2-Phenyl-4-quinolinecarboxylic acid
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2-Phenyl-4-quinolinecarboxylic acid
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CAS No:
132-60-5
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Formula:
C16H11NO2
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Chemical Name:
2-Phenyl-4-quinolinecarboxylic acid
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Synonyms:
4-Quinolinecarboxylic acid,2-phenyl-;Cinchoninic acid,2-phenyl-;2-Phenyl-4-quinolinecarboxylic acid;Agotan;Alutyl;Artam;Atocin;Atophan;Cinchophen;Cinchophene;Cinchophenic acid;Cinconal;Cincophen;Cincosal;Mylofanol;Phenoquin;2-Phenylcinchonic acid;2-Phenylcinchoninic acid;Quinophan;Rhematan;Rheumine;Tophol;Tophosan;Vantyl;Viophan;Quinophen;Aciphenochinolinium;Polyphlogin;Quinofen;Atofan;Artexin;Traubofan;Atigoa;Tervalon;Aminophan;Phenophan;Ikterosan;Aciphenochinoline;4-Carboxy-2-phenylquinoline;Rheumatan;Alutyo;Rheumin;NSC 2617;NSC 70178
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CAS No:
2-Phenyl-4-quinolinecarboxylic acid Basic Attributes
249.26
249.26
192803
205-067-1
39Y533Z02M
758887|70178|2617
DTXSID0040705
NEEDLES FROM METHANOL OR DILUTED ALCOHOL|WHITE OR YELLOWISH CRYSTALS OR POWDER|SMALL, WHITE, NEEDLE-LIKE CRYSTALS
M - Musculo-skeletal system
29334990
Characteristics
50.2
3.99
1.1426 (rough estimate)
218 °C
392.37°C (rough estimate)
230.1±25.4 °C
1.5300 (estimate)
Insoluble in water;alcohol: soluble 1g in 120ml(lit.)
Store below +30°C.
3.84E-09mmHg at 25°C
LD50 oral in dog: 1250mg/kg
ODORLESS
SLIGHTLY BITTER TASTE
154.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
OPTIC SIGN: +; ELONGATION: +; AXIAL ANGLE: 2V= 45 DEG /ORTHORHOMBIC SYSTEM/|OPTIC SIGN: -; AXIAL ANGLE: LARGE /TRICLINIC SYSTEM/|YELLOW CRYSTALLINE POWDER; SLIGHTLY BITTER, ASTRINGENT TASTE; MP: 223 °C; PRACTICALLY INSOL IN WATER; SLIGHTLY SOL IN ALCOHOL; SOL IN CHLOROFORM, ETHER /HYDROCHLORIDE/
Safety Information
III
6.1(b)
3249
3
22
36/37/39-26
GD4025000
Xn
STABLE TO AIR, BUT TURNS YELLOW UNDER THE INFLUENCE OF LIGHT
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 45 companies from 2 notifications to the ECHA C&L Inventory.
Toxicity
IN DOGS, CINCHOPHEN HAD NO EFFECT ON IOPANOIC ACID EXCRETIO BUT INCR BOTH BILIARY & URINARY EXCRETION OF IOPHENOXIC ACID.
Drug Information
Anti-Inflammatory Agents, Non-Steroidal|/IT WAS USED AS/ ANALGESIC IN ACUTE GOUT, ACTING MORE PROMPTLY THAN COLCHICUM & WITHOUT UNDESIRABLE SIDE EFFECTS. ... DOSE: ORAL, 0.5 G.|ONCE USED AS URICOSURIC, ANALGESIC & ANTI-INFLAMMATORY AGENT
THE OCCURRENCE OF JAUNDICE WITH CINCHOPHEN & ITS VARIOUS DERIV WAS OBSERVED WITH SUCH FREQUENCY & HERALDED SUCH SEVERE DEGENERATIVE & NECROTIZING CHANGES IN LIVER THAT THESE DRUGS HAVE BEEN LARGELE ABANDONED.|QUINIDINE, ADMIN PARENTERALLY SHORTLY AFTER OR SIMULTANEOUSLY WITH TUBOCURARINE, MAY ENHANCE OR CAUSE RECURRENT NEUROMUSCULAR EFFECTS OF TUBOCURARINE... ALTHOUGH NO DRUG INTERACTION HAS BEEN DOCUMENTED, OTHER CINCHONA ALKALOIDS (EG CINCHOPHEN & QUININE) MAY ALSO INTERACT WITH TUBOCURARINE.|CLINICAL & EXPTL STUDIES SHOW THAT ANTIARRHYTHMIC & CARDIODEPRESSANT EFFECTS OF QUINIDINE MAY BE ENHANCED BY ADMIN OF RESERPINE. ... CINCHOPHEN & QUININE ARE AGENTS RELATED TO QUINIDINE.|THE OTHER CINCHONA ALKALOIDS, CINCHOPHEN & QUININE, APPARENTLY EXERT DIRECT HYPOPROTHROMBINEMIC EFFECT BY DEPRESSING THE HEPATIC ENZYME SYSTEM THAT SYNTHESIZES VITAMIN K-DEPENDENT FACTORS...& COULD INTERACT WITH WARFARIN ALSO.
3. 3= MODERATELY TOXIC; PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).
2% 2-O-OXYPHENYLQUINOLINE-4-CARBOXYLIC ACID WAS EXCRETED IN URINE FROM HUMANS AFTER DOSAGE WITH CINCHOPHEN. /FROM TABLE/|YIELDS 8-HYDROXY-2-PHENYLQUINOLINE-4-CARBOXYLIC ACID & 2-(P-HYDROXYPHENYL)QUINOLINE-4-CARBOXYLIC ACID IN DOG: HARTIALA, K, TERHO, T & HAKKINEN, I; BIOCHEM PHARMAC, 16, 843 (1967). /FROM TABLE/
IN BLOOD OF HUMANS HALF LIFE AFTER DOSAGE OF CINCHOPHEN WAS 4-4.5 HR.
aciphenochinolium
2-Phenyl-4-quinolinecarboxylic acid Use and Manufacturing
The isatin is prepared as a sodium salt, which is ring-opened to form sodium anthranilate, and then cyclized with acetophenone to obtain cincofen sodium, which can be obtained by acidification with acetic acid or hydrochloric acid.
analgesic, antipyretic, antiinflammatory
IN COMBINATIONS WITH SODIUM SALICYLATE AS ATOPHANYL; ARTHROSAN; CINCOSAL. HYDROCHLORIDE, C16H12CLNO2, CHLOROXYL. ... LITHIUM SALT OCTAHYDRATE, C16H10LINO2, EKTOPHANOL.
TITRIMETRIC DETERMINATION OF CINCHOPHEN IN PRESENCE OF SALICYLATES & SODIUM BICARBONATE.|UV ABSORPTION DATA, INCL MAX WAVELENGTH & OTHER SOLVENTS FOR MORE THAN 150 DRUGS ARE GIVEN.|STRONGER BASES SUCH AS ACIPHENOQUINOLINE WERE DETERMINED IN PHARMACEUTICALS, SEPARATED OR IN PRESENCE OF ONE ANOTHER, BY TITRATION.
Pharmaceuticals
Computed Properties
Molecular Weight:249.26
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:249.078978594
Monoisotopic Mass:249.078978594
Topological Polar Surface Area:50.2
Heavy Atom Count:19
Complexity:325
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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