Chemical substance record

Pregabalin

148553-50-8C₈H₁₇NO₂159.229 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A γ-amino acid that is γ-aminobutyric acid (GABA) carrying an isobutyl substitutent at the β-position (the S-enantiomer). Binds with high affinity to the α2-δ site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	148553-50-8	ChEBI ↗
Molecular formula	C₈H₁₇NO₂	ChEBI ↗
Molar mass	159.229 g/mol	ChEBI ↗
Monoisotopic mass	159.12593 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:64356	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	159.23 g/mol	PubChem ↗
Exact mass	159.125928785 Da	PubChem ↗
Computed XLogP	-1.6	PubChem ↗
Topological polar surface area (Å²)	63.3	PubChem ↗
H-bond donors	2	PubChem ↗
H-bond acceptors	3	PubChem ↗
Rotatable bonds	5	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

pregabalin

IUPAC name

(3S)-3-(aminomethyl)-5-methylhexanoic acid

InChIKey

AYXYPKUFHZROOJ-ZETCQYMHSA-N

SMILES

CC(C)C[C@H](CN)CC(=O)O

InChI

InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1

Names & synonyms

(3S)-3-(aminomethyl)-5-methylhexanoic acidLyrica

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

gamma-amino acidChEBI parent class · 33707 ↗

carboxylic acid amino acid organic molecular entity

Roles recorded in ChEBI

antidepressantanxiolytic drugantipsychotic agentanalgesichypoglycemic agentantineoplastic agentanticonvulsantcalcium channel blockerantiemeticantitussive

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00628026 mol

Uses 159.229 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 8 atoms

60.35%

O

Oxygen · 2 atoms

20.10%

H

Hydrogen · 17 atoms

10.76%

N

Nitrogen · 1 atom

8.80%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

The cost-effectiveness of pregabalin in the treatment of fibromyalgia: US perspective. ↗Journal of medical economics · 2012 · PMID 22339078

Evaluation of efficacy and safety of gabapentin, duloxetine, and pregabalin in patients with painful diabetic peripheral neuropathy. ↗Indian journal of pharmacology · 2012 Jan · PMID 22345870

EP1178034 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

EP2418194 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US2008311635 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:64356

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 5486971 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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