U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26FN3O6
Molecular Weight 399.4139
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MERICITABINE

SMILES

CC(C)C(=O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@](C)(F)[C@@H]1OC(=O)C(C)C

InChI

InChIKey=MLESJYFEMSJZLZ-MAAOGQSESA-N
InChI=1S/C18H26FN3O6/c1-9(2)14(23)26-8-11-13(28-15(24)10(3)4)18(5,19)16(27-11)22-7-6-12(20)21-17(22)25/h6-7,9-11,13,16H,8H2,1-5H3,(H2,20,21,25)/t11-,13-,16-,18-/m1/s1

HIDE SMILES / InChI
Molecular Formula C18H26FN3O6
Molecular Weight 399.4139
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Mericitabine is a specific inhibitor of hepatitis C virus (HCV) replication that target NS5B polymerase. Mericitabine, a prodrug, is hydrolyzed in vivo to produce PSI-6130. It had been studied in phase II clinical trials for the treatment of chronic hepatitis C. However, while it showed a good safety profile in clinical trials, it was not sufficiently effective to be used as a standalone agent.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.61 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.557 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
0.854 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.361 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10.2 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.23 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
20.5 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.35 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
113 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
28.8 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: FASTED
21.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
19 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO5012433 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.54 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.96 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24025983
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RO4995855 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00G469
https://www.1pchem.com/search?query=1P00G469
AK Scientific
Y3208
https://aksci.com/item_detail.php?cat=Y3208
Achemo Scientific Limited
AC-81771
http://www.achemo.com/search/?Keyword=AC-81771
AstaTech
P11586
http://astatechinc.com/CPSResult.php?CRNO=P11586
BOC Sciences
817204-33-4
http://www.bocsci.com/description.asp?cas=817204-33-4
Cayman Chemical
13575
http://www.caymanchem.com/app/template/Product.vm/catalog/13575
Chem Scene
CS-0597
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0597
ChemDiv
H027-4240
http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=H027-4240
KeyOrganics
AS-63598
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-63598
Lab Network
LN00199862
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00199862
Lab Seeker
SC-50499
http://www.labseeker.com/search.php?keywords=SC-50499&category=0
LabSeeker
SC-50499
http://www.labseeker.com/search.php?keywords=SC-50499&category=0
Matrix Scientific
97930
http://www.matrixscientific.com/097930.html
MedChem Express
HY-10165
https://www.medchemexpress.com/search.html?q=HY-10165&ft=&fa=&fp=
MolPort
MolPort-027-835-126
https://www.molport.com/shop/molecule-link/MolPort-027-835-126
MolPort
MolPort-046-590-290
https://www.molport.com/shop/molecule-link/MolPort-046-590-290
ShangHai Biochempartner
BCP09351
http://www.biochempartner.com/search_BCP09351
Synthonix
13717
https://synthonix.com/catalogsearch/result/?q=13717
Synthonix
D13717
https://synthonix.com/catalogsearch/result/?q=D13717
Tetrahedron
TS94137
http://www.thsci.com/search.do?q=TS94137
eMolecules
44688924
https://orderbb.emolecules.com/search/#?query=44688924
mcule
MCULE-7926945296
https://mcule.com/MCULE-7926945296/
mcule
MCULE-8380582996
https://mcule.com/MCULE-8380582996/
mcule
MCULE-9836274954
https://mcule.com/MCULE-9836274954/
PubMed

PubMed

TitleDatePubMed
Patents

Patents

20070197463
2
US20130172239
2
WO2013178571A1
2

Sample Use Guides

In Vivo Use Guide
1500 mg doses twice daily for 2 weeks
Route of Administration: Oral
In Vitro Use Guide
A stable HCV 1b replicon cell (Gt 1b Con1) line was treated with the NS5B nucleoside inhibitor R7128 (prodrug PSI-6130). Inhibition of HCV replicon-encoded Renilla luciferase reporter activity after 3 days of incubation was calculated - EC50 = 0.61 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:41:09 GMT 2023
Edited
by admin
on Fri Dec 15 19:41:09 GMT 2023
Record UNII
TA63JX8X52
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MERICITABINE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
R-7128
Code English
2'-DEOXY-2'-FLUORO-2'-C-METHYLCYTIDINE DIISOBUTYRATE
Common Name English
mericitabine [INN]
Common Name English
RG7128
Code English
RO-5024048
Code English
MERICITABINE [USAN]
Common Name English
PSI6130 DIISOBUTYRATE
Code English
Mericitabine [WHO-DD]
Common Name English
RO5024048
Code English
CYTIDINE, 2'-DEOXY-2'-FLUORO-2'-METHYL-, 3',5'-BIS(2-METHYLPROPANOATE), (2'R)-
Common Name English
3',5'-DIISOBUTYRYL PSI6130
Code English
R7128
Code English
2'.ALPHA.-FLUORO-2'.BETA.-METHYL-3',5'-DIISOBUTYRYLDEOXYCYTIDINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
Code System Code Type Description
EVMPD
SUB89593
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
PUBCHEM
16122663
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID201025655
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
FDA UNII
TA63JX8X52
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
DRUG BANK
DB12045
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
USAN
ZZ-121
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
SMS_ID
100000140218
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
NCI_THESAURUS
C98959
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
CAS
940908-79-2
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL562967
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
INN
9293
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
WIKIPEDIA
Mericitabine
Created by admin on Fri Dec 15 19:41:09 GMT 2023 , Edited by admin on Fri Dec 15 19:41:09 GMT 2023
PRIMARY
Related Record Type Details
HEPATITIS C VIRUS
TARGET ORGANISM->INHIBITOR
HCV NS5B POLYMERASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of PSI-6130
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of PSI-6130
ACTIVE MOIETY
NIH
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