Page last updated: 2024-11-06

dextromoramide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dextromoramide is a synthetic opioid analgesic with a chemical structure similar to methadone. It is a potent μ-opioid receptor agonist, producing analgesia, sedation, and euphoria. Dextromoramide was synthesized in the 1950s and was initially marketed as a pain reliever. It has been studied for its potential to treat chronic pain conditions, including neuropathic pain, cancer pain, and post-operative pain. Its use has declined due to its high risk of addiction and abuse. Despite its potential clinical benefits, dextromoramide is a Schedule II controlled substance in many countries due to its addictive properties. Research continues to explore the therapeutic potential of dextromoramide, while acknowledging the challenges associated with its use.'

Dextromoramide: An opioid analgesic structurally related to METHADONE and used in the treatment of severe pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1070) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dextromoramide : An N-acylpyrrolidine arising by formal condensation of pyrrolidine with (3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenylbutanoic acid. An opioid analgesic that is structurally related to methadone, it is more poweful than morphine but shorter acting. It has been used (particularly as the hydrogen tartrate salt) for the treatment of severe pain, but was discontinued in the UK in 2004. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID92943
CHEMBL ID2365707
CHEBI ID74274
SCHEMBL ID25463
MeSH IDM0006142

Synonyms (60)

Synonym
jetrium
mcp 875
linfadol
jetrium r
palfium
moramide
(+)-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine
r 875
pyrrolamidolum
destromoramide [dcit]
dextromoramida [inn-spanish]
pyrrolidine, 1-(2,2-diphenyl-3-methyl-4-morpholinobutyryl)-, (+)-
troxilan
dextromoramide [inn:ban]
dauran
narcolo
einecs 206-613-1
skf 5137
dea no. 9613
palfadonna
yetrium
dextromoramidum [inn-latin]
alcoid
dextromoramide
(3s)-3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
357-56-2
dextromoramide (ban)
D07287
d-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine
pyrrolamidol
(+)-1-(3-methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine
(+)-4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
DB01529
palphium
1-((3s)-3-methyl-4-(4-morpholinyl)-1-oxo-2,2-diphenylbutyl)pyrrolidine
(3s)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-ylbutan-1-one
dextromoramida
(+)-3-methyl-4-morpholino-2,2-diphenyl-1-(pyrrolidin-1-yl)butanon
9s4s6ciy83 ,
destromoramide
unii-9s4s6ciy83
(+)-n-(3-methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidin
dextromoramidum
(+)-3-methyl-4-morpholino-2,2-diphenyl-1-(pyrrolidin-1-yl)butanone
skf-5137
CHEBI:74274 ,
SCHEMBL25463
dextromoramide [inn]
1-butanone, 3-methyl-4-(4-morpholinyl)-2,2-diphenyl-1-(1-pyrrolidinyl)-, (3s)-
dextromoramide [mart.]
dextromoramide [mi]
dextromoramide [who-dd]
pyrrolidine, 1-(3-methyl-4-morpholino-2,2-diphenylbutyryl)-, (-)-
4-[2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl]morpholine, (-)-
INUNXTSAACVKJS-OAQYLSRUSA-N
CHEMBL2365707
DTXSID8022909
3-methyl-4-morpholin-4-yl-2,2-di(phenyl)-1-pyrrolidin-1-ylbutan-1-one
Q408446

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"It has been shown in both mice and rats that the LD50 value for doxapram is reduced in rodents treated with narcotic analgesics."( A study of the enhanced toxicity of doxapram in rodents treated with narcotic analgesics.
Pleuvry, BJ, 1978
)
0.26

Pharmacokinetics

The extent of absorption and other pharmacokinetic parameters of dextromoramide following sublingual administration were assessed in five patients receiving chronic opioid analgesia. The data sets indicated short elimination half-life values (71 min, range 31-152 min)

ExcerptReferenceRelevance
" The pharmacokinetic parameters were calculated by computer using TRIOMPHE."( [Pharmacokinetics of dextromoramide in the surgical patient].
Athis, PD; Caillard, B; Lançon, JP; Obadia, JF; Pechinot, A; Pechinot, M; Pointaire, P, 1989
)
0.6
"The extent of absorption and other pharmacokinetic parameters of dextromoramide following sublingual administration were assessed in five patients receiving chronic opioid analgesia."( Dextromoramide pharmacokinetics following sublingual administration.
Jones, TE; Morris, RG; Saccoia, NC; Thorne, D, 1996
)
1.97
" Pharmacokinetic data sets for dextromoramide in each subject were conducted and analysed further, indicating short elimination half-life values (71 min, range 31-152 min)."( Determination and pharmacokinetics of dextromoramide in methadone maintenance therapy.
de Vos, JW; Ufkes, JG; van Brussel, GH, 1998
)
0.86

Dosage Studied

ExcerptRelevanceReference
" Two moderate respiratory depressions occurred in 1989 due to error in dosage with no consequence for the child."( [Intraoperative and postoperative analgesia in pediatric surgery. 1 years' experience].
Charles-Guillard, S; Heloury, Y; Meignier, M; Pannier, M; Ricard, P; Rogez, JM; Zaouter, M, 1990
)
0.28
"Dextromoramide (Palfium) was given by intravenous injection to a Thoroughbred horse at a dosage of 20 mg and urine was collected 2, 4, 6 and 8 h after drug administration."( Gas chromatographic mass-specific investigation of dextromoramide (Palfium) metabolism in the horse.
Duffield, AM; Reilly, PJ; Suann, CJ, 1990
)
1.97
" The concentration of the drug in a CSF sample collected 1 h after dosing was below the limit of detection (2 micrograms/L) in all subjects."( Pharmacokinetics of dextromoramide in surgical patients.
Barzaghi, N; Crema, F; Ego, D; Pagani, I; Perucca, E; Rovei, V, 1989
)
0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
opioid analgesicA narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
morpholinesAny compound containing morpholine as part of its structure.
N-acylpyrrolidine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (280)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990257 (91.79)18.7374
1990's17 (6.07)18.2507
2000's6 (2.14)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.29

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.29 (24.57)
Research Supply Index5.93 (2.92)
Research Growth Index3.98 (4.65)
Search Engine Demand Index50.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (4.74%)5.53%
Reviews7 (1.95%)6.00%
Case Studies14 (3.90%)4.05%
Observational0 (0.00%)0.25%
Other321 (89.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]