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

MedKoo CAT#: 529002

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

Description: Adefovir, also known as PMEA and GS-0393, is a DNA polymerase inhibitor potentially for the treatment of HBV infection.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 650
Size
Price

25mg
USD 250
200mg
USD 950
Size
Price

50mg
USD 450
500mg
USD 1450

Adefovir, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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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


Related CAS #: 142340-99-6 (Adefovir Dipivoxil)   142340-99-6 (Adefovir free acid)    

Synonym: GS-0393; GS-393; GS0393; GS393; GS 0393; GS 393; PMEA

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


Technical Data

Appearance:
Solid powder

Purity:
>98% (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).

Harmonized System Code:
293490


References

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.