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Substance Name: Acyclovir [USAN:USP]
RN: 59277-89-3
UNII: X4HES1O11F
InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N

Note

  • A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.

Molecular Formula

  • C8-H11-N5-O3

Molecular Weight

  • 225.2069
 

Classification Codes

Classification Codes

  • Anti-Infective Agents
  • Antiviral
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Aciclovir [INN]
  • Acyclovir
  • Acyclovir [USAN:USP]

MeSH Heading

  • Acyclovir

Synonyms

  • 2-Amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-6H-purin-6-one
  • 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-
  • 9-((2-Hydroxyethoxy)methyl)guanine
  • Aciclovir
  • Aciclovirum
  • Aciclovirum [INN-Latin]
  • Aciclovirum [Latin]
  • Activir
  • ACV
  • Acycloguanosine
  • Acyclovir
  • BW-248U
  • CCRIS 1953
  • DRG-0008
  • EINECS 261-685-1
  • Hascovir
  • HSDB 6511
  • NSC 645011
  • Sitavig
  • UNII-X4HES1O11F
  • Vipral
  • Virorax
  • W-248-U
  • Wellcome-248U
  • Zovirax

Systematic Names

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

Superlist Name

  • Aciclovir

Mixture Name

  • Xerese

Registry Numbers

CAS Registry Number

  • 59277-89-3

FDA UNII

  • X4HES1O11F

System Generated Number

  • 0059277893

Structure Descriptors

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)

InChIKey

MKUXAQIIEYXACX-UHFFFAOYSA-N

Smiles

c1nc2c(=O)[nH]c(nc2n1COCCO)N

Toxicity

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) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 American Journal of Kidney Diseases. Vol. 22, Pg. 611, 1993.
man TDLo oral 486mg/kg/17D- (486mg/kg) GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION		 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) BEHAVIORAL: COMA

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

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) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC

BRAIN AND COVERINGS: MENINGEAL CHANGES		 Southern Medical Journal. Vol. 87, Pg. 1227, 1994.
women TDLo oral 28mg/kg/2D-I (28mg/kg) LUNGS, THORAX, OR RESPIRATION: SPUTUM

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Southern Medical Journal. Vol. 87, Pg. 1227, 1994.
women TDLo oral 80mg/kg/4D-I (80mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 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.

Physical Properties

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

Physical property data is provided to ChemIDplus by SRC, Inc.