Phenylbutazone

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Phenylbutazone

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Catalog Number	PR50339
CAS	50-33-9
Description	A drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication).
Synonyms	4-Butyl-1,2-diphenylpyrazolidine-3,5-dione; Butapirazol; Butazolidin; Butadion
IUPAC Name	4-butyl-1,2-diphenylpyrazolidine-3,5-dione
Molecular Weight	308.4
Molecular Formula	C19H20N2O2
InChI	VYMDGNCVAMGZFE-UHFFFAOYSA-N
InChI Key	InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
Drug Categories	Agents causing hyperkalemia; Agents that produce hypertension; Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-Inflammatory Agents, Non-Steroidal; Anti-Inflammatory Agents, Non-Steroidal (Non-Selective); Antiinflammatory and Antirheumatic Products; Antiinflammatory and Antirheumatic Products, Non-Steroids; Antiinflammatory Preparations, Non-Steroids for Topical Use; Antirheumatic Agents; Butylpyrazolidines; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C9 Inhibitors (strength unknown); Cytochrome P-450 CYP2C9 Substrates; Cytochrome P-450 CYP3A Inducers; Cytochrome P-450 CYP3A4 Inducers; Cytochrome P-450 CYP3A4 Inducers (strength unknown); Cytochrome P-450 Enzyme Inducers; Cytochrome P-450 Enzyme Inhibitors; Cytochrome P-450 Substrates; Musculo-Skeletal System; Nephrotoxic agents; Non COX-2 selective NSAIDS; OAT1/SLC22A6 inhibitors; OAT3/SLC22A8 Inhibitors; Peripheral Nervous System Agents; Pyrazoles; Pyrazolones; Sensory System Agents; Topical Products for Joint and Muscular Pain
Drug Interactions	Abacavir-Phenylbutazone may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept-The metabolism of Phenylbutazone can be increased when combined with Abatacept. Abciximab-The risk or severity of bleeding and hemorrhage can be increased when Phenylbutazone is combined with Abciximab. Abemaciclib-The metabolism of Abemaciclib can be increased when combined with Phenylbutazone. Abrocitinib-The metabolism of Abrocitinib can be decreased when combined with Phenylbutazone.
Isomeric SMILES	CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
Type	Small Molecule
Therapeutic Category	Analgesics

Pharmacology

Indications

Phenylbutazone is primarily indicated for the treatment of backache and ankylosing spondylitis. These conditions often present with significant discomfort, and phenylbutazone can help alleviate this by targeting inflammation and pain at the source.

Pharmacodynamics

Phenylbutazone is a synthetic derivative of pyrazolone and is classified as a nonhormonal anti-inflammatory and antipyretic compound. This medication is beneficial in managing inflammatory conditions due to its ability to mitigate symptoms primarily through its anti-inflammatory effects. Its mechanism of action involves the reduction of prostaglandin H and prostacyclin production. Prostaglandins have varied actions on different cell types, including causing constriction or dilation of vascular smooth muscle cells, influencing platelet activity, and affecting spinal neurons involved in pain signaling. Prostacyclin plays a role in vascular constriction and platelet disaggregation, which can further explain the analgesic effects of phenylbutazone.

Mechanism of Action

Phenylbutazone operates by engaging with and inactivating prostaglandin H synthase and prostacyclin synthase, facilitated through a mechanism involving peroxide (H2O2) mediated deactivation. This interaction results in a diminished synthesis of prostaglandins, subsequently leading to decreased inflammation in the surrounding tissues. Through this process, Phenylbutazone effectively mitigates inflammatory responses, offering therapeutic benefits.

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