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Name	Entecavir hydrate	EINECS	606-668-5
CAS No.	209216-23-9	Density	1.81 g/cm³
PSA	139.28000	LogP	-0.31090
Solubility	N/A	Melting Point	>220°
Formula	C₁₂H₁₅N₅O₃^.H₂O	Boiling Point	734.2 °C at 760 mmHg
Molecular Weight	295.298	Flash Point	397.9 °C
Transport Information	N/A	Appearance	White crystalline powder
Safety	24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	2

Entecavir hydrate Synthetic route

: 209216-23-9
entecavir monohydrate

: 108-24-7
acetic anhydride

: C16H19N5O5

Conditions

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃;	88%

: 209216-23-9
entecavir monohydrate

: 544-63-8
n-tetradecanoic acid

: C26H41N5O4

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Entecavir hydrate Chemical Properties

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

Entecavir hydrate 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.

Entecavir hydrate 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.

Entecavir hydrate 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.

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