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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O3S
Molecular Weight 229.2576
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRICITABINE

SMILES

c1cn([C@@]2([H])CO[C@@]([H])(CO)S2)c(nc1=N)O

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 229.2576
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4920 ng/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9720 ng/mL
800 mg 2 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11500 ng/mL
1200 mg 2 times / day steady-state, oral
dose: 1200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
24100 ng × h/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
38100 ng × h/mL
800 mg 2 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
53200 ng × h/mL
1200 mg 2 times / day steady-state, oral
dose: 1200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.45 h
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.69 h
800 mg 2 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.91 h
1200 mg 2 times / day steady-state, oral
dose: 1200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
APRICITABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Anti-human immunodeficiency virus and anti-hepatitis-B virus activities and toxicities of the enantiomers of 2'-deoxy-3'-oxa-4'-thiocytidine and their 5-fluoro analogues in vitro.
1995 Jan 6
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
Antiviral activity of 2'-deoxy-3'-oxa-4'-thiocytidine (BCH-10652) against lamivudine-resistant human immunodeficiency virus type 1 in SCID-hu Thy/Liv mice.
2000 Mar
Selection and characterization of human immunodeficiency virus type 1 variants resistant to the (+) and (-) enantiomers of 2'-deoxy-3'-oxa-4'-thio-5-fluorocytidine.
2000 May
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.
2000 Nov
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.
2005 Mar
Pharmacokinetics of single oral doses of apricitabine, a novel deoxycytidine analogue reverse transcriptase inhibitor, in healthy volunteers.
2006
In vitro antiretroviral activity and in vitro toxicity profile of SPD754, a new deoxycytidine nucleoside reverse transcriptase inhibitor for treatment of human immunodeficiency virus infection.
2006 Feb
Efficacy and tolerability of 10-day monotherapy with apricitabine in antiretroviral-naive, HIV-infected patients.
2006 Jun 12
Effects of trimethoprim on the clearance of apricitabine, a deoxycytidine analog reverse transcriptase inhibitor, and Lamivudine in the isolated perfused rat kidney.
2006 Nov
Kinetics of inhibition of HIV type 1 reverse transcriptase-bearing NRTI-associated mutations by apricitabine triphosphate.
2007
Apricitabine: a novel deoxycytidine analogue nucleoside reverse transcriptase inhibitor for the treatment of nucleoside-resistant HIV infection.
2007
Gateways to clinical trials.
2007 Jan-Feb
Effects of apricitabine and other nucleoside reverse transcriptase inhibitors on replication of mitochondrial DNA in HepG2 cells.
2007 Oct
Multiple-dose pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in patients with HIV-1 infection.
2008
Influence of food on the pharmacokinetics of apricitabine, a novel deoxycytidine analogue reverse transcriptase inhibitor.
2008 Aug
Pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in healthy volunteers treated with trimethoprim-sulphamethoxazole.
2008 Feb
Apricitabine continues to show good results.
2008 Sep
Emerging antiviral drugs.
2008 Sep
Comparison of the pharmacokinetics of apricitabine in the presence and absence of ritonavir-boosted tipranavir: a phase I, open-label, controlled, single-centre study.
2009
Novel compounds for the treatment of HIV type-1 infection.
2009
Gateways to clinical trials.
2009 Apr
Effects of the K65R and K65R/M184V reverse transcriptase mutations in subtype C HIV on enzyme function and drug resistance.
2009 Feb 11
An analysis of enzyme kinetics data for mitochondrial DNA strand termination by nucleoside reverse transcription inhibitors.
2009 Jan
Pharmacotherapy of pediatric and adolescent HIV infection.
2009 Jun
Apricitabine: a nucleoside reverse transcriptase inhibitor for HIV infection.
2009 Oct
Resistance profile of the new nucleoside reverse transcriptase inhibitor apricitabine.
2010 Feb
Patents

Patents

Sample Use Guides

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
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
Created
by admin
on Sat Jun 26 03:42:46 UTC 2021
Edited
by admin
on Sat Jun 26 03:42:46 UTC 2021
Record UNII
K1YX059ML1
Record Status Validated (UNII)
Record Version
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Name Type Language
APRICITABINE
INN   MI  
INN  
Official Name English
AVX-754
Code English
BCH-10652, (-)-
Code English
4-AMINO-1-((2R,4R)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-4-YL)PYRIMIDIN-2(1H)-ONE
Systematic Name English
APRICITABINE [INN]
Common Name English
BCH-10618
Code English
SPD -754
Code English
APRICITABINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97452
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
Code System Code Type Description
WIKIPEDIA
APRICITABINE
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
EPA CompTox
160707-69-7
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
DRUG BANK
DB12855
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
MESH
C508042
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
PUBCHEM
455041
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
FDA UNII
K1YX059ML1
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
EVMPD
SUB33010
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
INN
8759
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
MERCK INDEX
M2012
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY Merck Index
CAS
160707-69-7
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
NCI_THESAURUS
C79871
Created by admin on Sat Jun 26 03:42:46 UTC 2021 , Edited by admin on Sat Jun 26 03:42:46 UTC 2021
PRIMARY
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