Compound: Pregabalin
SMILES: O=C(O)C[C@@H](CN)CC(C)C
InChIKey: AYXYPKUFHZROOJ-ZETCQYMHSA-N
Synonyms: Pregabalin, 148553-50-8, Lyrica, (S)-3-(Aminomethyl)-5-methylhexanoic acid, 3-isobutyl GABA, (3S)-3-(aminomethyl)-5-methylhexanoic acid, CI-1008, Pregabaline, Pregabalina, Vronogabic, Pregabalin mylan, Pregabalin sandoz, Pregabalin zentiva, (R-)-3-isobutyl GABA, PD-144723, Pregabalin sandoz gmbh, CI 1008, (S)-3-Isobutyl GABA, PD 144723, DTXSID1045950, LYRICA CR, 55JG375S6M, YNP-1807, NSC-759256, Hexanoic acid, 3-(aminomethyl)-5-methyl-, (S)-, PREGABALIN MYLAN PHARMA, DTXCID9025950, CHEBI:64356, pregabalinum, Lecaent, Rewisca, Alzain, Axalid, 3-(aminomethyl)-5-methyl-hexanoic acid, 3 isobutyl GABA, GABA, 3-isobutyl, BONQAT, RefChem:6163, (S+)-3-isobutyl GABA, Pregabalin Extended Release, PREGABALIN capsules, CV, N03AX16, CI1008, 1008, CI, 604-639-1, NSC729898, (S)-Pregabalin, Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3S)-, CHEMBL1059, (3S)-3-(aminomethyl)-5-methyl-hexanoic acid, Pregabalin [USAN], Nervalin, Pregablin, UNII-55JG375S6M, Pregabalin CRS, HSDB 7530, Pregabalin [USAN:INN:BAN:JAN], NCGC00095186-01, Lyrica (TN), (S)-3-aminomethyl-5-methylhexanoic acid, PREGABALIN [MI], (S)-3-(Aminomethyl)-5-methylhexanoicacid, PREGABALIN [INN], PREGABALIN [JAN], PREGABALIN [HSDB], PREGABALIN [VANDF], PREGABALIN [MART.], SCHEMBL8227, Pregabalin Impurity Standard, PREGABALIN [USP-RS], PREGABALIN [WHO-DD], orb389663, Pregabalin (JAN/USAN/INN), PREGABALIN [EMA EPAR], (S)-(+)-4-amino-3-(2-methylpropyl)butanoic acid, GTPL5484, DEA No. 2782, Pregabalin, 1mg/ml in Methanol, PREGABALIN [ORANGE BOOK], PREGABALIN [EP MONOGRAPH], GLXC-07956, HMS3715J16, PREGABALIN [USP MONOGRAPH], Pregabalin 1.0 mg/ml in Methanol, Tox21_111475, BDBM50164279, MFCD00917044, AKOS001476611, AKOS005145504, Lyrica;CI-1008;PD-144723, AC-1158, CCG-221247, CS-1247, DB00230, KS-5378, NSC 759256, NCGC00095186-11, NCGC00346738-01, 121GE001, HY-17414, PD144723, (S)-3-Aminomethyl-5-methyl-hexanoic acid, CAS-148553-50-8, NS00000537, P2840, (S)-(+)-3-Aminomethyl-5-Methylhexanoic Acid, D02716, AB01563007_01, F418830, Q412174, SR-01000942257, Hexanoic acid, 3-(aminomethyl)-5-ethyl-, (3S)-, Q-201617, SR-01000942257-2, BRD-K66786476-001-01-3, BRD-K66786476-003-01-9, Pregabalin, EuropePharmacopoeia (EP) Reference Standard, Pregabalin Working Standard (Secondary Reference Standard), 1414928-41-8
Theoretical properties:
molecular_formula: C8H17NO2
molecular_weight: 159.23 g/mol
exact_mass: 159.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 5
heavy_atom_count: 11
topological_polar_surface_area: 63.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline solid
color: White to off-white crystalline solid
solubility: Freely soluble
Descriptions:
{"pubchem": "Pregabalin is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It is functionally related to a gamma-aminobutyric acid.", "chebi": "A \u03b3-amino acid that is \u03b3-aminobutyric acid (GABA) carrying an isobutyl substitutent at the \u03b2-position (the <i>S</i>-enantiomer). Binds with high affinity to the \u03b1<small><sub>2</sub></small>-\u03b4 site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues.", "chembl": "PREGABALIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Pregabalin, sold under the brand names Axalid and Lyrica among others, is an anticonvulsant, analgesic, and anxiolytic amino acid medication used to treat epilepsy, neuropathic pain, fibromyalgia, restless legs syndrome, opioid withdrawal, generalized anxiety disorder (GAD), and postherpetic neuralgia (a type of nerve damage that can result from shingles). Pregabalin also has antiallodynic properties. Its use in epilepsy is as an add-on therapy for partial seizures. When used before surgery, it reduces pain but results in greater sedation and visual disturbances. It is taken by mouth.\nCommon side effects can include headache, dizziness, sleepiness, euphoria, confusion, trouble with memory, poor coordination, dry mouth, problems with vision, and weight gain. Serious side effects may include angioedema, kidney damage, and seizures.\nAs with all other drugs approved by the FDA for treating epilepsy, the pregabalin labeling warns of an increased suicide risk when combined with other drugs. When pregabalin is taken at high doses over a long period of time, addiction may occur, but if taken at usual doses the risk is low. Use during pregnancy or breastfeeding is of unclear safety.\nIt is a gabapentinoid medication which is a class of drugs within the derivatives of \u03b3-aminobutyric acid (GABA analogues), an inhibitory neurotransmitter. Although pregabalin is inactive at GABA receptors and GABA synapses, it acts by binding specifically to the \u03b12\u03b4-1 protein that was first described as an auxiliary subunit of voltage-gated calcium channels.\nPregabalin was approved for medical use in the United States in 2004. In the US, pregabalin is a Schedule V controlled substance under the Controlled Substances Act of 1970, which means that the drug has low abuse potential compared to substances in Schedules I-IV, however, there is still a potential for misuse. It is available as a generic medication. In 2023, it was the 78th most commonly prescribed medication in the United States, with more than 8 million prescriptions."}