Pranoprofen (HCID 4888)

Overview

Pranoprofen is a pyridochromene.

Names & identifiers

Preferred name: Pranoprofen
IUPAC: 2-(5H-chromeno[2,3-b]pyridin-7-yl)propanoic acid
English name: Pranoprofen
Molecular formula: C15H13NO3
Molecular weight: 255.27

Names & synonyms

pranoprofen52549-17-4pyranoprofenPranoprofenoPranoprofenePranoprofenumElicapricDTXSID1023497NSC-7598322R7O1ET613DTXCID603497alpha-Methyl-5H-(1)benzopyrano(2,3-b)pyridine-7-acetic acid

Show more names

Y 8004CesflanOftalarPralofenPraprofenranoprofen

(+-)-PranoprofenRefChem:868380S01BC09(2RS)-2-(10H-9-Oxa-1-azaanthracen-6-yl)propanoic acidNiflan2-(5H-chromeno[2,3-b]pyridin-7-yl)propanoic acidY-80042-(5H-[1]-Benzopyrano[2,3-b]pyridin-7-yl)propionic Acid

Database identifiers

CAS: 52549-17-4
PubChem CID: 4888
DTXSID: DTXSID1023497
ChEMBL: CHEMBL367463
ChEBI: CHEBI:32040
UNII: 2R7O1ET613
EC Number: 682-035-7
Nikkaji: J9.293B

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 59.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 19
Formal charge: 0
Complexity: 346

Experimental & physicochemical properties

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 182 · 182-183°
Boiling point: 398.5 °C · 398.5°C (rough estimate)
Density: 1.1654 · 1.1654 (rough estimate)
refractive index: 1.55 · 1.5500 (estimate)
storage temp.: 2 · 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 4.27 · 4.27±0.10(Predicted)
form: powder
color: white to beige
InChI: InChI=1S/C15H13NO3/c1-9(15(17)18)10-4-5-13-12(7-10)8-11-3-2-6-16-14(11)19-13/h2-7,9H,8H2,1H3,(H,17,18)
InChIKey: TVQZAMVBTVNYLA-UHFFFAOYSA-N
SMILES: C(C1C=CC2OC3=NC=CC=C3CC=2C=1)(C)C(=O)O
CAS DataBase Reference: 52549 · 52549-17-4(CAS DataBase Reference)
FDA UNII: 2 R7O1ET613 · 2R7O1ET613
ATC code: 1 BC09 · S01BC09
UNSPSC Code: 41106500 · 41106500
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301
Precautionary statements: 301 · P301+P310+P330
RIDADR: 2811 · UN 2811 6.1 / PGIII
WGK Germany: 1 · WGK 1
RTECS: 3100950 · DJ3100950
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 Oral · Acute Tox. 3 Oral
Toxicity: 50 in · LD50 in male mice, rats (mg/kg): 447.3, 87.3 orally (Edanaga)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Pranoprofen

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

wgk: WGK 1
rtecs: DJ3100950
ridadr: UN 2811 6.1 / PGIII
Toxicity: LD50 in male mice, rats (mg/kg): 447.3, 87.3 orally (Edanaga)
Signal word: Danger
Symbol(GHS): GHS06
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements: H301
Hazard Classifications: Acute Tox. 3 Oral
Precautionary statements: P301+P310+P330

Chemistry & industry

Pharmacology

ATC Code · 3 items

S01BC09

S - Sensory organs

QS - Sensory organs

Mechanism of ActionPranoprofen is a cyclo-oxygenase inhibitor.

MeSH Pharmacological Classification · 2 items

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.

Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout.

Cellular LocationsMembrane

Applications

UsesPranoprofen is an anti-inflammatory used in ophthalmology.

General DescriptionPranoprofen is an arylalkanoic acid and a non-steroidal anti-inflammatory drug.

Preparation methods · 1 item

PreparationUsing 2-chloronicotinic acid as a raw material, it is condensed with phenol under a strongly alkaline environment, then dehydrated by polyphosphoric acid, reduced by potassium borohydride, then hydrolyzed in acid, and finally acylated with chloroacetyl chloride. After hydrolysis under alkaline conditions, it is acylated by sulfonyl chloride and finally rearranged to obtain pranoprofen.