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Suprofen

pharmaceutical raw materials
Suprofen structure

Suprofen 

structure
  • CAS No:

    40828-46-4

  • Formula:

    C14H12O3S

  • Chemical Name:

    Suprofen

  • Synonyms:

    Benzeneacetic acid,α-methyl-4-(2-thienylcarbonyl)-;α-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid;Suprofen;R 25061;TN 762;Profenal;Racemic suprofen;(±)-Suprofen;Profenol;Sulproltin;Srendam;Masterfen;Topalgic;Sutoprofen;Suprol;Supranol;Suprocil;NSC 303611;2-[4-(Thiophene-2-carbonyl)phenyl]propanoic acid;p-(2-Thenoyl)hydratropic acid;64382-06-5

  • Categories:

    Active Pharmaceutical Ingredients  >  Antipyretic Analgesics

Description

Suprofen is a non-steroidal anti-inflammatory drug (NSAID). Target: PGE synthaseSuprofen is an NSAID.Suprofen is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. suprofen was clinically effective but the differential suppression of prostanoids favors 200mg which spares 6-keto PGF1a [1, 2].


Solid


Suprofen is an aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antirheumatic drug, a peripheral nervous system drug and a drug allergen. It is a member of thiophenes, a monocarboxylic acid and an aromatic ketone.|An ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. It is no longer approved for use in the United States.|An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.

Suprofen Basic Attributes

260.30828

260.31

255-096-9

757876|303611

DTXSID5045469

M - Musculo-skeletal system

2934999090

Characteristics

82.6

3.3

1.37 g/cm3

124.3 °C

442.6°C at 760 mmHg

221.5±24.6 °C

1.613

H2O: soluble

-20°C Freezer

LD50 (7 days post-drug) in mice, rats, guinea pigs, dogs (mg/kg): 590, 353, 280, 160 orally (Niemegeers)

3.91

157.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

6.1(b)

3249

6.1

Missing Phrase - N15.00950417

H301

Toxicity

Symptoms of overdose include bleeding in the eye or redness or swelling of the eye or the eyelid, blurred vision or other change in vision, fever or chills, itching or tearing, nausea or vomiting, pain, sensitivity to light, shortness of breath, sticky or matted eyelashes, swelling of face, throbbing pain, tightness in chest, troubled breathing, and wheezing.

20%

Drug Information

Used as eye drops to inhibit the miosis (pupil constriction) that may occur during ocular surgery.

Suprofen is a non-steroidal anti-inflammatory analgesic and antipyretic. Ophthalmic anti-inflammatory medicines are used in the eye to lessen problems that can occur during or after some kinds of eye surgery. Sometimes, the pupil of the eye gets smaller during an operation (pupil constriction), making it more difficult for the surgeon to reach some areas of the eye. Suprofen is used to help prevent this.

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.)|Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).|Suprofen has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-[4-(thiophene-2-carbonyl)phenyl]propanoyloxy]oxane-2-carboxylic acid, Suprofen -sulfoxide, and Thiophene-4,5-epoxide.

Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A2). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.

R 25061

Suprofen Use and Manufacturing

Methods of Manufacturing

Ethyl cyclopentenecarboxylate (I) is oxidized to diol (II) with N-methylmorpholine-N-oxide in the presence of a catalytic amount of osmium tetroxide. It is then split into dialdehyde (Ⅲ) under the action of sodium periodate, and its aqueous solution is converted into a bicyclic compound (Ⅳ) by Robinson-Schoepf reaction at Ph value 4. (IV) It is then reduced to alcohol (V) with sodium borohydride and reacted with dihydropyran to form tetrahydrofuran ether (VI) to protect the formed hydroxyl group. It is then converted to a tricyclide (VII), which is then reacted with acid chloride (VIII) in the presence of silver tetrafluoroborate to acylate to obtain dolasetron.

Uses

Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.

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

Computed Properties

Molecular Weight:260.31
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:260.05071541
Monoisotopic Mass:260.05071541
Topological Polar Surface Area:82.6
Heavy Atom Count:18
Complexity:321
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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