10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol[codeine]

ID: ALA485

Chembl Id: CHEMBL485

Max Phase: Approved

First Approval: 1952

Molecular Formula: C18H21NO3

Molecular Weight: 299.37

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Codeine | Codeine monohydrate | Codeinum | Codeinum monohydricum | Dea no. 9050 | IDS-NC-005(SECT.-2)

Synonyms from Alternative Forms(19): Codeine Sulfate | Codeine Monohydrate | Codeine phosphate | Codeine phosphate hydrate | Codeine phosphate anhydrous | Codeine phosphate bp | Codeine phosphate hemihydrate | Codeini phosphas | Methylmorphine | Bepro | Evacode | Galcodine | Codeine phosphate cii | Codeine polistirex | 3-Methoxy-Morphanin HCl | Codeine sulfate anhydrous | Codeine sulfate trihydrate | Codeine sulphate | Codeine sulfate cii

Canonical SMILES:  COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341

Standard InChI:  InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

Standard InChI Key:  OROGSEYTTFOCAN-DNJOTXNNSA-N

Alternative Forms

Associated Targets(Human)

SCN1A Tclin Sodium channel alpha subunits; brain (Types I, II, III) (374 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Opioid receptors; mu & delta (1530 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Skin (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A1 Tchem Solute carrier family 22 member 1 (646 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT2B4 Tbio UDP-glucuronosyltransferase 2B4 (139 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (7708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A10 Tbio UDP-glucuronosyltransferase 1-10 (257 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A8 Tbio UDP-glucuronosyltransferase 1-8 (233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A3 Tbio UDP-glucuronosyltransferase 1-3 (217 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT2B7 Tchem UDP-glucuronosyltransferase 2B7 (787 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Whole blood (398 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH2 Tclin Histamine H2 receptor (5428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR7 Tclin Serotonin 7 (5-HT7) receptor (5576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD4 Tchem Dopamine D4 receptor (7907 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TACR1 Tclin Neurokinin 1 receptor (6273 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABBR1 Tclin GABA-B receptor 1 (184 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SCN5A Tclin Sodium channel protein type V alpha subunit (3462 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GIPR Tchem Gastric inhibitory polypeptide receptor (542 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKBR Tclin Cholecystokinin B receptor (3550 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GCGR Tclin Glucagon receptor (2563 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GHSR Tclin Ghrelin receptor (6229 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR2 Tclin Estrogen receptor beta (9272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKAR Tclin Cholecystokinin A receptor (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRB Tclin Endothelin receptor ET-B (1928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB1 Tchem Bradykinin B1 receptor (1859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRHR1 Tclin Corticotropin releasing factor receptor 1 (2996 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRHR2 Tchem Corticotropin releasing factor receptor 2 (399 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC3R Tchem Melanocortin receptor 3 (5659 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC4R Tclin Melanocortin receptor 4 (10016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4D Tclin Phosphodiesterase 4D (3546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY1R Tchem Neuropeptide Y receptor type 1 (5019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MLNR Tchem Motilin receptor (1724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NTSR1 Tchem Neurotensin receptor 1 (1525 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY2R Tchem Neuropeptide Y receptor type 2 (3731 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Monkey (844 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp2d1 Cytochrome P450 2D1 (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp2d26 Cytochrome P450 2D2 (12 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp2d3 Cytochrome P450 2D3 (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp2d4 Cytochrome P450 2D18 (14 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (6060 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Opioid receptor (338 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Maoa Monoamine oxidase A (498 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Maob Monoamine oxidase B (346 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (10718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei (78846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichomonas vaginalis (2376 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Toxoplasma gondii (4585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pneumocystis carinii (749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania mexicana (936 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania major (2877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania infantum (5912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania amazonensis (3813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Entamoeba histolytica (2676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptosporidium parvum (1150 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brain (4256 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsome (4459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cacna1c Voltage-gated L-type calcium channel alpha-1C subunit (1321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin1 Glutamate (NMDA) receptor subunit zeta 1 (2166 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabra1 GABA receptor alpha-1 subunit (2848 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cacna1b Voltage-gated N-type calcium channel alpha-1B subunit (471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptgs1 Cyclooxygenase-1 (1373 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ar Androgen Receptor (5522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: YesChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: Yes
Chirality: YesAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 299.37Molecular Weight (Monoisotopic): 299.1521AlogP: 1.50#Rotatable Bonds: 1
Polar Surface Area: 41.93Molecular Species: BASEHBA: 4HBD: 1
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
CX Acidic pKa: 13.78CX Basic pKa: 9.19CX LogP: 1.34CX LogD: -0.45
Aromatic Rings: 1Heavy Atoms: 22QED Weighted: 0.80Np Likeness Score: 2.27

References

1. Kotick MP, Leland DL, Polazzi JO, Howes JF, Bousquet A..  (1983)  Analgesic narcotic antagonists. 15. Potent narcotic agonist 7 beta-(arylalkyl)-4,5 alpha-epoxymorphinans.,  26  (7): [PMID:6864732] [10.1021/jm00361a019]
2. Jorgensen WL, Duffy EM..  (2000)  Prediction of drug solubility from Monte Carlo simulations.,  10  (11): [PMID:10866370] [10.1016/s0960-894x(00)00172-4]
3. Lombardo F, Obach RS, Shalaeva MY, Gao F..  (2004)  Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics.,  47  (5): [PMID:14971904] [10.1021/jm030408h]
4. Mohacsi E, Leimgruber W, Baruth H..  (1982)  Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol.,  25  (10): [PMID:6292420] [10.1021/jm00352a037]
5. Leland DL, Kotick MP..  (1980)  Analgesic narcotic antagonists. 4. 7-Methyl-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones.,  23  (12): [PMID:7192744] [10.1021/jm00186a025]
6. Kotick MP, Leland DL, Polazzi JO, Howes JF, Bousquet AR..  (1981)  Analgesic narcotic antagonists. 8. 7 alpha-Alkyl-4,5 alpha-epoxymorphinan-6-ones.,  24  (12): [PMID:7310822] [10.1021/jm00144a015]
7. Polazzi JO, Schut RN, Kotick MP, Howes JF, Osgood PF, Razdan RK, Villarreal JE..  (1980)  Analgesic narcotic antagonists. 2. 8-Alkymorphinan-6-ones.,  23  (2): [PMID:6767032] [10.1021/jm00176a013]
8. May EL..  (1980)  Third Smissman Award address: reminiscences and musings of a classical medicinal chemist.,  23  (3): [PMID:7365738] [10.1021/jm00177a001]
9. Lombardo F, Shalaeva MY, Tupper KA, Gao F..  (2001)  ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.,  44  (15): [PMID:11448232] [10.1021/jm0100990]
10. Yoshida F, Topliss JG..  (2000)  QSAR model for drug human oral bioavailability.,  43  (13): [PMID:10891117] [10.1021/jm0000564]
11. May EL..  (1992)  Alfred Burger Award address. A half century in medicinal chemistry with major emphasis on pain-relieving drugs and their antagonists.,  35  (20): [PMID:1433169] [10.1021/jm00098a001]
12. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]
13. Musso DL, Cochran FR, Kelley JL, McLean EW, Selph JL, Rigdon GC, Orr GF, Davis RG, Cooper BR, Styles VL, Thompson JB, Hall WR..  (2003)  Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity.,  46  (3): [PMID:12540239] [10.1021/jm020067s]
14. Avdeef A, Barrett DA, Shaw PN, Knaggs RD, Davis SS..  (1996)  Octanol-, chloroform-, and propylene glycol dipelargonat-water partitioning of morphine-6-glucuronide and other related opiates.,  39  (22): [PMID:8893832] [10.1021/jm960073m]
15. Hanessian S, Parthasarathy S, Mauduit M, Payza K..  (2003)  The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.,  46  (1): [PMID:12502358] [10.1021/jm020164l]
16. Flouzat C, Bresson Y, Mattio A, Bonnet J, Guillaumet G..  (1993)  Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones.,  36  (4): [PMID:8386248] [10.1021/jm00056a010]
17. Cheney BV..  (1988)  Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.,  31  (3): [PMID:2831361] [10.1021/jm00398a007]
18. Awaya H, May EL, Aceto MD, Merz H, Rogers ME, Harris LS..  (1984)  Racemic and optically active 2,9-dimethyl-5-(m-hydroxyphenyl)morphans and pharmacological comparison with the 9-demethyl homologues.,  27  (4): [PMID:6708055] [10.1021/jm00370a019]
19. Harris A, Middlemiss D, Mills K, Gower AJ, Tyers MB..  (1983)  Synthesis of exo-3-phenylbicyclo[3.2.1]oct-3-en-2-amine and related compounds as potential analgesics.,  26  (1): [PMID:6681842] [10.1021/jm00355a012]
20. McKenzie TC, Epstein JW, Fanshawe WJ, Dixon JS, Osterberg AC, Wennogle LP, Regan BA, Abel MS, Meyerson LR..  (1984)  5-Aryl-3-azabicyclo[3.2.0]heptan-6-one ketals, compounds with morphine-like analgesic activity.,  27  (5): [PMID:6325691] [10.1021/jm00371a012]
21. Leland DL, Kotick MP..  (1981)  Analgesic narcotic antagonists. 5. 7,7-Dimethyldihydrocodeinones and 7,7-dimethyldihydromorphinones.,  24  (6): [PMID:6166748] [10.1021/jm00138a015]
22. Kotick MP..  (1981)  Analgesic narcotic antagonists. 6. 7 beta, 8 beta-Methano- and 7 beta, 8 beta-epoxydihydrocodeinone.,  24  (6): [PMID:6114178] [10.1021/jm00138a016]
23. Venhorst J, ter Laak AM, Commandeur JN, Funae Y, Hiroi T, Vermeulen NP..  (2003)  Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities.,  46  (1): [PMID:12502361] [10.1021/jm0209578]
24. Tobita M, Nishikawa T, Nagashima R..  (2005)  A discriminant model constructed by the support vector machine method for HERG potassium channel inhibitors.,  15  (11): [PMID:15911273] [10.1016/j.bmcl.2005.03.080]
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