatergic agents protect against soman-induced brain damage and cognitive dysfunction.
2003 Sep
Therapy against organophosphate poisoning: the importance of anticholinergic drugs with antiglutamatergic properties.
2008 Oct 15
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.
2010 Dec
Roles of perirhinal and posterior piriform cortices in control and generation of seizures: a microinfusion study in rats exposed to soman.
2010 Jan
Isobolographic analysis of caramiphen and lidocaine on spinal anesthesia in rats.
2010 Jan 18
[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats].
2010 May
Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test.
2010 Sep 13
The anticholinergic and antiglutamatergic drug caramiphen reduces seizure duration in soman-exposed rats: synergism with the benzodiazepine diazepam.
2012 Mar 15
Patents

Patents

EP0311677
3
EP0316434
3
EP0346445
3

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:00 UTC 2023
Edited
by admin
on Fri Dec 15 15:05:00 UTC 2023
Record UNII
09TQU5PG95
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARAMIPHEN EDISYLATE
GREEN BOOK   VANDF  
Common Name English
Caramiphen edisilate [WHO-DD]
Common Name English
CARAMIPHEN EDISILATE
MART.   WHO-DD  
Common Name English
CARAMIPHEN EDISYLATE [VANDF]
Common Name English
CARAMIPHEN ETHANEDISULFONATE
MI  
Common Name English
CARAMIPHEN EDISYLATE [GREEN BOOK]
Common Name English
CYCLOPENTANECARBOXYLIC ACID, 1-PHENYL-, 2-(DIETHYLAMINO)ETHYL ESTER, 1,2-ETHANEDISULPHONATE (2:1)
Common Name English
CYCLOPENTANECARBOXYLIC ACID, 1-PHENYL-, 2-(DIETHYLAMINO)ETHYL ESTER, 1,2-ETHANEDISULFONATE (2:1)
Common Name English
CARAMIPHEN EDISILATE [MART.]
Common Name English
CARAMIPHEN ETHANEDISULFONATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
CFR 21 CFR 520.301
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76459
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
MERCK INDEX
m3048
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY Merck Index
SMS_ID
100000084850
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID9047835
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
PUBCHEM
517304
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
DRUG BANK
DBSALT001670
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
RXCUI
133053
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY RxNorm
FDA UNII
09TQU5PG95
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
CAS
125-86-0
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
EVMPD
SUB01036MIG
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-759-0
Created by admin on Fri Dec 15 15:05:00 UTC 2023 , Edited by admin on Fri Dec 15 15:05:00 UTC 2023
PRIMARY
Related Record Type Details
Structure of CARAMIPHEN
PARENT -> SALT/SOLVATE
Structure of 1,2-ETHANEDISULFONIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CARAMIPHEN
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