becondogrel   Click here for help

GtoPdb Ligand ID: 13802

Synonyms: (4S)-2-Oxoclopidogrel | compound IV-1 [EP3290423B1] [3] | compound of formula I [US2022028976]
Compound class: Synthetic organic
Comment: Becondogrel is the INN for a platelet aggregation inhibitor (WHO proposed INN list 132, Feb 2025). It is a derivative of the irreversible P2Y12 receptor anti-platelet prodrug clopidogrel that has been modified to overcome individual differences in hepatic CYP450 enzyme activity that limit conversion of clopidogrel into its active metabolite [1-2] and conversion to an inactive carboxylic derivative by carboxylesterase 1 (CES1) [4]. Becondogrel is a prodrug that is converted to its active metabolite in vivo.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 71.91
Molecular weight 337.82
XLogP 0.71
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES COC(=O)[C@H](C1=C(C=CC=C1)Cl)N2CC[C@H]3C(=CC(=O)S3)C2
Isomeric SMILES COC(=O)[C@H](C1=CC=CC=C1Cl)N2CC[C@H]3C(=CC(=O)S3)C2
InChI InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13-,15-/m0/s1
InChI Key JBSAZVIMJUOBNB-ZFWWWQNUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Cen G, Yang M, Tan S. (2022)
Crystalline form b of tetrahydrothienopyridine compound, preparation method, composition and application thereof.
Patent number: US20220289761A1. Assignee: Chengdu Shibeikang Biomedical Technology Co Ltd. Priority date: 23/05/2022. Publication date: 15/09/2022.
2. Lau WC, Gurbel PA, Watkins PB, Neer CJ, Hopp AS, Carville DG, Guyer KE, Tait AR, Bates ER. (2004)
Contribution of hepatic cytochrome P450 3A4 metabolic activity to the phenomenon of clopidogrel resistance.
Circulation, 109 (2): 166-71. [PMID:14707025]
3. Sun H, Shan J, Zhang B, Yuan F. (2021)
Optically active 2-hydroxy tetrahydrothienopyridine derivatives, preparation method and use in manufacture of medicament thereof.
Patent number: EP3290423B1. Assignee: Jiangsu Vcare Pharmatech Co Ltd. Priority date: 28/01/2011. Publication date: 21/07/2021.
4. Tang M, Mukundan M, Yang J, Charpentier N, LeCluyse EL, Black C, Yang D, Shi D, Yan B. (2006)
Antiplatelet agents aspirin and clopidogrel are hydrolyzed by distinct carboxylesterases, and clopidogrel is transesterificated in the presence of ethyl alcohol.
J Pharmacol Exp Ther, 319 (3): 1467-76. [PMID:16943252]