Metabolism of brompheniramine

Bruce, Robert; Turnbull, Lennox B.; Newman, Jack; Pitts, Jefferson E.

doi:10.1021/jm00311a026

Cited by 21 publications

(4 citation statements)

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“…Evaporation of the solvent from the pale yellow band followed by trituration of the resulting pale yellow oil with 10 mL of Et 2 O afforded 3.9 g (65%) of 2 as a pale yellow solid; mp 45−47 °C (lit. 48−50,12b 37−40 °C 12c ). IR (cm -1 ) ν co 1667 (br, vs).…”

Section: Methodsmentioning

confidence: 99%

“…The oil was loaded onto a silica gel column and was eluted first with CH 2 Cl 2 /hexanes 1:1 until a sample of the eluent spotted on a TLC plate turned yellow-brown on exposure to UV lamp (after 400 mL collected). The column was then eluted with 4:1 CH 2 Cl 2 /hexanes to give the desired fraction in a pale yellow band prior to a yellow-orange band 12a. Evaporation of the solvent from the pale yellow band followed by trituration of the resulting pale yellow oil with 10 mL of Et 2 O afforded 3.9 g (65%) of 2 as a pale yellow solid; mp 45−47 °C (lit.…”

Section: Methodsmentioning

confidence: 99%

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Supramolecular Assembly and Solution Properties of Bis(bipyridyl)ruthenium(II) Coordination Complexes of Aryl(2-pyridyl)methanones

et al. 2002

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A series of mono- and bis(2-pyridyl)-arylmethanone ligands were prepared by utilizing the reaction between either bromobenzonitrile or dicyanobenzene and 2-lithiopyridine in either a 1:1 or a 2:1 mol ratio, respectively. They react with [Ru(bpy)2(EtOH)2][PF6]2 to yield the new complexes [N,O-PhC(O)(2-py)Ru(bpy)2][PF6]2 (6), [p-N,O-BrC6H4C-(O)(2-py)Ru(bpy)2][PF6]2 (7), [m-N,O-BrC6H4C(O)(2-py)Ru(bpy)2][PF6]2 (8), [p-[N,O-C(O)(2-py)2Ru(bpy)2]2(C6H4)]-[PF6]4 (9), and [m-[N,O-C(O)(2-py)2Ru(bpy)2]2(C6H4)][PF6]4 (10). The solid state structures of 6 and 7 show that the octahedral cations are arranged in sinusoidal chains by pi-pi stacking and CH-pi interactions between bipyridyl groups. Substitution of bromine for hydrogen at the para position of the aryl group in 7 causes the aryl group to become involved in pi-pi stacking interactions that organize the chains into a sheet structure. The complicated 1H and 13C NMR spectra of the complexes have been fully assigned using 2D methods. The optical spectra show two absorption maxima near 434 and 564 nm due to MLCT transitions. The compounds were found to be nonluminescent. Electrochemical data acquired for CH3CN solutions of the bimetallic derivatives indicate that there is no electronic communication between metal centers mediated either through space or through ligand orbitals. Crystallographic information: 6.0.5CH3CN is monoclinic, C2/c, a = 24.3474(11) A, b = 13.7721(6) A, c = 21.3184(10) A, beta = 103.9920(10) degrees, Z = 8; 7 is monoclinic, P2(1)/c, a = 10.6639(11) A, b = 23.690(3) A, c = 13.7634(14) A, beta = 91.440(2) degrees, Z = 4.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Supramolecular Assembly and Solution Properties of Bis(bipyridyl)ruthenium(II) Coordination Complexes of Aryl(2-pyridyl)methanones

et al. 2002

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“…The method was used for the late-stage derivatization of drug molecules, as shown with the efficient thioarylation of the pain-relief medicine, metaxalone. 44 The synthetic utility of the iron(III)-catalyzed thioarylation was also demonstrated with the use of this transformation as the key step in new syntheses of the antibiotic dapsone 45 and the antidepressant vortioxetine (Scheme 18b ). 46 The synthesis of vortioxetine showed that using a less activated arene ( meta -xylene) and an electron-deficient ortho -substituted N -(arylthio)succinimide, this reaction was still effective, giving the coupled product in 58% yield.…”

Section: Iron(iii)-catalyzed Thioarylation Of Arenesmentioning

confidence: 99%

Regioselective Functionalization of Arenes Using Iron Triflimide Catalysis

Sutherland¹,

Dodds²,

Waddell³

2023

Synlett

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Here we present our development of the super Lewis acid, iron(III) triflimide as an activating agent of N-halo- and N-thioaryl succinimides for the regioselective functionalization of arenes. We also describe how the iron(III)-catalyzed halogenation reactions were further exploited by combination with copper(I)-catalyzed Ullmann-type coupling reactions for the development of one-pot, multistep processes, including intermolecular aryl C–H amination. This Account also illustrates intramolecular versions of these one-pot processes for the preparation of benzannulated heterocycles, as well as the application of these methods for the synthesis of biologically active compounds and natural products.1 Introduction2 Iron(III)-Catalyzed Halogenation of Arenes3 One-Pot Intermolecular Aryl C–H Amination4 One-Pot Intramolecular C–N, C–O, and C–S Bond-Forming Processes5 Iron(III)-Catalyzed Thioarylation of Arenes6 Synthesis of Phenoxathiins and Phenothiazines Using Lewis Acid and Lewis Base Catalysis7 Conclusions

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“…Oral clearance was ∼3‐fold higher in children (20.2 versus 6.0 mL/min/kg), the terminal volume of distribution was ∼2‐fold larger in children (20 versus 11.7 L/kg), and the terminal exponential half‐life was decreased ∼50% in children (12.4 versus 24.9 hours). Brompheniramine is primarily metabolized to monodesmethyl and didesmethyl metabolites, with approximately 17% of the dose recovered unchanged in urine . The metabolic pathway(s) and pharmacological activity of the metabolites are unknown.…”

mentioning

confidence: 99%

Brompheniramine and Chlorpheniramine Pharmacokinetics Following Single‐Dose Oral Administration in Children Aged 2 to 17 Years

Pathirana

Jayawardena

Meeves

et al. 2017

The Journal of Clinical Pharma

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Two pediatric studies characterized brompheniramine and chlorpheniramine pharmacokinetics in a total of 72 subjects, aged 2 to 17 years. A single age-/weight-based oral dose, ranging from 1 to 4 mg, was administered with 2 to 6 oz of water at least 2 hours after a light breakfast. Plasma samples were obtained before and for 72 hours after dosing and analyzed using high-pressure liquid chromatography-tandem mass spectrometry. Pharmacokinetic parameters were estimated using noncompartmental methods; relationships with age were assessed using linear regression. Results indicated that for brompheniramine and chlorpheniramine, C was similar across age groups, although it tended to occur earlier in the youngest group. AUC was ∼15% to 30% higher in the oldest age group. As expected, CL and V /F increased with age; however, following allometric scaling, no age-related differences existed. Because the increase with age for both parameters was similar, no age-related differences in t existed (∼15 hours). Overall, the single doses were well tolerated. Sedation was the most common reported AE and appeared to be more prevalent in the 2- to 5-year-old group. Overall, these results indicate that an age/weight dosing nomogram using a 4-fold range of doses achieves similar C and AUC.

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Metabolism of brompheniramine

Cited by 21 publications

References 0 publications

Supramolecular Assembly and Solution Properties of Bis(bipyridyl)ruthenium(II) Coordination Complexes of Aryl(2-pyridyl)methanones

Supramolecular Assembly and Solution Properties of Bis(bipyridyl)ruthenium(II) Coordination Complexes of Aryl(2-pyridyl)methanones

Regioselective Functionalization of Arenes Using Iron Triflimide Catalysis

Brompheniramine and Chlorpheniramine Pharmacokinetics Following Single‐Dose Oral Administration in Children Aged 2 to 17 Years

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