Vidarabine
A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Vidarabine are summarized together with 3D and 2D structures and relevant physico-chemical properties.
Table of Contents
What is the Vidarabine?
The molecule Vidarabine presents a molecular formula of C10H13N5O4 and its IUPAC name is (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol.
Vidarabine, also known as 9-[2-hydroxy-1,9-bis(hydroxymethyl)propyl]adenine, is a nucleoside analogue antiviral medication used to treat herpes simplex virus and varicella zoster virus infections. It is also used as an immunosuppressive agent following organ transplantation. It was patented in 1967 and approved for medical use in 1977..
Vidarabine is used to treat herpes simplex virus and varicella zoster virus infections. It is also used as an immunosuppressive agent following organ transplantation..
Herpes simplex virus (HSV) is a DNA virus that causes infections in humans. HSV-1 is the most common type of HSV and is the cause of oral herpes, which is characterized by sores on the lips, mouth, or gums. HSV-2 is the most common cause of genital herpes, which is characterized by sores on the genitals..
Varicella zoster virus (VZV) is the virus that causes chickenpox. It is a DNA virus in the herpesvirus family. VZV is the cause of varicella, which is characterized by a rash of small, red, itchy bumps..
Vidarabine is an antiviral medication that is used to treat HSV and VZV infections. It is a nucleoside analogue that works by inhibiting the replication of HSV and VZV..
Vidarabine is used to treat HSV and VZV infections. It is also used as an immunosuppressive agent following organ transplantation..
Vidarabine is a nucleoside analogue antiviral medication. It is a white, crystalline powder that is soluble in water..
The recommended dose of vidarabine for the treatment of HSV or VZV infection is 10 mg/kg IV every 8 hours for 7 days. For the treatment of chickenpox, the recommended dose is 20 mg/kg IV every 8 hours for 7 days..
Vidarabine should be administered by a healthcare professional. It is given as an IV infusion over 30 minutes..
Common side effects of vidarabine include headache, nausea, and vomiting. Vidarabine can also cause dizziness..
Vidarabine is a nucleoside analogue antiviral medication used to treat herpes simplex virus and varicella zoster virus infections. It is also used as an immunosuppressive agent following organ transplantation. Vidarabine is a white, crystalline powder that is soluble in water. The recommended dose of vidarabine for the treatment of HSV or VZV infection is 10 mg/kg IV every 8 hours for 7 days. For the treatment of chickenpox, the recommended dose is 20 mg/kg IV every 8 hours for 7 days. Vidarabine should be administered by a healthcare professional. It is given as an IV infusion over 30 minutes. Common side effects of vidarabine include headache, nausea, and vomiting. Vidarabine can also cause dizziness..
3D structure
Cartesian coordinates
Geometry of Vidarabine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.
2D drawing
Molecule descriptors
| IUPAC name | (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| InChI code | InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1 |
| InChI Key | OIRDTQYFTABQOQ-UHTZMRCNSA-N |
| SMILES | Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O |
Other names (synonyms)
IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.
One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.
Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.
In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.
- (2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
- (2R,3S,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
- 2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
- 3XQD2MEW34
- 536V174
- 5536-17-4
- 6-Amino-9-b-D-arabinofuranosylpurine
- 6-Amino-9-beta-D-arabinofuranosylpurine
- 6-amino-9-(beta-D-arabinofuranosyl)purine
- 9-(beta-D-Arabinofuranosyl)adenine
- 9-(beta-D-arabinofuranosyl)-9H-adenine
- 9--D-arabinofuranosyl-9H-purin-6-amine
- 9-.beta.-D-Arabinofuranosyl-9H-purin-6-amine
- 9-.beta.-D-Arabinofuranosyl-9H-purine-6-amine
- 9-BETA-D-ARABINOFURANOSYL-ADENINE
- 9-b-d-arabinofuranosyladenine
- 9-beta-Arabinoadenosine
- 9-beta-D-Arabinofuranosyladenine
- 9-beta-D-arabinofuranosyl adenine
- 9-beta-D-arabinofuranosyl-9H-purin-6-amine
- 9-ss -D-Arabinofuranosyladenine
- 9H-Purin-6-amine, 9-.beta.-D-arabinofuranosyl-
- 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-
- 9H-Purin-6-amine, 9beta-D-arabinofuranosyl-
- 9H-adenin-9-yl beta-D-arabinofuranoside
- 9beta-D-Arabinofuranosyladenine
- AB00430250-08
- AB00430250-09
- AB00430250_11
- AB00430250_12
- AI3-52821
- Adenine 9-beta-D-arabinofuranoside
- Adenine 9-beta;-D-arabinofuranoside
- Adenine 9-ss -D-arabinofuranoside
- Adenine arabinoside
- Adenine beta-D-arabinofuranoside
- Adenine, 9-beta-D-arabinofuranosyl-
- Adenine, 9beta-D-arabinofuranosyl-
- Adenine-9-beta-D-arabinofuranoside
- Adenine-beta-D-arabinofuranoside
- Ara-A
- Araadenosine
- Arabinoside adenine
- Arabinosyl adenine
- Arabinosyladenine
- Arasena-A
- BCP27778
- BDBM50144936
- BRN 0624881
- BSPBio_002000
- CCG-39634
- CCRIS 3383
- CI 673
- CI-673
- D06298
- DB00194
- DS-1755
- DivK1c_000191
- GTPL4806
- HG1001
- HMS1921K05
- HMS2090F06
- HMS2092C16
- HMS2230N24
- HMS3259I08
- HMS3714I18
- HMS500J13
- HSDB 6514
- HY-B0277
- IDI1_000191
- KBio1_000191
- KBio2_002418
- KBio2_004986
- KBio2_007554
- KBio3_001500
- KBioGR_001224
- KBioSS_002424
- MFCD00065471
- MLS001066352
- MLS001333133
- MLS001333134
- NC00547
- NCGC00023673-08
- NCGC00178869-01
- NINDS_000191
- NSC 247519
- NSC-247519
- NSC-404241
- NSC-757383
- NSC757383
- PDSP1_001036
- PDSP2_001020
- Pharmakon1600-01500609
- Q415107
- RAB
- SBI-0051555.P002
- SMP1_000312
- SMR000471872
- SPECTRUM1500609
- SR-01000765435
- SR-01000765435-2
- SR-05000001737
- SR-05000001737-1
- SW199234-2
- Spongoadenosine
- V0098
- V0175
- Vidarabin
- Vidarabina
- Vidarabine
- Vidarabine (JAN)
- Vidarabine (Vira-A)
- Vidarabine anhydrous
- Vidarabine, anhydrous
- Vidarabinum
- Vira A
- Vira ATM
- Vira-A
- araA
- beta-D-Arabinofuranosyladenine
- beta-D-Arabinosyladenine
- s1784
Reference codes for other databases
There exist several different chemical codes commonly used in orded to identify molecules:- CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
- Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
- ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
- PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
- RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
- ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
- CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.
- ZINC970363
- UNII-3XQD2MEW34
- AKOS015919711
- DTXSID80873976
- CHEMBL1090
- CHEBI:45327
- EINECS 226-893-9
- SPBio_001491
- SCHEMBL110914
- Spectrum_001894
- Spectrum2_001336
- Spectrum3_000580
- Spectrum4_000782
- Spectrum5_001429
Physico-Chemical properties
| IUPAC name | (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| Molecular formula | C10H13N5O4 |
| Molecular weight | 267.241 |
| Melting point (ºC) | |
| Boiling point (ºC) | |
| Density (g/cm3) | |
| Molar refractivity | 62.67 |
| LogP | -1.4 |
| Topological polar surface area | 139.5 |
LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.
The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.
TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.
In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.
For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.