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 Source	ID
PubMed CID	162321
CHEBI ID	77841
SCHEMBL ID	4534058
MeSH ID	M0172928

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

Excerpt	Reference	Relevance
"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

Excerpt	Reference	Relevance
" 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

Excerpt	Relevance	Reference
" 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)

Role	Description
drug metabolite	null
NMDA receptor antagonist	Any 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)

Class	Description
ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate	An 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (5.88)	18.7374
1990's	2 (11.76)	18.2507
2000's	8 (47.06)	29.6817
2010's	6 (35.29)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	7 (41.18%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	1 (5.88%)	4.05%
Observational	1 (5.88%)	0.25%
Other	8 (47.06%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.03	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	1.99	1	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
trimipramine Trimipramine: Tricyclic antidepressant similar to IMIPRAMINE, but with more antihistaminic and sedative properties.. trimipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)-2-methylpropyl group at the nitrogen atom. It is used as an antidepressant.	2.03	1	0	dibenzoazepine; tertiary amino compound	antidepressant; environmental contaminant; xenobiotic
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	1.99	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	1.99	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	1.99	1	0	benzenes; phenyl acetates
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	3.5	1	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.43	1	1	1,2,3-triazole
voriconazole Voriconazole: A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.. voriconazole : A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.	3.43	1	1	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor
norketamine norketamine: metabolite of ketamine; RN given refers to cpd without isomeric designation	1.99	1	0	organochlorine compound
5,6-dehydronorketamine 5,6-dehydronorketamine: metabolite of ketamine; RN given refers to cpd without isomeric designation	1.99	1	0	organochlorine compound
norfentanyl norfentanyl: metabolite of fentanyl; RN given refers to parent cpd; structure given in first source. norfentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of 4-(N'-phenyl)piperidin-4-amine with propanoic acid. A major metabolite of fentanyl.	2.03	1	0	anilide; monocarboxylic acid amide; piperidines	drug metabolite; opioid analgesic
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	3.46	1	1	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
bisnortilidine bisnortilidine: active metabolite of tilidine; structure given in first source; RN given refers to (trans(+-)-isomer	6.3	10	4
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	10.01	3	3	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine-6-glucuronide morphine-6-glucuronide: RN given refers to (5alpha,6alpha)-isomer	2.03	1	0	morphinane alkaloid
morphine-3-glucuronide morphine-3-glucuronide: RN given refers to (5alpha,6alpha)-isomer	2.03	1	0	morphinane alkaloid
ent-dextilidine Tilidine: An opioid analgesic used similarly to MORPHINE in the control of moderate to severe pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1097). ent-dextilidine : An ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has R configuration at the carbon bearing the phenyl group and S configuration at the carbon bearing the dimethylamino group. It is the enantiomer of dextilidine; the opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and ent-dextilidine.. tilidine : A racemate that is an equimolar mixture of the two trans diastereoisomers of ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate, namely dextilidine and ent-dextilidine. It is used (commonly as the hydrochloride hemihydrate) as an opioid analgesic for the management of moderate to severe pain. A prodrug, it is metabolised in the body to nortilidine, which is responsible for the analgesic activity; virtually all of the opioid activity resides in the (1S,2R) isomer.	7.32	17	7	ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
pyrethrins [no description available]	2.03	1	0

Condition	Relationship Strength	Studies	Trials
Pain, Chronic [description not available]	2.15	1	0
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	2.15	1	0
Coronary Vessel Anomalies Malformations of CORONARY VESSELS, either arteries or veins. Included are anomalous origins of coronary arteries; ARTERIOVENOUS FISTULA; CORONARY ANEURYSM; MYOCARDIAL BRIDGING; and others.	2.03	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.99	1	0
Chronic Kidney Failure [description not available]	3.39	1	1
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	3.39	1	1

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