U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H25N3O.C4H4O4
Molecular Weight 391.4614
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PROPIRAM FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CCC(=O)N(C(C)CN1CCCCC1)C2=CC=CC=N2

InChI

InChIKey=WQTLOZFMTGYQDX-WLHGVMLRSA-N
InChI=1S/C16H25N3O.C4H4O4/c1-3-16(20)19(15-9-5-6-10-17-15)14(2)13-18-11-7-4-8-12-18;5-3(6)1-2-4(7)8/h5-6,9-10,14H,3-4,7-8,11-13H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C16H25N3O
Molecular Weight 275.3892
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Propiram is an orally administered analgesic with partial morphine-like agonist and weak antagonist properties. Analgesic efficacy of propiram, usually 50 or 100mg, appears comparable to that of standard dosages of other oral opioid drugs [i.e. pentazocine, pethidine (meperidine)] in patients with acute pain of moderate to severe intensity arising from various gynaecological and surgical procedures, and may be superior to codeine in gynaecological and postoperative dental pain. Propiram is a non-addictive analgesic for the relief of moderate-to-severe pain. Propiram reached Phase III clinical trials in the United States and Canada, but was discontinued. Propiram is a partial opioid mu receptor agonist.

Approval Year

PubMed

PubMed

TitleDatePubMed
Propiram Shire.
2002-03
Propiram. A review of its pharmacodynamic and pharmacokinetic properties, and clinical use as an analgesic.
1993-09
Patents

Sample Use Guides

Analgesic efficacy of propiram, usually 50 or 100mg, appears comparable to that of standard dosages of other oral opioid drugs
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:45:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:17 GMT 2025
Record UNII
AVG0GBV8AP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIRAME
Preferred Name English
PROPIRAM FUMARATE
MART.   MI   USAN  
USAN  
Official Name English
BAY 4503
Code English
PROPIRAM FUMARATE [USAN]
Common Name English
PROPIRAM FUMARATE [MI]
Common Name English
(±)-PROPIRAM FUMARATE
Common Name English
BAY-4503
Code English
PROPANAMIDE, N-(1-METHYL-2-(1-PIPERIDINYL)ETHYL)-N-2-PYRIDINYL-, (E)-2-BUTENEDIOATE (1:1)
Systematic Name English
PROPIRAM FUMARATE [MART.]
Common Name English
Propiram fumarate [WHO-DD]
Common Name English
N-(1-Methyl-2-piperidinoethyl)-N-2-pyridylpropionamide fumarate (1:1)
Systematic Name English
DL-PROPIRAM FUMARATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
NCI_THESAURUS C1506
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
Code System Code Type Description
FDA UNII
AVG0GBV8AP
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID301350227
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
MERCK INDEX
m1240
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY Merck Index
CAS
13717-04-9
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110985
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
PUBCHEM
6433584
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
237-270-6
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
NCI_THESAURUS
C66489
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
SMS_ID
300000055023
Created by admin on Mon Mar 31 18:45:17 GMT 2025 , Edited by admin on Mon Mar 31 18:45:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY