Natural Product (NP) Details

General Information of the NP (ID: NP3051)
Name
Pregabalin
Synonyms
Pregabalin; 148553-50-8; Lyrica; (S)-3-(Aminomethyl)-5-methylhexanoic acid; 3-isobutyl GABA; (3S)-3-(aminomethyl)-5-methylhexanoic acid; CI-1008; (S)-Pregabalin; Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3S)-; CI 1008; PD 144723; UNII-55JG375S6M; PD-144723; (S)-3-Isobutyl GABA; CHEMBL1059; CHEBI:64356; (3S)-3-(aminomethyl)-5-methyl-hexanoic acid; 55JG375S6M; MFCD00917044; Hexanoic acid, 3-(aminomethyl)-5-ethyl-, (3S)-; (R-)-3-isobutyl GABA; Hexanoic acid, 3-(aminomethyl)-5-methyl-, (S)-; Nervalin; Pregablin; HSDB 7530; Pregabalin [USAN:INN:BAN:JAN]; NCGC00095186-01; Lyrica (TN); (S)-3-(Aminomethyl)-5-methylhexanoicacid; SCHEMBL8227; DSSTox_CID_25950; DSSTox_RID_81246; DSSTox_GSID_45950; Pregabalin (JAN/USAN/INN); (S)-(+)-4-amino-3-(2-methylpropyl)butanoic acid; GTPL5484; ZINC5152; DEA No. 2782; Pregabalin, >=97% (NMR); DTXSID1045950; HMS3715J16; Pregabalin 1.0 mg/ml in Methanol; YNP-1807; Tox21_111475; BDBM50164279; CP0100; AKOS001476611; AKOS005145504; Lyrica;CI-1008;PD-144723; AC-1158; ACN-038395; CCG-221247; CM14412; CS-1247; DB00230; KS-5378; NSC 759256; (S)-3-aminomethyl-5-methylhexanoic acid; NCGC00346738-01; 121GE001; HY-17414; (S)-3-Aminomethyl-5-methyl-hexanoic acid; AB0074009; AM20080369; CAS-148553-50-8; EN300-92104; (3S)-3-(aminomethyl)-5-methyl hexanoic acid; (S)-(+)-3-Aminomethyl-5-Methylhexanoic Acid; D02716; W-5218; AB01563007_01; 553P508; A808784; Q412174; SR-01000942257; SR-01000942257-2; Pregabalin, EuropePharmacopoeia (EP) Reference Standard; Z2757554242; 1414928-41-8
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Chronic obstructive pulmonary disease [ICD-11: CA22] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.12
 
MDCK Permeability
 -4.735
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.049
 
PPB
 25.4%
 
BBB
 +++
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 ++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 2.362
 
T1/2
 1.308
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 +
 
Respiratory
 +++
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 ++
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 +++
 
Hematotoxicity
 -
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C8H17NO2
PubChem CID
5486971
Canonical SMILES
CC(C)CC(CC(=O)O)CN
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
CAS Number
CAS 148553-50-8
ChEBI ID
CHEBI:64356
TTD Drug ID
D00WUF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Tapentadol      Acute pain     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model For a xenograft model: Male Sprague Dawley rats (120-140 g) were anaesthetized with isoflurane, and arthritis was induced in the left knee by an intrarticular injection of 2 mg MIA in 25 ul of 0.9% saline.
                    Experimental
                    Result(s)		 The combination therapy of tapentadol and pregabalin restored descending noradrenergic inhibitory tone and also inhibited nociceptive transmission at the level of the spinal cord can provide superior analgesia.
Target and Pathway
Target(s) Calcium channel alpha-2/delta-1 (CACNA2D1)  Molecule Info  [3]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Cardiac muscle contraction
3 Adrenergic signaling in cardiomyocytes
4 Oxytocin signaling pathway
5 Hypertrophic cardiomyopathy (HCM)
6 Arrhythmogenic right ventricular cardiomyopathy (ARVC)
7 Dilated cardiomyopathy
Panther Pathway Muscarinic acetylcholine receptor 2 and 4 signaling pathway Click to Show/Hide
WikiPathways Arrhythmogenic Right Ventricular Cardiomyopathy Click to Show/Hide
2 miR-targeted genes in muscle cell - TarBase
3 miR-targeted genes in lymphocytes - TarBase
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5484).
Reference 2 A combination pharmacotherapy of tapentadol and pregabalin to tackle centrally driven osteoarthritis pain. Eur J Pain. 2019 Jul;23(6):1185-1195.
Reference 3 Pregabalin reduces the release of synaptic vesicles from cultured hippocampal neurons. Mol Pharmacol. 2006 Aug;70(2):467-76.
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