Chemical Formula and Systematic Names: Ibuprofen Drug - Essay Example

Ibuprofen Teacher               Ibuprofen Since the drug Ibuprofen was synthesized in 1969, it has become one of the most commonly used analgesic, antipyretic and anti-inflammatory chemicals. Ibuprofen is used to treat inflammatory conditions such as dysmenorrhea, vascular headache and fever, mild and moderate pain, osteoarthritis and rheumatoid arthritis (“Ibuprofen,” 2010; Bushra & Aslam, 2010). Its physical and chemical properties mostly account for its pharmacologic effects. Chemical Formula and Systematic Names The chemical formula of Ibuprofen is (CH3)2CHCH2C6H4CH(CH3)COOH. The molecular weight of the chemical is 206.29. The molecular formula is C13H18O2 (“Ibuprofen,” ChemicalLand21.com, 2012). Source: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=68518 Moreover, the systematic or IUPAC name of Ibuprofen is 2-[4-(2-methylpropyl)phenyl]propanoic acid (“Ibuprofen Compound Summary,” 2012). However, other websites say that it is 2-(4-isobutylphenyl)propanoic acid, where methylpropyl is replaced with isobutyl (Broyles, 2009). First of all, Ibuprofen is a propanoic acid, which is a carboxylic acid, characterized by a –COOH tail, and is an organic hydrocarbon molecule with three carbons, which is a property of the basic propane structure. Its being a propanoic acid gives Ibuprofen its pharmacologic properties – analgesic, antipyretic and antiinflammatory – because it is its carboxylic end that reacts with the enzymes that help produce pain hormones. Moreover, Ibuprofen is a chiral or aromatic compound because of its benzene ring or phenyl group, which is attached to the second carbon. Furthermore, there is an isobutyl group, which is made up of four carbons, attached to the second carbon of the phenyl group. Ibuprofen has two optical isomers, the R- and the S+ forms, and where the S+ form has distinct pharmacologic properties and has a significant role in inhibiting the synthesis of prostaglandins. The R- form, on the other hand, has no anti-inflammatory effect. Nevertheless, an enzyme in the human body naturally converts R- isomers of Ibuprofen into the useful S+ forms, thus increasing the total active forms of Ibuprofen in the body (“The Structure of Ibuprofen,” 2012). Physical Properties According to information from the University of Oxford Department of Chemistry, Ibuprofen is “only slightly soluble in water but readily soluble in organic solvents such as ethanol” (“Ibuprofen,” University of Oxford, 2012). Other sources, however, say that Ibuprofen is insoluble in cold water (“Material Safety,” 2012). The insolubility of Ibuprofen is due to the presence of the non-polar covalent bonds present in the hydrocarbon chains, which are not soluble in polar compounds like water. In fact, this particular physical property of Ibuprofen accounts for some of its less significant pharmacologic effects. Other physical properties of Ibuprofen include a melting point of 74-77°C (“Ibuprofen,” University of Oxford, 2012), its appearance as a white crystalline powder (“Ibuprofen,” ChemicalLand21.com, 2012), and its characteristic odor (“Ibuprofen,” 2010). These physical properties, however, do not have significant implications in the pharmacological effects of the drug. Chemical Properties A molecule of Ibuprofen contains a carboxyl end as its active part. The carboxylic part, or –C=O-OH, is made up of the double-bond carbonyl and single-bond hydroxyl parts, which are actually hydrogen-bond acceptors, thus making any carboxylic compound a participant in hydrogen bonding. Hydrogen bonding is actually the principle behind the pharmacological capacity of Ibuprofen in inhibiting prostaglandin production (“Cyclooxygenase Structure,” 2012). In short, the major pharmacologic properties of Ibuprofen rely heavily on its –COOH component. The isobutyl benzene part of Ibuprofen serves as the base chemical upon which Ibuprofen is manufactured. This particular component of the drug accounts for the insolubility of Ibuprofen and other properties that it shares with other hydrocarbon compounds. However, there are no known pharmacologic effects brought about by the isobutyl benzene part of Ibuprofen. Isobutyl benzene is also interestingly a raw material of perfumes (“Isobutyl Benzene,” 2012). Relevance of the Physical and Chemical Properties to the Pharmacological Properties The mere slight insolubility of Ibuprofen in water is characterized by a relatively slower pharmacologic effect, which means that one has to wait for a while before the analgesic and anti-inflammatory effects of Ibuprofen take place (“Nurofen Express,” 2012). Nevertheless, according to information from the National Institutes of Health, Ibuprofen is “rapidly absorbed after oral administration” and effects take place after 15-30 minutes (“Ibuprofen Compound Summary,” 2012). When it comes to the implications of its chemical properties on its pharmacologic role, one of the primary pharmacological properties of Ibuprofen associated with its carboxylic end or its being a carboxylic compound is that it inhibits cyclooxygenase, or COX, activity, which consequently reduces the synthesis of “prostaglandins, leukotrienes and thromboxane precursors” or the prostanoids (“Ibuprofen,” ChemicalLand21.com, 2012). The prostanoids each has a 5 to 6 carbon ring and a 20-carbon fatty acid chain. Prostanoids usually play significant roles in the pathophysiologic processes that include “inflammation, hemostasis, thrombosis, cytoprotection, ulceration, [and] hemodynamics” (“Ibuprofen,” ChemicalLand21.com, 2012). Ibuprofen inhibits the COX enzyme that converts arachidonic acid in order to produce the pain hormone prostaglandin. This is how Ibuprofen acts as an analgesic. Moreover, the COX enzyme occurs in either the COX-1 or the COX-2 type. When Ibuprofen has blocked the COX enzyme at the chemical level, then the conversion of arachidonic acid is inhibited, thus the production of prostaglandin does not take place (“Cyclooxegenase Structure,” 2012). Prostaglandins are chemicals that “deliver and strengthen pain signals and induce inflammation” (“Cyclooxygenase and NSAIDs,” 2012). Thus, if the inhibition of the production of prostaglandins ascribes the anti-inflammatory, antipyretic and most of all, analgesic, roles to Ibuprofen. As a nonselective COX inhibitor just like Aspirin, Ibuprofen may inhibit either COX-1 or COX-2. Since a COX enzyme has “two separate active sites for prostaglandin synthase,” the action of Ibuprofen as a nonselective COX inhibitor is to bind to the site of the COX enzyme where the prostaglandin is supposed to bind. Thus, the production of prostaglandin is inhibited if Ibuprofen binds to COX-1, and the inflammatory response is lessened if Ibuprofen binds to COX-2 (“Cyclooxygenase and NSAIDs,” 2012). The binding occurs at tyrosine 385 and arginine 120 in either COX enzyme, through the hydrophobic channel or the hydrophilic side pocket, and the part of Ibuprofen that binds is the carboxylic end, which forms a salt bridge between it and the arginine 120 of the COX enzyme through hydrogen bonding (“Cyclooxygenase Structure,” 2012). However, although the carboxylic end of the Ibuprofen molecule has a significant role in demonstrating its pharmacologic properties, the same part also has a role in the occurrence of the usual side effects associated with the use of Ibuprofen. The COX-1 enzyme is a “housekeeper enzyme” which directs the synthesis of prostaglandins for “[maintaining] normal gastric mucosa and influences kidney function” (“Cox 1 and 2,” 2005). Therefore, since Ibuprofen inhibits both COX-1 and COX-2 enzymes, then such an inhibitory effect affects the health of the stomach and the kidneys thus resulting in stomach irritation and other side effects associated with the stomach (Broyles, 2009). Other side effects would include “bleeding, ulceration, and perforation of the stomach or intestines,” which may even cause death to the patient (“Motrin,” 2012). However, since COX-2 is induced by inflammation, then its inhibition has a desirable effect (“Cox 1 and 2,” 2005). It is therefore the inhibition of COX-2 that gives COX-2 its therapeutic or pharmacologic benefits (“Ibuprofen,” ChemistryExplained.com, 2012). Nevertheless, among the NSAIDs, Ibuprofen is the safest as it has the “lowest incidence of serious gastrointestinal adverse effects” (“Ibuprofen,” 2010). Moreover, aside from the anti-inflammatory, antipyretic and analgesic effects of Ibuprofen, the drug also is a vasodilatory effect, which it fulfills by inhibiting COX activity in platelets, which may cause these platelets to accumulate. Thus, if such accumulation is prevented, then unnecessary blood clotting and coagulation is reduced, thus also accounting for the anticoagulant properties of Ibuprofen (Mitchell, 2010). Precautions When Taking the Painkiller When under medication with Ibuprofen, care should be taken to ensure that there are no undesirable side effects that would result. According to Bushra and Aslam (2010), Ibuprofen may in fact, “exacerbate severe asthma” and so it should not be administered to patients with asthma and other related respiratory disorders such as rhinitis and cystic fibrosis. Moreover, there should be precautions when giving the medicine to existing stomach, kidney and heart problems since most side effects of the drug affect these parts. Aside from the conditions mentioned above, Ibuprofen should also not be used with patients suffering from bleeding disorders (Bushra & Aslam, 2010). Other special precautions from the NIH that one should follow before he decides to take Ibuprofen also involve present medical conditions and the drugs that one presently takes. First, one should not take Ibuprofen if he is currently taking another pain medication as well as other previously prescribed medications like moexipril, quinapril, trandolapril, diuretics, lithium, methotrexate, benazepril, nutritional supplements, vitamins and herbal products. Moreover, a patient with phenylketonuria, lupus, swelling of the joints and extremities, runny nose or nasal polyps, or liver disease should not take Ibuprofen unless the physician says otherwise (“Ibuprofen,” NIH, 2012). References Broyles, R. (2009). “Ingredients in Ibuprofen and Their Chemical Properties.” Retrieved Oct. 4, 2012 from Brighthub.com: http://www.brighthub.com/science/medical/articles/33463.aspx Bushra, R. & Aslam, N. (2010). “An Overview of Clinical Pharmacology of Ibuprofen.” Oman Medical Journal, 25(3), 155-161. “Cox-1 and 2: The Cyclooxygenase Systems.” (2005). Retrieved Oct. 2, 2012 from the Arthritis Pages: http://www.arthritis.co.za/cox.html “Cyclooxygenase and NSAIDs.” (2012). Retrieved Oct. 4, 2012 from the State University of New York, University at Albany: http://www.albany.edu/faculty/cs812/bio366/Cyclooxygenase_ppt.pdf “Cyclooxygenase Structure and Mechanism.” (2012). Retrieved Oct. 4, 2012 from the University of Virginia: http://cti.itc.virginia.edu/~cmg/Demo/pdb/cycox/cycox.html “Ibuprofen Compound Summary.” (2012). Retrieved Oct. 4, 2012 from the National Institutes of Health PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3672#x27 “Ibuprofen.” (2010). Retrieved Oct. 5, 2012 from Pharma Ingredients: http://www.pharma-ingredients.basf.com/Statements/Technical%20Informations/EN/Pharma%20Solutions/03_030720e_Ibuprofen.pdf “Ibuprofen.” (2012). Retrieved Oct. 4, 2012 from ChemicalLand21.com: http://www.chemicalland21.com/lifescience/phar/IBUPROFEN.htm “Ibuprofen.” (2012). Retrieved Oct. 2, 2012 from ChemistryExplained.com: http://www.chemistryexplained.com/Hy-Kr/Ibuprofen.html#b “Ibuprofen.” (2012). Retrieved Oct. 2, 2012 from the University of Oxford Department of Chemistry: http://www.chem.ox.ac.uk/mom/ibuprofen/ibuprofen.html “Ibuprofen.” (2012). Retrieved Oct. 4, 2012 from the National Institutes of Health Medline Plus: http://www.nlm.nih.gov/medlineplus/druginfo/meds/a682159.html “Isobutyl Benzene.” (2012). Retrieved Oct. 4, 2012 from Primary Information Services: http://www.primaryinfo.com/scope/isobutyl-benzene.htm “Material Safety Data Sheet: Ibuprofen MSDS.” (2012). Retrieved Oct. 4, 2012 from Science Lab: http://www.sciencelab.com/msds.php?msdsId=9924344 Mitchell, V. (2010). “How Does Ibuprofen Work – A Pharmacological Guide.” Retrieved Oct. 2, 2012 from Suite.com: http://suite101.com/article/how-does-ibuprofen-work---a-pharmacological-guide-a323503 “Motrin.” (2012). Retrieved Oct. 2, 2012 from RXList.com: http://www.rxlist.com/ibuprofen-drug.htm “Nurofen Express.” (2012). Retrieved Oct. 3, 2012 from Chemistry in Your Cupboard: http://www.chemistryinyourcupboard.org/nurofen/8 “The Structure of Ibuprofen.” (2012). Retrieved Oct. 2, 2012 from Chemistry in Your Cupboard: http://www.chemistryinyourcupboard.org/nurofen/3 Read More

 

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