Multiple solubility maxima of oxolinic acid in mixed solvents and a new extension of Hildebrand solubility approach.

Abstract:

:A new extension of the Hildebrand solubility approach which describes drug solubility in solvent mixtures showing multiple solubility peaks, the chameleonic effect, is proposed. The experimental solubilities of oxolinic acid were measured at 25 degrees C in solvent mixtures of ethanol-water and ethanol-ethyl acetate. A plot of the mole fraction of the drug against the solubility parameter (delta) of the solvent mixtures displays two peaks at delta = 30.78 MPa1/2 (80% v/v of ethanol in water) and at delta = 20.90 MPa1/2 (30% v/v of ethanol in ethyl acetate). The new extension proposed reproduces two solubility peaks. The thermograms of the solid phase before and after equilibration with the solvent mixtures did not show significant changes. The new extension was also tested with experimental data previously reported for drugs showing two solubility peaks of different height. The accuracy of other published models for describing two solubility maxima is also compared.

authors

Jouyban-Gharamaleki A,Romero S,Bustamante P,Clark BJ

doi

10.1248/cpb.48.175

subject

Has Abstract

pub_date

2000-02-01 00:00:00

pages

175-8

issue

2

eissn

0009-2363

issn

1347-5223

journal_volume

48

pub_type

杂志文章
  • Pharmacologically active components of a Peruvian medicinal plant, huanarpo (Jatropha cilliata).

    abstract::From Jatropha cilliata M. Arg., a Peruvian medicinal plant, isoorientin and orientin were isolated as anxiolytic components by using the isolation guide of anti-conflict effect in mice. Several related flavonoids were also tested for this effect. Another bioassay-guided isolation using the acetic acid-induced writhing...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.333

    authors: Okuyama E,Okamoto Y,Yamazaki M,Satake M

    更新日期:1996-02-01 00:00:00

  • Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity.

    abstract::A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6-hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6-Alkyl-8-ergolinemethanols, prepared from...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1463

    authors: Ohno S,Adachi Y,Koumori M,Mizukoshi K,Nagasaka M,Ichihara K,Kato E

    更新日期:1994-07-01 00:00:00

  • Synthesis and antiviral activity of phthiobuzone analogues.

    abstract::A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4',4'' position, show more potent antiviral activity than phthiobuzone agai...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.208

    authors: Yang YJ,Zhao JH,Pan XD,Zhang PC

    更新日期:2010-02-01 00:00:00

  • Studies on anti-inflammatory agents. V. Synthesis and pharmacological properties of 3-(difluoromethyl)-1-(4-methoxyphenyl)-5- [4-(methylsulfinyl)phenyl]pyrazole and related compounds.

    abstract::A series of novel 1,5-diphenylpyrazole derivatives bearing hydrophilic substituents was prepared. The anti-inflammatory and analgesic activities of these compounds were evaluated by using the adjuvant arthritis and Randall-Selitto assays in rats, and the structure-activity relationships were studied. The optimal compo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1475

    authors: Tsuji K,Konishi N,Spears GW,Ogino T,Nakamura K,Tojo T,Ochi T,Shimojo F,Senoh H,Matsuo M

    更新日期:1997-09-01 00:00:00

  • Cycloartane glycosides from Cimicifuga dahurica.

    abstract::A new cycloartane bisdesmoside and two new trinorcycloartane glycosides, along with four known cycloartane compounds, were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-arabinopyranosyl cimigenol 15-O-beta-D-glucopyranoside, 24-hyd...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1468

    authors: Zhang QW,Ye WC,Hsiao WW,Zhao SX,Che CT

    更新日期:2001-11-01 00:00:00

  • Analysis of the phase solubility diagram of a phenacetin/competitor/beta-cyclodextrin ternary system, involving competitive inclusion complexation.

    abstract::The competitive inclusion complexations in the ternary phenacetin/competitors/beta-cyclodextrin (beta-CyD) systems were investigated by the solubility method, where m-bromobenzoic acid (m-BBA) and o-toluic acid (o-TA) were used as competitors. The solubility changes of the drug and competitors as a function of beta-Cy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.78

    authors: Ono N,Hirayama F,Arima H,Uekama K

    更新日期:2001-01-01 00:00:00

  • Fasciculic acids A, B and C as calmodulin antagonists from the mushroom Naematoloma fasciculare.

    abstract::Three new fasciculol esters, fasciculic acids A (1), B (2) and C (3), having potent calmodulin antagonistic activity were isolated from the toxic mushroom Naematoloma fasciculare (Fr.) Karst. Their structures were elucidated on the basis of spectral and chemical evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3247

    authors: Takahashi A,Kusano G,Ohta T,Ohizumi Y,Nozoe S

    更新日期:1989-12-01 00:00:00

  • Chemical modification of fumagillin. II. 6-Amino-6-deoxyfumagillol and its derivatives.

    abstract::6-Amino-6-deoxyfumagillol (5) was synthesized by reductive amination of 6-oxo-6-deoxyfumagillol (4), which was obtained by oxidation of fumagillol (2). The reduction proceeded stereoselectively by the equatorial attack of hydride and 5 was found to have the same stereochemistry as that of 2. Several derivatives of 5 w...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.575

    authors: Marui S,Kishimoto S

    更新日期:1992-03-01 00:00:00

  • Comparison of efficacy, toxicity and pharmacokinetics of free adriamycin and adriamycin linked to oxidized dextran in rats.

    abstract::Adriamycin linked to oxidized dextran (ADM-OXD) via Schiff's base formation was compared with free adriamycin with regard to antitumor activity, acute toxicity and plasma pharmacokinetics in rats following i.v. administration. ADM-OXD showed higher activity against Walker carcinosarcoma 256 than free adriamycin. On th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1639

    authors: Ueda Y,Munechika K,Kikukawa A,Kanoh Y,Yamanouchi K,Yokoyama K

    更新日期:1989-06-01 00:00:00

  • Synthesis and in Vitro Antibacterial Evaluation of Novel 4-Substituted 1-Menthyl-1,2,3-triazoles.

    abstract::Menthyl 1,4-disubstituted 1,2,3-triazole derivatives of hydroxybenzaldehydes, phenols and bile acids were synthesized via click chemistry. The novel synthesized compounds were evaluated for their in vitro antibacterial activity against Enterococcus faecium, and Staphylococcus aureus as Gram-positive bacteria. Some der...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00463

    authors: Khaligh P,Salehi P,Bararjanian M,Aliahmadi A,Khavasi HR,Nejad-Ebrahimi S

    更新日期:2016-01-01 00:00:00

  • Formal [4+2] cycloaddition of di-tert-butyl 2-ethoxycyclobutane-1,1-dicarboxylate with ketones or aldehydes and tandem lactonization.

    abstract::A catalytic amount of tin(IV) chloride catalyzed formal [4+2] cycloaddition reaction of di-tert-butyl 2-ethoxycyclobutane-1,1-carboxylate with ketones or aldehydes to give diethyl 6-ethoxydihydro-2H-pyran-3,3(4H)-dicarboxylates, whereas two equivalents of trimethylsilyl triflate promoted tandem [4+2] cycloaddition and...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.21

    authors: Okado R,Nowaki A,Matsuo J,Ishibashi H

    更新日期:2012-01-01 00:00:00

  • A mild and efficient stereoselective synthesis of (Z)- and (E)-allyl sulfides and potent antifungal agent, (Z)-3-(4-methoxybenzylidene)thiochroman-4-one from Morita-Baylis-Hillman acetates.

    abstract::A facile stereoselective synthesis of (Z)- and (E)-allyl sulfides has been accomplished from Morita-Baylis-Hillman acetates in one-pot by treatment with benzene thiol in the presence of catalytic amounts of 15% aqueous NaOH and TBAI in DMSO at room temperature. The method has been applied for the synthesis of (Z)-3-(4...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1274

    authors: Das B,Chowdhury N,Damodar K,Banerjee J

    更新日期:2007-08-01 00:00:00

  • Potential of Enzymomics Methodologies to Characterize Disease-Related Protein Functions.

    abstract::Enzymatic functions are often altered during disease onset and progression, and therefore chemical-biological studies, which utilize chemical knowledge to discover novel protein functions, are often employed to find proteins with functions closely related to disease phenotypes. Such studies are known as forward chemic...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c17-00144

    authors: Komatsu T

    更新日期:2017-01-01 00:00:00

  • The structure of a new cardenolide diglycoside and the biological activities of eleven cardenolide diglycosides from Nerium oleander.

    abstract::A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2-11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1-11 was examined on the basis of inhibitory activity aga...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.371

    authors: Zhao M,Bai L,Toki A,Hasegawa R,Sakai J,Hasegawa T,Ogura H,Kataoka T,Bai Y,Ando M,Hirose K,Ando M

    更新日期:2011-01-01 00:00:00

  • A synthetic study on antiviral and antioxidative chromene derivative.

    abstract::An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be syn...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.391

    authors: Mori J,Iwashima M,Takeuchi M,Saito H

    更新日期:2006-03-01 00:00:00

  • Three novel cantharidin-related compounds from the Chinese blister beetle, Mylabris phalerata Pall.

    abstract::Three novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.807

    authors: Nakatani T,Konishi T,Miyahara K,Noda N

    更新日期:2004-07-01 00:00:00

  • Selective Targeting of Cancer Stem Cells by 2-Aminodihydroquinoline Analogs.

    abstract::Many aminodihydroquinoline compounds have been studied to determine their cytotoxicity to cancer cells. However, anti-cancer stem cells (CSCs) activity of aminodihydroquinoline has not been tested in spite that CSC is believed to do an important roles in chemotherapy resistance and recurrence. The CSC selective target...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00726

    authors: Park H,Yu Y,Kim H,Lee E,Lee H,Jeon R,Kim WY

    更新日期:2017-04-01 00:00:00

  • Release kinetics of nicotinamide from fatty acid-nicotinamide equimolar complexes. II. Activation thermodynamic quantities.

    abstract::The rates of release of nicotinamide (NAA) from fatty acid (FA)-NAA complexes, FA-NAA, were determined at various temperatures, and the thermodynamic quantities for the release of NAA were estimated. The results were compared with the previous results obtained for FA-thiamine disulfide (TDS) complexes, (FA)6(TDS). The...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.3114

    authors: Yokoyama S,Ueda F,Fujie T

    更新日期:1991-12-01 00:00:00

  • Studies on antiulcer drugs. V. Synthesis and antiulcer activity of aralkylbenzazoles.

    abstract::A series of 2-alkylamino-5- or 6-aralkyl-substituted benzazoles were synthesized and tested for histamine H2-receptor antagonist and anti-stress ulcer activities. These new compounds showed little or no histamine H2-receptor antagonist activity in contrast to imidazo[1,2-a]pyridine analogues (I). On antiulcer assay, h...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2062

    authors: Katsura Y,Inoue Y,Tomoi M,Takasugi H

    更新日期:1992-08-01 00:00:00

  • Indonesian medicinal plants. IX. Chemical structures of gongganosides A, B, and C, three new quinovic acid glycosides from the bark of Bhesa paniculata (Celastraceae).

    abstract::Three new quinovic acid glycosides, named gongganosides A (1), B (2), and C (3), were isolated from the bark of Bhesa paniculata (Celastraceae), an Indonesian medicinal plant collected in Sumatra Island. The chemical structures have been elucidated on the basis of chemical and physicochemical evidence as quinovic acid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1596

    authors: Ohashi K,Kojima H,Tanikawa T,Okumura Y,Kawazoe K,Tatara N,Shibuya H,Kitagawa I

    更新日期:1994-08-01 00:00:00

  • New megastigmane glucosides from Excoecaria cochinchinensis LOUR. var. cochinchinensis.

    abstract::Two new megastigmane glucosides, called excoecariosides A and B were isolated from the leaves of a medicinal Vietnamese plant, Excoecaria cochinchinensis LOUR. var. cochinchinensis (Euphorbiaceae) together with seven known compounds. Their structures were elucidated by spectroscopic analyses and chemical reactions inc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1600

    authors: Giang PM,Son PT,Matsunami K,Otsuka H

    更新日期:2005-12-01 00:00:00

  • Three new diterpenoid alkaloids from roots of Aconitum ouvrardianum HAND.-MAZZ.

    abstract::A new C(19)-diterpenoid alkaloid, ouvrardiantine (1) and two new C(20)-diterpenoid alkaloids, ouvrardiandines A (2) and B (3) were isolated from the root of Aconitum ouvrardianum HAND.-MAZZ. The structure of the new alkaloids was established on the basis of spectral data (1D- and 2D-NMR, HR-MS). ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1090

    authors: Hou LH,Chen DL,Jian XX,Wang FP

    更新日期:2007-07-01 00:00:00

  • Biotransformation of a taxadiene by ginkgo cell cultures and the tumor multi-drug resistant reversal activities of the metabolites.

    abstract::The biotransformation of 2α,5α,10β-triacetoxy-14-oxo-taxa-4(20),11-diene (1) by cultured Gingko cells afforded four products. Their structures were identified on the basis of analyses of the chemical and spectroscopic (IR, MS, ¹H- and ¹³C-NMR) data. Among them, 2, 3 and 5 were three new compounds, and 4 displayed pote...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1038

    authors: Xie D,Zhang Y,Zou J,Yin D,Chen X,Dai J

    更新日期:2011-01-01 00:00:00

  • An enkephalin-degrading aminopeptidase from rat brain catalyzes the hydrolysis of a neuropeptide, kyotorphin (L-Tyr-L-Arg).

    abstract::We studied the hydrolysis of a neuropeptide kyotorphin (L-Tyr-L-Arg) by an enkephalin-degrading aminopeptidase purified from cytosol of rat brain in vitro. The purified enzyme was homogeneous as judged by sodium dodecyl sulfate (SDS)-polyacrylamide gel electrophoresis (PAGE), gel filtration and isoelectric focusing. T...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1883

    authors: Akasaki K,Tsuji H

    更新日期:1991-07-01 00:00:00

  • Technetium-99m complexes with steroid-2-aminooxyethyliminodiacetic acid conjugates.

    abstract::Conjugates of 2-aminooxyethyliminodiacetic acid with estrone, testosterone, epiandrosterone, 17-alpha-hydroxy-progesterone and progesterone were synthesized and their complexes with Tc-99m were successfully prepared in good yields, which indicated the agent to be promising for metal-labeling of biomolecules and relate...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.413

    authors: Yoda R,Karube Y,Takata J,Nagata Y,Matsushima Y

    更新日期:1999-03-01 00:00:00

  • Syntheses and doxorubicin-inclusion abilities of beta-cyclodextrin derivatives with a hydroquinone alpha-glycoside residue attached at the primary side.

    abstract::This paper describes syntheses and doxorubicin-inclusion abilities of beta-cyclodextrin (CyD) derivatives with a hydroquinone alpha-glycoside residue attached at the primary side. The hydroquinone glycoside having an alpha-D-glucosidic or 2-acetamido-2-deoxy-alpha-D-glucosidic linkage became a useful component for pro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.74

    authors: Oda Y,Miura M,Hattori K,Yamanoi T

    更新日期:2009-01-01 00:00:00

  • Characterization of secondary structure of neocarzinostatin apoprotein.

    abstract::Characteristics of the secondary structure of neocarzinostatin apoprotein (apo-NCS) were examined by various means. Gaussian analysis of the Fourier-transform infrared (FT-IR) curve and curve-fitting of the circular dichroism (CD) spectrum for apo-NCS revealed that this peptide was abundant in beta-structures. In the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3078

    authors: Saito K,Sato Y,Edo K,Akiyama-Murai Y,Koide Y,Ishida N,Mizugaki M

    更新日期:1989-11-01 00:00:00

  • Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.

    abstract::The Michael reaction of malonates with maleates afforded the corresponding adducts in high yields with high enantioselectivities (up to 98% enantiomeric excess (ee)) by using dilithium 3,3'-dichlorobinaphtholate as a catalyst. The obtained Michael adducts could be converted to optically active tricarboxylic acid (TCA)...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00993

    authors: Sakamoto M,Kaneko T,Orito Y,Shimoda Y,Nakajima M

    更新日期:2019-01-01 00:00:00

  • Slow release of tetracycline from a mucoadhesive complex with sucralfate for eradication of Helicobacter pylori.

    abstract::Treatment composed of a gastric mucoadhesive antibiotic with slow release drug delivery is expected to be effective for the eradication of Helicobacter pylori (H. pylori). In this study, we evaluated the slow release property of the tetracycline-sucralfate acidic complex. Tetracycline was the antibiotic selected becau...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1412

    authors: Higo S,Takeuchi H,Yamamoto H,Hino T,Kawashima Y

    更新日期:2008-10-01 00:00:00

  • Synthesis and Biological Evaluation of N-Aryl-5-aryloxazol-2-amine Derivatives as 5-Lipoxygenase Inhibitors.

    abstract::We describe the synthesis and biological evaluation of N-aryl-5-aryloxazol-2-amine derivatives that are able to inhibit 5-lipoxygenase (5-LOX), a key enzyme of leukotriene synthesis, for the treatment of inflammation-related diseases including asthma and rheumatoid arthritis. A novel structural moiety containing oxazo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00033

    authors: Suh JH,Yum EK,Cho YS

    更新日期:2015-01-01 00:00:00