NAV

Vicagrel

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Vicagrel
DrugBank Accession Number
DB16349
Background

Vicagrel is under investigation in clinical trial NCT03599284 (The Efficacy, Safety and Pharmacokinetic of Antiplatelet Therapy for Vicagrel).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 379.86
Monoisotopic: 379.0645069
Chemical Formula
C18H18ClNO4S
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UP2Y purinoceptor 12
antagonist
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
8A63K3TN0U
CAS number
1314081-53-2
InChI Key
GNHHCBSBCDGWND-KRWDZBQOSA-N
InChI
InChI=1S/C18H18ClNO4S/c1-11(21)24-16-9-12-10-20(8-7-15(12)25-16)17(18(22)23-2)13-5-3-4-6-14(13)19/h3-6,9,17H,7-8,10H2,1-2H3/t17-/m0/s1
IUPAC Name
methyl (2S)-2-[2-(acetyloxy)-4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl]-2-(2-chlorophenyl)acetate
SMILES
COC(=O)[C@@H](N1CCC2=C(C1)C=C(OC(C)=O)S2)C1=C(Cl)C=CC=C1

References

General References
Not Available
ChemSpider
28518813
ChEMBL
CHEMBL2042273
ZINC
ZINC000084654546

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCoronary Artery Disease (CAD) / Percutaneous Coronary Intervention (PCI) / Platelet Aggregation Inhibitors1
1CompletedOtherHealthy Adult Male1
1CompletedTreatmentAcute Coronary Syndrome (ACS)2
1CompletedTreatmentHealthy Subjects (HS) / PK/PD1
1RecruitingTreatmentHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00386 mg/mLALOGPS
logP3.67ALOGPS
logP3.81Chemaxon
logS-5ALOGPS
pKa (Strongest Basic)4.23Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area55.84 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity95.22 m3·mol-1Chemaxon
Polarizability38.04 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0009000000-aead0a0bc2326cf2fb6d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fi3-0029000000-bbc1e4e70fa3cba6d254
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-5fa05602aecb808ae7d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-5097000000-3224222c697e1412fc8e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003v-5197000000-9f5446c4e0d75e5cf41e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0291000000-3b3caee419106a5f8314
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. P2Y purinoceptor 12
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Inhibitor
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation.
Gene Name
P2RY12
Uniprot ID
Q9H244
Uniprot Name
P2Y purinoceptor 12
Molecular Weight
39438.355 Da
References
  1. Schilling U, Dingemanse J, Ufer M: Pharmacokinetics and Pharmacodynamics of Approved and Investigational P2Y12 Receptor Antagonists. Clin Pharmacokinet. 2020 May;59(5):545-566. doi: 10.1007/s40262-020-00864-4. [Article]
  2. Liu S, Wang Z, Tian X, Cai W: Corrigendum: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2021 Apr 16;12:668861. doi: 10.3389/fphar.2021.668861. eCollection 2021. [Article]
  3. Liu C, Lu Y, Sun H, Yang J, Liu Y, Lai X, Gong Y, Liu X, Li Y, Zhang Y, Chen X, Zhong D: Development and validation of a sensitive and rapid UHPLC-MS/MS method for the simultaneous quantification of the common active and inactive metabolites of vicagrel and clopidogrel in human plasma. J Pharm Biomed Anal. 2018 Feb 5;149:394-402. doi: 10.1016/j.jpba.2017.11.019. Epub 2017 Nov 6. [Article]
  4. Liu S, Wang Z, Tian X, Cai W: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2020 Dec 8;11:591854. doi: 10.3389/fphar.2020.591854. eCollection 2020. [Article]
  5. Li X, Liu C, Zhu X, Wei H, Zhang H, Chen H, Chen G, Yang D, Sun H, Shen Z, Zhang Y, Li W, Yang J, Liu Y, Lai X, Gong Y, Liu X, Li Y, Zhong D, Niu J, Liu B, Ding Y: Evaluation of Tolerability, Pharmacokinetics and Pharmacodynamics of Vicagrel, a Novel P2Y12 Antagonist, in Healthy Chinese Volunteers. Front Pharmacol. 2018 Jun 20;9:643. doi: 10.3389/fphar.2018.00643. eCollection 2018. [Article]
  6. Zhang Y, Zhu X, Zhan Y, Li X, Liu C, Zhu Y, Zhang H, Wei H, Xia Y, Sun H, Liu Y, Lai X, Gong Y, Liu X, Li Y, Ding Y, Zhong D: Impacts of CYP2C19 genetic polymorphisms on bioavailability and effect on platelet adhesion of vicagrel, a novel thienopyridine P2Y12 inhibitor. Br J Clin Pharmacol. 2020 Sep;86(9):1860-1874. doi: 10.1111/bcp.14296. Epub 2020 Jun 17. [Article]
  7. Liu C, Zhang Y, Chen W, Lu Y, Li W, Liu Y, Lai X, Gong Y, Liu X, Li Y, Chen X, Li X, Sun H, Yang J, Zhong D: Pharmacokinetics and pharmacokinetic/pharmacodynamic relationship of vicagrel, a novel thienopyridine P2Y12 inhibitor, compared with clopidogrel in healthy Chinese subjects following single oral dosing. Eur J Pharm Sci. 2019 Jan 15;127:151-160. doi: 10.1016/j.ejps.2018.10.011. Epub 2018 Oct 13. [Article]
  8. Zheng YD, Zhang H, Zhan Y, Bian YC, Ma S, Gan HX, Lai XJ, Liu YQ, Gong YC, Liu XF, Sun HB, Li YG, Zhong DF, Miao LY, Diao XX: Pharmacokinetics, mass balance, and metabolism of [(14)C]vicagrel, a novel irreversible P2Y12 inhibitor in humans. Acta Pharmacol Sin. 2021 Sep;42(9):1535-1546. doi: 10.1038/s41401-020-00547-7. Epub 2020 Nov 26. [Article]
  9. Li H, Chen H, Chen W, Xu H, Yuan F, Yang M, Sun H, Yang J, Liu Y, Lai X, Gong Y, Liu X, Li Y, Sheng L, Liu C, Li X: Platelet inhibitory activity, tolerability, and safety of vicagrel, a novel thienopyridine P2Y12 inhibitor. Medicine (Baltimore). 2020 Jan;99(4):e18683. doi: 10.1097/MD.0000000000018683. [Article]

Enzymes

Details1. Liver carboxylesterase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Liu S, Wang Z, Tian X, Cai W: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2020 Dec 8;11:591854. doi: 10.3389/fphar.2020.591854. eCollection 2020. [Article]
Details2. Intestinal-type alkaline phosphatase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Alkaline phosphatase activity
Gene Name
ALPI
Uniprot ID
P09923
Uniprot Name
Intestinal-type alkaline phosphatase
Molecular Weight
56811.695 Da
References
  1. Xie HG, Jia YM, Tai T, Ji JZ: Overcoming Clopidogrel Resistance: Three Promising Novel Antiplatelet Drugs Developed in China. J Cardiovasc Pharmacol. 2017 Dec;70(6):356-361. doi: 10.1097/FJC.0000000000000529. [Article]
Details3. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Liu S, Wang Z, Tian X, Cai W: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2020 Dec 8;11:591854. doi: 10.3389/fphar.2020.591854. eCollection 2020. [Article]
Details4. Cocaine esterase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Methylumbelliferyl-acetate deacetylase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and ...
Gene Name
CES2
Uniprot ID
O00748
Uniprot Name
Cocaine esterase
Molecular Weight
61806.41 Da
References
  1. Xie HG, Jia YM, Tai T, Ji JZ: Overcoming Clopidogrel Resistance: Three Promising Novel Antiplatelet Drugs Developed in China. J Cardiovasc Pharmacol. 2017 Dec;70(6):356-361. doi: 10.1097/FJC.0000000000000529. [Article]
  2. Qiu Z, Li N, Song L, Lu Y, Jing J, Parekha HS, Gao W, Tian F, Wang X, Ren S, Chen X: Contributions of intestine and plasma to the presystemic bioconversion of vicagrel, an acetate of clopidogrel. Pharm Res. 2014 Jan;31(1):238-51. doi: 10.1007/s11095-013-1158-5. Epub 2013 Sep 14. [Article]
  3. Liu S, Wang Z, Tian X, Cai W: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2020 Dec 8;11:591854. doi: 10.3389/fphar.2020.591854. eCollection 2020. [Article]
  4. Jiang J, Chen X, Zhong D: Arylacetamide Deacetylase Is Involved in Vicagrel Bioactivation in Humans. Front Pharmacol. 2017 Nov 20;8:846. doi: 10.3389/fphar.2017.00846. eCollection 2017. [Article]
Details5. Arylacetamide deacetylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Displays cellular triglyceride lipase activity in liver, increases the levels of intracellular fatty acids derived from the hydrolysis of newly formed triglyceride stores and plays a role in very low-density lipoprotein assembly. Displays serine esterase activity in liver. Deacetylates a variety of arylacetamide substrates, including xenobiotic compounds and procarcinogens, converting them to the primary arylamide compounds and increasing their toxicity.
Specific Function
Catalytic activity
Gene Name
AADAC
Uniprot ID
P22760
Uniprot Name
Arylacetamide deacetylase
Molecular Weight
45733.28 Da
References
  1. Jiang J, Chen X, Zhong D: Arylacetamide Deacetylase Is Involved in Vicagrel Bioactivation in Humans. Front Pharmacol. 2017 Nov 20;8:846. doi: 10.3389/fphar.2017.00846. eCollection 2017. [Article]

Drug created at December 15, 2020 20:03 / Updated at October 07, 2021 12:09