CILNIDIPINE, (+)-

Possibly Marketed Outside US

Details

Stereochemistry	UNKNOWN
Molecular Formula	C27H28N2O7
Molecular Weight	492.5204
Optical Activity	( + )
Additional Stereochemistry	Yes
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCCOC(=O)C1=C(C)NC(C)=C(C1C2=CC=CC(=C2)[N+]([O-])=O)C(=O)OC\C=C\C3=CC=CC=C3

InChI

InChIKey=KJEBULYHNRNJTE-DHZHZOJOSA-N

InChI=1S/C27H28N2O7/c1-18-23(26(30)35-14-8-11-20-9-5-4-6-10-20)25(21-12-7-13-22(17-21)29(32)33)24(19(2)28-18)27(31)36-16-15-34-3/h4-13,17,25,28H,14-16H2,1-3H3/b11-8+

HIDE SMILES / InChI

Molecular Formula	C27H28N2O7
Molecular Weight	492.5204
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: http://adis.springer.com/drugs/800001274
Curator's Comment: Description was created based on several sources, including http://www.nevapress.com/cdr/full/17/4/341.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19426250

Cilnidipine (FRC-8653) is a dihydropyridine (DHP) type of calcium channel antagonist. The L-type Ca2+ channel blockade by cilnidipine affects predominantly vascular smooth muscle, thereby producing vasodilation of peripheral resistance vessels and coronary arteries. The blockade of N-type Ca2+ channels affects predominantly peripheral nerve endings of sympathetic neurons, thereby dilating blood vessels by lowering plasma catecholamine levels. Furthermore, renoprotective and neuroprotective effects as well as cardioprotective action of cilnidipine have been demonstrated in clinical practice or animal examinations. Cilnidipine was originated by Fuji & Rebio Pharmaceutical Co., Ltd. and developed jointly with Ajinomoto for the treatment of hypertension. Cilnidipine has been launched in Japan.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 95 Target ID: CHEMBL2095177 Sources: http://www.nevapress.com/cdr/full/17/4/341.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10784100 \| https://www.ncbi.nlm.nih.gov/pubmed/10408255	Inhibitor 8504		4.77 null [pIC50]
Voltage-gated N-type calcium channel alpha-1B subunit 14 Target ID: CHEMBL5107 Sources: http://www.nevapress.com/cdr/full/17/4/341.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10784100 \| https://www.ncbi.nlm.nih.gov/pubmed/10408255	Inhibitor 8504		6.08 null [pIC50]

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 575 Sources: http://adis.springer.com/drugs/800001274 https://www.ncbi.nlm.nih.gov/pubmed/24407539 https://www.ncbi.nlm.nih.gov/pubmed/27734656	Primary	Approved 8583	ATELEC Approved Use Hypertension
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15340224	Primary	Preclinical	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841896	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
4.7 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.4 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15.7 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.5 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.5 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
16.5 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.4 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=17	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=18	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
23.7 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
27.5 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
60.1 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
51.4 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
101.8 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
95.5 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
11.6 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=17	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
46.1 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=18	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
5.2 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.1 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=38	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.8 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=17	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.9 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/340409_2149037F1105_1_003_1F.pdf#page=18	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	CILNIDIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.7% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/111890_2149037F1032_2_008_2F.pdf#page=41			CILNIDIPINE serum	Homo sapiens

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/	Other AEs: Skin eruption, Flushing of face... Other AEs: Skin eruption (grade 1, 7%) Flushing of face (grade 1, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/

AEs

AE	Significance	Dose	Population
Flushing of face	grade 1, 14%	20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/
Skin eruption	grade 1, 7%	20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9140677/

PubMed

Title	Date	PubMed
Renoprotective effect of the L/N-type calcium channel antagonist cilnidipine on puromycin aminonucleoside-induced nephrosis in rats.	2009	19338138
Prophylactic effects of an N- and L-type Ca2+ antagonist, cilnidipine, against cardiac hypertrophy and dysfunction in stroke-prone, spontaneously hypertensive rats.	2005-12-08	16333380
Comparison of the direct negative dromotropic effect of a new calcium channel blocker, cilnidipine, with that of nicardipine.	2005-05	15912307
[Effects of benidipine hydrochloride (Coniel) on blood pressure, heart rate and plasma norepinephrine concentration in spontaneously hypertensive rats].	1999-05	10480159
Comparison of 24-hour blood pressure, heart rate, and autonomic nerve activity in hypertensive patients treated with cilnidipine or nifedipine retard.	1998-08	9700998
Effect of cilnidipine, a novel dihydropyridine Ca++-channel antagonist, on N-type Ca++ channel in rat dorsal root ganglion neurons.	1997-03	9067302

Patents

Sample Use Guides

In Vivo Use Guide

Normally once daily 5 to 10 mg of cilnidipine after breakfast orally for adult patient. The dose can be increased or reduced according to the age and symptoms. If the above dose is not effective enough, the dose can be increased to 20 mg once daily. For severe hypertension, 10 to 20 mg of cilnidipine orally once daily after breakfast.

Route of Administration: Oral

In Vitro Use Guide

Cell viability of PC12 was not affected by low concentrations of cilnidipine up to 150 uM, but it was slightly decreased at 200 uM cilnidipine.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:10:02 GMT 2025` Edited by `admin` on `Mon Mar 31 23:10:02 GMT 2025`
Record UNII	S85436ZG85
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(+)-FRC-8653

Preferred Name

English

CILNIDIPINE, (+)-

Common Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 2-METHOXYETHYL 3-PHENYL-2-PROPENYL ESTER, (E)-(+)-

Systematic Name

English

Code System Code Type Description

FDA UNII

S85436ZG85

Created by admin on Mon Mar 31 23:10:02 GMT 2025 , Edited by admin on Mon Mar 31 23:10:02 GMT 2025

PRIMARY

CAS

118934-77-3

Created by admin on Mon Mar 31 23:10:02 GMT 2025 , Edited by admin on Mon Mar 31 23:10:02 GMT 2025

NON-SPECIFIC STEREOCHEMISTRY

PUBCHEM

5282138

Created by admin on Mon Mar 31 23:10:02 GMT 2025 , Edited by admin on Mon Mar 31 23:10:02 GMT 2025

PRIMARY

CAS

132338-87-5

Created by admin on Mon Mar 31 23:10:02 GMT 2025 , Edited by admin on Mon Mar 31 23:10:02 GMT 2025

PRIMARY

Related Record Type Details


					97T5AZ1JIP

CILNIDIPINE

RACEMATE -> ENANTIOMER

Details

SMILES

InChI

DescriptionSources: http://adis.springer.com/drugs/800001274Curator's Comment: Description was created based on several sources, including http://www.nevapress.com/cdr/full/17/4/341.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19426250

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

Description
Sources: http://adis.springer.com/drugs/800001274
Curator's Comment: Description was created based on several sources, including http://www.nevapress.com/cdr/full/17/4/341.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19426250

C_max

T_1/2

F_unbound