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| CAS No.: | 59277-89-3 |
|---|---|
| Name: | Acyclovir |
| Molecular Structure: | |
|
|
|
| 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 |
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- 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
- 59277-89-3
acycloguanosine
| 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 | 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 | 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 | Yield |
|---|---|
| In methanol | 90% |
- 81777-49-3
2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine
- 59277-89-3
acycloguanosine
| 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 | Yield |
|---|---|
| With phosphoric acid; adenosine deaminase Ambient temperature; pH=7.5; | 89% |
- 364634-35-5
9-(2-trimethylsilyloxyethoxymethyl)guanine
- 59277-89-3
acycloguanosine
| Conditions | Yield |
|---|---|
| With acetic acid In water at 80℃; for 2h; | 85% |
- 59277-89-3
acycloguanosine
| 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 | 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
| Conditions | Yield |
|---|---|
| With potassium chloride; potassium hydroxide In water at 25℃; pH=12; | A 80% B n/a |
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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: 
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.
