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59277-89-3

Basic Information
CAS No.: 59277-89-3
Name: Acyclovir
Article Data: 50
Cas Database
Molecular Structure:
Molecular Structure of 59277-89-3 (Acyclovir)
Formula: C8H11N5O3
Molecular Weight: 225.207
Synonyms: Acyclovir
EINECS: 261-685-1
Density: 1.77 g/cm3
Melting Point: 256-257 °C
Boiling Point: 595 °C at 760 mmHg
Flash Point: 313.6 °C
Solubility: Water: 0.7 mg/mL
Appearance: White to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
Transport Information: N/A
PSA: 119.05000
LogP: -0.75060
Synthetic route
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With sodium hydroxide In water at 85 - 95℃; for 3h;97.5%
With methylamine In water at 23℃; for 1h;93%
With sodium hydroxide92%
131490-71-6

1-<(2-hydroxyethoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With sodium hydroxide; copper diacetate for 1h; Heating;92%
With sodium hydroxide; copper(II) ion at 100℃; for 1h; Product distribution; further metal ions and reaction conditions investigatet; reaction also with H2O2 / Na2WO4;92%
112233-78-0

9-<(2-acetoxyethoxy)methyl>-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With ammonia In methanol; water at 60℃;91%
With ammonium hydroxide In methanol at 60℃; for 24h;91%
1336-21-6

ammonium hydroxide

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

59277-89-3

acycloguanosine

Conditions
ConditionsYield
In methanol90%
81777-49-3

2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With phosphoric acid; adenosine deaminase Ambient temperature; pH=7.5;89%
59277-86-0

2,6-diamino-9-{(2-hydroxyethoxy)methyl}purine

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With phosphoric acid; adenosine deaminase Ambient temperature; pH=7.5;89%
364634-35-5

9-(2-trimethylsilyloxyethoxymethyl)guanine

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With acetic acid In water at 80℃; for 2h;85%

9-<(2-acetoxyethoxy)methyl>-2-N-phenylacetylguanine

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 24h; Ambient temperature;84%
127218-19-3

Acetic acid 2-(2-bromo-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester

59277-89-3

acycloguanosine

Conditions
ConditionsYield
With ammonia In methanol at 120℃;80%
1400637-35-5

2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]ethyl pyrrolidinophosphate ammonium salt

A

59277-89-3

acycloguanosine

B

acyclovir monophosphate

Conditions
ConditionsYield
With potassium chloride; potassium hydroxide In water at 25℃; pH=12;A 80%
B n/a
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    Acyclovir (ACV), also known as acycloguano-sine. It is primarily used for the treatment of herpes simplex infections, chickenpox, and shingles. It can be taken by mouth, applied as a cream. Application of Acyclovir Acyclovir, also known as acyclovir,

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Specification

1. Introduction of Acyclovir
Acyclovir is one kind of white to light yellow crystal powder. IUPAC Name of IUPAC Name is 2-Amino-9-(2-hydroxyethoxymethyl)-3H-purin-6-one. Product Category of Acyclovir is Active Pharmaceutical Ingredients;Purine;Nucleotides and Nucleosides;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides, Nucleotides & Related Reagents. It can be soluble in water which is 0.7 mg/mL.

2. Properties of Acyclovir
Physical properties about Acyclovir are:
(1)Melting point: 256-257 °C; (2)Storage tempreture: -20 °C; (3)Water solubility: 0.7 mg/mL; (4)Index of Refraction: 1.762 ; (5)Density: 1.77 g/cm3 ; (6)Flash Point: 313.6 °C ; (7)Enthalpy of Vaporization: 93.25 kJ/mol ; (8)Boiling Point: 595 °C at 760 mmHg ; (9)Vapour Pressure: 5.29E-15 mmHg at 25 °C.

3. Structure Descriptors of Acyclovir
(1)InChI: InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15);
(2)InChIKey: InChIKey=MKUXAQIIEYXACX-UHFFFAOYSA-N;
(3)Smiles: c1nc2c(=O)[nH]c(nc2n1COCCO)N.

4. Toxicity of Acyclovir
Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 3gm/kg/22W-I (3000mg/kg) BLOOD: AGRANULOCYTOSIS
BLOOD: THROMBOCYTOPENIA
American Journal of Emergency Medicine. Vol. 16, Pg. 396, 1998.
mammal (species unspecified) LD50 intravenous 400mg/kg (400mg/kg)   Pharmacy International. Vol. 5, Pg. 191, 1984.
man TDLo intravenous 134ug/kg/1D-I (0.134mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Lancet. Vol. 2, Pg. 385, 1985.
man TDLo intravenous 107mg/kg/4D-I (107mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
American Journal of Kidney Diseases. Vol. 22, Pg. 611, 1993.
man TDLo oral 486mg/kg/17D- (486mg/kg) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
GASTROINTESTINAL: OTHER CHANGES
American Journal of Gastroenterology. Vol. 88, Pg. 2110, 1993.
mouse LD50 intraperitoneal 724mg/kg (724mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
mouse LD50 intravenous 1118mg/kg (1118mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 866, 1985.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Nature. Vol. 272, Pg. 583, 1978.
mouse LD50 subcutaneous 1118mg/kg (1118mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 866, 1985.
rat LD50 intraperitoneal 860mg/kg (860mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 866, 1985.
rat LD50 intravenous 750mg/kg (750mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
rat LD50 oral > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. -, Pg. 7, 1990.
rat LD50 subcutaneous 620mg/kg (620mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 866, 1985.
women LDLo multiple routes 36mg/kg/2D-I (36mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
BEHAVIORAL: COMA
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Journal of Kidney Diseases. Vol. 20, Pg. 647, 1992.
women TDLo intravenous 101mg/kg/2D-I (101mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
American Journal of Medicine. Vol. 94, Pg. 212, 1993.
women TDLo oral 12mg/kg/1D-I (12mg/kg) BRAIN AND COVERINGS: MENINGEAL CHANGES
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ANTIPSYCHOTIC
Southern Medical Journal. Vol. 87, Pg. 1227, 1994.
women TDLo oral 28mg/kg/2D-I (28mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG
BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
LUNGS, THORAX, OR RESPIRATION: SPUTUM
Southern Medical Journal. Vol. 87, Pg. 1227, 1994.
women TDLo oral 80mg/kg/4D-I (80mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Internal Medicine. Vol. 111, Pg. 187, 1989.
women TDLo oral 100mg/kg/5D-I (100mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 289, Pg. 1424, 1984.

5. Physical Properties of Acyclovir

Physical Property Value Units Temp (deg C) Source
Melting Point 255 deg C   EXP
log P (octanol-water) -1.56E+00 (none)   EXP
Water Solubility 1620 mg/L 22 EXP
Vapor Pressure 7.47E-15 mm Hg 25 EST
Henry's Law Constant 3.18E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.94E-11 cm3/molecule-sec 25 EST

6. Safety information of Acyclovir

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.

7. Uses of Acyclovir
Acyclovir is a commonly-used antiviral drug and is used for the treatment of herpes simplex virus infections. It is commonly marketed as tablets (200 mg, 400 mg, 800 mg and 1 gram), topical cream (5%), intravenous injection (25 mg/mL) and ophthalmic ointment (3%). It can be used especially against herpes. 

Aciclovir (INN) or acyclovir is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV.

8. Production of Acyclovir
(1)After Guanine trimethylsilyl and then react with 2-benzyloxyethoxy methyl chloride. Then remove the benzyl group to give acyclovir. The yield is 24%. The detailed steps are as follows:

Production of Acyclovir

(2)N, N'-diacetyl guanine and 2-oxa-butanediol diacetate in dimethyl sulfoxide can be used to manufacture the Acyclovir.

Production of Acyclovir