Prasugrel (CED0002966)

Record Information

Version

1.0

Creation Date

2016-05-25 18:29:21 UTC

Update Date

2026-08-20 05:19:40 UTC

Accession Number

CHEM022349

Identification

Common Name

Prasugrel

Class

Small Molecule

Description

Prasugrel is an organic compound with the formula C20H20FNO3S and an average molecular weight of 373.44 g/mol. Prasugrel belongs to the thienopyridines, a class of organoheterocyclic compounds within the organic compounds. It acts as an antagonist of the P2Y purinoceptor 12 (P2RY12) protein target. The compound is found in or released from two recorded sources: amplifiers within electrical and electronic equipment and antithrombotic agents within healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetic acid	Generator
CS-747	HMDB
747, CS	MeSH, HMDB
HCL, Prasugrel	MeSH, HMDB
Prasugrel HCL	MeSH, HMDB
Effient	MeSH, HMDB
Hydrochloride, prasugrel	MeSH, HMDB
Prasugrel hydrochloride	MeSH, HMDB
Efient	MeSH, HMDB
Prasugrel	MeSH

Chemical Formula

C₂₀H₂₀FNO₃S

Average Molecular Mass

373.441 g/mol

Monoisotopic Mass

373.115 g/mol

CAS Registry Number

150322-43-3

IUPAC Name

5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate

Traditional Name

prasugrel

SMILES

CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1

InChI Identifier

InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3

InChI Key

DTGLZDAWLRGWQN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienopyridines

Sub Class

Not Available

Direct Parent

Thienopyridines

Alternative Parents

Substituents

Thienopyridine
2,3,5-trisubstituted thiophene
Halobenzene
Fluorobenzene
Aralkylamine
Pyridine
Aryl fluoride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Thiophene
Alpha-aminoketone
Heteroaromatic compound
Tertiary aliphatic amine
Amino acid or derivatives
Ketone
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organonitrogen compound
Organooxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organofluoride
Organic oxygen compound
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:87723 )
acetate ester (CHEBI:87723 )
cyclopropanes (CHEBI:87723 )
ketone (CHEBI:87723 )
monofluorobenzenes (CHEBI:87723 )
thienopyridine (CHEBI:87723 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	3.67	ALOGPS
logP	4.31	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	5.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.81 m³·mol⁻¹	ChemAxon
Polarizability	37.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-03xu-5292000000-363487adeda2803edf87	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056s-2945000000-7653802e8e3994dc55bc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02mi-3109000000-5df287f035db2dd8d72e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9012000000-4c525511fe781201418c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-9110000000-e5719df9692a6db2952d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-4009000000-9044e8f3f643c0735a0a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-9148000000-99e7e9c97dd6cac360ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0596-9280000000-6aa7847fbc28ebfd9358	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-bb206404d6ff5af644df	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0109000000-7d582aadd109615619c5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9686000000-987d0f1a8e56ddbd1409	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0029000000-3ab5ac4bd79d4c163f1e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03e9-3093000000-d1df9adedf463fa6bb3f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1090000000-8ba5bc2b26647101aa32	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
759.0	Log mg/kg	[430:1400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
273	Antithrombotic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available

Pathways

3 pathways

Prasugrel Action Pathway

Prasugrel Drug Metabolism Action Pathway

Prasugrel Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	647.55
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	1275.17
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	905.698
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	1426.82
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	1388.91
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	1252.59
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	468.964
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	3340.04
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	2397.52
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	5814.48
Click to view 3D structure	Serine/threonine-protein kinase PLK1	P53350	Humans	Predicted (SEA)	3837.97
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	3702.12
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	2318.58
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	1963.67
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	5954.61
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	2397.21
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	2507.45
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	1720.31
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	2461.59
Click to view 3D structure	P2Y purinoceptor 12	Q9H244	Humans	Predicted (SEA)	143.865
Click to view 3D structure	Serine/threonine-protein kinase Nek2	P51955	Humans	Predicted (SEA)	4298.06
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	5470.15
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	4488.32
Click to view 3D structure	4-hydroxyphenylpyruvate dioxygenase	O23920	Daucus carota	Predicted (SEA)	57.7641
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	2384.6