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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 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

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparison of the direct negative dromotropic effect of a new calcium channel blocker, cilnidipine, with that of nicardipine.
2005 May
Patents

Sample Use Guides

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
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 Thu Jul 06 16:59:15 UTC 2023
Edited
by admin
on Thu Jul 06 16:59:15 UTC 2023
Record UNII
4LNU2SU262
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
(-)-FRC-8653
Code English
Code System Code Type Description
CAS
132295-21-7
Created by admin on Thu Jul 06 16:59:15 UTC 2023 , Edited by admin on Thu Jul 06 16:59:15 UTC 2023
PRIMARY
FDA UNII
4LNU2SU262
Created by admin on Thu Jul 06 16:59:15 UTC 2023 , Edited by admin on Thu Jul 06 16:59:15 UTC 2023
PRIMARY
CAS
118934-76-2
Created by admin on Thu Jul 06 16:59:15 UTC 2023 , Edited by admin on Thu Jul 06 16:59:15 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
Related Record Type Details
RACEMATE -> ENANTIOMER