Caramiphen

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Caramiphen
DrugBank Accession Number
DB11504
Background

Caramiphen is a cholinergic antagonist used in Parkinson's disease. Additionally, it is used, in combination with phenylpropanolamine, as a cough suppressant and nasal decongestant for the symptomatic treatment of seasonal respiratory conditions.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
Weight
Average: 289.419
Monoisotopic: 289.204179113
Chemical Formula
C18H27NO2
Synonyms
  • Caramifenio
  • Caramiphen
  • Caramiphenum

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Caramiphen edisylate09TQU5PG95125-86-0BANIDACEBXZGNK-UHFFFAOYSA-N
Caramiphen hydrochloride4858SN190E125-85-9MUPNXGNOIBYHSG-UHFFFAOYSA-N
International/Other Brands
Parpanil

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
97J7NP0XJY
CAS number
77-22-5
InChI Key
OFAIGZWCDGNZGT-UHFFFAOYSA-N
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
IUPAC Name
2-(diethylamino)ethyl 1-phenylcyclopentane-1-carboxylate
SMILES
CCN(CC)CCOC(=O)C1(CCCC1)C1=CC=CC=C1

References

General References
  1. Authors unspecified: CARAMIPHEN hydrochloride. J Am Med Assoc. 1959 Apr 25;169(17):2019. [Article]
  2. DeHaven-Hudkins DL, Allen JT, Hudkins RL, Stubbins JF, Tortella FC: Anticonvulsant activity of caramiphen analogs. Life Sci. 1995;56(19):1571-6. [Article]
  3. GLICK J: Codeine vs. caramiphen in cough control. Del Med J. 1963 Jul;35:180. [Article]
  4. Casselman AA, Bannard RA: Gas-liquid chromatography of caramiphen hydrochloride and its analogues. J Chromatogr. 1970 Oct 7;52(1):138-40. [Article]
  5. Hudkins RL, DeHaven-Hudkins DL, Stubbins JF: Muscarinic receptor binding profile of para-substituted caramiphen analogues. J Med Chem. 1991 Oct;34(10):2984-9. [Article]
  6. SNYDER GG: An evaluation of caramiphen ethane disulfonate as an antitussive agent. Laryngoscope. 1953 Oct;63(10):1008-13. [Article]
  7. Raveh L, Rabinovitz I, Gilat E, Egoz I, Kapon J, Stavitsky Z, Weissman BA, Brandeis R: Efficacy of antidotal treatment against sarin poisoning: the superiority of benactyzine and caramiphen. Toxicol Appl Pharmacol. 2008 Feb 15;227(1):155-62. [Article]
  8. Chen YW, Chu CC, Chen YC, Wang JJ, Hung CH: Isobolographic analysis of caramiphen and lidocaine on spinal anesthesia in rats. Neurosci Lett. 2010 Jan 18;469(1):174-8. doi: 10.1016/j.neulet.2009.11.071. Epub 2009 Dec 3. [Article]
  9. Leung YM, Tzeng JI, Gong CL, Wang YW, Chen YW, Wang JJ: Caramiphen-induced block of sodium currents and spinal anesthesia. Eur J Pharmacol. 2015 Jan 5;746:213-20. doi: 10.1016/j.ejphar.2014.10.035. Epub 2014 Oct 29. [Article]
  10. Raveh L, Eisenkraft A, Weissman BA: Caramiphen edisylate: an optimal antidote against organophosphate poisoning. Toxicology. 2014 Nov 5;325:115-24. doi: 10.1016/j.tox.2014.09.005. Epub 2014 Sep 6. [Article]
ChemSpider
6228
BindingDB
73402
RxNav
20191
ChEBI
135204
ChEMBL
CHEMBL61946
ZINC
ZINC000001847743
Wikipedia
Caramiphen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0437 mg/mLALOGPS
logP4.31ALOGPS
logP4.01Chemaxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.96Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity86.13 m3·mol-1Chemaxon
Polarizability34.2 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-6900000000-bc4d844b60043552f8d6
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9200000000-e8cc4f4a84fe6283a06c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-f3e5ab8e42799fc789ee
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-4970000000-42fb116b2506f69fc378
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1890000000-201b34f39ca497ee28a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6w-4910000000-665f221c98b2a6d7e40f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-1910000000-82bb543e11afdbc83321
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-a666c8ec7f9e5a87c73f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.0966446
predicted
DarkChem Lite v0.1.0
[M-H]-168.50859
predicted
DeepCCS 1.0 (2019)
[M+H]+178.5885446
predicted
DarkChem Lite v0.1.0
[M+H]+170.86658
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.1897446
predicted
DarkChem Lite v0.1.0
[M+Na]+176.95973
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:26 / Updated at February 21, 2021 18:53