Synonym
Bibw-22; Bibw 22; Bibw22
IUPAC/Chemical Name
2-Propanol, 1-((2,7-bis(2,6-dimethyl-4-morpholinyl)-6-phenyl-4-pteridinyl)(2-hydroxyethyl)amino)-2-methyl-, (cis(cis))-
InChi Key
JNHIGDFEPXMPAO-COPRSSIGSA-N
InChi Code
InChI=1S/C30H43N7O4/c1-19-14-36(15-20(2)40-19)27-24(23-10-8-7-9-11-23)31-25-26(32-27)33-29(37-16-21(3)41-22(4)17-37)34-28(25)35(12-13-38)18-30(5,6)39/h7-11,19-22,38-39H,12-18H2,1-6H3/t19-,20+,21-,22+
SMILES Code
CC(O)(C)CN(C1=C2N=C(C3=CC=CC=C3)C(N4C[C@H](C)O[C@H](C)C4)=NC2=NC(N5C[C@H](C)O[C@H](C)C5)=N1)CCO
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
565.72
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Chen HX, Bamberger U, Heckel A, Guo X, Cheng YC. BIBW 22, a dipyridamole analogue, acts as a bifunctional modulator on tumor cells by influencing both P-glycoprotein and nucleoside transport. Cancer Res. 1993 May 1;53(9):1974-7. PubMed PMID: 8097671.
2: Dieckmann-Schuppert A, Bamberger U, Schwarz RT. Chloroquine resistance in Plasmodium falciparum is not reversed by BIBW-22, a compound reversing the multidrug resistance phenotype in mammalian cancer cells. Biochem Pharmacol. 1993 Oct 19;46(8):1421-4. PubMed PMID: 8240391.
3: Jansen WJ, Pinedo HM, Kuiper CM, Lincke C, Bamberger U, Heckel A, Boven E. Biochemical modulation of 'classical' multidrug resistance by BIBW22BS, a potent derivative of dipyridamole. Ann Oncol. 1994 Oct;5(8):733-9. PubMed PMID: 7826906.
4: Liu Z, Lheureux F, Pouliot JF, Heckel A, Bamberger U, Georges E. BIBW22 BS, potent multidrug resistance-reversing agent, binds directly to P-glycoprotein and accumulates in drug-resistant cells. Mol Pharmacol. 1996 Sep;50(3):482-92. PubMed PMID: 8794885.
5: Jansen WJ, Pinedo HM, van der Wilt CL, Feller N, Bamberger U, Boven E. The influence of BIBW22BS, a dipyridamole derivative, on the antiproliferative effects of 5-fluorouracil, methotrexate and gemcitabine in vitro and in human tumour xenografts. Eur J Cancer. 1995 Dec;31A(13-14):2313-9. Erratum in: Eur J Cancer 1996 Jan;32A(1):185. PubMed PMID: 8652262.
6: Gaj CL, Anyanwutaku I, Chang YH, Cheng YC. Decreased drug accumulation without increased drug efflux in a novel MRP-overexpressing multidrug-resistant cell line. Biochem Pharmacol. 1998 Apr 15;55(8):1199-211. PubMed PMID: 9719474.
7: Schröder J, Esteban M, Müller MR, Kasimir-Bauer S, Bamberger U, Heckel A, Seeber S, Scheulen ME. Modulation of multidrug resistance by BIBW22BS in blasts of de novo or relapsed or persistent acute myeloid leukemia ex vivo. J Cancer Res Clin Oncol. 1996;122(5):307-12. PubMed PMID: 8609155.
