Adefovir Dipivoxil - Moligand™,≥99% , CAS No.142340-99-6

CAS: 142340-99-6 Cat. No.: A129786 Formula: C₂₀H₃₂N₅O₈P Molecular Weight: 501.47 EC Number: 634-317-6

GRADE & PURITY Moligand™, ≥99%

Synonyms

9-[2-[Bis(pivaloyloxymethoxy)phosphorylmethoxy]ethyl]adenine | 9-(2[bis(Pivaloyloxymethoxy)phosphorylmethoxy]ethyl)adenine

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Adefovir Dipivoxil works by blocking reverse transcriptase, an enzyme that is crucial for the hepatitis B virus (HBV) to reproduce in the body. Target: NRTIs; HBV Adefovir Dipivoxil works by blocking reverse transcriptase, an enzyme that is crucial for the hepatitis B virus (HBV) to reproduce in the body. Adefovir Dipivoxil is used for treatment of hepatitis B and herpes simplex virus infection [1-3]. Adefovir Dipivoxil is approved for the treatment of chronic hepatitis B in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (primarily ALT) or histologically active disease. Adefovir Dipivoxil is a failed treatment for HIV[3, 4].
Catalyst employed in the Sharpless Asymmetric Dihyroxylation of (E,E)- or (E,Z)-1,3-dienoates.¹ Also used in the preparation of ?-hydroxy-γ-lactones from ?,γ-unsaturated esters.²

Product Introduction:

Adefovir dipivoxil, an adenosine analogue, is an oral proagent of the nucleoside reverse transcriptase inhibitor Adefovir. Adefovir dipivoxil inhibits both the wild type and HBV Lamivudine-resistant strains. Adefovir dipivoxil shows anti-orthopoxvirus activity.

Specifications

Synonyms

9-[2-[Bis(pivaloyloxymethoxy)phosphorylmethoxy]ethyl]adenine | 9-(2[bis(Pivaloyloxymethoxy)phosphorylmethoxy]ethyl)adenine

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Powerful and selective nucleotide analogue reverse transcriptase inhibitor. Inhibition of viral DNA synthesis (IC 50=0.2-2.5 μ M. Human liver cancer cell lines transfected with HBV. Display antiviral effects in the body.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Product Properties

ALogP

1.8

Names and Identifiers

Pubchem Sid

488183410

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488183410

Canonical Smiles

CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C

IUPAC Name

[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate

InChIKey

WOZSCQDILHKSGG-UHFFFAOYSA-N

INCHI

1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

Isomeric SMILES

CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C

WGK Germany

3

RTECS

UA2459362

Molecular Weight

501.47

Reaxy-Rn

7060608

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7060608&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Imidazopyrimidines
      • Subclass Purines and purine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Imidazopyrimidines
• Subclass: Purines and purine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: 6-aminopurines
• Alternative Parents: Aminopyrimidines and derivatives Dialkyl alkylphosphonates Phosphonic acid esters N-substituted imidazoles Imidolactams Dicarboxylic acids and derivatives Heteroaromatic compounds Amino acids and derivatives Carboxylic acid esters Azacyclic compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Organophosphorus compounds Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 6-aminopurine - Aminopyrimidine - Dialkyl alkylphosphonate - Phosphonic acid diester - Dicarboxylic acid or derivatives - Imidolactam - Pyrimidine - Phosphonic acid ester - N-substituted imidazole - Azole - Heteroaromatic compound - Imidazole - Organophosphonic acid derivative - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Azacycle - Organophosphorus compound - Primary amine - Amine - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

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MC3R Tchem Melanocortin receptor 3 (5659 Activities)

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MLNR Tchem Motilin receptor (1724 Activities)

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Associated Targets(non-human)

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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Marmota monax (83 Activities)

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Human alphaherpesvirus 2 (4932 Activities)

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Rattus norvegicus (775804 Activities)

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Cowpox virus (428 Activities)

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Vaccinia virus (4609 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Hepatitis B virus (7925 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Human immunodeficiency virus 2 (5592 Activities)

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Duck hepatitis B virus (235 Activities)

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Vero (26788 Activities)

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Slc10a1 Bile acid transporter (65 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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ddn Putative uncharacterized protein (49 Activities)

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Woodchuck hepatitis virus (122 Activities)

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Plasma (328 Activities)

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Intestine (514 Activities)

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Kidney (1278 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : ≥ 100 mg/mL (199.41 mM) H2O : 0.67 mg/mL (1.34 mM; Need ultrasonic)
• Sensitivity: heat sensitive
• Melt Point(°C): 101 °C
• Molecular Weight: 501.500 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 15
• Exact Mass: 501.199 Da
• Monoisotopic Mass: 501.199 Da
• Topological Polar Surface Area: 167.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 705.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1