Details of the Drug

General Information of Drug (ID: DMXC1K9)

Drug Name
Alpha 1-PI
Synonyms
Ifenprodil; 23210-56-2; Vadilex; ifenprodil tartrate; Dilvax; Creocral; 4-(2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl)phenol; Ifenprodil [INN:DCF]; RC 61-91; Ifenprodilum [INN-Latin]; UNII-R8OE3P6O5S; EINECS 245-491-4; R8OE3P6O5S; CHEMBL305187; 4-Benzyl-alpha-(p-hydroxyphenyl)-beta-methyl-1-piperidineethanol; 2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)propanol; 4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol; NCGC00024643-03; IFENPRODIL HEMITARTRATE; alpha-(4-Hydroxyphenyl)-beta-methyl-4-(phenylmethyl)-1-piperidine
Indication
Disease Entry ICD 11 Status REF
Alpha-1 antitrypsin deficiency 5C5A Approved [1], [2]
Cancer related pain MG30 Withdrawn from market [3], [4]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 325.4
Topological Polar Surface Area (xlogp) 3.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 64.57 mL/min/kg [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.32 hours [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 18.99 L/kg [5]
Chemical Identifiers
Formula
C21H27NO2
IUPAC Name
4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Canonical SMILES
CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3
InChI
InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3
InChIKey
UYNVMODNBIQBMV-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3689
ChEBI ID
CHEBI:93829
CAS Number
23210-56-2
DrugBank ID
DB08954
TTD ID
D0I0DL

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glutamate receptor ionotropic NMDA 2B (NMDAR2B) TTN9D8E NMDE2_HUMAN Antagonist [6]
Pancreatic elastase 1 (CELA1) TT3NKIB CELA1_HUMAN Inhibitor [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003666)
3 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: 5472).
4 Effects of the novel 5-hydroxytryptamine reuptake inhibitor indalpine and ethanol on psychomotor performance. Arzneimittelforschung. 1988 Jan;38(1):98-102.
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 NMDA receptor stimulation induces reversible fission of the neuronal endoplasmic reticulum. PLoS One. 2009;4(4):e5250.
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10 Biological activity of WIN 63759, an orally bioavailable inhibitor of human neutrophil elastase. Drug Development Research Volume 34, Issue 3, pages 306-316, March 1995.
11 Pivotal role for alpha1-antichymotrypsin in skin repair. J Biol Chem. 2011 Aug 19;286(33):28889-901.
12 EP patent application no. 1292314, Method for treating respiratory disorders associated with pulmonary elastic fiber injury comprising the use of glycosaminoglycans.
13 CN patent application no. 1813706, Use of elastic protease inhibitor for preparing medicine for protecting cerebral hemorrhage.
14 Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J Med Chem. 2009 Sep 24;52(18):5732-47.
15 Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6.
16 4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine: a novel, potent, and selective NR1/2B NMDA receptor antagonist. J Med Chem. 1999 Jul 29;42(15):2993-3000.
17 NMDA receptors as targets for drug action in neuropathic pain. Eur J Pharmacol. 2001 Oct 19;429(1-3):71-8.
18 Inhibition of in vivo [(3)H]MK-801 binding by NMDA receptor open channel blockers and GluN2B antagonists in rats and mice. Eur J Pharmacol. 2015 Nov 5;766:1-8.
19 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
20 Clinical pipeline report, company report or official report of Cadent Therapeutics.
21 Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroaryl-4-oxo-1,2,... J Med Chem. 2001 Sep 13;44(19):3157-65.
22 Neu2000, an NR2B-selective, moderate NMDA receptor antagonist and potent spin trapping molecule for stroke. Drug News Perspect. 2010 Nov;23(9):549-56.
23 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
24 4,10-Dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with... Bioorg Med Chem Lett. 2000 May 15;10(10):1133-7.
25 Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17.