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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29NO2
Molecular Weight 339.4712
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPOXYPHENE

SMILES

CCC(=O)O[C@@](CC1=CC=CC=C1)([C@H](C)CN(C)C)C2=CC=CC=C2

InChI

InChIKey=XLMALTXPSGQGBX-GCJKJVERSA-N
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+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H29NO2
Molecular Weight 339.4712
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Propoxyphene is a centrally acting opiate analgesic. Propoxyphene is an odorless, freely soluble in water, white crystalline powder with a bitter taste. In vitro studies demonstrated propoxyphene and the metabolite norpropoxyphene inhibit sodium channels (local anesthetic effect) with norpropoxyphene being approximately 2 fold more potent than propoxyphene and propoxyphene approximately 10 fold more potent than lidocaine. Propoxyphene and norpropoxyphene inhibit the voltage-gated potassium current carried by cardiac rapidly activating delayed rectifier (hERG) channels with approximately equal potency. It is unclear if the effects on ion channels occur within therapeutic dose range. Propoxyphene is indicated for the relief of mild to moderate pain.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
53.0 nM [Kd]
140.0 nM [Kd]
2100.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DARVON COMPOUND-65

Cmax

ValueDoseCo-administeredAnalytePopulation
2310 ng/mL
7.5 mg/kg single, oral
NORPROPOXYPHENE plasma
Canis lupus
459 ng/mL
2 mg/kg single, intravenous
NORPROPOXYPHENE plasma
Canis lupus

AUC

ValueDoseCo-administeredAnalytePopulation
126000 ng × h/mL
7.5 mg/kg single, oral
NORPROPOXYPHENE plasma
Canis lupus
2440 ng × h/mL
2 mg/kg single, intravenous
NORPROPOXYPHENE plasma
Canis lupus

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
7.5 mg/kg single, oral
NORPROPOXYPHENE plasma
Canis lupus
4 h
2 mg/kg single, intravenous
NORPROPOXYPHENE plasma
Canis lupus

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Darvon-N (Propoxyphene) is given orally. The usual dosage is one 100 mg propoxyphene napsylate tablet every 4 hours as needed for pain. The maximum dose of Darvon-N is 6 tablets per day. Do not exceed the maximum daily dose.
Route of Administration: Oral
In Vitro Use Guide
Cell membrane preparation (Chemiscreen™ MOR) expressing recombinant human MOR were used for activity evaluation. The assays were performed in microtiter plates with 40 mkL of binding buffer or Propoxyphene (1–100,000 mkM), 10 mkL of radioligand (2 nM (3H)-DAMG), and 50 mkL of diluted membranes with three wells per group. The plates were then incubated at room temperature for 2h. The binding incubation was terminated by the addition of 100 mkL cold binding buffer to each well. The glass fiber filter plates were presoaked for 30–45 min with 0.33% PEI buffer. The PEI solution was removed from the filter plate with a vacuum manifold (Millipore) and the filters washed with 200 mkL priming buffer (50 mM HEPES, 0.5% BSA, pH 7.4) per well. The binding reaction was transferred to the filter plate and washed with 200 mkL washing buffer (50 mM HEPES with 500 mM NaCl and 0.1% BSA, pH 7.4).
Substance Class Chemical
Record UNII
S2F83W92TK
Record Status Validated (UNII)
Record Version