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Abacavir (hydrochloride)

CAT: 0804-HY-17423ESize: 1 EachDry Ice: NoHazardous: No
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Description
Abacavir hydrochloride is a competitive, orally active nucleoside reverse transcriptase inhibitor. Abacavir hydrochloride can inhibits the replication of HIV. Abacavir hydrochloride shows anticancer activity in prostate cancer cell lines. Abacavir hydrochloride can trespass the blood-brain-barrier and suppresses telomerase activity[1][2][3].
CAS Number
136777-48-5
UNSPSC
12352005
Target
Apoptosis; HIV; Reverse Transcriptase; Telomerase
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Cell Cycle/DNA Damage
Applications
COVID-19-anti-virus
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/abacavir-hydrochloride.html
Solubility
10 mM in DMSO
Smiles
NC1=NC(NC2CC2)=C3N=CN([C@H]4C=C[C@@H](CO)C4)C3=N1.[H]Cl
Molecular Formula
C14H19ClN6O
Molecular Weight
322.79
References & Citations
[1]Carlini F, et al. The reverse transcription inhibitor abacavir shows anticancer activity in prostate cancer cell lines. PLoS One. 2010 Dec 3;5 (12) :e14221.|[2]Collado-Diaz V, et al. Abacavir Induces Arterial Thrombosis in a Murine Model. J Infect Dis. 2018 Jun 20;218 (2) :228-233.|[3]Gringmuth M, et al. Enhanced Survival of High-Risk Medulloblastoma-Bearing Mice after Multimodal Treatment with Radiotherapy, Decitabine, and Abacavir. Int J Mol Sci. 2022 Mar 30;23 (7) :3815.|[4]McComsey GA, et al. Improvements in lipoatrophy, mitochondrial DNA levels and fat apoptosis after replacing stavudine with abacavir or zidovudine. AIDS. 2005 Jan 3;19 (1) :15-23.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Abacavir hydrochloride
CAS Number136777-48-5
PubChem CID67588134
IUPAC Name[(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol;hydrochloride
Molecular FormulaC14H19ClN6O
Molecular Weight322.79
Topological Polar Surface Area102
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count22
Formal Charge0
Complexity414
SMILES
C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO.Cl
InChI
InChI=1S/C14H18N6O.ClH/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21;/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);1H/t8-,10+;/m1./s1
InChIKey
QXNOPHSMRJNHHG-SCYNACPDSA-N
Chemical Structure
2D Structure
2D structure of Abacavir hydrochloride
CAS: 136777-48-5
CID: 67588134
Formula: C14H19ClN6O
MW: 322.79
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight322.79
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass322.1308869
Monoisotopic Mass322.1308869
Topological Polar Surface Area102 Ų
Heavy Atom Count22
Formal Charge0
Complexity414
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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sc-358732Abacavir hydrochloride
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