Adefovir | PMEA | GS-0393 | DNA polymerase inhibitor | CAS#106941-25-7

MedKoo Cat#: 529002 | Name: Adefovir

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Adefovir, also known as PMEA and GS-0393, is a DNA polymerase inhibitor known as a landmark medication for the treatment of chronic Hepatitis B virus infection. It had significantly less resistance accumulation and side effects than other therapies available. In hepatitis B e antigen-negative chronic hepatitis B, adefovir dipivoxil, its prodrug, was recently found to maintain its efficacy even after 3 years of therapy. Adefovir dipivoxil is effective in patients with compensated or decompensated chronic viral B liver disease, and in pre- and post-transplant hepatitis B virus patients who develop resistance to lamivudine. It is well-tolerated and safe even after the third year of long-term therapy, and is associated with low rates of viral resistance. All these characteristics make adefovir dipivoxil an important drug for the treatment of hepatitis B virus infection and an excellent candidate for long-term maintenance therapy in chronic viral B liver disease.

Chemical Structure

Adefovir

CAS#106941-25-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 529002

Name: Adefovir

CAS#: 106941-25-7 (free acid)

Chemical Formula: C8H12N5O4P

Exact Mass: 273.0627

Molecular Weight: 273.18

Elemental Analysis: C, 35.17; H, 4.43; N, 25.64; O, 23.43; P, 11.34

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks

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Related CAS #

142340-99-6 (dipivoxil) 106941-25-7 (free acid) 129556-87-2 (monophosphate)

Synonym

GS-0393; GS-393; GS0393; GS393; GS 0393; GS 393; PMEA; Adefovir

IUPAC/Chemical Name

((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid

InChi Key

SUPKOOSCJHTBAH-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

SMILES Code

NC1=C2N=CN(CCOCP(O)(O)=O)C2=NC=N1

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 273.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Yamamoto T, Maruyama Y, Ohashi N, Yasuda H, Shinozaki M. Hypophosphatemia predicts a failure to recover from adefovir-related renal injury after dose reduction in lamivudine-resistant hepatitis B patients. Hepatol Res. 2017 Jan 12. doi: 10.1111/hepr.12865. [Epub ahead of print] PubMed PMID: 28079295. 2: Laho T, Clarke JD, Dzierlenga AL, Li H, Klein DM, Goedken M, Micuda S, Cherrington NJ. Effect of nonalcoholic steatohepatitis on renal filtration and secretion of adefovir. Biochem Pharmacol. 2016 Sep 1;115:144-51. doi: 10.1016/j.bcp.2016.07.001. PubMed PMID: 27381944. 3: Lian J, Han T, Xiang H, Liu F, Lyu H, Gao Y, Wang F. [A randomized controlled trial on 240-week monotherapy with entecavir or adefovir in patients with chronic hepatitis B and cirrhosis]. Zhonghua Gan Zang Bing Za Zhi. 2015 Oct;23(10):733-7. doi: 10.3760/cma.j.issn.1007-3418.2015.10.005. Chinese. PubMed PMID: 26573188. 4: Maeda K, Tian Y, Fujita T, Ikeda Y, Kumagai Y, Kondo T, Tanabe K, Nakayama H, Horita S, Kusuhara H, Sugiyama Y. Inhibitory effects of p-aminohippurate and probenecid on the renal clearance of adefovir and benzylpenicillin as probe drugs for organic anion transporter (OAT) 1 and OAT3 in humans. Eur J Pharm Sci. 2014 Aug 1;59:94-103. doi: 10.1016/j.ejps.2014.04.004. PubMed PMID: 24747579. 5: Yang S, Xing H, Wang Q, Wang X, Liu S, Cheng J. De novo entecavir+adefovir dipivoxil+lamivudine triple-resistance mutations resulting from sequential therapy with adefovir dipivoxil, and lamivudine. Ann Clin Microbiol Antimicrob. 2016 Apr 14;15:24. doi: 10.1186/s12941-016-0138-0. PubMed PMID: 27079793; PubMed Central PMCID: PMC4832522. 6: Pourfarzib M, Dinarvand R, Akbari-Adergani B, Mehramizi A, Rastegar H, Shekarchi M. Water-compatible molecularly imprinted polymer as a sorbent for the selective extraction and purification of adefovir from human serum and urine. J Sep Sci. 2015 May;38(10):1755-62. doi: 10.1002/jssc.201401492. PubMed PMID: 25763883. 7: Ma LN, Ding XC, Liu XY, Xu CQ, Liu SW, Yan X. De novo combination therapy adefovir plus lamivudine as a treatment for women of child-bearing age with HBeAg-positive chronic hepatitis B before pregnancy. J Med Virol. 2014 Mar;86(3):433-6. doi: 10.1002/jmv.23828. PubMed PMID: 24166586. 8: Lin Y, Pan F, Wang Y, Chen Z, Lin C, Yao L, Zhang X, Zhou R, Pan C. Adefovir dipivoxil-induced Fanconi syndrome and its predictive factors: A study of 28 cases. Oncol Lett. 2017 Jan;13(1):307-314. doi: 10.3892/ol.2016.5393. PubMed PMID: 28123560; PubMed Central PMCID: PMC5244885. 9: Yoon IS, Son JH, Kim SB, Choi MK, Maeng HJ. Effects of 1α,25-Dihydroxyvitamin D3 on Intestinal Absorption and Disposition of Adefovir Dipivoxil and Its Metabolite, Adefovir, in Rats. Biol Pharm Bull. 2015;38(11):1732-7. doi: 10.1248/bpb.b15-00356. PubMed PMID: 26521823. 10: Luo Q, Deng Y, Cheng F, Kang J, Zhong S, Zhang D, Zeng W. Relationship between nephrotoxicity and long-term adefovir dipivoxil therapy for chronic hepatitis B: A meta-analysis. Medicine (Baltimore). 2016 Dec;95(50):e5578. PubMed PMID: 27977591; PubMed Central PMCID: PMC5268037. 11: Huang ZB, Zhao SS, Huang Y, Dai XH, Zhou RR, Yi PP, Chen RC, Li WT, Zhang BX, Li N, Fan XG. Comparison of the efficacy of Lamivudine plus adefovir versus entecavir in the treatment of Lamivudine-resistant chronic hepatitis B: a systematic review and meta-analysis. Clin Ther. 2013 Dec;35(12):1997-2006. doi: 10.1016/j.clinthera.2013.10.002. Review. PubMed PMID: 24238791. 12: Kim SB, Kim SU, Kim BK, Park JY, Kim do Y, Ahn SH, Han KH. Outcome of adefovir add-on lamivudine rescue therapy of up to 5 years in patients with lamivudine-resistant chronic hepatitis B. J Gastroenterol Hepatol. 2016 Jan;31(1):241-7. doi: 10.1111/jgh.13046. PubMed PMID: 26204913. 13: George N, Basu G, Mohapatra A, Zachariah U, Abraham P, Korula A, Varughese S, Jacob CK, Tamilarasi V. Adefovir nephrotoxicity in a renal allograft recipient. Indian J Nephrol. 2015 May-Jun;25(3):180-3. doi: 10.4103/0971-4065.144423. PubMed PMID: 26060371; PubMed Central PMCID: PMC4446926. 14: Chung GE, Cho EJ, Lee JH, Yoo JJ, Lee M, Cho Y, Lee DH, Kim HY, Yu SJ, Kim YJ, Yoon JH, Zoulim F. Tenofovir has inferior efficacy in adefovir-experienced chronic hepatitis B patients compared to nucleos(t)ide-naïve patients. Clin Mol Hepatol. 2017 Feb 14. doi: 10.3350/cmh.2016.0060. [Epub ahead of print] PubMed PMID: 28190329. 15: Gu J, Sun R, Shen S, Yu Z. The curative effect of adefovir dipivoxil treating HBeAg negative chronic hepatitis B and treating HBeAg positive chronic hepatitis B combining interferon α-2b. Pak J Pharm Sci. 2015 Jul;28(4 Suppl):1493-7. PubMed PMID: 26431662. 16: Ko SY, Kim BK, Kwon SY, Kim KH, Kim JH, Choe WH, Lee CH. Clonal evolution of hepatitis B virus polymerase gene mutations during lamivudine-adefovir combination treatment. World J Gastroenterol. 2012 Nov 28;18(44):6437-46; discussion p.6445. doi: 10.3748/wjg.v18.i44.6437. PubMed PMID: 23197889; PubMed Central PMCID: PMC3508638. 17: Lim YS, Lee JY, Lee D, Shim JH, Lee HC, Lee YS, Suh DJ. Randomized trial of the virologic response during up to two years of entecavir-adefovir combination therapy in multiple-drug-refractory chronic hepatitis B virus patients. Antimicrob Agents Chemother. 2013 Jul;57(7):3369-74. doi: 10.1128/AAC.00587-13. PubMed PMID: 23650172; PubMed Central PMCID: PMC3697381. 18: Hartono JL, Aung MO, Dan YY, Gowans M, Lim K, Lee YM, Lee GH, Low HC, Tan PS, Thwin MA, Soon C, Chiu LL, Khoo MJ, Koay E, Lim SG. Resolution of adefovir-related nephrotoxicity by adefovir dose-reduction in patients with chronic hepatitis B. Aliment Pharmacol Ther. 2013 Apr;37(7):710-9. doi: 10.1111/apt.12251. PubMed PMID: 23432107. 19: Kim du H, Sung DH, Min YK. Hypophosphatemic osteomalacia induced by low-dose adefovir therapy: focus on manifestations in the skeletal system and literature review. J Bone Miner Metab. 2013 Mar;31(2):240-6. doi: 10.1007/s00774-012-0384-y. Review. PubMed PMID: 22976054. 20: Berg T, Zoulim F, Moeller B, Trinh H, Marcellin P, Chan S, Kitrinos KM, Dinh P, Flaherty JF Jr, McHutchison JG, Manns M. Long-term efficacy and safety of emtricitabine plus tenofovir DF vs. tenofovir DF monotherapy in adefovir-experienced chronic hepatitis B patients. J Hepatol. 2014 Apr;60(4):715-22. doi: 10.1016/j.jhep.2013.11.024. PubMed PMID: 24295873.