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 555	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 8504
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 555	11.4 nM [Kd]
Calcium uptake 2 Target ID: Calcium uptake Sources: http://www.ncbi.nlm.nih.gov/pubmed/9612662	Inhibitor 8504
Calcium channel 4 Target ID: Calcium channel Sources: http://link.springer.com/article/10.2165/00126839-200203050-00007	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Atherosclerosis 76 Sources: http://adisinsight.springer.com/drugs/800001931 https://www.ncbi.nlm.nih.gov/pubmed/11116287	Primary	Preclinical	Unknown Approved Use Unknown
Hypertension 575 Sources: http://adisinsight.springer.com/drugs/800001931 https://www.ncbi.nlm.nih.gov/pubmed/11116287	Primary	Phase II 1147	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 1147	Unknown Approved Use Unknown
Hypertension 575 Sources: http://link.springer.com/article/10.2165/00126839-200203050-00007	Primary	Phase III 665	Unknown Approved Use Unknown
Atherosclerosis 76 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 1147	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Vatanidipine hydrochloride: a new long-lasting antihypertensive agent.	2001-01	11116287
Inhibitory effects of AE0047, a new dihydropyridine Ca(2+) channel blocker, on renal nerve stimulation-induced renal actions in anesthetized dogs.	2000-06	10869409
Therapeutic effects of AE0047, a novel calcium antagonist, on progression of brain damage after stroke in stroke-prone spontaneously hypertensive rats.	1998-03	9510090
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.	1997-09	9306262

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

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

Preferred Name

English

vatanidipine [INN]

Common Name

English

Watanidipine

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C333