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G-29701

Names

[ CAS No. ]:
129-20-4

[ Name ]:
G-29701

[Synonym ]:
p-Oxyphenylbutazone
oxyphenbutazon
4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione G 27202
Oxazolidin
ossifenbutazone
EINECS 204-936-2
oxyphenylbutazone
MFCD00057278
Idrobutazina
Oxyphenbutazone
Tanderil
Oxiphenbutazone
Oxi-Fenibutol
Oxifenylbutazon
Etrozolidina

Biological Activity

[Description]:

Oxyphenbutazone is a phenylbutazone derivative, with anti-inflammatory effect. Oxyphenbutazone is a non-selective COX inhibitor. Oxyphenbutazone selectively kills non-replicating Mycobaterium tuberculosis[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Immunology/Inflammation >> COX
Signaling Pathways >> Anti-infection >> Bacterial

[Target]

COX[1]


[In Vitro]

Oxyphenbutazone enhances the anticancer efficiency of methotrexate (MTX) in Hep3B cells[1]. Oxyphenbutazone (2.5 -7.5 µM; 48 hours) co-treatment with (MTX, 0.25-1.0 µM) shows potential cytotoxicity against Hep3B cells[1]. Oxyphenbutazone exhibits reparative effects in the hepatocytes[1]. Cell Cytotoxicity Assay[1] Cell Line: Hep3B cells Concentration: 2.5 µM, 5 µM, 7.5 µM Incubation Time: 48 hours Result: Enhanced the cytotoxicity of MTX.

[In Vivo]

Oxyphenbutazone (70 mg/kg/week; p.o.; in two divided doses; for 13 weeks) exerts potential anticancer activity when co-treatment with MTX (5.0 or 2.5 mg/kg/week; i.p.)[1]. Animal Model: 5–6 weeks Wistar strain albino male rats (150–220 g)[1] Dosage: 70 mg/kg/week (co-treatment with MTX 5.0 or 2.5 mg/kg/week) Administration: Oral administration; once a week; in two divided doses; for 13 weeks Result: Exerted potential anticancer activity in rats when co-treatment with MTX.

[References]

[1]. Saleem S, et al. Oxyphenbutazone promotes cytotoxicity in rats and Hep3B cellsvia suppression of PGE2 and deactivation of Wnt/β-catenin signaling pathway. Mol Cell Biochem. 2018 Jul;444(1-2):187-196.

[2]. Gold B, et al. Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials. Proc Natl Acad Sci U S A. 2012 Oct 2;109(40):16004-11.

Chemical & Physical Properties

[ Density]:
1.241g/cm3

[ Boiling Point ]:
485.6ºC at 760mmHg

[ Melting Point ]:
109-111°C

[ Molecular Formula ]:
C19H20N2O3

[ Molecular Weight ]:
324.37400

[ Flash Point ]:
247.5ºC

[ Exact Mass ]:
324.14700

[ PSA ]:
60.85000

[ LogP ]:
3.62340

[ Vapour Pressure ]:
4.7E-10mmHg at 25°C

[ Index of Refraction ]:
1.61

[ Storage condition ]:
Hygroscopic, -20°C Freezer, Under Inert Atmosphere

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UQ8400000
CHEMICAL NAME :
3,5-Pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-
CAS REGISTRY NUMBER :
129-20-4
BEILSTEIN REFERENCE NO. :
0307474
LAST UPDATED :
199612
DATA ITEMS CITED :
24
MOLECULAR FORMULA :
C19-H20-N2-O3
MOLECULAR WEIGHT :
324.41
WISWESSER LINE NOTATION :
T5VNNV EHJ BR DQ& CR& E4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
420 mg/kg/4W-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), diffuse Blood - agranulocytosis Blood - thrombocytopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
27 mg/kg/14D
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Blood - hemorrhage
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
50 mg/kg/7D
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
24 mg/kg/4D
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Endocrine - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
329 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
145 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
68 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
104 mg/kg
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Behavioral - excitement Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1165 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
1180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
560 mg/kg
SEX/DURATION :
male 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
female 10-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)

MUTATION DATA

TYPE OF TEST :
Sex chromosome loss and nondisjunction
TEST SYSTEM :
Mold - Aspergillus nidulans
DOSE/DURATION :
1 gm/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 26,159,1974 *** REVIEWS *** IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,183,1977 IARC Cancer Review:Animal No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,183,1977 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5469 No. of Facilities: 25 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 290 (estimated) No. of Female Employees: 121 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
22-50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Bone marrow depression due to mianserin, phenylbutazone, oxyphenbutazone, and chloramphenicol--Part I.

Adverse Drug React. Acute Poisoning Rev. 5(2) , 97-136, (1986)

Bone marrow depression due to mianserin, phenylbutazone, oxyphenbutazone, and chloramphenicol--Part II.

Adverse Drug React. Acute Poisoning Rev. 5(3) , 181-96, (1986)

Disposition and tolerance of suxibuzone in horses.

Equine Vet. J. 31(5) , 411-6, (1999)

Suxibuzone (SBZ), a nonsteroidal anti-inflammatory drug, was administered to 6 horses at a dose rate of 7.5 mg/kg bwt by intravenous (i.v.) route. Plasma and synovial fluid concentrations of suxibuzon...


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