VATANIDIPINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C41H42N4O6
Molecular Weight	686.7954
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=C(C)NC(C)=C(C1C2=CC(=CC=C2)[N+]([O-])=O)C(=O)OCCC3=CC=C(C=C3)N4CCN(CC4)C(C5=CC=CC=C5)C6=CC=CC=C6

InChI

InChIKey=OTTHUQAYARCXLP-UHFFFAOYSA-N

InChI=1S/C41H42N4O6/c1-28-36(40(46)50-3)38(33-15-10-16-35(27-33)45(48)49)37(29(2)42-28)41(47)51-26-21-30-17-19-34(20-18-30)43-22-24-44(25-23-43)39(31-11-6-4-7-12-31)32-13-8-5-9-14-32/h4-20,27,38-39,42H,21-26H2,1-3H3

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11116287http://en.pharmacodia.com/yaodu/html/v1/chemicals/d4667ee8a72fe0f6700a7b985f9b8a97.html | http://adisinsight.springer.com/drugs/800001931 | https://www.ncbi.nlm.nih.gov/pubmed/9306262
Curator's Comment: Description was created based on several sources, including http://link.springer.com/article/10.2165/00126839-200203050-00007 and http://www.ncbi.nlm.nih.gov/pubmed/9612662

Watanidipine (AE0047) had been NDA filed for the treatment of hypertension in Japan. Watanidipine (as Calbren®) was awaiting registration with Mitsubishi Pharma Corporation in Japan. However, Mitsubishi Pharma Corporation has discontinued the development of this drug. Watanidipine had also been in phase II clinical trials for the treatment of stroke and preclinical trials for atherosclerosis. However, no recent development has been reported. Watanidipine (AE0047) has being shown to be a calcium antagonist with protective effects against cerebral ischaemia and the occurrence of stroke in several animal models.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
calcium ion transmembrane transport 3 Target ID: GO:0070588 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9378237 \| https://www.ncbi.nlm.nih.gov/pubmed/7590520 \| http://www.kegg.jp/dbget-bin/www_bget?dr:D01933 \| https://www.ncbi.nlm.nih.gov/pubmed/9612662	Blocker 537	11.4 nM [Kd]
Low-density lipoprotein (LDL) oxidation 2 Target ID: Low-density lipoprotein (LDL) oxidation Sources: http://www.ncbi.nlm.nih.gov/pubmed/9493553	Inhibitor 8297
L-type calcium current, Cavia porcellus 2 Target ID: L-type calcium current, Cavia porcellus Sources: http://www.ncbi.nlm.nih.gov/pubmed/9612662	Blocker 537	11.4 nM [Kd]
Calcium uptake 2 Target ID: Calcium uptake Sources: http://www.ncbi.nlm.nih.gov/pubmed/9612662	Inhibitor 8297
Calcium channel 4 Target ID: Calcium channel Sources: http://link.springer.com/article/10.2165/00126839-200203050-00007	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Atherosclerosis 74 Sources: http://adisinsight.springer.com/drugs/800001931 https://www.ncbi.nlm.nih.gov/pubmed/11116287	Primary	Preclinical	Unknown Approved Use Unknown
Hypertension 567 Sources: http://adisinsight.springer.com/drugs/800001931 https://www.ncbi.nlm.nih.gov/pubmed/11116287	Primary	Phase II 1132	Unknown Approved Use Unknown
Stroke 144 Sources: http://adisinsight.springer.com/drugs/800001931 https://www.ncbi.nlm.nih.gov/pubmed/11116287 https://www.ncbi.nlm.nih.gov/pubmed/7853209	Primary	Phase II 1132	Unknown Approved Use Unknown
Hypertension 567 Sources: http://link.springer.com/article/10.2165/00126839-200203050-00007	Primary	Phase III 656	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: http://adisinsight.springer.com/drugs/800001931	Primary	Preclinical	Unknown Approved Use Unknown
Stroke 144 Sources: http://link.springer.com/article/10.2165/00126839-200203050-00007	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of the calcium antagonist AE0047 on the development of neurological deficit and infarction after middle cerebral artery occlusion in stroke-prone spontaneously hypertensive rats.	1997 Sep	9306262
Therapeutic effects of AE0047, a novel calcium antagonist, on progression of brain damage after stroke in stroke-prone spontaneously hypertensive rats.	1998 Mar	9510090
Inhibitory effects of AE0047, a new dihydropyridine Ca(2+) channel blocker, on renal nerve stimulation-induced renal actions in anesthetized dogs.	2000 Jun	10869409
Vatanidipine hydrochloride: a new long-lasting antihypertensive agent.	2001 Jan	11116287

Patents

Sample Use Guides

In Vivo Use Guide

For essential hypertension - orally, once-daily 2-8 mg/day

Route of Administration: Oral

In Vitro Use Guide

After 1-hr treatment with Vatanidipine (10(-6) M), K(+)-induced contraction in rat aortic strip was slightly depressed

Name

Type

Language

VATANIDIPINE

Official Name

English

vatanidipine [INN]

Common Name

English

Watanidipine

Common Name

English

(±)-P-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)PHENETHYL)METHYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C333