About the Author

Richard L. Apodaca is a software developer and Ph.D. chemist living in La Jolla, California. His company, Metamolecular, creates innovative solutions to chemical information problems.

E-mail: rich.apodaca@gmail.com

Education and Work

Peer-Reviewed Publications

  1. John M. Keith; Mark S. Tichenor; Richard L. Apodaca; Wei Xiao; William M. Jones; Mark Seierstad; Joan M. Pierce; James A.Palmer; Michael Webb; Mark J. Karbarz; Brian P. Scott; Sandy J. Wilson; Michelle L. Wennerholm; Michele Rizzolio; Raymond Rynberg; Sandra R.Chaplan; J. Guy Breitenbucher The SAR of brain penetration for a series of heteroaryl urea FAAH inhibitors Bioorg. Med Chem. Lett. 2016, 26, 3109-3114.
  2. Michael A. Letavic; Leah Aluisio; Richard Apodaca; Manoj Bajpai; Ann J. Barbier; Anne Bonneville; Pascal Bonaventure; Nicholas I. Carruthers; Christine Dugovic; Ian C. Fraser; Michelle L. Kramer; Brian Lord; Timothy W. Lovenberg; Lilian Y. Li; Kiev S. Ly; Heather Mcallister; Neelakandha S. Mani; Kirsten L. Morton; Anthony Ndifor; S. Diane Nepomuceno; Chennagiri R. Pandit; Steven B. Sands; Chandra R. Shah; Jonathan E. Shelton; Sandra S. Snook; Devin M. Swanson; and Wei Xiao Novel Benzamide-Based Histamine H3 Receptor Antagonists: The Identification of Two Candidates for Clinical Development ACS Med. Chem. Lett. 2015, 6, 450-454.
  3. John M.Keith; Natalie Hawryluk; Richard L. Apodaca; Allison Chambers; Joan M. Pierce; Mark Seierstad; James A. Palmer; Michael Webb; Mark J.Karbarz; Brian P. Scott; Sandy J. Wilson; Lin Luo; Michelle L. Wennerholm; Leon Chang; Michele Rizzolio; Sandra R. Chaplan; J. Guy Breitenbucher 1-Aryl-2-((6-aryl)pyrimidin-4-yl)amino)ethanols as competitive inhibitors of fatty acid amide hydrolase Bioorg. Med. Chem. Lett. 2014, 24, 1280-1284.
  4. Williams, Antony K.; Ekins, Sean; Clark, Alex M.; Jack, James; Apodaca, Richard L. Mobile apps for chemistry in the world of drug discovery Drug Discovery Today 2011, 16, 928.
  5. Karbarz, M.J.; Luo, L.; Chang, L.; Tham, C-S; Palmer, J.A.; Wilson, S.J.; Wennerholm, M.L.; Brown, S.M.; Scott, B.P.; Apodaca, R.L.; Keith, J.M.; Wu, J.; Breitenbucher, J.G.; Chaplan, S.R.; Webb, M. Biochemical and Biological Properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a Mechanism-Based Inhibitor of Fatty Acid Amide Hydrolase Anesth. Analg. 2009, 108, 316-329.
  6. Keith, J.M.; Apodaca, R.; Xiao, W.; Seierstad, M.; Pattabiraman, K.; Wu, J.; Webb, M.; Karbarz, M.J.; Brown, S.; Wilson, S.; Scott, B.; Tham, Cc; Luo, L.; Palmer, J.; Wennerholm, M.; Chaplan, S.; Breitenbucher, J.G. Thiadiazolopiperazinyl ureas as inhibitors of fatty acid amide hydrolase Bioorg. Med. Chem. Lett. 2008, 18, 4838-4843.
  7. Bembenek, S.D.; Keith, J.M.; Letavic, M.A.; Apodaca, R.; Barbier, A.J.; Dvorak, L.; Aluisio, L.; Miller, K.L.; Lovenberg, T.W.; Carruthers, N.I. Lead identification of acetylcholinesterase inhibitors–histamine H3 receptor antagonists from molecular modeling Bioorg. Med. Chem. 2008, 16, 2968-2937.
  8. Timmons, A.; Seierstad, M.; Apodaca, R.; Epperson, M.; Pippel, D.; Brown, S.; Chang, L.; Scott, B.; Webb, M.; Chaplan, S.R.; Breitenbucher, J.G. Novel ketooxazole based inhibitors of fatty acid amide hydrolase (FAAH) Bioorg. Med. Chem. Lett. 2008, 18, 2109-2113.
  9. Romero, F.A.; Du, W.; Hwang, I.; Rayl, T.J.; Kimball, F. S.; Leung, D.; Hoover, H.S.; Apodaca, R.L.; Breitenbucher, J.G.; Cravatt, B.F.; Boger, D. L. Potent and Selective α-Ketoheterocycle-Based Inhibitors of the Anandamide and Oleamide Catabolizing Enzyme, Fatty Acid Amide Hydrolase J. Med. Chem. 2007, 50, 1058-1068.
  10. Swanson, D.M.; Wilson, S.J.; Boggs, J.D.; Xiao, W.; Apodaca, R.; Barbier, A.J.; Lovenberg, T.W.; Carruthers, N.I. Aplysamine-1 and Related Analogs as Histamine H3 Receptor Antagonists. Bioorg. Med. Chem. Lett. 2006, 16, 897-900.
  11. Dvorak, C. A.; Apodaca, R.; Barbier, A.J.; Berridge, C.W.; Wilson, S.J.; Boggs, J.D.; Xiao, W.; Lovenberg, T.W; Carruthers, N.I. 4-Phenoxypiperidines: Potent, Conformationally Restricted, Non-Imidazole Histamine H3 Antagonists. J. Med. Chem. 2005, 48, 2229-2238.
  12. Barbier, A.J.; Berridge, C.; Dugovic, C.; Laposky, A.D.; Wilson, S.J.; Boggs, J.; Aluisio, L.; Lord, B.; Mazur, C.; Pudiak, C.M.; Langlois, X.; Xiao, W.; Apodaca, R.; Carruthers, N.I.; Lovenberg, T.W. Acute wake-promoting actions of JNJ-5207852, a novel, diamine-based H3 antagonist. Br. J. Pharmacol. 2004, 143, 649-661.
  13. Apodaca, Richard; Dvorak, Curt A.; Xiao, Wei; Barbier, Ann J.; Boggs, Jamin D.; Wilson, Sandy J.; Lovenberg, Timothy W.; Carruthers, Nicholas I. A New Class of Diamine-Based Human Histamine H3 Receptor Antagonists: 4-(Aminoalkoxy)benzylamines. J. Med. Chem. 2003, 46, 3938-3944.
  14. Apodaca, R.; Xiao, W. Direct Reductive Amination of Aldehydes and Ketones: Catalysis by Dibutyltin Dichloride. Org. Lett. 2001, 3, 1745-1748.
  15. Lynch, Vincent M.; Apodaca, Richard; Whitesell, James K.; Chou, Ming I. Trans-(R,R)-2,2'-(cyclopenta-1,2-diyl)diphenyl bis[(R)-O-methylmandelate]. Acta Crystallographica, Section C: Crystal Structure Communications 1998, 10, C54.
  16. Apodaca R. Comprehensive Organic Functional Group Transformations. (Book Review) J. Am. Chem Soc. 1997, 119, 2343.
  17. Whitesell, J.K.; Apodaca, R. Synthesis and Resolution of a New Chiral C2‑Symmetrical Bisphenol: trans-1,2-Bis(2-hydroxyphenyl)cyclopentane. Tetrahedron Lett. 1997, 38, 2589-2592.
  18. Whitesell, J.K.; Apodaca, R. A Convenient Synthesis of Protected and Free Homallylic Alcohols: Catalytic Use of Dibutyltin Dichloride in the Allylation of Aldehydes with Allyltributyltin. Tetrahedron Lett. 1996, 37, 3955-3958.
  19. Whitesell, J.K.; Apodaca, R. Trimethylsilylcyanation of Aldehydes and Ketones Catalyzed by Diorganotin Dichlorides. Tetrahedron Lett. 1996, 37, 2525-2528.

Issued Patents

  1. Richard Apodaca, J. Guy Breitenbucher, Kanaka Pattabiraman, Mark Seierstad, Wei Xiao Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase US 9,169,224
  2. Natalie A. Hawryluk J. Guy Breitenbucher William M. Jones Alison L. Chambers John M. Keith Mark Seierstad Ethylene diamine modulators of fatty acid hydrolase US 8,906,914
  3. Richard Apodaca, J. Guy Breitenbucher, Alison L. Chambers, Xiaohu Deng, Natalie A. Hawryluk, John M. Keith, Neelakandha S. Mani, Jeffrey E. Merit, Joan M. Pierce, Mark Seierstad, Wei Xiao Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase US 8,598,202
  4. Richard Apodaca, J. Guy Breitenbucher, Kanaka Pattabiraman, Mark Seierstad, Wei Xiao Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase US 8,530,476
  5. Apodaca; Richard, Barbier; Ann J.; Carruthers; Nicholas I.; Gomez; Leslie A.; Keith; John M., Lovenberg; Timothy W., Wolin; Ronald L. Hexahydro-pyrrolo-isoquinoline compounds US 8,273,762
  6. Apodaca; Richard, Barbier; Ann J., Carruthers; Nicholas I., Gomez; Leslie A., Keith; John M., Lovenberg; Timothy W., Wolin; Ronald L. Hexahydro-pyrrolo-isoquinoline compounds US 7,754,882
  7. Apodaca; Richard, Breitenbucher; J. Guy, Pattabiraman; Kanaka, Seierstad; Mark, Xiao; Wei Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase US 7,598,249
  8. Apodaca; Richard, Breitenbucher; J. Guy, Pattabiraman; Kanaka, Seierstad; Mark, Xiao; Wei N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase US 7,541,359
  9. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,482,364
  10. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,446,104
  11. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Rudolph; Dale A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxyalkylamines US 7,429,586
  12. Apodaca; Richard L., Jablonowski; Jill A., Ly; Kiev S., Shah; Chandravadan R., Swanson; Devin M., Xiao; Wei Piperazinyl and diazapanyl benzamides and benzthioamides US 7,414,047
  13. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,288,540
  14. Apodaca; Richard L., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Phenylpiperidines and phenylpyrrolidines US 7,279,491
  15. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxypiperidines US 7,241,778
  16. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Rudolph; Dale A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxyalkylamines US 7,186,732
  17. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxypiperidines US 7,071,191
  18. Apodaca; Richard, Xiao; Wei, Jablonowski; Jill A. Phenylalkynes US 6,884,803

Patent Applications

  1. Apodaca, Richard; Barbier, Ann J.; Carruthers, Nicholas I.; Gomez, Leslie A.; Keith, John M.; Lovenberg, Timothy W.; Wolin, Ronald L. Hexahydro-pyrrolo-isoquinoline Compounds US 20120321559
  2. Apodaca, Richard; Breitenbucher, J., Guy; Chambers, Alison, L.; Deng, Xiaohu; Hawryluk, Natalie, A.; Keith, John, M.; Mani, Neelakandha, S.; Merit, Jeffrey, E.; Pierce, Joan, M.; Seierstad, Mark; Xiao, Wei Aryl - Hydroxyethylamino - Pyrimidines and Triazines as Modulators of Fatty Acid amide Hydrolase. WO 2009/105220
  3. Apodaca, Richard; Breitenbucher, J., Guy; Hawryluk, Natalie, A.; Jones, William, M.; Keith, John, M.; Merit, Jeffrey, E.; Tichenor, Mark, S.; Timmons, Amy, K. Heteroaryl-Substituted Urea Modulators of Fatty Acid Amide Hydrolase. WO 2008153752
  4. Apodaca, Richard; Breitenbucher, J. Guy; Pattabiraman, Kanaka; Seierstad, Mark; Xiao, Wei. Preparation of thiadiazolylpiperazinecarboxamides as modulators of fatty acid amide hydrolase (FAAH). US 2007004741
  5. Apodaca, Richard; Breitenbucher, James, Guy; Chambers, Alison L.; Seierstad, Mark; Xiao, Wei Oxazolyl Piperidine Modulators of Fatty Acid Amide Hydrolase WO 2007140005
  6. Apodaca, Richard; Breitenbucher, J., Guy; Epperson, Matthew, T.; Fried, Amy, K.; Pippel, Daniel, J.; Seierstad, Mark 2-Keto-Oxazoles as Modulators of Fatty Acid Amide Hydrolase WO 2007061862
  7. Apodaca, Richard; Breitenbucher, J., Guy; Pattabiraman, Kanaka; Seierstad, Mark; Xiao, Wei N-Heteroarylpiperazinly Ureas as Modulators of Fatty Acid Amide Hydrolase WO 2007005510
  8. Apodaca, Richard; Barbier, Ann J.; Carruthers, Nicholas I.; Gomez, Leslie A.; Keith, John M.; Lovenberg, Timothy W.; Wolin, Ronald L. Hexahydropyrroloisoquinoline compounds as histamine H3 receptor and serotonin transporter modulators and their preparation, pharmaceutical compositions and use in the treatment of CNS disorders WO 2006138604
  9. Apodaca, Richard; Breitenbucher, J. Guy; Pattabiraman, Kanaka; Seierstad, Mark; Xiao, Wei. Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase WO 2006074025
  10. Apodaca, Richard L.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of phenylpiperidines and phenylpyrrolidines as histamine H3 receptor inhibitors US 2004087573
  11. Apodaca, Richard L.; Jablonowski, Jill A.; Ly, Kiev S.; Shah, Chandravadan R.; Swanson, Devin M.; Xiao, Wei. Preparation of piperazinyl and diazepanyl benzamides and benzothioamides as inhibitors of histamine H3 receptor WO 2004037801
  12. Apodaca, Richard L.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of phenylpiperidines and phenylpyrrolidines as histamine H3 receptor modulators WO 2004037257
  13. Apodaca, Richard; Deng, Xiaohu; Jablonowski, Jill A.; Mani, Neelakandha; Pandit, Chennagiri R.; Xiao, Wei. Preparation of substituted phenylalkynes as H3 receptor ligands US 2004002604
  14. Apodaca, Richard; Xiao, Wei; Jablonoski, Jill A. Preparation of substituted phenylalkynes for use in histamine-mediated disorders 2003050099
  15. Apodaca, Richard; Carruthers, Nicholas I.; Carson, John R.; Chai, Wenying; Kwok, Annette K.; Li, Xiaobing; Lovenberg, Timothy W.; Rudolph, Dale A.; Shah, Chandravadan R. Octahydroindolizine and quinolizine and hexahydropyrrolizine derivatives as histaminic H1 and H3 antagonists WO 2002024695
  16. Apodaca, Richard; Carruthers, Nicholas I.; Dvorak, Curt A.; Rudolph, Dale A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of non-imidazole aryloxyalkylamines as histamine H3 receptor antagonists. WO 2002012214
  17. Apodaca, Richard; Carruthers, Nicholas I.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of aryloxypiperidines as histamine H3 receptor antagonists WO 2002012190