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MedKoo Cat#: 555901 | Name: ent-Entecavir

Description:

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

ent-Entecavir is an enantiomeric impurity of the antiviral drug Entecavir. Entecavir is an oral antiviral drug used in the treatment of hepatitis B virus (HBV) infection. Entecavir is a reverse transcriptase inhibitor. It prevents the hepatitis B virus from multiplying and reduces the amount of virus in the body. More specifically, it is a deoxyguanosine analogue belonging to a class of carbocyclic nucleosides, that inhibits reverse transcription, DNA replication and transcription in the viral replication process.

Chemical Structure

ent-Entecavir
ent-Entecavir
CAS#188399-46-4 (enantiomer)

Theoretical Analysis

MedKoo Cat#: 555901

Name: ent-Entecavir

CAS#: 188399-46-4 (enantiomer)

Chemical Formula: C12H15N5O3

Exact Mass: 277.1175

Molecular Weight: 277.28

Elemental Analysis: C, 51.98; H, 5.45; N, 25.26; O, 17.31

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Related CAS #
142217-69-4 (free) 209216-23-9 (hydrate) 911138-73-3 (maleate) 188399-46-4 (enantiomer)
Synonym
ent-Entecavir, ent-BMS 200475; ent-BMS-200475; ent-BMS200475; ent-Baraclude; ent-SQ 34676; ent-SQ-34676; ent-SQ34676; FT-0083013; FT0083013; FT0083013; D07896;
IUPAC/Chemical Name
2-Amino-1,9-dihydro-9-[(1R,3S,4R)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-Purin-6-one
InChi Key
QDGZDCVAUDNJFG-BWZBUEFSSA-N
InChi Code
InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m1/s1
SMILES Code
O=C1NC(N)=NC2=C1N=CN2[C@H]3C([C@@H](CO)[C@H](O)C3)=C
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 277.28 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.

Recalculate based on batch purity %
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: Kuo MH, Tseng CW, Lu MC, Tung CH, Tseng KC, Huang KY, Lee CH, Lai NS. Risk of Hepatitis B Virus Reactivation in Rheumatoid Arthritis Patients Undergoing Tocilizumab-Containing Treatment. Dig Dis Sci. 2021 Jan 2. doi: 10.1007/s10620-020-06725-1. Epub ahead of print. PMID: 33387124. 2: Araujo NM, Teles SA, Spitz N. Comprehensive Analysis of Clinically Significant Hepatitis B Virus Mutations in Relation to Genotype, Subgenotype and Geographic Region. Front Microbiol. 2020 Dec 14;11:616023. doi: 10.3389/fmicb.2020.616023. PMID: 33381105; PMCID: PMC7767914. 3: Manolakopoulos S, Kranidioti H, Kourikou A, Deutsch MM, Triantos C, Tsolias C, Manesis EK, Mathou N, Alexopoulou A, Hadziyannis E, Papatheodoridis G. Long- term clinical outcome of HBeAg-negative chronic hepatitis B patients who discontinued nucleos(t)ide analogues. Liver Int. 2021 Jan;41(1):48-57. doi: 10.1111/liv.14654. PMID: 33373114. 4: Ahn YE, Suh SJ, Kim TH, Jung YK, Yim HJ. Maintaining Antiviral Efficacy after Switching to Generic Entecavir 1 mg for Antiviral-resistant Chronic Hepatitis B. Korean J Gastroenterol. 2020 Dec 30. doi: 10.4166/kjg.2020.0144. Epub ahead of print. PMID: 33372170. 5: Broquetas T, Garcia-Retortillo M, Micó M, Canillas L, Puigvehí M, Cañete N, Coll S, Viu A, Hernandez JJ, Bessa X, Carrión JA. Hepatitis B surface antigen and hepatitis B core-related antigen kinetics after adding pegylated-interferon to nucleos(t)ids analogues in hepatitis B e antigen-negative patients. World J Hepatol. 2020 Nov 27;12(11):1076-1088. doi: 10.4254/wjh.v12.i11.1076. PMID: 33312431; PMCID: PMC7701972. 6: Yu YF, Chen Y, Shen XF, Wang RJ, Shen JW, Fang ZH. [Entecavir improves the reproductive function of male patients with chronic hepatitis B]. Zhonghua Nan Ke Xue. 2020 Apr;26(4):326-330. Chinese. PMID: 33351299. 7: Inoue J, Akahane T, Kobayashi T, Obara N, Umetsu T, Kakazu E, Ninomiya M, Iwata T, Sano A, Tsuruoka M, Sato K, Masamune A. Switching to tenofovir disoproxil fumarate in entecavir-treated chronic hepatitis B patients: A pilot randomized controlled study. Biomed Rep. 2021 Feb;14(2):20. doi: 10.3892/br.2020.1396. Epub 2020 Dec 1. PMID: 33335726; PMCID: PMC7739848. 8: Wu CJ, Chau GY, Lee IC, Huo TI, Su CW, Hou MC, Huang YH. Early and late recurrence of surgically resected hepatitis B virus-related hepatocellular carcinoma on nucleos(t)ide analogues therapy. J Formos Med Assoc. 2020 Dec 14:S0929-6646(20)30596-9. doi: 10.1016/j.jfma.2020.11.019. Epub ahead of print. PMID: 33334659. 9: Wani MA, Sodhi JS, Yatoo GN, Shah A, Geelani S, Zargar SA, Gulzar GM, Khan M, Aziz SA. Clinical Profile and Efficacy of Antivirals in Hepatitis B Virus Reactivation, in Patients With Cancer Receiving Chemotherapy. J Clin Exp Hepatol. 2020 Nov-Dec;10(6):590-598. doi: 10.1016/j.jceh.2020.06.008. Epub 2020 Jul 8. PMID: 33311896; PMCID: PMC7719970. 10: Chang JW, Kim SU. Authors' response: Additional more factors should be included in predicting risk of hepatocellular carcinoma in patients with chronic hepatitis B virus infection. J Viral Hepat. 2020 Dec 11. doi: 10.1111/jvh.13450. Epub ahead of print. PMID: 33305419. 11: Chen CH, Chen CY, Wang JH, Lai HC, Hung CH, Lu SN, Peng CY. Comparison of incidence of hepatocellular carcinoma between chronic hepatitis B patients with cirrhosis treated with entecavir or tenofovir in Taiwan - a retrospective study. Am J Cancer Res. 2020 Nov 1;10(11):3882-3895. PMID: 33294274; PMCID: PMC7716174. 12: Gu X, Zhang Y, Zou Y, Li X, Guan M, Zhou Q, Qiu J. Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents. Bioorg Med Chem. 2020 Nov 28;29:115892. doi: 10.1016/j.bmc.2020.115892. Epub ahead of print. PMID: 33285406. 13: Reynolds G, Stewart T, Harrison SJ, Spencer A, Teh BW. Hepatitis B reverse seroconversion despite entecavir prophylaxis in a myeloma patient on multiple novel agents: a case report and review of the literature. Leuk Lymphoma. 2020 Dec 4:1-7. doi: 10.1080/10428194.2020.1855343. Epub ahead of print. PMID: 33275059. 14: Peng CW, Jeng WJ, Chien RN, Liaw YF. The impact of hepatitis flare on HBeAg loss was effective mainly in the first year of Nucleot(s)ide therapy in chronic hepatitis B. J Viral Hepat. 2020 Dec 3. doi: 10.1111/jvh.13449. Epub ahead of print. PMID: 33274536. 15: Mohamed K, Yazdanpanah N, Saghazadeh A, Rezaei N. Computational drug discovery and repurposing for the treatment of COVID-19: A systematic review. Bioorg Chem. 2021 Jan;106:104490. doi: 10.1016/j.bioorg.2020.104490. Epub 2020 Nov 19. PMID: 33261845; PMCID: PMC7676368. 16: Kim HL, Kim GA, Park JA, Kang HR, Lee EK, Lim YS. Cost-effectiveness of antiviral treatment in adult patients with immune-tolerant phase chronic hepatitis B. Gut. 2020 Nov 25:gutjnl-2020-321309. doi: 10.1136/gutjnl-2020-321309. Epub ahead of print. PMID: 33239344. 17: Suzuki K, Suda G, Yamamoto Y, Furuya K, Baba M, Nakamura A, Miyoshi H, Kimura M, Maehara O, Yamada R, Kitagataya T, Yamamoto K, Shigesawa T, Nakamura A, Ohara M, Kawagishi N, Nakai M, Sho T, Natsuizaka M, Morikawa K, Ogawa K, Ohnishi S, Sakamoto N; NORTE Study Group. Tenofovir-disoproxil-fumarate modulates lipid metabolism via hepatic CD36/PPAR-alpha activation in hepatitis B virus infection. J Gastroenterol. 2020 Nov 19. doi: 10.1007/s00535-020-01750-3. Epub ahead of print. PMID: 33211179. 18: Luo M, Wu S, Kalkeri R, Ptak RG, Zhou T, Van Mellaert L, Wang C, Dumbre SG, Block T, Groaz E, De Jonghe S, Li Y, Herdewijn P. Scalable Synthesis, In Vitro cccDNA Reduction, and In Vivo Antihepatitis B Virus Activity of a Phosphonomethoxydeoxythreosyl Adenine Prodrug. J Med Chem. 2020 Nov 25;63(22):13851-13860. doi: 10.1021/acs.jmedchem.0c01381. Epub 2020 Nov 16. PMID: 33191744. 19: Mak LY, Cloherty G, Wong DK, Gersch J, Seto WK, Fung J, Yuen MF. HBV RNA profiles in chronic hepatitis B patients under different disease phases and anti-viral therapy. Hepatology. 2020 Nov 6. doi: 10.1002/hep.31616. Epub ahead of print. PMID: 33159329. 20: Huang HH, Hsiao FY, Chen HM, Wang CY, Ko BS. Antiviral prophylaxis for hepatitis B carriers improves the prognosis of diffuse large B-cell lymphoma in Taiwan - a population-based study. Br J Haematol. 2021 Jan;192(1):110-118. doi: 10.1111/bjh.17142. Epub 2020 Oct 31. PMID: 33131074.