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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
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
Selection of resistance-conferring mutations in HIV-1 by the nucleoside reverse transcriptase inhibitors (+/-)dOTC and (+/-)dOTFC.
2000 Nov
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
Gateways to clinical trials.
2007 Jan-Feb
Apricitabine continues to show good results.
2008 Sep
Emerging antiviral drugs.
2008 Sep
Effects of the K65R and K65R/M184V reverse transcriptase mutations in subtype C HIV on enzyme function and drug resistance.
2009 Feb 11
Pharmacotherapy of pediatric and adolescent HIV infection.
2009 Jun
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.
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 Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
Code System Code Type Description
WIKIPEDIA
APRICITABINE
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID60166974
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
DRUG BANK
DB12855
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
MESH
C508042
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
PUBCHEM
455041
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
FDA UNII
K1YX059ML1
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
EVMPD
SUB33010
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
INN
8759
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
SMS_ID
100000126376
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
MERCK INDEX
m2012
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY Merck Index
CAS
160707-69-7
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
NCI_THESAURUS
C79871
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY