6-methoxy-2-naphthylacetic acid: major metabolite of nabumetone; inhibits cyclooxygenase-2 (COX-2) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
(6-methoxy-2-naphthyl)acetic acid : A monocarboxylic acid consisting of 2-naphthylacetic acid having a methoxy substituent at the 6-position. The active metabolite of the prodrug nabumetone. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 32176 |
| CHEMBL ID | 1105 |
| CHEBI ID | 35628 |
| SCHEMBL ID | 253759 |
| MeSH ID | M0130195 |
| Synonym |
|---|
| CHEMBL1105 |
| 23981-47-7 |
| 6-mnaa |
| (6-methoxynaphthalen-2-yl)acetic acid |
| 6-methoxynaphth-2-ylacetic acid |
| 6-methoxy-2-naphthylacetic acid |
| (6-methoxy-2-naphthyl)acetic acid |
| CHEBI:35628 , |
| 6-mna |
| 2-naphthaleneacetic acid, 6-methoxy- |
| 6mna |
| 6-methoxy-2-naphthaleneacetic acid |
| einecs 245-967-1 |
| 6-metossi-2-naphtil acetico [italian] |
| brn 2371586 |
| brl 10720 |
| 6-methoxynaphthalene-2-acetic acid |
| UNM-0000306103 , |
| 2-(6-methoxynaphthalen-2-yl)acetic acid |
| AKOS005256647 |
| 9h7k3yod7q , |
| 6-metossi-2-naphtil acetico |
| 3-10-00-01106 (beilstein handbook reference) |
| unii-9h7k3yod7q |
| FT-0638373 |
| naproxen sodium impurity i [ep impurity] |
| naproxen impurity i [ep impurity] |
| 2-(6-methoxy-2-naphthyl)acetic acid |
| SCHEMBL253759 |
| PHJFLPMVEFKEPL-UHFFFAOYSA-N |
| ksc-419-062 |
| KUC114374N |
| 6-methoxy naphthalene acetic acid |
| cid_32176 |
| 2-(6-methoxy-2-naphthalenyl)acetic acid |
| 2-(6-methoxynaphthalen-2-yl)ethanoic acid |
| bdbm54706 |
| HMS3649O21 |
| DTXSID70178705 |
| mfcd00033105 |
| 2-(6-methoxynaphthalen-2-yl)acetic acid, pharmaceutical impurity standard |
| 6-methoxy-2-naphthylacetic acid, aldrichcpr |
| H11907 |
| alpha-demethylnaproxen |
| (6-methoxynaphthalen-2-yl)acetic acid; alpha-demethylnaproxen; naproxen imp. i (ep); naproxen impurity i |
| J-015303 |
| (6-methoxy-naphthalen-2-yl)-acetic acid |
| (6-methoxynaphthalen-2-yl)-acetic acid |
| DS-15868 |
| Q27116532 |
| naproxen ep impurity i |
| desmethyl naproxen; 2-(6-methoxy-2-naphthyl)acetic acid; 6-methoxy-2-naphthylacetic acid; 6-methoxy-2-naphthaleneacetic acid |
| SR-01000946589-1 |
| sr-01000946589 |
| PWY , |
| AMY32137 |
| HY-W086896 |
| 6-methoxy-2-naphthaleneacetic acid (desmethyl naproxen) |
| CS-0127451 |
| EN300-94917 |
| Z1269762978 |
6-methoxy-2-naphthylacetic acid, BRL 10720. In the patients with liver insufficiency the mean values of Cmax and AUC0-24 h for 6-MNA were 26. The study compared results of young healthy volunteers with those of a group of elderly arthritic patients.
| Excerpt | Reference | Relevance |
|---|---|---|
| "We have performed a detailed pharmacokinetic study of the plasma concentrations of the major active metabolite of nabumetone, 6-methoxy-2-naphthylacetic acid (6 MNA), attained after a single dose and during chronic administration comparing the results of a group of young healthy volunteers with those of a group of elderly arthritic patients." | ( A pharmacokinetic study of the active metabolite of nabumetone in young healthy subjects and older arthritis patients. Chellingsworth, MC; Jubb, R; Kendall, MJ; Kill, DC; Thawley, AR; Undre, NA, 1989) | 0.48 |
| " Pharmacokinetic assessment was made on the presence of the major and active metabolite found in the plasma, 6-methoxy-2-naphthylacetic acid, BRL 10720." | ( Nabumetone pharmacokinetics in patients with varying degrees of renal impairment. Boelaert, JR; Cooper, DL; Daneels, RF; Jonnaert, HA; Schurgers, ML; Thawley, AR; Undre, NA, 1987) | 0.49 |
| " In the patients with liver insufficiency the mean values of Cmax and AUC0-24 h for 6-methoxy-2-naphthylacetic acid were 26." | ( Liver insufficiency as a factor modifying the pharmacokinetic characteristic of the preparation nabumetone. Bacracheva, N; Dierdorf, D; Gruev, I; Kostova, N; Maleev, A; Vlahov, V, 1986) | 0.5 |
There is a tendency towards a reduced bioavailability of 6-methoxy-2-naphthylacetic acid after nabumetone administration in patients with a more severely expressed pathologic impairment.
| Excerpt | Reference | Relevance |
|---|---|---|
| " There is a tendency towards a reduced bioavailability of 6-methoxy-2-naphthylacetic acid after nabumetone administration in patients with a more severely expressed pathologic impairment, compared to patients with slight morphologic changes of the liver parenchyma." | ( Liver insufficiency as a factor modifying the pharmacokinetic characteristic of the preparation nabumetone. Bacracheva, N; Dierdorf, D; Gruev, I; Kostova, N; Maleev, A; Vlahov, V, 1986) | 0.52 |
| "The bioavailability of nabumetone after different multiple dosing regimens was investigated in healthy male volunteers by determining the main plasma metabolite 6-methoxy-2-naphthylacetic acid." | ( Nabumetone--a novel anti-inflammatory drug: bioavailability after different dosage regimens. Buscher, G; Dierdorf, D; Mügge, H; von Schrader, HW; Wolf, D, 1984) | 0.46 |
| Excerpt | Relevance | Reference |
|---|---|---|
| "6MNA, the active metabolite of the non-acidic anti-inflammatory drug nabumetone, was investigated using intravenous administration for effects on (a) carrageenan paw oedema and gastric irritancy compared to either oral nabumetone or both oral and intravenous indomethacin when given acutely and (b) gastrointestinal irritancy when given in repeat dosing studies." | ( Anti-inflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6MNA (6-methoxy-2-naphthylacetic acid): comparison with indomethacin. Blower, PR; Gentry, C; Kelvin, AS; Melarange, R; Neil, C; O'Connell, C; Toseland, CD, 1992) | 0.5 |
| "6MNA, the active metabolite of the nonacidic antiinflammatory drug nabumetone, was investigated using intravenous administration for effects on (1) carrageenan paw edema and gastric irritancy compared with either oral nabumetone or both oral and intravenous indomethacin when given acutely and (2) gastrointestinal irritancy when given in repeat dosing studies." | ( Antiinflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6-methoxy-2-naphthylacetic acid (6MNA). Comparative studies with indomethacin. Blower, PR; Gentry, C; Kelvin, AS; Melarange, R; Neil, C; O'Connell, C; Toseland, CD, 1992) | 0.51 |
| "The bioavailability of nabumetone after different multiple dosing regimens was investigated in healthy male volunteers by determining the main plasma metabolite 6-methoxy-2-naphthylacetic acid." | ( Nabumetone--a novel anti-inflammatory drug: bioavailability after different dosage regimens. Buscher, G; Dierdorf, D; Mügge, H; von Schrader, HW; Wolf, D, 1984) | 0.46 |
| Role | Description |
|---|---|
| EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. |
| drug metabolite | null |
| xenobiotic metabolite | Any metabolite produced by metabolism of a xenobiotic compound. |
| [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] | |
| Class | Description |
|---|---|
| monocarboxylic acid | An oxoacid containing a single carboxy group. |
| methoxynaphthalene | Any alkyloxynaphthalene bearing one or more methoxy substituents. |
| [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] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Prostaglandin G/H synthase 1 | Homo sapiens (human) | IC50 (µMol) | 4.1130 | 0.0002 | 1.5574 | 10.0000 | AID625243 |
| Aldo-keto reductase family 1 member C3 | Homo sapiens (human) | IC50 (µMol) | 0.6500 | 0.0500 | 2.2070 | 10.0000 | AID1628930 |
| Aldo-keto reductase family 1 member C2 | Homo sapiens (human) | IC50 (µMol) | 19.0400 | 0.3700 | 4.0951 | 9.2800 | AID1628931 |
| Prostaglandin G/H synthase 2 | Mus musculus (house mouse) | IC50 (µMol) | 1.4000 | 0.0005 | 0.4008 | 6.2000 | AID692689 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| GTP-binding protein (rab7) | Canis lupus familiaris (dog) | EC50 (µMol) | 30.0000 | 0.0220 | 1.2146 | 6.4190 | AID2036 |
| ras protein, partial | Homo sapiens (human) | EC50 (µMol) | 30.0000 | 0.0200 | 0.2237 | 1.9660 | AID2038; AID2043 |
| Rac1 protein | Homo sapiens (human) | EC50 (µMol) | 30.0000 | 0.0202 | 5.9860 | 29.5100 | AID2039; AID2040 |
| cell division cycle 42 (GTP binding protein, 25kDa), partial | Homo sapiens (human) | EC50 (µMol) | 30.0000 | 0.0563 | 3.0554 | 13.5100 | AID2021; AID2022 |
| Ras-related protein Rab-2A | Canis lupus familiaris (dog) | EC50 (µMol) | 30.0000 | 0.1580 | 0.3777 | 0.7042 | AID2046 |
| Sigma non-opioid intracellular receptor 1 | Rattus norvegicus (Norway rat) | EC50 (µMol) | 30.0000 | 0.1060 | 1.0765 | 1.7000 | AID2038; AID2043 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID692689 | Inhibition of mouse COX2-mediated 2-arachidonoylglycerol oxygenation preincubated for 3 mins before 2-arachidonoylglycerol addition measured after 30 seconds | 2012 | ACS medicinal chemistry letters, Sep-13, Volume: 3, Issue:9 | Substrate-Selective Inhibition of Cyclooxygenase-2: Development and Evaluation of Achiral Profen Probes. |
| AID692691 | Inhibition of mouse COX2-mediated arachidonic acid oxygenation at 10 uM preincubated for 3 mins before 2-arachidonoylglycerol addition measured after 30 seconds | 2012 | ACS medicinal chemistry letters, Sep-13, Volume: 3, Issue:9 | Substrate-Selective Inhibition of Cyclooxygenase-2: Development and Evaluation of Achiral Profen Probes. |
| AID42809 | Compound was evaluated for in vitro inhibition of [Fe(2+)]/ascorbate-induced oxidation of bovine heart membranes(antioxidant BHMLO); not determined | 1999 | Journal of medicinal chemistry, Jan-28, Volume: 42, Issue:2 | Novel esters and amides of nonsteroidal antiinflammatory carboxylic acids as antioxidants and antiproliferative agents. |
| AID1148675 | Antiinflammatory activity in Wistar rat assessed as inhibition of cotton pellet-induced granuloma formation at 50 mg/kg, po after 5 days relative to control | 1978 | Journal of medicinal chemistry, Dec, Volume: 21, Issue:12 | 4-(6-Methoxy-2-naphthyl)butan-2-one and related analogues, a novel structural class of antiinflammatory compounds. |
| AID1628930 | Inhibition of human recombinant AKR1C3 using S-tetralol as substrate assessed as reduction in NADP+-dependent S-tetralol oxidation preincubated for 10 mins followed by protein addition by fluorometric assay | 2016 | Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16 | Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. |
| AID81332 | Compound was evaluated for in vitro inhibition of proliferation measured by inhibition of [3H]thymidine incorporation by HMVEC-L cells | 1999 | Journal of medicinal chemistry, Jan-28, Volume: 42, Issue:2 | Novel esters and amides of nonsteroidal antiinflammatory carboxylic acids as antioxidants and antiproliferative agents. |
| AID243647 | In vitro inhibitory activity against ovine cyclooxygenase-1 (COX-1) at 200 uM; Inactive | 2004 | Journal of medicinal chemistry, Sep-23, Volume: 47, Issue:20 | Novel cyclooxygenase-1 inhibitors discovered using affinity fingerprints. |
| AID1628932 | Selectivity ratio of IC50 for human recombinant AKR1C2 to IC50 for human recombinant AKR1C3 | 2016 | Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16 | Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. |
| AID1628931 | Inhibition of human recombinant AKR1C2 using S-tetralol as substrate assessed as reduction in NADP+-dependent S-tetralol oxidation preincubated for 10 mins followed by protein addition by fluorometric assay | 2016 | Journal of medicinal chemistry, 08-25, Volume: 59, Issue:16 | Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 7 (12.07) | 18.7374 |
| 1990's | 20 (34.48) | 18.2507 |
| 2000's | 17 (29.31) | 29.6817 |
| 2010's | 12 (20.69) | 24.3611 |
| 2020's | 2 (3.45) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (21.16) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 6 (9.84%) | 5.53% |
| Reviews | 1 (1.64%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 54 (88.52%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||