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Lymphatic Drug Transport
Lymphatic transport approach is taken for facilitating enhanced uptake of the drug into the body’s lymphocytes. Current studies demonstrate the enhancement of immunomodulatory effects by the delivery of the drug into lymphocytes that reside in lymph. Different classes of lymph-directing pro-drugs can be synthesized. One is the alkyl chain derivatives, like octadecyl mycophenolamide (MPA-C18AM), octadecyl mycophenolate (MPA-C18E) and octyl mycophenolate (MPA-C8E). This is for promotion of passive partitioning in lymphatic pathways of transport into lipids. The other one is a triglyceride mimetic pro-drug (1,3-dipalmitoyl-2-mycophenoloyl glycerol, 2-MPA-TG) that is used for facilitating metabolism into triglyceride reacylation -deacylation pathways (2). One effective strategy for enhancing the effectiveness of lymphatic drug transport is the usage of the lipidic pro-drug. It may be the triglyceride mimetic pro-drug. Fatty acid substituents are present at the 1- and 3- positions in the triglyceride pro-drug. This results in rapid metabolism in contrast to slow hydrolysis when the position is at 2-position. These triglycerides mimetic pro-drugs have the feature of being metabolically stable, unlike the pro-drugs that are simple fatty acid ester linked. This allows the reasonable absorption in the enterocytes. Integration into triglyceride synthesis pathways occurs due to which there is the production of MPA monoglyceride (MPA-MG) which have less molecular weight and good permeability. MPA-MG is synthesized again along with lipids. This makes the drugs to partition into the intestinal lipoproteins. This is for transport of the lymphatic drug (3).
This is evident from a research (1). In the study, Plasma pharmacokinetics, lymphocyte uptake and lymphatic transport were assessed in rats after lipid-based formulations being infused intraduodenally. These formulations had MPA pro-drugs. The rats were administered with 2,3-dipalmitoyl-2-mycophenolic acid glycerol (2-MPA-TG), which is a triglyceride mimetic pro-drug. An 80 fold increase was found in the transport of 2-MPA-TG, i.e. 13.4% of the dose, whereas the parent MPA was 0.17% of the dose. The subsequent result is increased the amount of MPA derivatives. A significant development in MPA was also observed in the nodes of mesenteric lymph. This was achieved after the conversion into the active form of the pro-drug. The lymph system is known to be rich in its content of lymphocyte. Thus, an increase in the immunomodulator MPA-TGA can enhance the therapeutic value of it. The data indicates that triglyceride mimetic prodrugs enhance the immunotherapy by targeting the drug to lymph nodes and lymphocytes.
MPA C 18 alkyl chain derivatives and testosterone undecanoate are not useful to be used as a drug because they have the characteristics of poor absorption and rapid hydrolysis. Testosterone undecanoate is an ester of testosterone. Intestinal lymphatic delivery is achieved by it, but the level is not good when compared to triglyceride mimetic. They have hyaluronidase, oxidative, and thermal degradation. Esterases lead to fast hydrolysis of the different ester linkages as esterases are pervasive in the body. Poor absorption is a result of the additional weight of molecules that has an association with the fatty acids that are substituted in nature (4).
1. Han S, Quach T, Hu L, Wahab A, Simpson J. Targeted delivery of a model immunomodulator to the lymphatic system: Comparison of alkyl ester versus triglyceride mimetic lipid prodrug strategies. Journal of controlled release. 2014;177(10):1-10.
2. Trevaskis N, Caliph S, Nguyen G, Tso P, Charman W, Porter C. A Mouse Model to Evaluate the Impact of Species, Sex, and Lipid Load on Lymphatic Drug Transport. Pharm Res. 2013;30(12):3254-3270.
3. Caliph S, Trevaskis N, Charman W, Porter C. Intravenous dosing conditions may affect systemic clearance for highly lipophilic drugs: Implications for lymphatic transport and absolute bioavailability studies. Journal of Pharmaceutical Sciences. 2012;101(9):3540-3546.
4. Ullrich T. 3-Alkoxy-pyrrolo[1,2-b]pyrazolines as Selective Androgen Receptor Modulators with Ideal Physicochemical Properties for Transdermal Administration - Journal of Medicinal Chemistry (ACS Publications) [Internet]. Pubs.acs.org. 2015 [cited 18 August 2015]. Available from: http://pubs.acs.org/doi/abs/10.1021/jm5009049
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