Nabumetone

Modify Date: 2024-01-03 17:36:15

Nabumetone Structure
Nabumetone structure
 Common Name Nabumetone
CAS Number 42924-53-8 Molecular Weight 228.286
Density 1.1±0.1 g/cm3 Boiling Point 371.1±17.0 °C at 760 mmHg
Molecular Formula C15H16O2 Melting Point 80-81ºC
MSDS Chinese USA Flash Point 165.4±14.5 °C

 Use of Nabumetone


Nabumetone is an orally active non-acidic anti-inflammatory agent, acts as a potent and selective COX-2 inhibitor, and is the prodrug of the active metabolite 6MNA.

 Names

Name nabumetone
Synonym More Synonyms

 Nabumetone Biological Activity

Description Nabumetone is an orally active non-acidic anti-inflammatory agent, acts as a potent and selective COX-2 inhibitor, and is the prodrug of the active metabolite 6MNA.
Related Catalog
Target

COX-2

In Vitro Nabumetone is a potent and selective COX-2 inhibitor. Nabumetone (50 μmol-2 mmol) dose-dependently inhibits the proliferation of K-562 and Meg-01 cells, but shows no obvious apoptotic effect. Nabumetone potentiates the apoptotic effect of ADR in the K-562 cell line. Moreover, Nabumetone reduces Bcl-2 expression[1].
In Vivo Nabumetone (79 mg/kg, p.o.) inhibits paw oedema and paw exudate PGE2 in rats. Nabumetone does not induce gastric damage and causes only 57% inhibition of gastric mucosal 6-keto-PGF1α production in rats[2]. Nabumetone (25, 50, 100 mg/kg, i.p.) dose-dependently inhibits the increase of DDC-induced mucus secretion and stimulates stress-induced mucus secretion in rats. Nabumetone (25 mg/kg, i.p.) significantly suppresses stress-induced ulcer index in rats[3].
Cell Assay Every cell line is plated into 6-well plates at a concentration of 3 × 105/mL with or without drugs (Nabumetone, etc.) and incubated for 48 h. Viable cells are then counted using the trypan blue dye exclusion test. The percentage of proliferation inhibition is calculated as 1-(viable cells exposed to drug/viable cells in control) ×100[1].
Animal Admin Rats[3] Albino male rats (250- to 300-g body weight) are used in the study. The animals are maintained in a single cage and are deprived of food for 16 h before the onset of experiments. Free access to water is allowed until 1 h before the beginning of experiments. There are eight rats in each group. The animals are pretreated with intraperitoneal injections of Nabumetone or dipyrone at 25-, 50-, or 100-mg/kg doses for 3 days[3].
References

[1]. Vural F, et al. Cyclo-oxygenase 2 inhibitor, nabumetone, inhibits proliferation in chronic myeloid leukemia cell lines. Leuk Lymphoma. 2005 May;46(5):753-6.

[2]. Melarange R, et al. Anti-inflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6MNA (6-methoxy-2-naphthylacetic acid): comparison with indomethacin. Agents Actions. 1992;Spec No:C82-3.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 371.1±17.0 °C at 760 mmHg
Melting Point 80-81ºC
Molecular Formula C15H16O2
Molecular Weight 228.286
Flash Point 165.4±14.5 °C
Exact Mass 228.115036
PSA 26.30000
LogP 2.82
Vapour Pressure 0.0±0.8 mmHg at 25°C
Index of Refraction 1.576
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EL9085000
CHEMICAL NAME :
2-Butanone, 4-(6-methoxy-2-naphthalenyl)-
CAS REGISTRY NUMBER :
42924-53-8
LAST UPDATED :
199612
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C15-H16-O2
MOLECULAR WEIGHT :
228.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1260 mg/kg/6W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - fibrosis (interstitial) Lungs, Thorax, or Respiration - cough Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 67,1021,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3880 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - other changes
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1520 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - other changes Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4290 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Gastrointestinal - other changes
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2380 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle contraction or spasticity Gastrointestinal - ulceration or bleeding from stomach
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
3200 mg/kg
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Nutritional and Gross Metabolic - weight loss or decreased weight gain Nutritional and Gross Metabolic - other changes
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2939,1988 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
58240 mg/kg/26W-I
TOXIC EFFECTS :
Gastrointestinal - peritonitis Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2953,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
58240 mg/kg/26W-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2953,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
81900 mg/kg/52W-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - other changes Endocrine - changes in thymus weight
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2953,1988 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1760 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2975,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8960 mg/kg
SEX/DURATION :
female 15-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2953,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4160 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 22,2975,1988

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases 22-40
Safety Phrases 36/37
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS EL9085000
HS Code 2914399090

 Synthetic Route

 Customs

HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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 Synonyms

4-(6-méthoxynaphtalén-2-yl)butan-2-one
Mebutan
Relifen
4-(6-Methoxy-2-naphthyl)-butan-2-one
Arthaxan
Relif
4-(6-Methoxynaphthalen-2-yl)butan-2-on
4-(6-methoxynaphthalen-2-yl)butan-2-one
Nabumetona
4-(6-Methoxy-2-naphthyl)butan-2-one
MFCD00079518
Nabumetone
Relafen
Listran
2-Butanone, 4-(6-methoxy-2-naphthalenyl)-
Nabuser
Relifex
Dolsinal
4-(6-Methoxy-2-naphthyl)-2-butanone
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343272-51-5
Nabumetone-d6 Dimer Impurity
1346600-45-0
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