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Indoprofen

Indoprofen structure

CAS No:
31842-01-0
Formula:
C17H15NO3
Chemical Name:
Indoprofen
Synonyms:
Benzeneacetic acid,4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-α-methyl-;4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)-α-methylbenzeneacetic acid;1-Oxo-2-[p-[(α-methyl)carboxymethyl]phenyl]isoindoline;K 4277;Indoprofen;2-[4-(1-Oxo-2-isoindolinyl)phenyl]propanoic acid;dl-α-[4-(1-Oxo-2-isoindolinyl)phenyl]propionic acid;(±)-Indoprofen;Racemic Indoprofen;Isindone;IPP;Bor-ind;Flosin;Praxis;Flosint;Reumofene;p-(1-Oxo-2-isoindolinyl)hydratropic acid;53022-60-9
Categories:
Analytical Chemistry > Standard

Description

Indoprofen is a non-steroidal anti-inflammatory drug, provide insight into treatments for spinal muscular atrophies.

Indoprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a monocarboxylic acid, a member of isoindoles and a gamma-lactam. It derives from a propionic acid.|A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide.|A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p21)

Indoprofen Basic Attributes

Molecular Weight：

281.31

Exact Mass：

281.31

EC Number：

250-833-0

NSC Number：

757065

DSSTox ID：

DTXSID5045831

ATC Code：

M - Musculo-skeletal system

HScode：

2918300090

Characteristics

PSA：

57.6

XLogP3：

2.8

Density：

1.308g/cm3

Melting Point：

213-214 °C

Flash Point：

263ºC

Refractive Index：

1.642

Water Solubility：

>42.2 [ug/mL]

Toxicity：

LD50 in rats (mg/kg): 58.66 i.v.; 60.83 orally (Buttinoni)

Collision Cross Section：

166.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|166.4 Å² [M+H]+ [CCS Type: TW]

Safety Information

Packing level：

Ⅲ

Transport codes：

UN 2811 6.1 / PGIII

wgk germany：

hazard class code：

25-40

safety instructions：

22-36/37/39-45

RTECS Number：

MU6645000

Marks：

Precautionary statement(s)：

P281-P301 + P310

Hazard Statements：

H301-H351

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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.)

Absorption：

Renal.

Metabolism/Metabolites：

Glucuronidation.

Biological Half-Life：

2.3 hours.

MeSH Entry Terms：

Dexindoprofen

Indoprofen Use and Manufacturing

Uses

analgesic, antiinflammatory

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:281.30
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:281.10519334
Monoisotopic Mass:281.10519334
Topological Polar Surface Area:57.6
Heavy Atom Count:21
Complexity:414
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes