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148553-50-8 molecular structure
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(3S)-3-(aminomethyl)-5-methylhexanoic acid

ChemBase ID: 115
Molecular Formular: C8H17NO2
Molecular Mass: 159.22608
Monoisotopic Mass: 159.12592879
SMILES and InChIs

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

Cite this record

CBID:115 http://www.chembase.cn/molecule-115.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3S)-3-(aminomethyl)-5-methylhexanoic acid
IUPAC Traditional name
pregabalin
Brand Name
Lyrica
Synonyms
pregabalin
Pregabalin
(S)-3-(Aminomethyl)-5-methylhexanoic acid
CI-1008
(S)-3-(Aminomethyl)-5-methylhexanoic acid
(3S)-3-(Aminomethyl)-5-methylhexanoic Acid
(S)-(+)-3-(Aminomethyl)-5-methylhexanoic Acid
(S)-3-(Ammoniomethyl)-5-methylhexanoate
CI 1008
Lyrica
PD 144723
(S)-Pregabalin
PD-144723
Pregabalin
CAS Number
148553-50-8
MDL Number
MFCD00917044
PubChem SID
46504934
160963578
PubChem CID
5486971

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.8009205  H Acceptors
H Donor LogD (pH = 5.5) -1.4076396 
LogD (pH = 7.4) -1.3444575  Log P -1.3455846 
Molar Refractivity 43.68 cm3 Polarizability 17.506392 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.35  LOG S -1.15 
Solubility (Water) 1.13e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
deionized water: ≥10 mg/mL expand Show data source
Water expand Show data source
Apperance
Off-White Solid expand Show data source
white powder expand Show data source
Melting Point
194-196°C expand Show data source
Hydrophobicity(logP)
1.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-48/22 expand Show data source
Safety Statements
22-36/37 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H318-H361 expand Show data source
GHS Precautionary statements
P280-P305 + P351 + P338 expand Show data source
Drug Control
USDEA Schedule V expand Show data source
Storage Temperature
room temp expand Show data source
Purity
≥97% (NMR) expand Show data source
95+% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C8H17NO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00230 external link
Item Information
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 external link
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 external link
S-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • : 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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