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nortilidine

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

Description

nortilidine: active metabolite of tilidine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(1R,2S)-nortilidine : An ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate that is ent-dextilidine in which one of the methyl groups attached to the nitrogen is replaced by hydrogen. ent-Dextilidine is metabolised to (1R,2S)-nortilidine by the liver. [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 CID162321
CHEBI ID77841
SCHEMBL ID4534058
MeSH IDM0172928

Synonyms (18)

Synonym
nortilidine
38677-94-0
ethyl (1r,2s)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
7145g6817j ,
unii-7145g6817j
3-cyclohexene-1-carboxylic acid, 2-(methylamino)-1-phenyl-, ethyl ester, trans-(+-)-
CHEBI:77841
(1r,2s)-nortilidine
(-)-nortilidine
(1r,2s)-(-)-nortilidine
ethyl trans-(-)-2-(methylamino)-1-phenyl-3-cyclohexene-1-carboxylate
SCHEMBL4534058
3-cyclohexene-1-carboxylic acid, 2-(methylamino)-1-phenyl-, ethyl ester, (1r,2s)-rel-
1-phenyl-1-trans-carbethoxy-2-methylaminocyclohex-3-ene
3-cyclohexene-1-carboxylic acid, 2-(methylamino)-1-phenyl-, ethyl ester, trans-
3-cyclohexene-1-carboxylic acid, 2-(methylamino)-1-phenyl-, ethyl ester, trans-(+/-)-
DTXSID10191973
Q27147451

Research Excerpts

Actions

ExcerptReferenceRelevance
"Nortilidine had a much lower volume of distribution (275 +/- 79 vs."( Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine.
Hajda, JP; Jähnchen, E; Oie, S; Trenk, D, 2002
)
1.31

Bioavailability

ExcerptReferenceRelevance
" The systemic bioavailability of tilidine was low (7."( Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine.
Hajda, JP; Jähnchen, E; Oie, S; Trenk, D, 2002
)
0.59

Dosage Studied

ExcerptRelevanceReference
" Because of the equivalence of different dose strengths of Valoron N tablets, patients are able to exchange low dosed Valoron N retard tablets for higher-dosed ones (50 mg, 100 mg and 200 mg tilidine/tablet), if necessary."( Pharmacokinetics of nortilidine and naloxone after administration of tilidine/naloxone solution or tilidine/naloxone sustained release tablets.
Brennscheidt, U; Seiler, KU; Thomann, P, 2000
)
0.63
" Thus, although two-thirds of the dose of tilidine is metabolized to nortilidine, only one-third of the dose is available systemically as nortilidine for interaction with the opiate receptors after both intravenous and oral dosing of tilidine."( Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine.
Hajda, JP; Jähnchen, E; Oie, S; Trenk, D, 2002
)
0.82
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
drug metabolitenull
NMDA receptor antagonistAny substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
[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 (1)

ClassDescription
ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylateAn amino acid ester that is the ethyl ester of cyclohex-3-ene-1-carboxylic acid in which the cyclohexane ring is substituted at positions 1 and 2 by phenyl and methylamino groups, respectively.
[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 (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.88)18.7374
1990's2 (11.76)18.2507
2000's8 (47.06)29.6817
2010's6 (35.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (41.18%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (5.88%)4.05%
Observational1 (5.88%)0.25%
Other8 (47.06%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]