Freeman, David S.

Thompson, Charles M.

English

University of Montana

University of Montana ScholarWorks at University of Montana Syllabi Course Syllabi Fall 9-1-2000 PHAR 421.01: Medicinal Chemistry I David S. Freeman University of Montana - Missoula Charles M. Thompson The University Of Montana Follow this and additional works at: https://scholarworks.umt.edu/syllabi Let us know how access to this document benefits you. Recommended Citation Freeman, David S. and Thompson, Charles M., "PHAR 421.01: Medicinal Chemistry I" (2000). Syllabi. 5290. https://scholarworks.umt.edu/syllabi/5290 This Syllabus is brought to you for free and open access by the Course Syllabi at ScholarWorks at University of Montana. It has been accepted for inclusion in Syllabi by an authorized administrator of ScholarWorks at University of Montana. For more information, please contact scholarworks@mso.umt.edu. PHARMACY 421 - MEDICINAL CHEMISTRY I AUTUMN SEMESTER, 2000INSTRUCTORS: David Freeman, Office: SB 308 Office Phone: 243-4772 Home Phone: 728-6 551E-m ail: dfreeman@selwav.umt.edu Internet Site: www.umt.edu/pharmacvChuck Thompson, Office: SB 383 Office Phone: 243-4643E-m ail: cmthomp@selwav.umt.edu Internet Site: www.umt.edu/medchemEXAMS AND GRADING:First Exam: Tuesday, Oct. 3 ........................50 pointsSecond Exam: Thursday, Nov. 2  ............. 70 pointsThird Exam: Tuesday, Dec. 12 .........................80 pointsFinal Exam: ...............100 points10 Point Quizzes: Best 5 out of 6 scores 50 pointsTotal Points: 350 90-100% = A 80-89 % = B 70-79 % = C 65-69 % = ­D* All EXAMS are comprehensive* All exams and quizzes must be taken at scheduled times* Instructor must be informed BEFORE missing a scheduled exam periodand must be based on GOOD REASONS* Missed exam periods must be made up within 2 days* No make up quizzesSTUDENT PERFORMANCE OBJECTIVES:1) Identify organic functional groups and know their polar/lipophilic and acid/base properties2) Know the relationships between organic functional groups and biological activity3) Know the possible modes of metabolism in the body for organic functional groups4) Know the chemical structures of important neurotransmitters or hormones and the biochemical pathways for their syntheses and metabolism5) Know the major biochemical events triggered by the activation of receptors important for drug action6) Given the chemical structure of a drug, know its pharmacologic or therapeutic class7) Given the chemical structure of a drug, khow important chemical features (acid/base or lipophilic properties, chemical groups affecting absorption, distribution, or metabolism, chemical groups affecting potency or receptor interaction, chemical groups affecting storage or formulation)that contribute to the drug's pharmacological activity8) Given the chemical structure of a drug, know important chemical changes that will predictably alter the pharmacological properties (potency, duration of action, etc.) of the drug9) Given the chemical structure of a drug, know the important biological receptors it interacts with and the biochemical events produced by these interactions10) Given the common or generic name of a drug, know its pharmacologic or therapeutic class, some of its important chemical properties (structural skeleton or chemical class, acid/base, etc.), the receptors it interacts with and the biochemical events produced by these interactionsTEXTBOOK: Goodman & Gilman's "The Pharmacological Basis of Therapeutics", Ninth EditionReading In TextI. Physicochemical Properties of Drugs Related to Pharmacological Activity and MetabolismA. Organic Functional Groups in Medicinal Chemistry 3-4 1 ■ Physicochemical Properties11-16 2. Metabolic FateB. Acid/Base Review1. Equilibrium 3-4 2. pKa valuesC. Quantitative Structure-Activity Relationships1. Concept of Linear Free Energy Relationships2. Hydrophobicity and Log P values3. Electronic Effects and Sigma valuesD. Problem Solving in Medicinal ChemistryII. Biochemical Processes Affecting Drugs and Pharmacological ActivityA. Processes Affecting Drug Distribution 9-11 1. Non-specific binding sites and plasma protein binding11-16 2. Biotransformation reactions (metabolism)ReadingIn Text8. Processes Affecting Drug Action at the Active Site 31-33 . 1. Structural families of receptors39-40 2. Binding events initiating the pharmacological responsea. Occupancy and conformational changes of receptorb. Agonist vs. antagonist events34-37 3. Events propagating and amplifying pharmacological response4. Events terminating the pharmacological responseIII. Processes and Overview of Drugs Affecting Cholinergic ReceptorsA, Biochemical Events at the Cholinergic Synapse 115-119 1. Synthesis and metabolism of acetylcholine2. Muscarinic and nicotinic receptors3. Processes following receptor activationB. Overview on Cholinergic DrugsIV. Muscarinic Receptor Agonists141-143 A. Chemistry of Acetylcholine1. Important functional groups2. Conformations of acetylcholineB. SAR and Chemistry of Selected Agonists* METHACHOLINE CARBACHOL BETHANECHOL PILOCARPINE GEVIMELINE *V. Cholinergic Antagonists 148-150 A. Muscarinic Blocking Agents1. Natural product and model agent - atropine2. SAR and chemistry of selected antimuscarinic agentsa. Tertiary agiines* ATROPINE SCOPOLAMINE HOMATROPINE 'DICYCLOMINE CYCLOPENTOLATE*b. Quaternary amines* GLYCOPYRROLATE METHANTHELINE *'PROPANTHELINE IPRATROPIUM *VI. Anticholinesterase Agents161-164 A. Mechanism of Acetylcholine Hydrolysis1. Individual steps involved in hydrolysis2. Rates of reaction steps162-165 B. Mechanisms of Cholinesterase Inhibition1. Competitive binding at active site2. Covalent binding at active site 165-167 C. SAR and Chemistry of Cholinesterase inhibitors1. Natural product and model agent * PHYSOSTIGMINE '2. Competitive inhibitors * EDROPHONIUM *3. Carbamates - "reversible" inhibitors'NEOSTIGMINE PYRIDOSTIGMINE'4. Organophosphates - "irreversible" inhibitors* ECHOTHIOPHATE ISOFLUROPHATE PARATHION MALATHION * 170-171 D. Reactivation of Inhibited Cholinesterase * PRALIDOXIME *VII. Agents Acting At Nicotinic Receptors177-178 A. Properties of the Nicotinic Cholinergic Receptor178-182 B. Neuromuscular blocking agents1. Natural product and model agent * TUBOCURARINE *2. Competitive agents '  MIVACURIUM ATRACURIUM PANCURONIUM *3. Depolarizing agents ‘ DECAMETHONIUM SUCCINYLCHOLINE * 193-195 C. Ganglionic blocking agents* HEXAMETHONIUM TRIMETHAPHAN MECAMYLAMINE *ReadingIn TextVIII. Processes and Overview of Drugs Affecting Adrenergic ReceptorsA. Biochemical Events at the Adrenergic Synapse118-123 1 • Synthesis and storage of norepinephrine123-1 24 2. Termination and metabolism of catecholamines124-1 27 3. Alpha and beta receptors and subtypes127-1 30 4. Processes following receptor activationB. Overview on Adrenergic DrugsIX. Adrenergic Receptor AgonistsA. Chemistry of Norepinephrine and Epinephrine1. Oxidative and acid/base properties2. Stereochemistry200-203 B. SAR and Chemistry of Selected Agonists1. Differentiating alpha and beta activity2. Decreasing metabolism3. Peripheral vs. CNS effects4. Direct and indirect effects* DOPAMINE ISOPROTERENOL TERBUTALINE METAPROTERENOL ** ALBUTEROL SALMETEROL EPHEDRINE PHENYLPROPANOLAMINE ** RITODRINE CLONIDINE AMPHETAMINE TETRAHYDROZOLINE ** METHYLPHENIDATE DOBUTAMINE METHOXAMINE PHENYLEPHRINE •PHENTERMINE FENFLURAMINE METHYLPHENlDATE PEMOLINE COCAINE*203-204 5. Physiological and biochemical mechanismsX. Adrenergic Receptor Antagonists225-227 A. Alpha Blocking Agents v227-228 1. Chemistry of haloaikylamines * PHENOXYBENZAMINE *228-229 2. Chemistry of imidazolines * PHENTOLAMiNE TOLAZOLINE*229-230 3. Selective blockers * PRAZOSIN TERAZOSIN DOXAZOSIN*232-233 B. Beta Blocking Agents237 1. Nonselective blockers* PROPRANOLOL NADOLOL TIMOLOL PINDOLOL CARTEOLOL*238-239 2. Selective blockers * METOPROLOL ATENOLOL ACEBUTOLOL ESMOLOL *3. Blockers with intrinsic sympathomimetic activity {ISA blockers)4. Combined alpha and beta blocker * LABETALOL *XI. Antihistamines and Other Agents581-586 A. Biochemistry of Histamine Synthesis, Metabolism, and Receptors586-592 B. Hi receptor antagonists* DIPHENHYDRAMINE CHLORPHENIRAMINE CYCUZINE PYRILAMINE ** PROMETHAZINE TERFENADINE LORATADINE ASTEMtZOLE FEXOFENADINE * 901-906 C. H2 receptor blocking agents* CIMETIDINE RANITIDINE FAMOTIDINE NIZATIDINE*907-909 D. Inhibitors of H+/K+ ATPase‘ OMEPRAZOLE LANSOPRAZOLE RABEPRAZOLE PANTOPRAZOLE*667-669 E. Inhibitors of histamine release* CROMOLYN SODIUM NEDOCROMIL SODIUM *XII. Local and General Anesthetics331-332 A. SAR and Chemistry of Local Anesthetic Agents1. Natural product and model compound * COCAINE *2. Synthetic esters and amides•PROCAINE LIDOCAINE TETRACAINE ETIDOCAINE ** BENZOCAINE PRAMOXINE *332-333 B. Nonspecific and Specific Effects on Neural Membranes333-336 C. Factors Affecting Activity of Agents337-338 D. Adverse effects and metabolismE. Structure and Chemical Properties of General Anesthetic Agents* DIETHYL ETHER NITROUS OXIDE HALOTHANE ISOFLURANE *ReadingIn TextXIII. Sedative/Hypnotic AgentsA. Benzodiazepines362-364 1. Structure, Chemical Properties, and SAR364-367 2. Biochemical effects* DIAZEPAM CHLORD1AZEPOXIDE FLURAZEPAM OXAZEPAM * ‘ TRIAZOLAM MIDAZOLAM LORAZEPAM ZOLPIDEM*373-377 B. Barbiturates1. Chemical properties and SAR of agents2. Biochemical effects* PHENOBARBITAL PENTOBARBITAL SECOBARBITAL** BUTABARBITAL THIOPENTAL *381 C. Non-barbiturates * CHLORAL HYDRATE *XIV. Opioid Analgesic Agents521-527 A. Biochemistry of Endorphins, Enkephalins, and Their ReceptorsB. Natural Product and Model Agent * MORPHINE*527-530 C. SAR, Stereochemistry, and Chemical Properties1. Chemical features of morphine2 N-Substituents producing agonist, partial agonist, or antagonist effects3. Synthetic agents‘ HEROIN HYDROMORPHONE CODEINE MEPERIDINE LEVORPHANOL* ‘ BUTORPHANOL METHADONE FENTANYL PENTAZOCINE ETORPHINE * * NALOXONE NALTREXONE DEXTROMETHORPHAN *XV. Antineoplastic Agents v1233-1238 A. Chemistry and Mechanisms of Action for Alkylating and Cross-linking Agents /* MECHLORETHAMINE CHLORAMBUCIL CYCLOPHOSPHAMIDE IPOSFAMIDE * \ .* BUSULFAN CARMUSTINE LOMUSTINE DACARBAZINE PROCARBAZINE*1269-1272 * CISPLATIN CARBOPLATIN*B. Mechanisms of Action for Antimetabolite Agents1243-1247 * METHOTREXATE LEUCOVORIN FLUOROURACIL FLOXURIDINE *1252-1257 * CYTARAB1NE GEMCITABINE CLADRIBINE PENTOSTATlN MERCAPTOPURINE *C. Mechanisms of Action for Natural Products and Miscellaneous Agents1258-1262 * VINCRISTINE VINBLASTINE PACLITAXEL ETGPOSIDE *1268, 1271 * ASPARAGINASE HYDROXYUREA*D. Mechanisms of Action for Antibiotic Type Agents1263-1267 * DAUNORUBICIN DOXORUBICIN IDARUBICIN BLEOMYCIN*1268 * MITOXANTRONE MITOMYCIN DACTJNOMYCIN*-V  . : . :- -

PHAR 421.01: Medicinal Chemistry I

University of Montana ScholarWorks at University of Montana Syllabi Course Syllabi Fall 9-1-2001 PHAR 421.01: Medicinal Chemistry I David S. Freeman University of Montana - Missoula Charles M. Thompson University of Montana, Missoula Follow this and additional works at: https://scholarworks.umt.edu/syllabi Let us know how access to this document benefits you. Recommended Citation Freeman, David S. and Thompson, Charles M., "PHAR 421.01: Medicinal Chemistry I" (2001). Syllabi. 6219. https://scholarworks.umt.edu/syllabi/6219 This Syllabus is brought to you for free and open access by the Course Syllabi at ScholarWorks at University of Montana. It has been accepted for inclusion in Syllabi by an authorized administrator of ScholarWorks at University of Montana. For more information, please contact scholarworks@mso.umt.edu. PHARMACY 421 -  MEDICINAL CHEMISTRY  I  AUTUMN SEMESTER, 2001  INSTRUCTORS:   David Freeman, Office: SB 308          Office Phone: 243-4772        Home Phone: 728-6551   E-mail: dfreeman@selway.umt.edu  Internet Site: http://skaggs-06.pharmacy.umt.edu/pharm-sci/Freeman/PHAR%20421/    Chuck Thompson, Office: SB 383  Office Phone: 243-4643   E-mail:  cmthomp@selway.umt.edu   Internet Site: http://www.umt.edu/medchem/teaching/part1syl.htm  EXAMS AND GRADING:   First Exam:  Friday, Oct. 5  . . . . . . . . . .   50 points   Second Exam:  Friday, Nov. 2  . . . . . . . . . .   70 points   Third Exam:  Friday, Dec. 7 . . . . . . . . . .    80 points   Final Exam:  Wednesday, Dec. 19 . . . . .  100 points    10 Point Quizzes: Best 5 out of 6 scores . . . . . .   50 points   Total Points:  350        90-100% = A        80-89 % = B        70-79 % = C        65-69 % = D     * All EXAMS are comprehensive     * All exams and quizzes must be taken at scheduled times     * Instructor must be informed BEFORE missing a scheduled exam period       and must be based on GOOD REASONS      * Missed exam periods must be made up within 2 days     * No make up quizzes  STUDENT PERFORMANCE OBJECTIVES: 1) Identify organic functional groups and know their polar/lipophilic and acid/base properties  2) Know the relationships between organic functional groups and biological activity 3) Know the possible modes of metabolism in the body for organic functional groups 4) Know the chemical structures of important neurotransmitters or hormones and the biochemical     pathways for their syntheses and metabolism   5) Know the major biochemical events triggered by the activation of receptors important for drug action   6) Given the chemical structure of a drug, know its pharmacologic or therapeutic class   7) Given the chemical structure of a drug, know important chemical features (acid/base or lipophilic       properties, chemical groups affecting absorption, distribution, or metabolism, chemical groups      affecting potency or receptor interaction, chemical groups affecting storage or formulation)      that contribute to the drug's pharmacological activity   8) Given the chemical structure of a drug, know important chemical changes that will predictably      alter the pharmacological properties (potency, duration of action, etc.) of the drug   9) Given the chemical structure of a drug, know the important biological receptors it interacts      with and the biochemical events produced by these interactions   10) Given the common or generic name of a drug, know its pharmacologic or therapeutic class,      some of its important chemical properties (structural skeleton or chemical class, acid/base, etc.),      the receptors it interacts with and the biochemical events produced by these interactions    TEXTBOOK:  Goodman & Gilman's "The Pharmacological Basis of Therapeutics",  Tenth Edition     I. Physicochemical Properties of Drugs Related to Pharmacological Activity and Metabolism A. Organic Functional Groups in Medicinal Chemistry  1.  Physicochemical Properties     2.  Metabolic Fate   B.  Acid/Base Review     1.  Equilibrium    2.  pKa values C. Quantitative Structure-Activity Relationships 1. Concept of Linear Free Energy Relationships 2. Hydrophobicity and Log P values 3. Electronic Effects and Sigma values D.  Problem Solving in Medicinal Chemistry   II.  Biochemical Processes Affecting Drugs and Pharmacological Activity   A.  Processes Affecting Drug Distribution     1.  Non-specific binding sites and plasma protein binding    2.  Biotransformation reactions (metabolism)      B.  Processes Affecting Drug Action at the Active Site    1. Structural families of receptors    2.  Binding events initiating the pharmacological response     a.  Occupancy and conformational changes of receptor      b.  Agonist vs. antagonist events     3.  Events propagating and amplifying pharmacological response    4.  Events terminating the pharmacological response   III.  Processes and Overview of Drugs Affecting Cholinergic Receptors   A. Biochemical Events at the Cholinergic Synapse    1.  Synthesis and metabolism of acetylcholine     2.  Muscarinic and nicotinic receptors     3.  Processes following receptor activation    B.  Overview on Cholinergic Drugs   IV.  Muscarinic Receptor Agonists  A.  Chemistry of Acetylcholine    1.  Important functional groups     2.  Conformations of acetylcholine   B.  SAR and Chemistry of Selected Agonists     * METHACHOLINE  CARBACHOL  BETHANECHOL  PILOCARPINE  CEVIMELINE *     V.  Anticholinesterase Agents    A.  Mechanism of Acetylcholine Hydrolysis     1.  Individual steps involved in hydrolysis     2.  Rates of reaction steps    B.  Mechanisms of Cholinesterase Inhibition     1.  Competitive binding at active site     2.  Covalent binding at active site    C.  SAR and Chemistry of Cholinesterase Inhibitors     1.  Natural product and model agent   * PHYSOSTIGMINE *     2.  Competitive inhibitors  * EDROPHONIUM *    3.  Carbamates - "reversible" inhibitors     * NEOSTIGMINE   PYRIDOSTIGMINE *    4.  Organophosphates - "irreversible" inhibitors      * ECHOTHIOPHATE  ISOFLUROPHATE  PARATHION  MALATHION *   D.  Reactivation of Inhibited Cholinesterase    * PRALIDOXIME *    VI.  Cholinergic Antagonists   A.  Muscarinic Blocking Agents     1.  Natural product and model agent - atropine     2.  SAR and chemistry of selected antimuscarinic agents      a.  Tertiary amines       * ATROPINE  SCOPOLAMINE  HOMATROPINE         * DICYCLOMINE  CYCLOPENTOLATE *     b.  Quaternary amines       * GLYCOPYRROLATE  METHANTHELINE *      * PROPANTHELINE   IPRATROPIUM *    VII.  Agents Acting At Nicotinic Receptors   A. Properties of the Nicotinic Cholinergic Receptor   B.  Neuromuscular blocking agents     1.  Natural product and model agent   * TUBOCURARINE *    2.  Competitive agents   * MIVACURIUM   ATRACURIUM   PANCURONIUM *     3.  Depolarizing agents    * DECAMETHONIUM  SUCCINYLCHOLINE  *   C.  Ganglionic blocking agents      * HEXAMETHONIUM  TRIMETHAPHAN   MECAMYLAMINE *     VIII.  Processes and Overview of Drugs Affecting Adrenergic Receptors   A.  Biochemical Events at the Adrenergic Synapse     1.  Synthesis and storage of norepinephrine     2.  Termination and metabolism of catecholamines    3.  Alpha and beta receptors and subtypes     4.  Processes following receptor activation    B.  Overview on Adrenergic Drugs    IX.  Adrenergic Receptor Agonists   A.  Chemistry of Norepinephrine and Epinephrine     1.  Oxidative and acid/base properties     2.  Stereochemistry   B.  SAR and Chemistry of Selected Agonists     1.  Differentiating alpha and beta activity     2.  Decreasing metabolism     3.  Peripheral vs. CNS effects     4.  Direct and indirect effects      * DOPAMINE  ISOPROTERENOL  TERBUTALINE  METAPROTERENOL *     * ALBUTEROL  SALMETEROL  EPHEDRINE  PHENYLPROPANOLAMINE *     * RITODRINE   CLONIDINE   AMPHETAMINE  TETRAHYDROZOLINE *     * METHYLPHENIDATE   DOBUTAMINE   METHOXAMINE  PHENYLEPHRINE     * PHENTERMINE  FENFLURAMINE  METHYLPHENIDATE  PEMOLINE  COCAINE *    5.  Physiological and biochemical mechanisms   X.  Adrenergic Receptor Antagonists    A.  Alpha Blocking Agents     1.  Chemistry of haloalkylamines  * PHENOXYBENZAMINE *    2.  Chemistry of imidazolines  * PHENTOLAMINE   TOLAZOLINE *    3.  Selective blockers         * PRAZOSIN   TERAZOSIN   DOXAZOSIN *    B.  Beta Blocking Agents     1.  Nonselective blockers      * PROPRANOLOL  NADOLOL  TIMOLOL   PINDOLOL   CARTEOLOL *     2.  Selective blockers  * METOPROLOL  ATENOLOL  ACEBUTOLOL   ESMOLOL *     3.  Blockers with intrinsic sympathomimetic activity (ISA blockers)    4.  Combined alpha and beta blocker   * LABETALOL *   XI.  Antihistamines and Other Agents   A.  Biochemistry of Histamine Synthesis, Metabolism, and Receptors   B.  H1 receptor antagonists    * DIPHENHYDRAMINE   CHLORPHENIRAMINE  CYCLIZINE  PYRILAMINE *    * PROMETHAZINE  TERFENADINE  LORATADINE  ASTEMIZOLE  FEXOFENADINE *   C.  H2 receptor blocking agents    * CIMETIDINE  RANITIDINE  FAMOTIDINE  NIZATIDINE *   D.  Inhibitors of H+/K+ ATPase     * OMEPRAZOLE   LANSOPRAZOLE  RABEPRAZOLE  PANTOPRAZOLE *   E.  Inhibitors of histamine release    * CROMOLYN SODIUM    NEDOCROMIL SODIUM *    XII.  Local and General Anesthetics   A.  SAR and Chemistry of Local Anesthetic Agents    1.  Natural product and model compound    * COCAINE *    2.  Synthetic esters and amides        * PROCAINE  LIDOCAINE  TETRACAINE  ETIDOCAINE *     * BENZOCAINE   PRAMOXINE *   B.  Nonspecific and Specific Effects on Neural Membranes   C.  Factors Affecting Activity of Agents   D.  Adverse effects and metabolism     E.  Structure and Chemical Properties of General Anesthetic Agents    * DIETHYL ETHER   NITROUS OXIDE   HALOTHANE  ISOFLURANE *      XIII.  Sedative/Hypnotic Agents   A.  Benzodiazepines    1.  Structure, Chemical Properties, and SAR    2.  Biochemical effects     * DIAZEPAM  CHLORDIAZEPOXIDE  FLURAZEPAM  OXAZEPAM *     * TRIAZOLAM  MIDAZOLAM  LORAZEPAM   ZOLPIDEM *   B.  Barbiturates    1.  Chemical properties and SAR of agents    2.  Biochemical effects     * PHENOBARBITAL   PENTOBARBITAL   SECOBARBITAL *     * BUTABARBITAL THIOPENTAL *   C.  Non-barbiturates * CHLORAL HYDRATE  *    XIV.  Opioid Analgesic Agents   A.  Biochemistry of Endorphins, Enkephalins, and Their Receptors   B.  Natural Product and Model Agent     * MORPHINE *   C.  SAR, Stereochemistry, and Chemical Properties     1.  Chemical features of morphine    2.  N-Substituents producing agonist, partial agonist, or antagonist effects         3.  Synthetic agents    * HEROIN   HYDROMORPHONE   CODEINE   MEPERIDINE  LEVORPHANOL *    * BUTORPHANOL   METHADONE   FENTANYL   PENTAZOCINE   ETORPHINE *    * NALOXONE   NALTREXONE   DEXTROMETHORPHAN *    XV.  Antineoplastic Agents  A.  Chemistry and Mechanisms of Action for Alkylating and Cross-linking Agents * MECHLORETHAMINE  CHLORAMBUCIL  CYCLOPHOSPHAMIDE  IFOSFAMIDE *    * BUSULFAN  CARMUSTINE   LOMUSTINE  DACARBAZINE  PROCARBAZINE *   * CISPLATIN   CARBOPLATIN *   B.  Mechanisms of Action for Antimetabolite Agents   * METHOTREXATE  LEUCOVORIN  FLUOROURACIL  FLOXURIDINE *   * CYTARABINE  GEMCITABINE  CLADRIBINE PENTOSTATIN  MERCAPTOPURINE *   C.  Mechanisms of Action for Natural Products and Miscellaneous Agents   * VINCRISTINE   VINBLASTINE  PACLITAXEL  ETOPOSIDE *   *  ASPARAGINASE   HYDROXYUREA *   D.  Mechanisms of Action for Antibiotic Type Agents   * DAUNORUBICIN  DOXORUBICIN  IDARUBICIN  BLEOMYCIN *   * MITOXANTRONE  MITOMYCIN  DACTINOMYCIN *  

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PHAR 421.01: Medicinal Chemistry I

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