BERBAMINE DIHYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H40N2O6.2ClH
Molecular Weight	681.645
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.[H][C@@]12CC3=CC=C(OC4=CC(C[C@@]5([H])N(C)CCC6=C5C(OC7=C(OC)C=C(CCN1C)C2=C7)=C(OC)C(OC)=C6)=CC=C4O)C=C3

InChI

InChIKey=USRXDYNDPPUBSG-KKXMJGKMSA-N

InChI=1S/C37H40N2O6.2ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33;;/h6-11,18-21,28-29,40H,12-17H2,1-5H3;2*1H/t28-,29+;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	C37H40N2O6
Molecular Weight	608.7233
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CaM kinase II gamma 4 Target ID: CHEMBL3829 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23960096 \| https://www.ncbi.nlm.nih.gov/pubmed/23074277	Inhibitor 8297

PubMed

Title	Date	PubMed
Effects of various principles from Chinese herbal medicine on rhodamine123 accumulation in brain capillary endothelial cells.	2002 Jul	12100750
Effect of Mahonia aquifolium active compounds on interleukin-8 production in the human monocytic cell line THP-1.	2002 Mar	11914967
Interaction of multidrug resistance reversal agents with P-glycoprotein ATPase activity on blood-brain barrier.	2002 May	11978192
Inhibition of Na(+),K(+)-ATPase by the extract of Stephania cephararantha HAYATA and bisbenzylisoquinoline alkaloid cycleanine, a major constituent.	2003 Aug 1	12907236
[Reversal effect of berbamine on multidrug resistance of K562/A02 cells and its mechanism].	2003 Dec	14706144
Integrity of actin-network is involved in uridine 5'-triphosphate evoked store-operated Ca2+ entry in bovine adrenocortical fasciculata cells.	2003 Jan	12686727
Effect of E6, a novel calmodulin inhibitor, on activity of P-glycoprotein in purified primary cultured rat brain microvessel endothelial cells.	2003 Nov	14627500
[Distribution of four alkaloids in plants of Berberis].	2004 Feb	22454993
[Comparison of the anti-arrhythmic effects of matrine and berbamine with amiodarone and RP58866].	2004 Sep	15606015
[The mechanism of apoptosis of chronic myeloid leukemia cells induced by the novel p210 bcr/abl inhibitor berbamine].	2006 Aug 29	17064567
Berbamine: a novel inhibitor of bcr/abl fusion gene with potent anti-leukemia activity.	2006 Jan	16023722
Berbamine induces apoptosis in human hepatoma cell line SMMC7721 by loss in mitochondrial transmembrane potential and caspase activation.	2007 Apr	17444599
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007 Jul 16	17634120
Berbamine selectively induces apoptosis of human acute promyelocytic leukemia cells via survivin-mediated pathway.	2007 May 5	17531122
Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine.	2008 Aug	18618524
Novel immunomodulatory properties of berbamine through selective down-regulation of STAT4 and action of IFN-gamma in experimental autoimmune encephalomyelitis.	2008 Jul 15	18606704
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008 Mar	17968851
Harnessing gene expression to identify the genetic basis of drug resistance.	2009	19888205
Berbamine induces Fas-mediated apoptosis in human hepatocellular carcinoma HepG2 cells and inhibits its tumor growth in nude mice.	2009	19408145
Effects of theanine on growth of human lung cancer and leukemia cells as well as migration and invasion of human lung cancer cells.	2009 Apr	19760127
Berbamine exhibits potent antitumor effects on imatinib-resistant CML cells in vitro and in vivo.	2009 Apr	19270722
Berbamine derivatives: a novel class of compounds for anti-leukemia activity.	2009 Aug	19285759
Berbamine, a novel nuclear factor kappaB inhibitor, inhibits growth and induces apoptosis in human myeloma cells.	2009 Dec	19960011
[Mechanism related to inhibition of leukemia K562 cells by berbamine].	2009 Jul	19693977
The antiproliferation effect of berbamine on k562 resistant cells by inhibiting NF-kappaB pathway.	2009 Jul	19548306
Probing the binding sites and the effect of berbamine on the structure of bovine serum albumin.	2009 Jun	19185535
A new dawn for the use of traditional Chinese medicine in cancer therapy.	2009 Mar 20	19298677
Antihyperglycemic and antioxidant effect of Berberis aristata root extract and its role in regulating carbohydrate metabolism in diabetic rats.	2009 May 4	19429334
Suppression of growth, migration and invasion of highly-metastatic human breast cancer cells by berbamine and its molecular mechanisms of action.	2009 Oct 1	19796390
[Berbamine induces apoptosis of multiple myeloma RPMI 8226 cells by activating GADD45/JNK pathway].	2009 Sep	19830854
Suppression of human lung cancer cell growth and migration by berbamine.	2010 Aug	19967402
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010 Dec 13	21144003
A novel calmodulin antagonist O-(4-ethoxyl-butyl)-berbamine overcomes multidrug resistance in drug-resistant MCF-7/ADR breast carcinoma cells.	2010 Jul	20112430
Degradation of HER2/neu by ANT2 shRNA suppresses migration and invasiveness of breast cancer cells.	2010 Jul 23	20650008
Circumvention of multi-drug resistance of cancer cells by Chinese herbal medicines.	2010 Jul 25	20653978
4-Chlorobenzoyl berbamine induces apoptosis and G2/M cell cycle arrest through the PI3K/Akt and NF-kappaB signal pathway in lymphoma cells.	2010 Mar	20127010
Tissue culture and generation of autotetraploid plants of Sophora ﬂavescens Aiton.	2010 Oct	21120030

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:32:28 GMT 2023` Edited by `admin` on `Sat Dec 16 09:32:28 GMT 2023`
Record UNII	K44OC6U989
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BERBAMINE DIHYDROCHLORIDE

Common Name

English

BERBAMAN-12-OL, 6,6',7-TRIMETHOXY-2,2'-DIMETHYL-, DIHYDROCHLORIDE

Common Name

English

BERBAMINE HYDROCHLORIDE

Common Name

English

Berbamine hydrochloride [WHO-DD]

Common Name

English

16H-1,24:6,9-DIETHENO-11,15-METHENO-2H-PYRIDO(2',3':17,18)(1,11)DIOXACYCLOEICOSINO(2,3,4-IJ)ISOQUINOLIN-12-OL, 3,4,4A,5,16A,17,18,19-OCTAHYDRO-21,22,26-TRIMETHOXY-4,17-DIMETHYL-, HYDROCHLORIDE (1:2), (4AS,16AR)-

Systematic Name

English

Code System Code Type Description

EVMPD

SUB182701