Levopropoxyphene

Identification

Name
Levopropoxyphene
Accession Number
DB06793
Type
Small Molecule
Groups
Withdrawn
Description

Levopropoxyphene is a stereoisomer of propoxyphene in the form of 2S, 3R enantiomer. It was sold as an antitussive, but it was removed from the market in the 70s.[3] Levopropoxyphene was developed by Lilly and FDA approved on March 21st, 1962. This drug presented different dosages and it was administered as a capsule or suspension.

Structure
Thumb
Synonyms
  • (-)-Propoxyphene
  • (l)-Propoxyphene
  • levopropoxifeno
  • Levopropoxyphene
Product Ingredients
IngredientUNIICASInChI Key
Levopropoxyphene napsylate anhydrousW7DQT6KY5S5714-90-9VZPXFHVJUUSVLH-VNJAQMQMSA-N
Categories
UNII
U75VZ9PK1J
CAS number
2338-37-6
Weight
Average: 339.479
Monoisotopic: 339.219829178
Chemical Formula
C22H29NO2
InChI Key
XLMALTXPSGQGBX-PGRDOPGGSA-N
InChI
InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m0/s1
IUPAC Name
(2R,3S)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
SMILES
[H][C@](C)(CN(C)C)[C@@](CC1=CC=CC=C1)(OC(=O)CC)C1=CC=CC=C1

Pharmacology

Indication

Levopropoxyphene was used as an antitussive. An antitussive is a medication often recommended for the treatment of cough and associated respiratory tract disorders.[1] Its enantiomer, dextropropoxyphene, presents an analgesic effect.[2]

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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7-NitroindazoleThe therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Levopropoxyphene.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Levopropoxyphene.
AmifampridineThe risk or severity of seizure can be increased when Levopropoxyphene is combined with Amifampridine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Levopropoxyphene.
BarbexacloneThe therapeutic efficacy of Barbexaclone can be decreased when used in combination with Levopropoxyphene.
BarbitalThe therapeutic efficacy of Barbital can be decreased when used in combination with Levopropoxyphene.
BeclamideThe therapeutic efficacy of Beclamide can be decreased when used in combination with Levopropoxyphene.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Levopropoxyphene.
ButalbitalThe therapeutic efficacy of Butalbital can be decreased when used in combination with Levopropoxyphene.
CannabidivarinThe therapeutic efficacy of Cannabidivarin can be decreased when used in combination with Levopropoxyphene.
Food Interactions
Not Available

References

General References
  1. Dicpinigaitis PV, Morice AH, Birring SS, McGarvey L, Smith JA, Canning BJ, Page CP: Antitussive drugs--past, present, and future. Pharmacol Rev. 2014 Mar 26;66(2):468-512. doi: 10.1124/pr.111.005116. Print 2014. [PubMed:24671376]
  2. de Vries EJ, Janssen DB: Biocatalytic conversion of epoxides. Curr Opin Biotechnol. 2003 Aug;14(4):414-20. [PubMed:12943851]
  3. Tyrell J. (2014). Fundamentals of Industrial Chemistry. Wiley.
External Links
PubChem Compound
200742
PubChem Substance
310264889
ChemSpider
173777
ChEBI
51174
ChEMBL
CHEMBL1738990
Wikipedia
Levopropoxyphene
MSDS
Download (22.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75-76ºCThe Merck Index. 9th edition. (1976)
water solubility3.32 mg/L at 25ºCMcFarland, and Raevsky O. Chem Inf Comput Sci. (2001)
logP4.11EPA
Predicted Properties
PropertyValueSource
Water Solubility0.00419 mg/mLALOGPS
logP4.06ALOGPS
logP4.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.88 m3·mol-1ChemAxon
Polarizability38.92 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Phenylbutylamines / Benzyloxycarbonyls / Phenylpropanes / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Stilbene / Phenylbutylamine / Benzyloxycarbonyl / Phenylpropane / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid ester
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on September 14, 2010 10:21 / Updated on December 16, 2018 06:53