Preformulation of FK506 Prodrugs for Improving Solubility
In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506‐G or FK506‐S) such as FK506‐M32‐LS‐G (FK506‐G) and FK506‐M32‐LS‐SL (FK506‐S) were synthesized. Two prodrugs (FK506‐G or FK506‐S), including FK506, were characterized by differential scanning calorimetr...
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| Published in | Bulletin of the Korean Chemical Society Vol. 37; no. 8; pp. 1313 - 1319 |
|---|---|
| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
01.08.2016
Wiley Wiley‐VCH Verlag GmbH & Co. KGaA 대한화학회 |
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| Online Access | Get full text |
| ISSN | 1229-5949 0253-2964 1229-5949 |
| DOI | 10.1002/bkcs.10861 |
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| Abstract | In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506‐G or FK506‐S) such as FK506‐M32‐LS‐G (FK506‐G) and FK506‐M32‐LS‐SL (FK506‐S) were synthesized. Two prodrugs (FK506‐G or FK506‐S), including FK506, were characterized by differential scanning calorimetry (DSC), X‐ray diffractometry (XRD), scanning electron microscopy (SEM), enzymatic kinetics, and cytotoxicity. A phase solubility test was conducted in distilled water, and the solubility of two prodrugs (FK506‐G or FK506‐S) was measured in various pH values for pH solubility profiles. Most interesting was that FK506‐S showed the highest solubility, 866 μg/mL in water. In vitro enzymatic kinetics of two prodrugs (FK506‐G or FK506‐S) in human plasma was evaluated by measuring the decrease of FK506‐G or FK506‐S as well as the increase of FK506 by HPLC, and FK506‐G or FK506‐S was metabolized in 1 h in human plasma. Two prodrugs (FK506‐G or FK506‐S) including FK506 showed an IC50
of 336.6 μg/mL for FK506, 337.9 μg/mL for FK506‐G, or 480.1 μg/mL for FK506‐S against a conjunctive cell line, Clone 1‐5c‐4 cells. Taken together, FK506‐S could be the most optimal prodrug for aqueous preparations based on preformulation data. |
|---|---|
| AbstractList | In order to improve water solubility of a lipophilic drug, tacrolimus (
FK506
), two prodrugs (
FK506
‐G or
FK506
‐S) such as
FK506‐M32‐LS
‐G (
FK506
‐G) and
FK506‐M32‐LS‐SL
(
FK506
‐S) were synthesized. Two prodrugs (
FK506
‐G or
FK506
‐S), including
FK506
, were characterized by differential scanning calorimetry (
DSC
), X‐ray diffractometry (
XRD
), scanning electron microscopy (
SEM
), enzymatic kinetics, and cytotoxicity. A phase solubility test was conducted in distilled water, and the solubility of two prodrugs (
FK506
‐G or
FK506
‐S) was measured in various
pH
values for
pH
solubility profiles. Most interesting was that
FK506
‐S showed the highest solubility, 866 μg/
mL
in water.
In vitro
enzymatic kinetics of two prodrugs (
FK506
‐G or
FK506
‐S) in human plasma was evaluated by measuring the decrease of
FK506
‐G or
FK506
‐S as well as the increase of
FK506
by
HPLC
, and
FK506
‐G or
FK506
‐S was metabolized in 1 h in human plasma. Two prodrugs (
FK506
‐G or
FK506
‐S) including
FK506
showed an
IC
50
of 336.6 μg/
mL
for
FK506
, 337.9 μg/
mL
for
FK506
‐G, or 480.1 μg/
mL
for
FK506
‐S against a conjunctive cell line, Clone 1‐5c‐4 cells. Taken together,
FK506
‐S could be the most optimal prodrug for aqueous preparations based on preformulation data. In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506-G or FK506-S) such as FK506-M32-LS-G (FK506-G) and FK506-M32-LS-SL (FK506-S) were synthesized. Two prodrugs (FK506-G or FK506-S), including FK506, were characterized by differential scanning calorimetry (DSC), X-ray diffractometry (XRD), scanning electron microscopy (SEM), enzymatic kinetics, and cytotoxicity. A phase solubility test was conducted in distilled water, and the solubility of two prodrugs (FK506-G or FK506-S) was measured in various pH values for pH solubility profiles. Most interesting was that FK506-S showed the highest solubility, 866 μg/mL in water. In vitro enzymatic kinetics of two prodrugs (FK506-G or FK506-S) in human plasma was evaluated by measuring the decrease of FK506-G or FK506-S as well as the increase of FK506 by HPLC, and FK506-G or FK506-S was metabolized in 1 h in human plasma. Two prodrugs (FK506-G or FK506-S) including FK506 showed an IC50 of 336.6 μg/mL for FK506, 337.9 μg/mL for FK506-G, or 480.1 μg/mL for FK506-S against a conjunctive cell line, Clone 1-5c-4 cells. Taken together, FK506-S could be the most optimal prodrug for aqueous preparations based on preformulation data. KCI Citation Count: 1 In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506‐G or FK506‐S) such as FK506‐M32‐LS‐G (FK506‐G) and FK506‐M32‐LS‐SL (FK506‐S) were synthesized. Two prodrugs (FK506‐G or FK506‐S), including FK506, were characterized by differential scanning calorimetry (DSC), X‐ray diffractometry (XRD), scanning electron microscopy (SEM), enzymatic kinetics, and cytotoxicity. A phase solubility test was conducted in distilled water, and the solubility of two prodrugs (FK506‐G or FK506‐S) was measured in various pH values for pH solubility profiles. Most interesting was that FK506‐S showed the highest solubility, 866 μg/mL in water. In vitro enzymatic kinetics of two prodrugs (FK506‐G or FK506‐S) in human plasma was evaluated by measuring the decrease of FK506‐G or FK506‐S as well as the increase of FK506 by HPLC, and FK506‐G or FK506‐S was metabolized in 1 h in human plasma. Two prodrugs (FK506‐G or FK506‐S) including FK506 showed an IC50 of 336.6 μg/mL for FK506, 337.9 μg/mL for FK506‐G, or 480.1 μg/mL for FK506‐S against a conjunctive cell line, Clone 1‐5c‐4 cells. Taken together, FK506‐S could be the most optimal prodrug for aqueous preparations based on preformulation data. |
| Author | Lee, Ki-Ho Na, Young-Guk Park, Byong-Chul Lim, Si-Kyu Park, Jeong-Sook Jung, Sang-Hun Hwang, Sung-Joo Kim, Daehee Jun, Hye-Suk Cho, Cheong-Weon |
| Author_xml | – sequence: 1 givenname: Young-Guk surname: Na fullname: Na, Young-Guk organization: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Korea – sequence: 2 givenname: Hye-Suk surname: Jun fullname: Jun, Hye-Suk organization: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Korea – sequence: 3 givenname: Daehee surname: Kim fullname: Kim, Daehee organization: GeneChem Inc., Daejeon 305-343, Korea – sequence: 4 givenname: Byong-Chul surname: Park fullname: Park, Byong-Chul organization: Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Korea – sequence: 5 givenname: Si-Kyu surname: Lim fullname: Lim, Si-Kyu organization: Genotech Inc., Daejeon 305-343, Korea – sequence: 6 givenname: Ki-Ho surname: Lee fullname: Lee, Ki-Ho organization: College of Pharmacy, Korea University, Sejong 30019, Korea – sequence: 7 givenname: Sung-Joo surname: Hwang fullname: Hwang, Sung-Joo organization: College of Pharmacy, Yonsei University, Incheon 406-840, Korea – sequence: 8 givenname: Jeong-Sook surname: Park fullname: Park, Jeong-Sook organization: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Korea – sequence: 9 givenname: Sang-Hun surname: Jung fullname: Jung, Sang-Hun organization: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Korea – sequence: 10 givenname: Cheong-Weon surname: Cho fullname: Cho, Cheong-Weon email: chocw@cnu.ac.kr organization: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Korea |
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| CitedBy_id | crossref_primary_10_1016_j_ejps_2017_12_017 crossref_primary_10_3389_fbioe_2024_1351583 crossref_primary_10_1021_acsabm_2c00946 |
| Cites_doi | 10.1016/j.colsurfb.2014.03.005 10.1016/j.ijpharm.2007.07.042 10.1016/j.chemphyslip.2011.03.006 10.1002/jps.10506 10.1016/j.ijpharm.2013.12.027 10.1023/A:1018967107612 10.7164/antibiotics.40.1256 10.1097/00007890-199204000-00002 10.1016/j.jcis.2014.08.019 10.7164/antibiotics.40.1249 10.1039/C3RA44257H 10.1016/S0378-5173(03)00389-2 10.1002/jps.2600720808 10.1002/jps.20067 10.1016/S0168-3659(03)00271-2 10.1016/j.bmc.2007.04.002 10.1016/j.ejpb.2011.08.005 10.1093/annonc/mdh218 10.1016/j.jcis.2015.10.022 10.1016/j.jpba.2011.06.023 10.4049/jimmunol.139.6.1797 10.1016/S0959-8049(97)00351-1 |
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| References | M. R. Caira, Y. Robbertse, J. J. Bergh, M. Song, M. M. De Villiers, J. Pharm. Sci. 2003, 92, 2519. A. B. Jain, R. Venkataramana, E. Cadoff, J. J. Fung, S. Todo, A. Krajack, T. E. Starzl, Transplant. Proc. 1990, 22, 57. T. Higuchi, K. Connors, Adv. Anal. Chem. Instrum. 1965, 4, 117. R. Hanafi, S. Mosad, K. Abouzid, R. Nie, H. Spahn-Langguth, J. Pharm. Biomed. Anal. 2011, 56, 569. M. L. Immordino, P. Brusa, S. Arpicco, J. Control. Release 2003, 91, 417. A. Alexopoulos, M. V. Karamouzis, H. Stavrinides, Ann. Oncol. 2004, 15, 891. W. Du, L. Hong, T. Yao, X. Yang, Q. He, B. Yang, Y. Hu, Bioorg. Med. Chem. 2007, 5, 6323. Y. He, P. Li, S. H. Yalkowsky, Int. J. Pharm. 2003, 264, 25. T. Kino, H. Hatanaka, S. Miyata, J. Antibiot. (Tokyo) 1987, 40, 1256. S. H. Yalkowsky, S. C. Valvani, T. J. Roseman, J. Pharm. Sci. 1981, 72, 866. S. Jambhrunkar, S. Karmakar, A. Popat, M. Yu, C. Yu, RSC Adv. 2014b, 4, 709. M. H. Park, C. G. Keum, J. Y. Song, D. Kim, C. W. Cho, Int. J. Pharm. 2014, 462, 1. E. Soo, S. Thakur, S. Jambhrunkar, H. S. Parekh, A. Popat, J. Colloid Interface Sci. 2016, 462, 368. S. Dhaneshwar, K. Tewari, S. Joshi, D. Godbole, P. Ghosh, Chem. Phys. Lipids 2011, 164, 307. A. Kagayama, S. Tanimoto, J. Fujisaki, A. Kaibara, K. Ohara, K. Iwsaki, Y. Hirano, T. Hata, Pharm. Res. 1993, 10, 1446. P. Y. Grosse, F. Bressolle, F. Pingue, Eur. J. Cancer 1998, 34, 168. S. Sawada, G. Suzuki, Y. Kawase, F. Takaku, J. Immunol. 1987, 139, 1797. T. Honbo, M. Kobayashi, K. Hane, T. Hata, Y. Ueda, Transplant. Proc. 1987, 6, 17. A. Popat, S. Karmakar, S. Jambhrunkar, C. Xu, C. Yu, Colloids Surf. B Biointerfaces 2014, 117, 520. T. Kino, H. Hatanaka, M. Hashmoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Apla, H. Imanaka, J. Antibiot. (Tokyo) 1987, 40, 1249. M. L. Branham, T. Moyo, T. Govender, Eur. J. Pharm. Biopharm. 2012, 80, 194. H. Fukukawa, O. Imventarza, R. Venkataramana, M. Suzuki, Y. Zhu, V. S. Warty, J. Fung, S. Todo, T. E. Starzl, Transplantation 1992, 53, 722. J. J. Kim, J. S. Woo, S. K. Kim, D. H. Kim, S. Y. Kang, M. O. Lee, B. M. Lee, T. H. Youm, K. H. Lee, C. W. Cho, B. C. Park, Korean Patent 2013, 10. A. Swaminathan, G. Burckart, R. Venkataramanan, Pharm. Res. 1993, 10, S389. T. Kino, N. Inamura, F. Sakai, Transplant. Proc. 1987, 19, 36. K. Kawakami, K. Miyoshi, Y. Ida, J. Pharm. Sci. 2004, 93, 1471. S. Jambhrunkar, Z. Qu, A. Popat, S. Karmakar, C. Xu, C. Yu, J. Colloid Interface Sci. 2014a, 434, 218. Q. Mekki, C. Lee, S. Carrier, G. Klintmalm, M. Shaefer, P. Burke, P. Schechte, Clin. Pharmacol. Ther. 1994, 53, 229. A. Nornoo, D. W. Osborne, D. S. Chow, Int. J. Pharm. 2008, 349, 108. J. S. Woo, K. H. Lee, B. C. Park, C. W. Cho, S. Y. Kang, D. H. Kim, W. M. Seo, J. Y. Yang, S. W. Paek, S. M. Lee, S. E. Yoo, Korean Patent 2011, 10. 2014b; 4 2014; 117 2012; 80 2011 1987; 6 2014a; 434 2008; 349 2016; 462 2011; 56 1992; 53 1987; 19 1990; 22 1987; 40 2003; 91 2004; 93 2003; 92 1987; 139 1993; 10 2004; 15 1965; 4 2007; 5 2013 1981; 72 2014; 462 1998; 34 2003; 264 1994; 53 2011; 164 e_1_2_5_27_1 e_1_2_5_28_1 e_1_2_5_26_1 e_1_2_5_24_1 e_1_2_5_21_1 Honbo T. (e_1_2_5_6_1) 1987; 6 e_1_2_5_22_1 Jain A. B. (e_1_2_5_7_1) 1990; 22 Kino T. (e_1_2_5_5_1) 1987; 19 Higuchi T. (e_1_2_5_25_1) 1965; 4 e_1_2_5_29_1 Swaminathan A. (e_1_2_5_10_1) 1993; 10 Mekki Q. (e_1_2_5_11_1) 1994; 53 Woo J. S. (e_1_2_5_30_1) 2011 e_1_2_5_20_1 e_1_2_5_15_1 e_1_2_5_14_1 e_1_2_5_17_1 e_1_2_5_9_1 e_1_2_5_16_1 e_1_2_5_8_1 e_1_2_5_13_1 e_1_2_5_12_1 e_1_2_5_4_1 e_1_2_5_3_1 e_1_2_5_2_1 e_1_2_5_19_1 e_1_2_5_18_1 Kim J. J. (e_1_2_5_23_1) 2013 e_1_2_5_31_1 |
| References_xml | – reference: H. Fukukawa, O. Imventarza, R. Venkataramana, M. Suzuki, Y. Zhu, V. S. Warty, J. Fung, S. Todo, T. E. Starzl, Transplantation 1992, 53, 722. – reference: S. Sawada, G. Suzuki, Y. Kawase, F. Takaku, J. Immunol. 1987, 139, 1797. – reference: E. Soo, S. Thakur, S. Jambhrunkar, H. S. Parekh, A. Popat, J. Colloid Interface Sci. 2016, 462, 368. – reference: A. Nornoo, D. W. Osborne, D. S. Chow, Int. J. Pharm. 2008, 349, 108. – reference: S. Jambhrunkar, S. Karmakar, A. Popat, M. Yu, C. Yu, RSC Adv. 2014b, 4, 709. – reference: K. Kawakami, K. Miyoshi, Y. Ida, J. Pharm. Sci. 2004, 93, 1471. – reference: Y. He, P. Li, S. H. Yalkowsky, Int. J. Pharm. 2003, 264, 25. – reference: A. Alexopoulos, M. V. Karamouzis, H. Stavrinides, Ann. Oncol. 2004, 15, 891. – reference: A. Swaminathan, G. Burckart, R. Venkataramanan, Pharm. Res. 1993, 10, S389. – reference: P. Y. Grosse, F. Bressolle, F. Pingue, Eur. J. Cancer 1998, 34, 168. – reference: S. Dhaneshwar, K. Tewari, S. Joshi, D. Godbole, P. Ghosh, Chem. Phys. Lipids 2011, 164, 307. – reference: T. Kino, N. Inamura, F. Sakai, Transplant. Proc. 1987, 19, 36. – reference: T. Honbo, M. Kobayashi, K. Hane, T. Hata, Y. Ueda, Transplant. Proc. 1987, 6, 17. – reference: M. L. Immordino, P. Brusa, S. Arpicco, J. Control. Release 2003, 91, 417. – reference: W. Du, L. Hong, T. Yao, X. Yang, Q. He, B. Yang, Y. Hu, Bioorg. Med. Chem. 2007, 5, 6323. – reference: J. S. Woo, K. H. Lee, B. C. Park, C. W. Cho, S. Y. Kang, D. H. Kim, W. M. Seo, J. Y. Yang, S. W. Paek, S. M. Lee, S. E. Yoo, Korean Patent 2011, 10. – reference: R. Hanafi, S. Mosad, K. Abouzid, R. Nie, H. Spahn-Langguth, J. Pharm. Biomed. Anal. 2011, 56, 569. – reference: A. Kagayama, S. Tanimoto, J. Fujisaki, A. Kaibara, K. Ohara, K. Iwsaki, Y. Hirano, T. Hata, Pharm. Res. 1993, 10, 1446. – reference: A. Popat, S. Karmakar, S. Jambhrunkar, C. Xu, C. Yu, Colloids Surf. B Biointerfaces 2014, 117, 520. – reference: T. Higuchi, K. Connors, Adv. Anal. Chem. Instrum. 1965, 4, 117. – reference: Q. Mekki, C. Lee, S. Carrier, G. Klintmalm, M. Shaefer, P. Burke, P. Schechte, Clin. Pharmacol. Ther. 1994, 53, 229. – reference: S. Jambhrunkar, Z. Qu, A. Popat, S. Karmakar, C. Xu, C. Yu, J. Colloid Interface Sci. 2014a, 434, 218. – reference: T. Kino, H. Hatanaka, S. Miyata, J. Antibiot. (Tokyo) 1987, 40, 1256. – reference: A. B. Jain, R. Venkataramana, E. Cadoff, J. J. Fung, S. Todo, A. Krajack, T. E. Starzl, Transplant. Proc. 1990, 22, 57. – reference: S. H. Yalkowsky, S. C. Valvani, T. J. Roseman, J. Pharm. Sci. 1981, 72, 866. – reference: J. J. Kim, J. S. Woo, S. K. Kim, D. H. Kim, S. Y. Kang, M. O. Lee, B. M. Lee, T. H. Youm, K. H. Lee, C. W. Cho, B. C. Park, Korean Patent 2013, 10. – reference: M. R. Caira, Y. Robbertse, J. J. Bergh, M. Song, M. M. De Villiers, J. Pharm. Sci. 2003, 92, 2519. – reference: M. H. Park, C. G. Keum, J. Y. Song, D. Kim, C. W. Cho, Int. J. Pharm. 2014, 462, 1. – reference: T. Kino, H. Hatanaka, M. Hashmoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Apla, H. Imanaka, J. Antibiot. (Tokyo) 1987, 40, 1249. – reference: M. L. Branham, T. Moyo, T. Govender, Eur. J. Pharm. Biopharm. 2012, 80, 194. – volume: 19 start-page: 36 year: 1987 publication-title: Transplant. Proc. – volume: 264 start-page: 25 year: 2003 publication-title: Int. J. Pharm. – volume: 4 start-page: 709 year: 2014b publication-title: RSC Adv. – volume: 34 start-page: 168 year: 1998 publication-title: Eur. J. Cancer – volume: 4 start-page: 117 year: 1965 publication-title: Adv. Anal. Chem. Instrum. – start-page: 10 year: 2011 publication-title: Korean Patent – volume: 93 start-page: 1471 year: 2004 publication-title: J. Pharm. Sci. – volume: 15 start-page: 891 year: 2004 publication-title: Ann. Oncol. – start-page: 10 year: 2013 publication-title: Korean Patent – volume: 22 start-page: 57 year: 1990 publication-title: Transplant. Proc. – volume: 139 start-page: 1797 year: 1987 publication-title: J. Immunol. – volume: 40 start-page: 1249 year: 1987 publication-title: J. Antibiot. (Tokyo) – volume: 10 start-page: 1446 year: 1993 publication-title: Pharm. Res. – volume: 434 start-page: 218 year: 2014a publication-title: J. Colloid Interface Sci. – volume: 462 start-page: 368 year: 2016 publication-title: J. Colloid Interface Sci. – volume: 164 start-page: 307 year: 2011 publication-title: Chem. Phys. Lipids – volume: 10 start-page: S389 year: 1993 publication-title: Pharm. Res. – volume: 53 start-page: 229 year: 1994 publication-title: Clin. Pharmacol. Ther. – volume: 92 start-page: 2519 year: 2003 publication-title: J. Pharm. Sci. – volume: 6 start-page: 17 year: 1987 publication-title: Transplant. Proc. – volume: 349 start-page: 108 year: 2008 publication-title: Int. J. Pharm. – volume: 117 start-page: 520 year: 2014 publication-title: Colloids Surf. B Biointerfaces – volume: 5 start-page: 6323 year: 2007 publication-title: Bioorg. Med. Chem. – volume: 462 start-page: 1 year: 2014 publication-title: Int. J. Pharm. – volume: 40 start-page: 1256 year: 1987 publication-title: J. Antibiot. (Tokyo) – volume: 53 start-page: 722 year: 1992 publication-title: Transplantation – volume: 80 start-page: 194 year: 2012 publication-title: Eur. J. Pharm. Biopharm. – volume: 91 start-page: 417 year: 2003 publication-title: J. Control. Release – volume: 56 start-page: 569 year: 2011 publication-title: J. Pharm. Biomed. Anal. – volume: 72 start-page: 866 year: 1981 publication-title: J. Pharm. Sci. – ident: e_1_2_5_20_1 doi: 10.1016/j.colsurfb.2014.03.005 – ident: e_1_2_5_26_1 doi: 10.1016/j.ijpharm.2007.07.042 – ident: e_1_2_5_31_1 doi: 10.1016/j.chemphyslip.2011.03.006 – ident: e_1_2_5_28_1 doi: 10.1002/jps.10506 – start-page: 10 year: 2011 ident: e_1_2_5_30_1 publication-title: Korean Patent – ident: e_1_2_5_24_1 doi: 10.1016/j.ijpharm.2013.12.027 – volume: 10 start-page: S389 year: 1993 ident: e_1_2_5_10_1 publication-title: Pharm. Res. – ident: e_1_2_5_18_1 doi: 10.1023/A:1018967107612 – ident: e_1_2_5_4_1 doi: 10.7164/antibiotics.40.1256 – ident: e_1_2_5_8_1 doi: 10.1097/00007890-199204000-00002 – volume: 6 start-page: 17 year: 1987 ident: e_1_2_5_6_1 publication-title: Transplant. Proc. – ident: e_1_2_5_21_1 doi: 10.1016/j.jcis.2014.08.019 – ident: e_1_2_5_2_1 doi: 10.7164/antibiotics.40.1249 – ident: e_1_2_5_19_1 doi: 10.1039/C3RA44257H – volume: 19 start-page: 36 year: 1987 ident: e_1_2_5_5_1 publication-title: Transplant. Proc. – ident: e_1_2_5_16_1 doi: 10.1016/S0378-5173(03)00389-2 – volume: 4 start-page: 117 year: 1965 ident: e_1_2_5_25_1 publication-title: Adv. Anal. Chem. Instrum. – volume: 53 start-page: 229 year: 1994 ident: e_1_2_5_11_1 publication-title: Clin. Pharmacol. Ther. – start-page: 10 year: 2013 ident: e_1_2_5_23_1 publication-title: Korean Patent – ident: e_1_2_5_17_1 doi: 10.1002/jps.2600720808 – ident: e_1_2_5_9_1 doi: 10.1002/jps.20067 – volume: 22 start-page: 57 year: 1990 ident: e_1_2_5_7_1 publication-title: Transplant. Proc. – ident: e_1_2_5_12_1 doi: 10.1016/S0168-3659(03)00271-2 – ident: e_1_2_5_14_1 doi: 10.1016/j.bmc.2007.04.002 – ident: e_1_2_5_29_1 doi: 10.1016/j.ejpb.2011.08.005 – ident: e_1_2_5_13_1 doi: 10.1093/annonc/mdh218 – ident: e_1_2_5_22_1 doi: 10.1016/j.jcis.2015.10.022 – ident: e_1_2_5_27_1 doi: 10.1016/j.jpba.2011.06.023 – ident: e_1_2_5_3_1 doi: 10.4049/jimmunol.139.6.1797 – ident: e_1_2_5_15_1 doi: 10.1016/S0959-8049(97)00351-1 |
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| Snippet | In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506‐G or FK506‐S) such as FK506‐M32‐LS‐G (FK506‐G) and... In order to improve water solubility of a lipophilic drug, tacrolimus ( FK506 ), two prodrugs ( FK506 ‐G or FK506 ‐S) such as FK506‐M32‐LS ‐G ( FK506 ‐G) and... In order to improve water solubility of a lipophilic drug, tacrolimus (FK506), two prodrugs (FK506-G or FK506-S) such as FK506-M32-LS-G (FK506-G) and... |
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| Title | Preformulation of FK506 Prodrugs for Improving Solubility |
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