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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H53N5O8S
Molecular Weight 799.975
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOVAPREVIR

SMILES

COC1=CC=C2C(O[C@@H]3C[C@H](N(C3)C(=O)[C@@H](CC(=O)N4CCCCC4)C(C)(C)C)C(=O)N[C@@]5(C[C@H]5C=C)C(=O)NS(=O)(=O)C6CC6)=CC(=NC2=C1)C7=CC=CC=C7

InChI

InChIKey=MHFMTUBUVQZIRE-WINRQGAFSA-N
InChI=1S/C43H53N5O8S/c1-6-28-25-43(28,41(52)46-57(53,54)31-16-17-31)45-39(50)36-22-30(26-48(36)40(51)33(42(2,3)4)23-38(49)47-19-11-8-12-20-47)56-37-24-34(27-13-9-7-10-14-27)44-35-21-29(55-5)15-18-32(35)37/h6-7,9-10,13-15,18,21,24,28,30-31,33,36H,1,8,11-12,16-17,19-20,22-23,25-26H2,2-5H3,(H,45,50)(H,46,52)/t28-,30-,33-,36+,43-/m1/s1

HIDE SMILES / InChI

Molecular Formula C43H53N5O8S
Molecular Weight 799.975
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Sovaprevir (formerly ACH-1625) is an oral, once-daily, small molecule inhibitor of HCV protease being developed by Achillion Pharmaceuticals for the treatment of Hepatitis C. ACH-1625 is a linear peptidomimetic inhibitor that non-covalently binds to HCV NS3 protease with high potency and specificity. Short-term monotherapy of HCV genotype-1 infection with ACH-1625 was found to be safe and resulted in ≥3.3 log(10) IU/ml mean viral load reduction. Sovaprevir was developed as a therapy for patients with chronic HCV. Approximately 550 patients already have been treated with the drug in two phase 2 studies with 12-week treatment programs. One study included treatment with sovaprevir combined with pegylated interferon and ribavirin, and the other monitored the use of sovaprevir in combination with ACH-3102, Achillions second-generation NS5A inhibitor. In the second study, all of the patients with HCV genotype 1b achieved sustained virologic response.

Approval Year

PubMed

PubMed

TitleDatePubMed
Rapid and sharp decline in HCV upon monotherapy with NS3 protease inhibitor, ACH-1625.
2012
Current race in the development of DAAs (direct-acting antivirals) against HCV.
2014 Jun 15
Patents

Sample Use Guides

Hepatitis C, Chronic: Sovaprevir 200-400 mg QD + ACH-3102 150 mg loading dose on Day 1 followed by 50 mg QD + RBV weight-based 1000-1200mg QD for 12 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:11:05 UTC 2023
Edited
by admin
on Sat Dec 16 17:11:05 UTC 2023
Record UNII
2ND9V3MN6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SOVAPREVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
Sovaprevir [WHO-DD]
Common Name English
ACH-0141625
Code English
sovaprevir [INN]
Common Name English
SOVAPREVIR [USAN]
Common Name English
(2S,4R)-1-((2S)-2-TERT-BUTYL-4-OXO-4-(PIPERIDIN-1-YL)BUTANOYL)-N-((1R,2S)-1-((CYCLOPROPANESULFONYL)CARBAMOYL)-2-ETHENYLCYCLOPROPYL)-4-((7-METHOXY-2-PHENYLQUINOLIN-4-YL)OXY)PYRROLIDINE-2-CARBOXAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
Code System Code Type Description
WIKIPEDIA
Sovaprevir
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
FDA UNII
2ND9V3MN6O
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID00142994
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
DRUG BANK
DB12069
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
NCI_THESAURUS
C152411
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
USAN
YY-83
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
CAS
1001667-23-7
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105750
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
INN
9531
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
SMS_ID
100000175095
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
PUBCHEM
53362096
Created by admin on Sat Dec 16 17:11:06 UTC 2023 , Edited by admin on Sat Dec 16 17:11:06 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
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ACTIVE MOIETY