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209216-23-9

Basic Information
CAS No.: 209216-23-9
Name: Entecavir hydrate
Article Data: 2
Molecular Structure:
Molecular Structure of 209216-23-9 (Entecavir hydrate)
Formula: C12H15N5O3.H2O
Molecular Weight: 295.298
Synonyms: Baraclude;6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-, monohydrate;Intermediates of drug, pesticide and dye;Enticavir;Entecavir hydrate / 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one monohydrate;Entecavir monohydrate;Entecavir API in stock;Entecavir(monohydrate)--Fine Product;
EINECS: 606-668-5
Density: 1.81 g/cm3
Melting Point: >220°
Boiling Point: 734.2 °C at 760 mmHg
Flash Point: 397.9 °C
Appearance: White crystalline powder
Safety: 24/25
PSA: 139.28000
LogP: -0.31090
Synthetic route
209216-23-9

entecavir monohydrate

108-24-7

acetic anhydride

C16H19N5O5

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile at 20℃;88%
209216-23-9

entecavir monohydrate

544-63-8

n-tetradecanoic acid

C26H41N5O4

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h;
209216-23-9

entecavir monohydrate

57-10-3

1-hexadecylcarboxylic acid

entecavir 5'-palmitate

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h;
209216-23-9

entecavir monohydrate

57-11-4

stearic acid

entecavir 5'-stearate

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h;
209216-23-9

entecavir monohydrate

1383812-22-3

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; N,N-dimethyl-aniline / 1 h / 70 °C / Cooling with ice
View Scheme
209216-23-9

entecavir monohydrate

701278-58-2

6-chloro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-9H-purine-2-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; N,N-dimethyl-aniline / 1 h / 70 °C / Cooling with ice
3: ammonia / methanol / 5 h / 20 °C
View Scheme
209216-23-9

entecavir monohydrate

C12H15N5O2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; N,N-dimethyl-aniline / 1 h / 70 °C / Cooling with ice
3: ammonia / methanol / 5 h / 20 °C
4: zinc; ammonium hydroxide / 55 °C
View Scheme
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Chemistry

Molecular Structure of Entecavir hydrate (CAS NO.209216-23-9):

IUPAC Name: 2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one hydrate
Molecular Formula: C12H15N5O3.H2O
Molecular Weight: 295.30
H bond acceptors: 9
H bond donors: 7
Freely Rotating Bonds: 4
Polar Surface Area: 125.76 Å2
Density:1.81g/cm3
Flash Point: 397.9 °C
Enthalpy of Vaporization: 112.46 kJ/mol
Boiling Point: 734.2 °C at 760 mmHg
Vapour Pressure: 1.24E-22 mmHg at 25°C
Appearance: White crystalline powder
Classification Code: Anti-Infective Agents; Antiviral Agents; Antiviral used in the treatment of hepatitis B infection; Treatment of hepatitis B infection
InChI
InChI=1/C12H15N5O3.H2O/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);1H2/t6-,7+,8-;/m0./s1
Smiles
[nH]1c(N)nc2[n@](cnc2c1=O)[C@H]1C([C@@H]([C@H](C1)O)CO)=C.O

History

1992: SQ-34676 at Squibb as part of anti-herpes virus program.
1997: BMS 200475 developed at BMS pharmaceutical research institute as antiviral nucleoside analogue à Activity demonstrated against HBV, HSV-1, HCMV, VZV in cell lines & no or little activity against HIV or influenza.Superior activity observed against HBV pushed research towards BMS 200475, its base analogues and its enantiomer against HBV in HepG2.2.15 cell line Comparison to other NAs, proven more selective potent inhibitor of HBV by virtue of being Guanine NA.
1998: Inhibition of hepadnaviral polymerases was demonstrated in vitro in comparison to a number of NAs-TP. Metabolic studies showed more efficient phosphorylation to triphosphate active form.
3 year treatment of woodchuck model of CHB sustained antiviral efficacy and prolonged life spans without detectable emergence of resistance.

Safety Profile

 Entecavir hydrate (CAS NO.209216-23-9)  may cause lactic acidosis and severe hepatomegaly with steatosis (including fatal cases) when used alone or in combination with antiretrovirals. Severe acute hepatitis B exacerbations have occurred in patients who discontinued anti-hepatitis B therapy, including entecavir. Monitor hepatic function for at least several months after discontinuation. If appropriate, initiate anti-hepatitis B therapy.

Specification

  Entecavir hydrate , with CAS number of 209216-23-9, can be called entecavir hydrate ; Entecavir monohydrate ; 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one monohydrate ; Entecavir hydrate / 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one monohydrate . Entecavir hydrate (CAS NO.209216-23-9)  is an oral antiviral drug used in the treatment of hepatitis B infection.