CAS 59277-89-3|Acyclovir

Introduction：Basic information about CAS 59277-89-3|Acyclovir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Acyclovir BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles117
8. Synonyms

Common Name	Acyclovir
CAS Number	59277-89-3	Molecular Weight	225.205
Density	1.8±0.1 g/cm3	Boiling Point	576.5±58.0 °C at 760 mmHg
Molecular Formula	C₈H₁₁N₅O₃	Melting Point	256-257°C
MSDS	ChineseUSA	Flash Point	302.4±32.3 °C

Names

Name	acyclovir
Synonym	More Synonyms

Acyclovir BiologicalActivity

Description	Acyclovir, a molecule tailored to inactivate the thymidine kinase of the herpesvirus, is a guanosine analogue antiviral drug. It is a drug for HSV infection by GlaxoSmithKline.IC50 Value: 0.53-0.75 uM [3]Target: HSVin vitro: Acyclovir sensitivity was determined in a plaque-reduction assay in Vero cells. IC50 Values were consistently 2-3 fold lower in B2 compared with the H strain of Vero cells. HSV Type 2 strains were 2-10-fold less sensitive than Type 1 strains [2]. in vivo: two patients experienced a recurrence during treatment with oral acyclovir (200 mg 4 times daily) for up to 12 weeks, compared with nine during placebo treatment (P = 0.016). There was no difference between acyclovir and placebo in the time to the next recurrence following completion of treatment [3]. low-dose oral acyclovirmay be effective in the prevention of HSV infection during OKT3 treatment of seropositive patients. Continuation of acyclovir prophylaxis for two to four weeks following the conclusion of OKT3 therapy may prevent occurrence of delayed infections [4].Clinical trial: Acyclovir to Treat Patients Co-infected With HIV and Herpes Viruses in Uganda. Phage2
Related Catalog	Signaling Pathways >>Anti-infection >>HSVResearch Areas >>Infection
References	[1]. Li Z, et al. Acyclovir treatment of skin lesions results in immune deviation in mice infected cutaneously with herpes simplex virus. Antivir Chem Chemother. 1999 Sep;10(5):251-7. [2]. Shelley WB, Hashim M, Shelley ED. Acyclovir in the treatment of hand-foot-and-mouth disease. Cutis. 1996 Apr;57(4):232-4. [3]. Collins P, Oliver NM. Sensitivity monitoring of herpes simplex virus isolates from patients receiving acyclovir. J Antimicrob Chemother. 1986 Oct;18 Suppl B:103-12. [4]. Meyrick Thomas RH, Dodd HJ, Yeo JM, Oral acyclovir in the suppression of recurrent non-genital herpes simplex virus infection. Br J Dermatol. 1985 Dec;113(6):731-5. [5]. Tang IY, Maddux MS, Veremis SA, Low-dose oral acyclovir for prevention of herpes simplex virus infection during OKT3 therapy. Transplant Proc. 1989 Feb;21(1 Pt 2):1758-60.

Description

Acyclovir, a molecule tailored to inactivate the thymidine kinase of the herpesvirus, is a guanosine analogue antiviral drug. It is a drug for HSV infection by GlaxoSmithKline.IC50 Value: 0.53-0.75 uM [3]Target: HSVin vitro: Acyclovir sensitivity was determined in a plaque-reduction assay in Vero cells. IC50 Values were consistently 2-3 fold lower in B2 compared with the H strain of Vero cells. HSV Type 2 strains were 2-10-fold less sensitive than Type 1 strains [2]. in vivo: two patients experienced a recurrence during treatment with oral acyclovir (200 mg 4 times daily) for up to 12 weeks, compared with nine during placebo treatment (P = 0.016). There was no difference between acyclovir and placebo in the time to the next recurrence following completion of treatment [3]. low-dose oral acyclovirmay be effective in the prevention of HSV infection during OKT3 treatment of seropositive patients. Continuation of acyclovir prophylaxis for two to four weeks following the conclusion of OKT3 therapy may prevent occurrence of delayed infections [4].Clinical trial: Acyclovir to Treat Patients Co-infected With HIV and Herpes Viruses in Uganda. Phage2

Related Catalog

Signaling Pathways >>Anti-infection >>HSVResearch Areas >>Infection

References

[1]. Li Z, et al. Acyclovir treatment of skin lesions results in immune deviation in mice infected cutaneously with herpes simplex virus. Antivir Chem Chemother. 1999 Sep;10(5):251-7.

[2]. Shelley WB, Hashim M, Shelley ED. Acyclovir in the treatment of hand-foot-and-mouth disease. Cutis. 1996 Apr;57(4):232-4.

[3]. Collins P, Oliver NM. Sensitivity monitoring of herpes simplex virus isolates from patients receiving acyclovir. J Antimicrob Chemother. 1986 Oct;18 Suppl B:103-12.

[4]. Meyrick Thomas RH, Dodd HJ, Yeo JM, Oral acyclovir in the suppression of recurrent non-genital herpes simplex virus infection. Br J Dermatol. 1985 Dec;113(6):731-5.

[5]. Tang IY, Maddux MS, Veremis SA, Low-dose oral acyclovir for prevention of herpes simplex virus infection during OKT3 therapy. Transplant Proc. 1989 Feb;21(1 Pt 2):1758-60.

Chemical & Physical Properties

Density	1.8±0.1 g/cm3
Boiling Point	576.5±58.0 °C at 760 mmHg
Melting Point	256-257°C
Molecular Formula	C₈H₁₁N₅O₃
Molecular Weight	225.205
Flash Point	302.4±32.3 °C
Exact Mass	225.086182
PSA	119.05000
LogP	-3.31
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.762
Stability	Stable. Incompatible with strong oxidizing agents.
Water Solubility	H2O: 0.7 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0791400

CHEMICAL NAME :: 6H-Purin-6-one, 1,9-dihydro-2-amino-9-((2-hydroxyethoxy)methyl)-

CAS REGISTRY NUMBER :: 59277-89-3

LAST UPDATED :: 199712

DATA ITEMS CITED :: 30

MOLECULAR FORMULA :: C8-H11-N5-O3

MOLECULAR WEIGHT :: 225.24

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ D1O2Q GZ IQ &T56 BN DN FVM INJ B1O2Q HZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 28 mg/kg/2D-I

TOXIC EFFECTS :: Brain and Coverings - changes in surface EEG Behavioral - hallucinations, distorted perceptions Lungs, Thorax, or Respiration - sputum

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 12 mg/kg/1D-I

TOXIC EFFECTS :: Brain and Coverings - meningeal changes Behavioral - somnolence (general depressed activity) Behavioral - antipsychotic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 100 mg/kg/5D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, allergic (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 80 mg/kg/4D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - hallucinations, distorted perceptions Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 486 mg/kg/17D-I

TOXIC EFFECTS :: Gastrointestinal - decreased motility or constipation Gastrointestinal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 134 ug/kg/1D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 101 mg/kg/2D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - muscle contraction or spasticity

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 107 mg/kg/4D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Multiple routes

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 36 mg/kg/2D-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Behavioral - coma Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 860 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 724 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1118 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1118 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg/5D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes primarily in glomeruli Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 60 mg/kg

SEX/DURATION :: female 5-6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 200 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1200 mg/kg

SEX/DURATION :: female 1-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - rabbit Kidney

DOSE/DURATION :: 6800 ug/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 38,1771,1989

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xi
Risk Phrases	36/37/38
Safety Phrases	S22-S24/25
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	UP0791400
HS Code	2933790090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles117

Liquid chromatography tandem mass spectrometry quantitation of intracellular concentrations of ganciclovir and its phosphorylated forms.

Anal. Bioanal. Chem 407(12) , 3449-56, (2015)

Ganciclovir (GCV) is prescribed for cytomegalovirus infection which is a major issue in immunodepressed patients. It is however characterized by hematological toxicity. A better understanding of GCV c...

Comparison of in vitro release rates of acyclovir from cream formulations using vertical diffusion cells.

AAPS PharmSciTech 15(4) , 994-9, (2014)

Acyclovir, indicated in the treatment of herpes labialis ("cold sores"), is formulated as semisolid topical dosage forms and marketed in numerous countries. Since the formulations of the various acycl...

Transporter-mediated uptake of UDP-glucuronic acid by human liver microsomes: assay conditions, kinetics, and inhibition.

Drug Metab. Dispos. 43(1) , 147-53, (2014)

This study characterized the kinetics, variability, and factors that affect UDP-glucuronic acid (UDP-GlcUA) uptake by human liver microsomes (HLM). Biphasic kinetics were observed for UDP-GlcUA uptake...

Synonyms

Zovir

9-((2-Hydroxyethoxy)methyl)guanine

EINECS 261-685-1

Poviral

aclovir

bw248u

Acyclo-V

Maynar

9-(2-Hydroxyethoxy)methylguanine

Vimrax

Zoviax

Aciclovir

Zyclir

Cycloviran

2-Amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one

Viroraxl

Azone

w-248-u

BW 248U

2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one

2-amino-9-{[(2-hydroxyethyl)oxy]methyl}-1,9-dihydro-6H-purin-6-one

6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-

9-[(2-Hydroxyethoxy)methyl]guanine

Wellcome 248U

Cargosil

Zovirax

Acyclovir

9-(2-Hydroxyethyloxymethyl)guanine

6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-

ACV

MFCD00057880

Acycloguanosine

vipral

Herpevir

Gerpevir

virorax

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