NAV

Levopropoxyphene

Identification

Generic Name
Levopropoxyphene
DrugBank Accession Number
DB06793
Background

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.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 339.479
Monoisotopic: 339.219829178
Chemical Formula
C22H29NO2
Synonyms
  • (-)-Propoxyphene
  • (l)-Propoxyphene
  • levopropoxifeno
  • Levopropoxyphene
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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

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Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
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interactions in your software
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.
BrexanoloneThe therapeutic efficacy of Brexanolone can be decreased when used in combination with Levopropoxyphene.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Levopropoxyphene.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Levopropoxyphene napsylate anhydrousW7DQT6KY5S5714-90-9VZPXFHVJUUSVLH-VNJAQMQMSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Amino acid or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
U75VZ9PK1J
CAS number
2338-37-6
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

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. [Article]
  2. de Vries EJ, Janssen DB: Biocatalytic conversion of epoxides. Curr Opin Biotechnol. 2003 Aug;14(4):414-20. [Article]
  3. Tyrell J. (2014). Fundamentals of Industrial Chemistry. Wiley.
PubChem Compound
200742
PubChem Substance
310264889
ChemSpider
173777
RxNav
6377
ChEBI
51174
ChEMBL
CHEMBL1738990
ZINC
ZINC000001530767
Wikipedia
Levopropoxyphene
MSDS
Download (22.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSsplash10-0a4i-3190000000-23a4e1c3e4e618c63c87
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9120000000-f76f3d90103e0de058a4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9150000000-07d3369247f880b91798
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-4980000000-2aa2d32e113bce505fb7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9140000000-cdacdd2543f8eb2c60b9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufv-0690000000-6be347209ba89b1056b0
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]-198.0436793
predicted
DarkChem Lite v0.1.0
[M-H]-179.594
predicted
DeepCCS 1.0 (2019)
[M+H]+198.1223793
predicted
DarkChem Lite v0.1.0
[M+H]+181.95201
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.56422
predicted
DeepCCS 1.0 (2019)

Drug created at September 14, 2010 16:21 / Updated at February 02, 2024 22:54