CAS No.59277-89-3,Acyclovir Suppliers

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Basic Information

Molecular Structure:
CAS No.:	59277-89-3
Name:	Acyclovir
Article Data:	50
Cas Database

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:	Xi
Risk Codes:	36/37/38
Safety:	22-24/25-36-26
PSA:	119.05000
LogP:	-0.75060

Synthetic route

: 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

: 59277-89-3
acycloguanosine

Conditions

Conditions	Yield
With sodium hydroxide In water at 85 - 95℃; for 3h;	97.5%
With methylamine In water at 23℃; for 1h;	93%
With sodium hydroxide	92%

: 131490-71-6
1-<(2-hydroxyethoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide

: 59277-89-3
acycloguanosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In methanol	90%

: 81777-49-3
2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine

: 59277-89-3
acycloguanosine

Conditions

Conditions	Yield
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

Conditions	Yield
With phosphoric acid; adenosine deaminase Ambient temperature; pH=7.5;	89%

: 364634-35-5
9-(2-trimethylsilyloxyethoxymethyl)guanine

: 59277-89-3
acycloguanosine

Conditions

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

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

: 59277-89-3
acycloguanosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium chloride; potassium hydroxide In water at 25℃; pH=12;	A 80% B n/a

Raw Materials

73-40-5

Downstream Products

73-40-5

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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: Irritant Xi
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:

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

Production of Acyclovir