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BIBX 1382

(CAS: 196612-93-8)

Suppliers of BIBX 1382

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AOBIOUS INC [email protected] (508) 306-0937 USA

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Price and Availability: USD20/1mg ()

BOC Sciences [email protected] 1-631-504-6093

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Biochempartner Co., Ltd [email protected] 0086-13720134139; 0086-15971444841 China

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CHEMSCENE, LLC [email protected] 732-484-9848 USA

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Quality Control & MSDS Files: LCMS HNMR MSDS

MedKoo Biosciences, Inc. [email protected] 919-279-0682 USA

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Shanghai Haoyuan Chemexpress Co., Ltd. [email protected] +86 (21) 5187-0955 / +86 (21) 5895-5995 China

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Background Information of BIBX 1382

BIBX 1382 is a potent, selective inhibitor of EGFR tyrosine kinase (IC50 = 3 nM); displays > 1000-fold lower potency against ErbB2 (IC50 = 3.4 μM) and a range of other related tyrosine kinases (IC50 > 10 μM).

Solubility of BIBX 1382

Solubility Sources
DMSO ≥50 mg/mL; Water ≥50 mg/mL MedChemexpress Co., Ltd.

Storage Condition of BIBX 1382

Storage Condition Sources

MSDS Information

MSDS Sources
MedChemexpress Co., Ltd.

Quality Control and Spectral Data

QC Reports Sources
[LCMS] [HNMR] MedChemexpress Co., Ltd.

Mechanism and Indications

Signaling Pathways JAK/STAT Signaling Protein Tyrosine Kinase/RTK
Target EGFR
Research Area Cancer
Indications Solid tumor

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
BIBX 1382 European Organisation for Research and Treatment of Cancer (EORTC) Solid tumor 1999/2/28 Phase 1 Clinical
BIBX 1382 - Discontinued
BIBX 1382 - Phase 1

Chemical Information

M.Wt Formula CAS No. Synonyms
387.84 C18H19ClFN7 196612-93-8 Falnidamol;BIBX-1382;BIBX1382; N8-(3-chloro-4-fluorophenyl)-N2-(1-methylpiperidin-4-yl)pyrimido[5,4-d]pyrimidine-2,8-diamine

Structure Information of BIBX 1382

Smiles ClC1=CC(NC2=NC=NC3=CN=C(NC(CC4)CCN4C)N=C23)=CC=C1F
InChI InChI=1S/C18H19ClFN7/c1-27-6-4-11(5-7-27)25-18-21-9-15-16(26-18)17(23-10-22-15)24-12-2-3-14(20)13(19)8-12/h2-3,8-11H,4-7H2,1H3,(H,21,25,26)(H,22,23,24)

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Chemical and Physical Properties

Appearance:light yellow to khaki Solid Melting point:
Boiling point: Flash Point:
Water Solubility: Solubility:
Density:1.427 Merck:
BRN: Refractive Index:
Vapour: EINECS:
Optical Rotation: alpha:

Reference

[1].Solca FF, et al. Inhibition of epidermal growth factor receptor activity by two pyrimidopyrimidine derivatives. J Pharmacol Exp Ther. 2004 Nov;311(2):502-9.
Overexpression of the epidermal growth factor receptors (EGFRs) and human epidermal growth factor receptor 2 occurs frequently in human cancers and is associated with aggressive tumor behavior and poor patient prognosis. We have investigated the effects in vitro and in vivo of a new class of inhibitor molecules on the growth of several human cancer cell lines. BIBX1382 [N8-(3-chloro-4-fluoro-phenyl)-N2-(1-methyl-piperidin-4-yl)-pyrimido[5,4-d]pyrimidine-2,8-diamine] and BIBU1361 [(3-chloro-4-fluoro-phenyl)-[6-(4-diethylaminomethyl-piperidin-1yl)-pyrimido[5,4-d]pyrimidin-4-yl]-amine] are two new selective EGFR kinase inhibitors that do not block the activity of other tyrosine kinases. BIBU1361 blocked epidermal growth factor-induced phosphorylation of EGFR and also prevented downstream responses such as mitogen-activated protein kinase kinase (MAPK/extracellular signal-regulated kinase kinase) and MAPK activation in cells. In accordance with these observations thymidine incorporation into EGFR-expressing KB cells was selectively and potently inhibited by BIBX1382 and BIBU1361 with half-maximally effective doses in the nanomolar range. Oral administration of these compounds inhibited the growth of established human xenografts in athymic mice, including vulval and head and neck squamous cell carcinomas. Tumor growth inhibition by BIBX1382 coincided with reduced pEGFR and Ki-67 levels in vivo, which is in accordance with the expected effect of EGFR inhibitors. Collectively, these results show that the structural class of pyrimidopyrimidines, exemplified here by BIBX1382 and BIBU1361, represents an interesting scaffold for the design of EGFR inhibitors.

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