MERICITABINE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22440918 | https://www.ncbi.nlm.nih.gov/pubmed/20942646 | https://www.pharmacodia.com/web/drug/1_827.html

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

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus NS5B RNA-dependent RNA polymerase 14 Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24154738 \| http://www.fullertreacymoney.com/system/data/images/archive/2012-08-30/PharmaforBeginners82912.pdf	Inhibitor 8297		0.61 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20942646 https://www.ncbi.nlm.nih.gov/pubmed/20951424 https://www.ncbi.nlm.nih.gov/pubmed/26752189	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Tetrazole and triazole as bioisosteres of carboxylic acid: discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents.	2013 Aug 15	23856047
Highly efficient infectious cell culture of three hepatitis C virus genotype 2b strains and sensitivity to lead protease, nonstructural protein 5A, and polymerase inhibitors.	2014 Feb	23913364
The combination of alisporivir plus an NS5A inhibitor provides additive to synergistic anti-hepatitis C virus activity without detectable cross-resistance.	2014 Jun	24687498
Mericitabine and Either Boceprevir or Telaprevir in Combination with Peginterferon Alfa-2a plus Ribavirin for Patients with Chronic Hepatitis C Genotype 1 Infection and Prior Null Response: The Randomized DYNAMO 1 and DYNAMO 2 Studies.	2016	26752189
Modelling the interaction between danoprevir and mericitabine in the treatment of chronic HCV infection.	2016	26555159
Ritonavir-boosted danoprevir-based regimens in treatment-naive and prior null responders with HCV genotype 1 or 4 and compensated cirrhosis.	2016 May	26886127

Patents

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 UTC 2023` Edited by `admin` on `Fri Dec 15 19:41:09 UTC 2023`
Record UNII	TA63JX8X52
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MERICITABINE

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