Details of the Drug

General Information of Drug (ID: DMMBAIH)

Drug Name
NXN-188
Synonyms 6634-56-6; 4,4-bis[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]pentanoic acid; NSC51920; AC1Q5VTF; AC1L6AFP; CTK5C4317; ZINC4721635; NSC-51920; AKOS030583716; KB-274877
Indication
Disease Entry ICD 11 Status REF
Migraine 8A80 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 484.6
Topological Polar Surface Area (xlogp) 0
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C27H36N2O6
IUPAC Name
4,4-bis[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]pentanoic acid
Canonical SMILES
CC(CCC(=O)O)(C1=CC(=C(C=C1)O)CN2CCOCC2)C3=CC(=C(C=C3)O)CN4CCOCC4
InChI
InChI=1S/C27H36N2O6/c1-27(7-6-26(32)33,22-2-4-24(30)20(16-22)18-28-8-12-34-13-9-28)23-3-5-25(31)21(17-23)19-29-10-14-35-15-11-29/h2-5,16-17,30-31H,6-15,18-19H2,1H3,(H,32,33)
InChIKey
JWNUBAIGCVTLMJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
242911
CAS Number
6634-56-6
DrugBank ID
DB06096
TTD ID
D0O2XJ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1B receptor (HTR1B) TTK8CXU 5HT1B_HUMAN Modulator [2]
5-HT 1D receptor (HTR1D) TT6MSOK 5HT1D_HUMAN Modulator [2]
Nitric-oxide synthase brain (NOS1) TTZUFI5 NOS1_HUMAN Inhibitor [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00920686) Study of NXN 188 for the Treatment of Migraine With Aura. U.S. National Institutes of Health.
2 Company report (NeurAxon)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors. J Neurochem. 1996 Nov;67(5):2096-103.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Triptans in pregnancy. Ther Drug Monit. 2008 Feb;30(1):5-9.
7 Clinical pipeline report, company report or official report of Jazz Pharmaceuticals.
8 5-HT1B and other related serotonergic proteins are altered in APPswe mutation. Neurosci Lett. 2015 May 6;594:137-43.
9 Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65.
10 Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. Mol Pharmacol. 1991 Aug;40(2):143-8.
11 Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32.
12 An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210.
13 Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study. Clin Ther. 2001 Nov;23(11):1867-75.
14 Clinical pipeline report, company report or official report of Neurim Pharmaceuticals.
15 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
16 Company report (Fabrekramer)
17 ClinicalTrials.gov (NCT01748877) Efficacy, Tolerability, and Safety of NXN-462 in Patients With Post-Herpetic Neuralgia. U.S. National Institutes of Health.
18 Discovery of a series of aminopiperidines as novel iNOS inhibitors. Bioorg Med Chem Lett. 2008 Jan 1;18(1):336-43.
19 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
20 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
21 Design and synthesis of 2-amino-4-methylpyridine analogues as inhibitors for inducible nitric oxide synthase and in vivo evaluation of [18F]6-(2-fl... J Med Chem. 2009 Apr 23;52(8):2443-53.
22 Synthesis of analogs of (1,4)-3- and 5-imino oxazepane, thiazepane, and diazepane as inhibitors of nitric oxide synthases. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5907-11.