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Details

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

SHOW SMILES / InChI
Structure of CILNIDIPINE

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
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

CNS Active
4002
Curator's Comment: Cilnidipine is brain penetrant and CNS active in animal studies. No human data available.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 4.77 null [pIC50]
Inhibitor
8504
 6.08 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ATELEC

Approved Use

Hypertension
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Renoprotective effect of the L/N-type calcium channel antagonist cilnidipine on puromycin aminonucleoside-induced nephrosis in rats.
2009
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
Comparison of the direct negative dromotropic effect of a new calcium channel blocker, cilnidipine, with that of nicardipine.
2005-05
[Effects of benidipine hydrochloride (Coniel) on blood pressure, heart rate and plasma norepinephrine concentration in spontaneously hypertensive rats].
1999-05
Comparison of 24-hour blood pressure, heart rate, and autonomic nerve activity in hypertensive patients treated with cilnidipine or nifedipine retard.
1998-08
Effect of cilnidipine, a novel dihydropyridine Ca++-channel antagonist, on N-type Ca++ channel in rat dorsal root ganglion neurons.
1997-03
Patents

Patents

JP2004359675A
3
US4672068
3

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 18:30:20 GMT 2025
Edited
by admin
on Mon Mar 31 18:30:20 GMT 2025
Record UNII
97T5AZ1JIP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CILNIDIPINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
ATELEC
Preferred Name English
CILNIDIPINE [JAN]
Common Name English
cilnidipine [INN]
Common Name English
SISCARD
Brand Name English
FRC-8653
Code English
Cilnidipine [WHO-DD]
Common Name English
CILNIDIPINE [MART.]
Common Name English
(±)-(E)-CINNAMYL 2-METHOXYETHYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLATE
Systematic Name English
CINALONG
Brand Name English
CILNIDIPINE [MI]
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-(2-METHOXYETHYL) 5-((2E)-3-PHENYL-2-PROPEN-1-YL) ESTER
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC08CA14
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
WHO-ATC C08CA14
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
Code System Code Type Description
MESH
C065927
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
CAS
132203-70-4
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
CAS
102106-21-8
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C171754
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
MERCK INDEX
m3548
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY Merck Index
FDA UNII
97T5AZ1JIP
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
DRUG CENTRAL
642
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
IUPHAR
7767
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID0046309
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
SMS_ID
100000091319
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
WIKIPEDIA
Cilnidipine
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL452076
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
EVMPD
SUB06268MIG
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
INN
6880
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
DRUG BANK
DB09232
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
CHEBI
31399
Created by admin on Mon Mar 31 18:30:20 GMT 2025 , Edited by admin on Mon Mar 31 18:30:20 GMT 2025
PRIMARY
Related Record Type Details
VOLTAGE-DEPENDENT L-TYPE CALCIUM CHANNEL SUBUNIT ALPHA-1D
TARGET -> INHIBITOR
Structure of CILNIDIPINE, (+)-
ENANTIOMER -> RACEMATE
Structure of CILNIDIPINE, (-)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of CILNIDIPINE
ACTIVE MOIETY
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