 Home > Encyclopedia > Oxazolidin

Oxazolidin

Oxazolidin structure

CAS No:
129-20-4
Formula:
C19H20N2O3
Chemical Name:
Oxazolidin
Synonyms:
3,5-Pyrazolidinedione,4-butyl-1-(4-hydroxyphenyl)-2-phenyl-;3,5-Pyrazolidinedione,4-butyl-1-(p-hydroxyphenyl)-2-phenyl-;4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione;G 27202;4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione;1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione;1-p-Hydroxyphenyl-2-phenyl-3,5-dioxo-4-n-butylpyrazolidine;Metabolite I;Oxazolidin;Oxyphenbutazone;Oxyphenobutazone;Oxyphenylbutazone;1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine;Tandearil;Tanderil;Tendearil;p-Hydroxyphenylbutazone;4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine;1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine;4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,4-pyrazolidinedione;p-Oxyphenylbutazone;Flogoril;Crovaril;Oxalid;Tandacote;Floghene;Telidal;Flogitolo;Butapirone;Neo-Farmadol;Flamaril;Offitril;Suganril;Romaxin;Ro 04-4410;Rapostan;Visubutina;Frabel;Californit;NSC 526053
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

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].

Oxyphenbutazone is a metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, a gout suppressant, a drug metabolite, a xenobiotic metabolite, an antineoplastic agent and an antimicrobial agent. It is a member of pyrazolidines and a member of phenols. It derives from a phenylbutazone.|Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.|A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27)

Oxazolidin Basic Attributes

Molecular Weight：

324.37

Exact Mass：

324.37

EC Number：

204-936-2

NSC Number：

757261|526053

DSSTox ID：

DTXSID1045291

Color/Form：

WHITE TO YELLOWISH WHITE, CRYSTALLINE POWDER

ATC Code：

M - Musculo-skeletal system|S - Sensory organs

HScode：

2933990090

Characteristics

PSA：

60.8

XLogP3：

2.72

Appearance：

white to brown

Density：

1.241g/cm3

Melting Point：

96 °C

Boiling Point：

485.6ºC at 760mmHg

Flash Point：

247.5ºC

Refractive Index：

1.61

Water Solubility：

DMSO: soluble 10mg/mL, clear

Storage Conditions：

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Odor：

ODORLESS

Collision Cross Section：

177.2 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|184.74 Å² [M-H]-

Safety Information

Transport codes：

UN 3077 9 / PGIII

wgk germany：

hazard class code：

22-50

safety instructions：

Marks：

Xn,N

Precautionary statement(s)：

P273

Hazard Statements：

H302-H400

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Interactions：

SOME TRICYCLIC COMPD HAVE BEEN SHOWN TO DELAY OXYPHENYLBUTAZONE ABSORPTION IN RAT BY INCR GASTRIC EMPTYING TIME.|...OXYPHENBUTAZONE MAY PROLONG PROTHROMBIN TIME IN PT RECEIVING COUMARIN ANTICOAGULANTS CONCOMITANTLY & MAY INCR HYPOGLYCEMIC EFFECT OF INSULIN & ORAL HYPOGLYCEMIC AGENTS.|WHEN OXYPHENBUTAZONE & METHANDROSTENOLONE ARE ADMIN CONCURRENTLY IN HUMANS, SERUM OXYPHENBUTAZONE LEVELS MAY BE ELEVATED. PT TREATED WITH THESE CONCURRENTLY SHOULD BE MONITORED FOR SIGNS OF OXYPHENBUTAZONE-INDUCED ADVERSE EFFECTS.|OXYPHENBUTAZONE ABSORPTION...IS DECR BY DESIPRAMINE.|For more Interactions (Complete) data for OXYPHENBUTAZONE (6 total), please visit the HSDB record page.

Drug Information

Therapeutic Uses：

Anti-Inflammatory Agents, Non-Steroidal; Anti-Inflammatory Agents, Topical|EPISCLERITIS & UVEITIS ASSOC WITH RHEUMATOID ARTHRITIS HAVE SOMETIMES BEEN TREATED SUCCESSFULLY WITH...OXYPHENBUTAZONE.|...HAS MILD URICOSURIC EFFECT IN EXPTL ANIMALS & MAN, PROBABLY ATTRIBUTABLE TO ONE OF ITS METABOLITES.|...HAS MILD URICOSURIC EFFECT IN EXPTL ANIMALS & MAN... URICOSURIC EFFECT RESULTS FROM DIMINISHED TUBULAR REABSORPTION OF URIC ACID. ...CAUSES SIGNIFICANT RETENTION OF SODIUM & CHLORIDE, ACCOMPANIED BY REDN IN URINE VOL... REDUCES UPTAKE OF IODINE BY THYROID GLAND...ALSO INHIBITS ENZYMES OF KREBS CYCLE... /PHENYLBUTAZONE/|For more Therapeutic Uses (Complete) data for OXYPHENBUTAZONE (7 total), please visit the HSDB record page.

Drug Warnings：

...40-YR OLD MAN RECEIVED TOTAL DOSE OF 1 G OXYPHENBUTAZONE OVER APPROX 5 DAYS, 2 MO BEFORE ADMISSION TO HOSPITAL WITH SEVERE ANEMIA & LEUCOCYTOSIS; HE DIED ON THIRD DAY AFTER DEVELOPING THIS CONDITION.|...WHITE-BLOOD CELL DISORDER CONCERNED 47-YR-OLD MAN WHO, 13 MO BEFORE ADMISSION WITH TEMP, HAD BEEN GIVEN 1.9 G OXYPHENBUTAZONE OVER 2-WK PERIOD. ON ADMISSION, HE WAS GIVEN 0.6 G OF DRUG; BLOOD EXAM SHOWED THAT HE HAD LEUKEMIA, OF WHICH HE DIED APPROX 4 MO LATER.|IT SHOULD ALWAYS BE TAKEN IMMEDIATELY AFTER MEALS OR WITH FULL GLASS OF MILK, TO MINIMIZE GASTRIC IRRITATION.|OXYPHENBUTAZONE IS SAID TO CAUSE SOMEWHAT LESS GASTRIC IRRITATION /THAN PHENYLBUTAZONE/. ... IT SHOULD BE TAKEN IN 3 OR 4 DIVIDED PORTIONS AFTER MEALS TO LESSEN GASTRIC IRRITATION.|For more Drug Warnings (Complete) data for OXYPHENBUTAZONE (8 total), please visit the HSDB record page.

MeSH：

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Absorption：

...OXYPHENBUTAZONE IS EXTENSIVELY BOUND TO PLASMA PROTEINS & HAS PLASMA HALF-TIME OF SEVERAL DAYS. ...ONLY SLOWLY EXCRETED IN URINE, SINCE BINDING TO PLASMA PROTEIN LIMITS...GLOMERULAR FILTRATION, &...RELATIVELY HIGH PKA, WHICH FAVORS PASSIVE REABSORPTION IN DISTAL TUBULE.

Metabolism/Metabolites：

OXIDN OF PHENYLBUTAZONE DURING CHRONIC DOSING BY MEASURING URINARY EXCRETION OF 3 METABOLITES, OXYPHENBUTAZONE GAMMA-HYDROXYPHENBUTAZONE & P,GAMMA-HYDROXYPHENBUTAZONE DURING INFUSION OF HYDROCORTISONE SODIUM SUCCINATE IS REPORTED.

Biological Half-Life：

IN MAN, OXYPHENBUTAZONE HAS BIOLOGICAL HALF-LIFE OF ABOUT 2 DAYS.

Mechanism of Action：

...HAS PROMINENT ANTI-INFLAMMATORY EFFECTS IN ANIMALS, & COMPARABLE EFFECTS... IN PT WITH RHEUMATOID ARTHRITIS & RELATED DISORDERS. ...INHIBITS BIOSYNTHESIS OF PROSTAGLANDINS, UNCOUPLES OXIDATIVE PHOSPHORYLATION, & INHIBITS ATP-DEPENDENT BIOSYNTHESIS OF MUCOPOLYSACCHARIDE SULFATES IN CARTILAGE. /PHENYLBUTAZONE/

Human Toxicity Excerpts：

NAUSEA, VOMITING, EPIGASTRIC DISCOMFORT, & SKIN RASHES ARE MOST FREQUENTLY REPORTED UNTOWARD EFFECTS. DIARRHEA, VERTIGO, INSOMNIA, EUPHORIA, NERVOUSNESS, HEMATURIA...& BLURRED VISION HAVE ALSO BEEN OBSERVED. ...WATER & ELECTROLYTE RETENTION & EDEMA FORMATION OCCUR. /PHENYLBUTAZONE/|MORE SERIOUS FORMS OF ADVERSE EFFECTS INCL PEPTIC ULCER...WITH HEMORRHAGE OR PERFORATION, HYPERSENSITIVITY REACTIONS OF SERUM-SICKNESS TYPE, ULCERATIVE STOMATITIS, HEPATITIS, NEPHRITIS, APLASTIC ANEMIA, LEUKOPENIA, AGRANULOCYTOSIS, & THROMBOCYTOPENIA. NUMBER OF DEATHS HAVE OCCURRED... /PHENYLBUTAZONE/|...32-YR OLD WOMAN WHO WAS TREATED WITH 2.5 G OXYPHENBUTAZONE OVER 7 DAYS; SHE...DEVELOPED SEVERE LEUCOCYTOSIS FOLLOWED BY LEUCOPENIA & ANEMIA...SUBSEQUENT RECOVERY.|ADMIN OF PHENYLBUTAZONE...IS ASSOC WITH...BONE MARROW SUPPRESSION. TOXICITY OF OXYPHENBUTAZONE IS SIMILAR TO THAT OF PARENT COMPD... /PHENYLBUTAZONE/|NUMBER OF CASES OF LEUKEMIA WERE REPORTED BETWEEN 1960 & 1966 IN SUBJECTS TREATED WITH PHENYLBUTAZONE OR OXYPHENBUTAZONE. AVAIL EVIDENCE IS, HOWEVER, INSUFFICIENT TO SUBSTANTIATE SUGGESTION THAT USE...IS RELATED TO SUBSEQUENT DEVELOPMENT OF LEUKEMIA.

MeSH Entry Terms：

Diflamil

Oxazolidin Use and Manufacturing

Methods of Manufacturing

HAFLIGER, US PATENT 2,745,783 (1956 TO GEIGY): PFISTER, HAFLIGER, HELV CHIM ACTA 40, 395 (1957).

Uses

Anti-inflammatory;Cyclooxygenase inhibito

Formulations：

OXYPHENBUTAZONE, NF (TANDEARIL), IS MARKETED IN 100-MG TABLETS.

Manufacturing Info：

OXYPHENBUTAZONE IS HYDROXY ANALOG OF PHENYLBUTAZONE & ONE OF MAJOR ACTIVE METABOLITES OF PARENT DRUG. ... OXYPHENBUTAZONE HAS SAME SPECTRUM OF ACTIVITY, THERAPEUTIC USES, INTERACTIONS, & TOXICITY AS PARENT COMPD, & IT SHARES SAME INDICATIONS, DANGERS, & CONTRAINDICATIONS FOR CLINICAL USE.

Analytic Methods：

THIN-LAYER CHROMATOGRAPHY.

Laboratory Methods：

HIGH SPEED LIQUID CHROMATOGRAPHIC DETERMINATION OF OXYPHENBUTAZONE IN PLASMA.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:324.4
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:324.14739250
Monoisotopic Mass:324.14739250
Topological Polar Surface Area:60.8
Heavy Atom Count:24
Complexity:454
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Not yet clear

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Hydroxybutazone Tablets
Ingredients	The main ingredient of this product is hydroxybutazone.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	0.1g

Hydroxybutazone Tablets
Ingredients	The main ingredient of this product is hydroxybutazone.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	0.1g