Details of the Drug

General Information of Drug (ID: DM0HS92)

Drug Name
Merimepodib
Synonyms
Merimebodib; Merimepodib [USAN:INN]; Tyverb/Tykerb; MMPD; 198821-22-6; 2ZL2BA06FU; C23H24N4O6; CHEMBL304087; MERIMEPODIB, VI-21497, VX-497; UNII-2ZL2BA06FU; VI-21497; VX-497; VX497; Vx 497; carbamic acid
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1]
Gastric adenocarcinoma 2B72 Phase 3 [1]
Head and neck cancer 2D42 Phase 2 [1]
Hepatitis C virus infection 1E51.1 Patented [2]
Hepatitis virus infection 1E50-1E51 Discontinued in Phase 2 [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 452.5
Topological Polar Surface Area (xlogp) 2.1
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C23H24N4O6
IUPAC Name
[(3S)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate
Canonical SMILES
COC1=C(C=CC(=C1)NC(=O)NC2=CC=CC(=C2)CNC(=O)O[C@H]3CCOC3)C4=CN=CO4
InChI
InChI=1S/C23H24N4O6/c1-30-20-10-17(5-6-19(20)21-12-24-14-32-21)27-22(28)26-16-4-2-3-15(9-16)11-25-23(29)33-18-7-8-31-13-18/h2-6,9-10,12,14,18H,7-8,11,13H2,1H3,(H,25,29)(H2,26,27,28)/t18-/m0/s1
InChIKey
JBPUGFODGPKTDW-SFHVURJKSA-N
Cross-matching ID
PubChem CID
153241
CAS Number
198821-22-6
DrugBank ID
DB04862
TTD ID
D0F0ZE

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Epidermal growth factor receptor (EGFR) TTGKNB4 EGFR_HUMAN Inhibitor [4]
Erbb2 tyrosine kinase receptor (HER2) TT6EO5L ERBB2_HUMAN Inhibitor [4]
Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1) TTL7C8Q IMDH1_HUMAN Inhibitor [5], [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Head and neck tissue
The Studied Disease Head and neck cancer [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Epidermal growth factor receptor (EGFR) DTT EGFR 5.84E-05 0.32 0.55
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 022059.
2 Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitors: a patent and scientific literature review (2002-2016).Expert Opin Ther Pat. 2017 Jun;27(6):677-690.
3 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800008158)
4 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
5 VX-497: a novel, selective IMPDH inhibitor and immunosuppressive agent. J Pharm Sci. 2001 May;90(5):625-37.
6 Triple negative breast cancer--current status and prospective targeted treatment based on HER1 (EGFR), TOP2A and C-MYC gene assessment. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2009 Mar;153(1):13-7.
7 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: 7422).
8 Boehringer Ingelheim. Product Development Pipeline. June 2 2009.
9 2017 FDA drug approvals.Nat Rev Drug Discov. 2018 Feb;17(2):81-85.
10 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
11 Her2/neu is not a commonly expressed therapeutic target in melanoma -- a large cohort tissue microarray study. Melanoma Res. 2004 Jun;14(3):207-10.
12 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
13 Clinical pipeline report, company report or official report of Roche (2009).
14 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
15 A comparison of physicochemical property profiles of marketed oral drugs and orally bioavailable anti-cancer protein kinase inhibitors in clinical development. Curr Top Med Chem. 2007;7(14):1408-22.
16 Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67.
17 Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13.
18 In vitro and in vivo antiproliferative activity of IPCAR, a new pyrazole nucleoside analog. Anticancer Res. 1998 Jul-Aug;18(4A):2623-30.
19 Antiviral agents active against influenza A viruses. Nat Rev Drug Discov. 2006 Dec;5(12):1015-25.
20 Characterization of pharmacological efficacy of VX-148, a new, potent immunosuppressive inosine 5'-monophosphate dehydrogenase inhibitor. J Pharmacol Exp Ther. 2002 Sep;302(3):1272-7.
21 Nasopharyngeal carcinoma: Current treatment options and future directions. J Nasopharyng Carcinoma, 2014, 1(16): e16.
22 Gefitinib ('Iressa', ZD1839) and new epidermal growth factor receptor inhibitors. Br J Cancer. 2004 Feb 9;90(3):566-72.
23 Quantitative prediction of fold resistance for inhibitors of EGFR. Biochemistry. 2009 Sep 8;48(35):8435-48.
24 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. (Target id: 1797).
25 Synthesis and Src kinase inhibitory activity of a series of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-furyl-3-quinolinecarbonitriles. J Med Chem. 2006 Dec 28;49(26):7868-76.
26 Emerging drugs for diabetic foot ulcers. Expert Opin Emerg Drugs. 2006 Nov;11(4):709-24.