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Compound Detail

CHEMBL1213351

PROPOXYPHENE
💊 Approved Drug
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💊 Approved Drug
CCC(=O)O[C@](Cc1ccccc1)(c1ccccc1)[C@H](C)CN(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1213351
Name PROPOXYPHENE
Phase Approved
Structure Type MOL
InChI Key XLMALTXPSGQGBX-GCJKJVERSA-N
Therapeutic ✓ Yes

Known Names

Algafan D-propoxyphene Depromic Dextropropoxifeno Dextropropoxyphen Dextropropoxyphene IDS-ND-004(SECT.2) J5.928E Propoxyphene, d- SK-65
0
Targets
0
Activities
0
Assay Types
5
PK Parameters
20
Publications
10
Known Names
1
Indications

Molecular Properties

339.5
MW (Da)
4.28
ALogP
3
HBA
0
HBD
29.5
PSA (Ų)
0.67
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1957
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Year 1964

Extended Properties

Molecular Formula C22H29NO2
MW 339.48
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.24

Indications

Pain

ATC Classification

N02AC04
dextropropoxyphene
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Withdrawn
cardiotoxicity
Serious abnormal heart rhythms
Country: Canada; New Zealand; Vietnam   Year: 2010
Withdrawn
General Warning
Risk of serious abnormal heart rhythms that have been linked to serious adverse effects including sudden death
Country: Canada; New Zealand; Vietnam   Year: 2010
Withdrawn
cardiotoxicity
Risk of serious abnormal heart rhythms that have been linked to serious adverse effects including sudden death
Country: Canada; New Zealand; Vietnam   Year: 2010
Withdrawn
drug misuse
Deaths. More dangerous than other simple analgesics in overdose, particularly when combined with alcohol
Country: Canada; New Zealand; Vietnam   Year: 2010
Withdrawn
General Warning
Deaths. More dangerous than other simple analgesics in overdose, particularly when combined with alcohol
Country: Canada; New Zealand; Vietnam   Year: 2010
Withdrawn
cardiotoxicity
Prolong the PR interval, widen the QRS complex, prolong the QT interval and therefore increase the risk of serious abnormal heart rhythms.
Country: European Union; New Zealand; Canada; Iraq; United States   Year: 2009
Withdrawn
drug misuse
Risk of potentially fatal overdose
Country: European Union; New Zealand; Canada; Iraq; United States   Year: 2009
Withdrawn
General Warning
Adverse drug reactions
Country: European Union; New Zealand; Canada; Iraq; United States   Year: 2009
Withdrawn
cardiotoxicity
Prolong the PR interval, widen the QRS complex, prolong the QT interval and therefore increase the risk of serious abnormal heart rhythms.
Country: European Union; New Zealand; Canada; Iraq; United States   Year: 2009
Withdrawn
cardiotoxicity
Prolong the PR interval, widen the QRS complex, prolong the QT interval and therefore increase the risk of serious abnormal heart rhythms.
Country: European Union; New Zealand; Canada; Iraq; United States   Year: 2009

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
F 49.0 % Homo sapiens
Fu 0.24 - Homo sapiens
MRT 13.33 hr Homo sapiens
T1/2 18.0 hr Homo sapiens

Literature References

PubMed DOI Target Context # Activities
309950 10.1021/jm00207a023 Rattus norvegicus 29
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
6167716 10.1021/jm00135a006 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18426954 10.1124/dmd.108.020479 ADMET 4
628000 10.1021/jm00201a004 Mus musculus 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
448682 10.1021/jm00193a016 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
10891117 10.1021/jm0000564 No relevant target 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2

Data from ChEMBL 36 via Core Engine