Apricitabine
Basic information
- CAS
143338-12-9- Standard SMILES
Nc1ccn([C@H]2CO[C@@H](CO)S2)c(=O)n1- InChIKey
RYMCFYKJDVMSIR-RNFRBKRXSA-N- Molecular formula
- C8H11N3O3S
- Average molar mass
- 229.26 g/mol
- Monoisotopic mass
- 229.05211239
Overview
Apricitabine has been used in trials studying the treatment of HIV Infections.
Names & identifiers
- Preferred name
- Apricitabine
- IUPAC
- 4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one
- English name
- Apricitabine
- Molecular formula
- C8H11N3O3S
- Molecular weight
- 229.26
Names & synonyms
Apricitabine160707-69-7AVX754SPD754AVX-754SPD-754BCH-10618BCH 10618ApricitabinaK1YX059ML1(-)-BCH 10652SPD 754
Show more names
CS-1026Avx 754(-)-dOTCUnii-K1yx059ml1Apricitabine [(-)-BCH10652
BCH-106192(1H)-Pyrimidinone, 4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]-BCH-10652, (-)-DTXSID60166974BCH106192(1H)-Pyrimidinone, 4-amino-1-((2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl)-apricitabinumRefChem:558432
Database identifiers
- CAS
143338-12-9、160707-69-7- PubChem CID
- 455041
- DTXSID
DTXSID60166974- ChEMBL
CHEMBL210651- UNII
- DND9Y3G72C、K1YX059ML1
- Nikkaji
- J1.147.915D、J645.730D
Properties
Computed structural properties
- XLogP
- -1.2
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 331
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 475.4 · 475.4±55.0 °C(Predicted)
- Density
- 1.73 · 1.73
- solubility
- DMSO: soluble
- form
- A solid
- pka
- 13.83 · 13.83±0.10(Predicted)
- FDA UNII
- 1 YX059ML1 · K1YX059ML1
Chemistry & industry
Pharmacology
Mechanism of ActionApricitabine is a type of medicine called a nucleoside reverse transcriptase inhibitor (NRTI). NRTIs work by blocking reverse transcriptase, a protein that HIV needs to make more copies of itself.
Applications
DescriptionApricitabine (formerly known as BCH-10618, SPD754, and AVX754) is a deoxycytidine nucleoside reverse transcriptase inhibitor (NRTI) in clinical development for the treatment of HIV disease. Specifically, apricitabine is the (–)-enantiomer of the heterosubstituted analog 2udeoxy-3u-oxa-4u-thiocytidine and has the molecular formula C8H11N3O3S. Apricitabine is structurally similar to lamivudine, but differs in the inversion of the oxygen and sulfur in the furanosyl ring. Apricitabine has a molecular weight of 229.26 (1 mM = 0.229 mg/ml).
DescriptionIn common with other NRTIs, apricitabine is activated by intra-cellular phosphorylation. The initial phosphorylation to apricitabine monophosphate is catalyzed by deoxycytidine kinase. After further phosphorylation, the triphosphate form of the molecule competes with endogenous deoxycytidine triphosphate for binding to HIV-1 reverse transcriptase. The subsequent incorporation of apricitabine triphosphate into nascent DNA by this enzyme interrupts viral replication by terminating the elongation of the DNA chain. Apricitabine triphosphate is a potent and highly selective inhibitor of HIV-1 reverse transcriptase in vitro. Its inhibitory constant (Ki) for reverse transcriptase from wild-type HIV-1 (0.08 mM) was half that of lamivudine triphosphate under the same conditions and 150- to 3750- fold lower than for human DNA polymerases, including the mitochondrial DNA polymerase γ .
Uses(-)-2''-Deoxy-3''-oxa-4''-thiocytidine (Apricitabine) is a drug that is used in the treatment of HIV aids. It as also been shown to be useful against lamivudine and zidovudine resistant virus strains
Related reactions
1 records
Compound notes
Loading…