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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O3S
Molecular Weight 229.256
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Apricitabine

SMILES

NC1=NC(=O)N(C=C1)[C@H]2CO[C@@H](CO)S2

InChI

InChIKey=RYMCFYKJDVMSIR-RNFRBKRXSA-N
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1

HIDE SMILES / InChI

Molecular Formula C8H11N3O3S
Molecular Weight 229.256
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Apricitabine (ATC) is an investigational drug that was being studied for the treatment of HIV infection. Apricitabine belongs to a class (group) of HIV drugs called nucleoside reverse transcriptase inhibitors (NRTIs). NRTIs block an HIV reverse transcriptase. By blocking reverse transcriptase, NRTIs prevent HIV from multiplying and can reduce the amount of HIV in the body. In vitro studies have shown that apricitabine appears to work on certain HIV strains against which other FDA-approved NRTIs, such as lamivudine (brand name: Epivir), may no longer work. Apricitabine shows antiviral activity in vitro against HIV-1 strains and clinical isolates with mutations in the reverse transcriptase that confer resistance to other NRTIs, including M184V, thymidine analogue mutations (TAMs), nucleoside-associated mutations such as L74V and certain mutations at codon 69. Apricitabine has shown activity in treatment-experienced HIV-1-infected patients with NRTI resistance (with M184V and up to five TAMs) as well as in treatment-naive patients. The study of apricitabine as an HIV medicine was discontinued in 2016. The company developing the drug decided to stop their clinical trials due to a lack of funding and a lack of interest in apricitabine’s early access program.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.08 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
9720 ng/mL
800 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
11500 ng/mL
1200 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
4920 ng/mL
400 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
38100 ng × h/mL
800 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
53200 ng × h/mL
1200 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
24100 ng × h/mL
400 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.69 h
800 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
1.91 h
1200 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens
2.45 h
400 mg 2 times / day steady-state, oral
APRICITABINE plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In this Phase II randomized, double-blind study, 51 treatment-experienced HIV-1-infected patients with the reverse transcriptase mutation M184V who were failing therapy which included lamivudine (3TC) were randomized to receive twice-daily 600 mg Apricitabine (ATC), 800 mg ATC or 150 mg 3TC for 21 days.
Route of Administration: Oral
In Vitro Use Guide
Apricitabine (ATC) showed similar activity (IC50: 10–50 uM) against isolates of various group M HIV-1 clades, including A/G, B, C, D, A(E), D/F, F and H.
Substance Class Chemical
Record UNII
K1YX059ML1
Record Status Validated (UNII)
Record Version