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

• ChemBase ID: 115
• Molecular Formular: C8H17NO2
• Molecular Mass: 159.22608
• Monoisotopic Mass: 159.12592879
• SMILES: OC(=O)C[C@H](CC(C)C)CN
• Canonical SMILES: NC[C@H](CC(=O)O)CC(C)C
• 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
• InChIKey: AYXYPKUFHZROOJ-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-(aminomethyl)-5-methylhexanoic acid
• IUPAC Traditional name: pregabalin
• Brand Name: Lyrica
• Synonyms: (S)-3-(Aminomethyl)-5-methylhexanoic acid; pregabalin; Pregabalin; (S)-3-(Aminomethyl)-5-methylhexanoic acid; CI-1008; PD-144723; Pregabalin; (3S)-3-(Aminomethyl)-5-methylhexanoic Acid; (S)-(+)-3-(Aminomethyl)-5-methylhexanoic Acid; (S)-3-(Ammoniomethyl)-5-methylhexanoate; CI 1008; Lyrica; PD 144723; (S)-Pregabalin

Database IDs

• CAS Number: 148553-50-8
• MDL Number: MFCD00917044
• PubChem SID: 46504934; 160963578
• PubChem CID: 5486971

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.8009205
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.4076396
• LogD (pH = 7.4): -1.3444575
• Log P: -1.3455846
• Molar Refractivity: 43.68 cm^3
• Polarizability: 17.506392 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.35
• LOG S: -1.15
• Solubility (Water): 1.13e+01 g/l

PROPERTIES

Physical Property

• Solubility: deionized water: ≥10 mg/mL; Water
• Apperance: Off-White Solid; white powder
• Melting Point: 194-196°C
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-48/22
• Safety Statements: 22-36/37
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H318-H361
• GHS Precautionary statements: P280-P305 + P351 + P338
• Drug Control: USDEA Schedule V
• Storage Temperature: room temp

Product Information

• Purity: ≥97% (NMR); 95+%; 97%
• Empirical Formula (Hill Notation): C8H17NO2

DETAILS

DrugBank - DB00230

• Drug Groups: illicit; approved; investigational
• Description: Pregabalin is an anticonvulsant drug used for neuropathic pain, as an adjunct therapy for partial seizures, and in generalized anxiety disorder. It was designed as a more potent successor to gabapentin. Pregabalin is marketed by Pfizer under the trade name Lyrica. It is considered to have a dependence liability if misused, and is classified as a Schedule V drug in the U.S. [Wikipedia]
• Indication: For management of neuropathic pain associated with diabetic peripheral neuropathy and postherpetic neuralgia.
• Pharmacology: Pregabalin is a new anticonvulsant drug indicated as an add on therapy for partial onset seizures and for certain types of neuropathic pain. It was designed as a more potent successor to a related drug, gabapentin. Pregabalin binds to the alpha2-delta subunit of the voltage-gated calcium channel in the central nervous system. While pregabalin is a structural derivative of the inhibitory neurotransmitter gamma- aminobutyric acid (GABA), it does not bind directly to GABAA, GABAB, or benzodiazepine receptors, does not augment GABAA responses in cultured neurons, does not alter rat brain GABA concentration or have acute effects on GABA uptake or degradation. However, in cultured neurons prolonged application of pregabalin increases the density of GABA transporter protein and increases the rate of functional GABA transport. Pregabalin does not block sodium channels, is not active at opiate receptors, and does not alter cyclooxygenase enzyme activity. It is inactive at serotonin and dopamine receptors and does not inhibit dopamine, serotonin, or noradrenaline reuptake.
• Affected Organisms: Humans and other mammals
• Biotransformation: Negligible
• Absorption: Well absorbed after oral administration.
• Half Life: ~6 hours
• Elimination: Pregabalin is eliminated from the systemic circulation primarily by renal excretion as unchanged drug.
• Distribution: * 0.5 L/kg
• Clearance: * Renal cl=67.0 – 80.9 mL/min [young healthy subjects]
• References: : Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - PZ0010

Biochem/physiol Actions
Pregabalin is a lipophilic GABA analog/ligand at α2δ subunit of voltage-dependent Ca2+ channels. Pregabalin is an anticonvulsant, anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - P704790

S-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

REFERENCES

• : Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. Pubmed
• Taylor, C.P., at al.: Epilepsy Res., 14, 11 (1993)
• Field, M.J., et al.: Pain, 80, 391 (1999)