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Home> Encyclopedia >   /  Antibiotic and antimicrobial agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate  /  Pharmaceuticals and Biochemicals
Acyclovir structure
Acyclovir structure

Acyclovir

Iupac Name:2-amino-9-(2-hydroxyethoxymethyl)-3H-purin-6-one
CAS No.:59277-89-3
Molecular Weight:225.20464
Introduction: Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered intravenously, orally, or topically.
1. Names and Identifiers
1.1 Name
Acyclovir
1.2 Synonyms

9-(2-Hydroxyethoxymethyl)guanine 9-[(2-Hydroxyethoxy)methyl]guanine aciclovir Acycloguanosine Acyclovir Acyclovir (Patented-No Supply) N(9)-Oxyethoxymethylguanine (Acyclovir)

1.3 CAS No.
59277-89-3
1.4 CID
135398513
1.5 EINECS(EC#)
261-685-1
1.6 Molecular Formula
C8H11N5O3 (isomer)
1.7 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)
1.8 InChkey
MKUXAQIIEYXACX-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=NC2=C(N1COCCO)N=C(NC2=O)N
1.10 Isomers Smiles
C1=NC2=C(N1COCCO)N=C(NC2=O)N
2. Properties
3.1 Density
1.77
3.2 Melting Point
256-257℃
3.3 Boiling Point
595 °C at 760 mmHg
3.4 Vapour
5.4X10-15 mm Hg at 25 °C (est)
3.5 Refractive Index
1.8000 (estimate)
3.6 Flash Point
595 °C at 760 mmHg
3.7 Appearance
White to light yellow crystal powder
3.8 Chemical Properties
white to light yellow crystal powder
3.9 Color/Form
Powder
3.10 pKa
[2.52]
3.11 Solubility
H2O: 0.7?mg/mL
3.12 Stability
Stable. Incompatible with strong oxidizing agents.
3.13 StorageTemp
?20°C
3.14 Water Solubility
Water solubility: 0.7 mg/mL
3. Use and Manufacturing
4.1 Definition
ChEBI: An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9.
4.2 Storage
Ambient temperatures.
4.3 Usage
Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered intravenously, orally, or topically.
4. Safety and Handling
5.1 Hazard Codes
Xi
5.2 Risk Statements
36/37/38
5.3 Safety Statements
S22;S24/25;S36;S26
5.4 HazardClass
IRRITANT
5.5 Transport
OTH
5.6 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
5.7 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl acyclovir sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Acyclovir Sodium/
5.8 Formulations/Preparations
Topical: Ointment: 5%, Zovirax (Biovail)
Oral: Capsules: 200 mg Zovirax (with parabens), (GlaxoSmithKline); Suspension: 200 mg/5mL Acyclovir Suspension (with parabens), (Alpharma), Zovirax (with glycerin parabens and sorbitol), (GlaxoSmithKline); Tablets: 400 mg Zovirax (with povidone), GlaxoSmithKline, 800 mg Zovirax (with povidone), GlaxoSmithKline.
Acyclovir sodium: Parenteral: For injection, concentrate, for IV infusion only: 25 mg (of acyclovir) per mL (500 mg, 1 g) Acyclovir Sodium Injection (Mayne), 50 mg (of acyclovir) per mL (500 mg, 1 g) Acyclovir Sodium Injection (American Pharmaceutical Partners), For Injection, for IV infusion only: 500 mg (of acyclovir) Acyclovir Sodium for Injection (Abbott, American Pharmaceutical Partners, Bedford), Zovirax (GlaxoSmithKline), 1 g (of acyclovir) Acyclovir Sodium for Injection (Abbott, Bedford), Zovirax (GlaxoSmithKline).
5.9 Octanol/Water Partition Coefficient
log Kow = -1.56
5.10 Safety

Hazard Codes:?IrritantXi
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.

5.11 Specification

?Acyclovir , its cas register number is 59277-89-3. It also can be called 9-[(2-Hydroxyethoxy)methyl]guanine ; 2-Amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-6H-purin-6-one ; and Acycloguanosine . 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%).

5.12 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) 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. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Computational chemical data
  • Molecular Weight:225.20464g/mol
  • Molecular Formula:C8H11N5O3
  • Compound Is Canonicalized:True
  • XLogP3-AA:_1.9
  • Exact Mass:225.08618923
  • Monoisotopic Mass:225.08618923
  • Complexity:308
  • Rotatable Bond Count:4
  • Hydrogen Bond Donor Count:3
  • Hydrogen Bond Acceptor Count:5
  • Topological Polar Surface Area:115
  • Heavy Atom Count:16
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
10. Question & Answer
  • Acyclovir is an antiviral drug. However, it is not a cure for these infections. The viruses that cause these infections continue to live in the body even between outbreaks. Acyclovir decreases the severity and length of these outbreaks. It helps the sores heal faster, keeps new sores from forming, ...
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