Photochemical Fate of Pharmaceuticals in the Environment: Cimetidine and Ranitidine
The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1Δg)) and hydroxyl radical (•OH), two transient oxidants formed in sunl...
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| Published in | Environmental science & technology Vol. 37; no. 15; pp. 3342 - 3350 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Washington, DC
American Chemical Society
01.08.2003
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1Δg)) and hydroxyl radical (•OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with •OH in water is 6.5 ± 0.5 × 109 M-1 s-1. Over the pH range 4−10, cimetidine reacts with 1O2 with bimolecular rate constants ranging from 3.3 ± 0.3 × 106 M-1 s-1 at low pH to 2.5 ± 0.2 × 108 M-1 s-1 in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 1O2 in water ranges from 1.6 ± 0.2 × 107 M-1 s-1 at pH 6−6.4 ± 0.2 × 107 M-1 s-1 at pH 10. Reaction of ranitidine hydrochloride with •OH proceeds with a rate constant of 1.5 ± 0.2 × 1010 M-1 s-1. Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 ° latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 1O2 and •OH, indicate that photooxidation mediated by 1O2 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 1O2. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 1O2, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. |
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| AbstractList | The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1delta(g))) and hydroxyl radical (*OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with *OH in water is 6.5 +/- 0.5 x 10(9) M(-1) s(-1). Over the pH range 4-10, cimetidine reacts with 1O2 with bimolecular rate constants ranging from 3.3 +/- 0.3 x 10(6) M(-1) s(-1) at low pH to 2.5 +/- 0.2 x 10(8) M(-1) s(-1) in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 1O2 in water ranges from 1.6 +/- 0.2 x 10(7) M(-1) s(-1) at pH 6-6.4 +/- 0.2 x 10(7) M(-1) s(-1) at pH 10. Reaction of ranitidine hydrochloride with *OH proceeds with a rate constant of 1.5 +/- 0.2 x 10(10) M(-1) s(-1). Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 degrees latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 1O2 and *OH, indicate that photooxidation mediated by 1O2 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 1O2. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 1O2, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis.The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1delta(g))) and hydroxyl radical (*OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with *OH in water is 6.5 +/- 0.5 x 10(9) M(-1) s(-1). Over the pH range 4-10, cimetidine reacts with 1O2 with bimolecular rate constants ranging from 3.3 +/- 0.3 x 10(6) M(-1) s(-1) at low pH to 2.5 +/- 0.2 x 10(8) M(-1) s(-1) in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 1O2 in water ranges from 1.6 +/- 0.2 x 10(7) M(-1) s(-1) at pH 6-6.4 +/- 0.2 x 10(7) M(-1) s(-1) at pH 10. Reaction of ranitidine hydrochloride with *OH proceeds with a rate constant of 1.5 +/- 0.2 x 10(10) M(-1) s(-1). Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 degrees latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 1O2 and *OH, indicate that photooxidation mediated by 1O2 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 1O2. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 1O2, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. The photochemical fate of the pharmaceuticals, cimetidine and ranitidine, which display disparate degradation mechanisms, was investigated. Photolysis experiments with sunlight in natural water were performed, as were steady-state photolysis experiments and laser flash photolysis experiments. The second-order rate constant for the reaction of the pharmaceuticals with hydroxyl radical was determined using Fenton's reagent. In Mississippi River water, singlet-oxygenation formed from the interaction of sunlight with dissolved organic carbon appeared to be the dominant decay process for cimetidine, while ranitidine was subject to direct photolysis, and reaction with singlet oxygen was an additional loss process. Chemical reaction was the primary pathway by which ranitidine and cimetidine interacted with singlet oxygen, while the contribution of the physical quenching pathway was negligible. For cimetidine, the data indicated that the dialkylimidazole ring was the most reactive group, while for ranitidine, the furan displayed the highest reactivity. The direct photodegradation rate of ranitidine was insensitive to pH, while the reaction with singlet oxygen exhibited a pH-dependence. The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1delta(g))) and hydroxyl radical (*OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with *OH in water is 6.5 +/- 0.5 x 10(9) M(-1) s(-1). Over the pH range 4-10, cimetidine reacts with 1O2 with bimolecular rate constants ranging from 3.3 +/- 0.3 x 10(6) M(-1) s(-1) at low pH to 2.5 +/- 0.2 x 10(8) M(-1) s(-1) in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 1O2 in water ranges from 1.6 +/- 0.2 x 10(7) M(-1) s(-1) at pH 6-6.4 +/- 0.2 x 10(7) M(-1) s(-1) at pH 10. Reaction of ranitidine hydrochloride with *OH proceeds with a rate constant of 1.5 +/- 0.2 x 10(10) M(-1) s(-1). Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 degrees latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 1O2 and *OH, indicate that photooxidation mediated by 1O2 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 1O2. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 1O2, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (102, 02('deltag)) and hydroxyl radical (*OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with *OH in water is 6.5 ± 0.5 x 109 M-1 s-1. Over the pH range 4-10, cimetidine reacts with 102 with bimolecular rate constants ranging from 3.3 ± 0.3 x 106 M-1 s-1 at low pH to 2.5 ± 0.2 x 108 M-1 s-1 in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 102 in water ranges from 1.6 ± 0.2 x 107 M-1 s-I at pH 6-6.4 ± 0.2 x 107 M-1 S-I at pH 10. Reaction of ranitidine hydrochloride with 'OH proceeds with a rate constant of 1.5 ± 0.2 x 1010 M-1 s-1. Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 ' latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 102 and *OH, indicate that photooxidation mediated by 102 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 102. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to sing let-oxyg e nation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 102, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. [PUBLICATION ABSTRACT] The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen (1O2, O2(1Δg)) and hydroxyl radical (•OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with •OH in water is 6.5 ± 0.5 × 109 M-1 s-1. Over the pH range 4−10, cimetidine reacts with 1O2 with bimolecular rate constants ranging from 3.3 ± 0.3 × 106 M-1 s-1 at low pH to 2.5 ± 0.2 × 108 M-1 s-1 in alkaline solutions. The bimolecular rate constants for ranitidine reacting with 1O2 in water ranges from 1.6 ± 0.2 × 107 M-1 s-1 at pH 6−6.4 ± 0.2 × 107 M-1 s-1 at pH 10. Reaction of ranitidine hydrochloride with •OH proceeds with a rate constant of 1.5 ± 0.2 × 1010 M-1 s-1. Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 ° latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of 1O2 and •OH, indicate that photooxidation mediated by 1O2 is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by 1O2. These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with 1O2, as evidenced by the high relative rate constants of the furan and imidazole models. The nitroacetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. The photochemical fates of the histamine H sub(2)-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant pharmaceuticals displayed high rates of reaction with both singlet oxygen ( super(1)O sub(2), O sub(2)( super(1) Delta sub(g))) and hydroxyl radical ( times OH), two transient oxidants formed in sunlit natural waters. For cimetidine, the bimolecular rate constant for reaction with times OH in water is 6.5 plus or minus 0.5 x 10 super(9) M super(-1) s super(-1). Over the pH range 4-10, cimetidine reacts with super(1)O sub(2) with bimolecular rate constants ranging from 3.3 plus or minus 0.3 x 10 super(6) M super(-1) s super(-1) at low pH to 2.5 plus or minus 0.2 x 10 super(8) M super(-1) s super(-1) in alkaline solutions. The bimolecular rate constants for ranitidine reacting with super(1)O sub(2) in water ranges from 1.6 plus or minus 0.2 x 10 super(7) M super(-1) s super(-1) at pH 6-6.4 plus or minus 0.2 x 10 super(7) M super(-1) s super(-1) at pH 10. Reaction of ranitidine hydrochloride with times OH proceeds with a rate constant of 1.5 plus or minus 0.2 x 10 super(10) M super(-1) s super(-1). Ranitidine was also degraded in direct photolysis experiments with a half-life of 35 min under noon summertime sunlight at 45 degree latitude, while cimetidine was shown to be resistant to direct photolysis. The results of these experiments, combined with the expected steady-state near surface concentrations of super(1)O sub(2) and times OH, indicate that photooxidation mediated by super(1)O sub(2) is the likely degradation pathway for cimetidine in most natural waters, and photodegradation by direct photolysis is expected to be the major pathway for ranitidine, with some degradation caused by super(1)O sub(2). These predictions were verified in studies using Mississippi River water. Model compounds were analyzed by laser flash photolysis experiments to assess which functionalities within ranitidine and cimetidine are most susceptible to singlet-oxygenation and direct photolysis. The heterocyclic moieties of the pharmaceuticals were clearly implicated as the sites of reaction with super(1)O sub(2), as evidenced by the high relative rate constants of the furan and imidazole models. The nitro-acetamidine portion of ranitidine has been shown to be the moiety active in direct photolysis. |
| Author | Latch, Douglas E Arnold, William A McNeill, Kristopher Packer, Jennifer L Stender, Brian L |
| Author_xml | – sequence: 1 givenname: Douglas E surname: Latch fullname: Latch, Douglas E – sequence: 2 givenname: Brian L surname: Stender fullname: Stender, Brian L – sequence: 3 givenname: Jennifer L surname: Packer fullname: Packer, Jennifer L – sequence: 4 givenname: William A surname: Arnold fullname: Arnold, William A – sequence: 5 givenname: Kristopher surname: McNeill fullname: McNeill, Kristopher |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15043021$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/12966980$$D View this record in MEDLINE/PubMed |
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| Snippet | The photochemical fates of the histamine H2-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant... The photochemical fate of the pharmaceuticals, cimetidine and ranitidine, which display disparate degradation mechanisms, was investigated. Photolysis... The photochemical fates of the histamine H sub(2)-receptor antagonists cimetidine and ranitidine were studied. Each of the two environmentally relevant... |
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| SubjectTerms | Applied sciences Biological and physicochemical phenomena Chemical reactions cimetidine Cimetidine - analysis Cimetidine - chemistry Earth sciences Earth, ocean, space Electrons Engineering and environment geology. Geothermics Environmental Monitoring Environmental Pollutants Exact sciences and technology Experiments Half-Life Histamine H2 Antagonists - analysis Histamine H2 Antagonists - chemistry Hydroxyl Radical - chemistry Natural water pollution Oxidants - chemistry Oxidation Pharmaceuticals Photochemistry Pollution Pollution, environment geology ranitidine Ranitidine - analysis Ranitidine - chemistry Water pollution Water treatment and pollution |
| Title | Photochemical Fate of Pharmaceuticals in the Environment: Cimetidine and Ranitidine |
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