Controlling ADME through Chemical Design. Marty Mulvihill Chris Vulpe
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1 Controlling ADME through Chemical Design Marty Mulvihill Chris Vulpe
2 ADME
3 Chemical Processes in ADME Wang and Skolnik, Chemistry and Biodiversity, 2009, 1887.
4 Controlling toxicity through ADME Toward molecular design for hazard reduction fundamental relationships between chemical properties and toxicity Anastas et al. Tetrahedron, 2010, 1031, and Chem. Rev. 2010, 110, Highly toxic Moderately toxic
5 Molecular Property considerations Voutchkova et al.chem. Rev. 2010, 110, 5845
6 General Absorption Parameters Voutchkova et al.chem. Rev. 2010, 110, 5845
7 Absorption in Digestive Tract Parameters to Consider Particles: > 100nm Unionized or highly charged at ph 2 (eg SO 3- ) log P ow : < 0 or > 5 Molecular Weight: > 500 Da Phase: Solids absorbed less then liquids Hydrogen Bonds: Maximize to minimize abosrbtion best > 5 H-bond donors. Hydrolyzable Linkages will break in body, esp. amides and esters. - Moderately Greasy stuff gets absorbed - Charged or very soluble things get excreted. Chem. Rev. 2010, 110, 5845.
8 Oral Bioavailability and Log P
9 ph changes in digestive tract from 0-7 Need to consider ionizability of your compound
10 More absorption than expected? Lipinski Rule Violations More absorption than expected? Less absorption than expected? Lo Lipophilicity Hi Log P and Log D (ph 7.4) vs. F a for 86 commercial drugs Zhu, C.et al. Eur. J. Med. Chem. 37, pp ,2002
11 Transport mechanisms (1) passive, transcellular; (2) active or secondary active; (3) facilitated diffusion; (4) passive, paracellular; (5) absorption limited by P-gp and/or other efflux transporters; (6) intestinal first-pass metabolism followed by absorption of parent and metabolite; and (7) receptor-mediated transport. Current Industrial Practices of Assessing Permeability and P-Glycoprotein Interaction. AAPS Journal. 2006; 8(1): E1-E13.
12 Many Nutrient Transporters
13 Generic Amino Acid Glucose Phosphate
14 Example Oligopeptide Transporter Substrates dipeptides and tripeptides Model of the essential structural elements of substrates that enable them to be accommodated within the substrate-binding domain of mammalian peptide transporters TRENDS in Pharmacological Sciences Vol.23 No.9 September 2002
15 Absorption in Respiratory Tract Parameters to Consider Particles: > 5 um mass median aerodynamic diameter. Blood to Gas Partitioning P BG : < 1 Molecular Weight: > 400 Da (more importantly is a low Vapor pressure!) Vapor Pressure: < mmhg Chem. Rev. 2010, 110, 5845.
16 Chem. Rev. 2010, 110, Dermal Adsorption
17 Metabolism- CYP 450
18 Phase I and Phase II metabolism X is often: 1) Glucuronic Acid 2) Sulfate Esters 3) Glycine 4) Glutamine
19 A lot of P450s UGT indicates uridine dinucleotide phosphate (UDP) glucuronosyl transferase; FMO, flavin-containing monooxygenase; NAT, N- acetyltransferase; MAO, monoamine oxidase; P450, cytochrome P450. Contribution of individual enzyme systems to metabolism of marketed drugs Contribution of individual P450s in metabolism of drugs.
20 The mechanism of CYP-450 Chemical Reviews 2004:
21 Metabolism can increase or Decrease toxicity
22 Metabolism can increase and decrease toxicity TCE
23 Metabolism can increase or decrease toxicity
24 Structural Alerts associated with Bio-activation Annu. Rev. Pharmacol. Toxicol :145 67
25 Strategies to reduce Risk (a) eliminating the suspect functional group, (b) blocking the potential for metabolism (c) making metabolism less favorable (most frequently by use of steric hindrance or reducing oxidation potential) (d ) incorporating metabolic soft spots to direct metabolism away from the suspect group. Annu. Rev. Pharmacol. Toxicol :145 67
26 Metabolic Soft Spot Addition The metabolism of alpidem to an arene oxide which is hepatoxic. Zolpidem is a close structural analog of alpidem, but it has metabolic soft spots (benzylic methyl and N-methyl groups), which shift metabolism away from arene-oxide formation.
27 Metabolic Soft Spots
28 SmartCYP How To Interpret SMARTCyp Results Explanation of output The results are shown in form of a structure and a table for each molecule. The 3 top ranking atoms are highlighted both in the structure and table. The figure can be switched to showing atom numbers by hovering the mouse pointer over the figure. The atom numbers will be hidden if you move the pointer away from the figure. The table gives the Rank, Atom (type and number), Score, Energy, and Accessibility The atoms in the tables are ranked by Score, with the lowest score resulting in the lowest rank, and thus the highest probability of being a site of metabolism. If the score and energy are noted with a hyphen ("-"), then there is no matching energy rule. Such sites are not considered as possible sites of metabolism. While the top three sites are coloured for easier identification this does not mean there is a cutoff saying that there are always three likely sites, the score is what matters.
29 Blocking Bio-activation felbamate Add Fluorine to Methine group prevents bio-activation
30 H to Fluorine to block Bio-activation Replacement of H with F at these sites prevents bioactivation
31 Biodegradability vs. ADME design trade-offs
32 Homework Using these parameters predict the reparatory, dermal, and digestive absorption of your compounds. And predict the primary metabolite based on SMART Cyp. Note: Chemspider has all of the values you except blood/air partition ratio, which can be estimated: S B = C w ( K ow ) S B = Blood solubility (mmol/l) C w = Water solubility (mmol/l) Paterson and Mackay, British Journal of Industrial Medicine, 1989, 46:
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