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59277-89-3 , Acyclovir, CAS:59277-89-3

59277-89-3 , Acyclovir ,
CAS:59277-89-3
C8H11N5O3 / 225.20
MFCD00057880

Acyclovir , 阿昔洛韦

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

Acyclovir is an antiviral drug that inhibits the replication of herpes viruses by selectively inhibiting viral DNA polymerase. The drug is active against a broad range of herpes viruses, including both types of herpes simplex virus (HSV-1 and HSV-2) and varicella zoster virus. Acyclovir has also been shown to be effective against aciclovir-resistant mutants. This drug can be used as a prophylaxis or in combination with other antiviral agents for the treatment of active infections. Acyclovir can cause headaches, nausea, vomiting, and diarrhea when taken orally. It should not be taken with certain medicines such as aminoglycosides or high doses of aspirin because this may increase the risk for kidney problems.

Title: Acyclovir

CAS Registry Number: 59277-89-3

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

Additional Names: acycloguanosine; 9-[(2-hydroxyethoxy)methyl]guanine

Manufacturers' Codes: BW-248U; Wellcome 248U

Trademarks: Acicloftal (Bruschettini); Avirase (Lampugnani); Cycloviran (Sigma-Tau); Maynar (Ferrer); Virmen (Menarini); Viruseen (Hommel); Zoliparin (Mann); Zovir (GSK); Zovirax (GSK)

Molecular Formula: C8H11N5O3

Molecular Weight: 225.20

Percent Composition: C 42.67%, H 4.92%, N 31.10%, O 21.31%

Literature References: Orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Prepn: H. J. Schaeffer, DE 2539963; idem, US 4199574 (1976, 1980 to Wellcome). Convenient synthesis from guanine: H. Matsumoto et al., Chem. Pharm. Bull. 36, 1153 (1988). Selectivity of action: G. B. Elion et al., Proc. Natl. Acad. Sci. USA 74, 5716 (1977). Chemistry, antiviral activity, metabolism: H. J. Schaeffer et al., Nature 272, 583 (1978). In vitro activity: P. Collins, D. J. Bauer, J. Antimicrob. Chemother. 5, 431 (1979). Effect on herpes simplex infections in mice: H. J. Field et al., Antimicrob. Agents Chemother. 15, 554 (1979); on herpes zoster in immunocompromised patients: H. H. Balfour et al., N. Engl. J. Med. 308, 1448 (1983). Treatment of primary episodes of genital herpes simplex infection: Y. J. Bryson et al., ibid. 916; of recurrent genital herpes: S. E. Straus et al., ibid. 310, 1545 (1984); J. M. Douglas et al., ibid. 1551. HPLC determn in serum and clinical pharmacokinetics: G. Bahrami et al., J. Chromatogr. B 816, 327 (2005). Symposia on pharmacology and clinical studies: Am. J. Med. 73, Suppl. 1A, 1-392 (1982); J. Antimicrob. Chemother. 12, Suppl. B, 1-202 (1983); Scand. J. Infect. Dis. Suppl. 47, 1-176 (1985). Review: R. J. Whitley, J. W. Gnann, Jr., N. Engl. J. Med. 327, 782-789 (1992).

Properties: Crystals from methanol, mp 256.5-257°. LD50 in mice (mg/kg): >10,000 orally; 1000 i.p. (Schaeffer).

Melting point: mp 256.5-257°

Toxicity data: LD50 in mice (mg/kg): >10,000 orally; 1000 i.p. (Schaeffer)

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones.

CAS Number59277-89-3
Product NameAcyclovir
IUPAC Name2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
Molecular FormulaC8H11N5O3
Molecular Weight225.2 g/mol
InChIInChI=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)
InChI KeyMKUXAQIIEYXACX-UHFFFAOYSA-N
SMILESC1=NC2=C(N1COCCO)N=C(NC2=O)N
SynonymsAciclovir; Acycloguanosine; 59277-89-3; Zovirax; Vipral
Canonical SMILESC1=NC2=C(N1COCCO)NC(=NC2=O)N
Isomeric SMILESC1=NC2=C(N1COCCO)NC(=NC2=O)N


CAS No: 59277-89-3 Synonyms: AcyclovirValaciclovir hydrochloride anhydrous impurity BAcycloguanosine9-(2-Hydroxyethoxymethyl)guanine MDL No: MFCD00057880 Chemical Formula: C8H11N5O3 Molecular Weight: 225.20


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