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Session ID: 1ed288dbeb0994576ae66f4b6ce4d725

Search Type: drug

Started at: 2010-07-01 11:32:25

Finished at: 2010-07-01 11:34:13

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Field Result Source
Name
nimodipine External
Drugbank ID
DB00393 DrugBank
Description
Nimodipine (marketed by Bayer as Nimotop) is a dihydropyridine calcium channel blocker originally developed for the treatment of high blood pressure. It is not frequently used for this indication, but has shown good results in preventing a major complication of subarachnoid hemorrhage (a form of cerebral hemorrhage) termed vasospasm; this is now the main use of nimodipine. Wikipedia
Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured congenital aneurysms who are in good neurological condition post-ictus (e.g., Hunt and Hess Grades I-III). The contractile processes of smooth muscle cells are dependent upon calcium ions, which enter these cells during depolarization as slow ionic transmembrane currents. Nimodipine inhibits calcium ion transfer into these cells and thus inhibits contractions of vascular smooth muscle. In animal experiments, nimodipine had a greater effect on cerebral arteries than on arteries elsewhere in the body perhaps because it is highly lipophilic, allowing it to cross the blood brain barrier. DrugBank
The regular dosage is 60 mg tablets every four hours. If the patient is unable to take tablets orally, it was previously given via intravenous infusion at a rate of 1–2 mg/hour (lower dosage if the body weight is <70 kg or blood pressure is too low), but since the withdrawal of the IV preparation, administration by nasogastric tube is an alternative. Wikipedia
Chemical Kingdom
Organic BioSpider
Chemical Class
Not Available Not Applicable
Chemical Species
aromatic compound Checkmol
carboxylic acid ester Checkmol
dialkyl ether Checkmol
enamine Checkmol
heterocyclic compound Checkmol
nitro compound Checkmol
Synonym
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)- Pubchem
2-Methoxyethyl-1-methylethyl ester Pubchem
Admon NIST
N149_SIGMA Pubchem
Nimodipine (usan/inn) Pubchem
Nimodipino Pubchem
Nimodipino [inn-spanish] Pubchem
Nimodipinum Pubchem
Nimodipinum [inn-latin] Pubchem
Nimotop NIST
Nimotop (TN) Pubchem
Nimotop - Cap 30mg DPD
Nimotop(TM) Pubchem
Periplum NIST
UNII-57WA9QZ5WH Pubchem
Brand Mixture
Not Available Not Applicable
CAS
66085-59-4 DrugBank
InChI Identifier 
InChI=1/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-1
0-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H
2,1-5H3
 ChemSpider
IUPAC
O5-(2-methoxyethyl) O3-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate DrugBank
Chemical Formula
C21H26N2O7 PubChem
Chemical Structure
Chemical Structure Molconvert
Average Molecular Weight (g/mol)
418.440340 BioSpider
Monoisotopic Molecular Weight (g/mol)
418.174000 BioSpider
SMILES (Isomeric) 
O=C(OC(C)C)\C1=C(\N/C(=C(/C(=O)OCCOC)C1c2cccc([N+]([O-])=O)c2)C)C
 ChemSpider
SMILES (Canonical) 
CC1=C(C(C(=C(N1)C)C(=O)OC(C)C)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OCCO
C
 PubChem
Kegg Drug
D00438 DrugBank
Kegg Compound
C07267 DrugBank
Pubchem Compound ID
4497 DrugBank
Pubchem Substance ID
10473530 Pubchem
11119999 Pubchem
11120487 Pubchem
11120975 Pubchem
11121462 Pubchem
11121942 Pubchem
11147082 Pubchem
11341987 Pubchem
11362170 Pubchem
11362531 Pubchem
11364815 Pubchem
11365093 Pubchem
11367377 Pubchem
11367655 Pubchem
11369939 Pubchem
11370333 Pubchem
11370334 Pubchem
11371732 Pubchem
11373256 Pubchem
11374401 Pubchem
11375817 Pubchem
11378106 Pubchem
11466946 Pubchem
11468066 Pubchem
11485200 Pubchem
11486721 Pubchem
11487572 Pubchem
11489378 Pubchem
11490582 Pubchem
11492606 Pubchem
11495694 Pubchem
11528721 Pubchem
12013716 Pubchem
14831516 Pubchem
17405450 Pubchem
187034 Pubchem
24277858 Pubchem
26612490 Pubchem
26663021 Pubchem
26680672 Pubchem
26747118 Pubchem
26747119 Pubchem
26747120 Pubchem
26751792 Pubchem
26751793 Pubchem
26759246 Pubchem
29223591 Pubchem
3153214 Pubchem
36529021 Pubchem
4444853 Pubchem
46386964 Pubchem
46508497 Pubchem
47364914 Pubchem
47364915 Pubchem
47364916 Pubchem
47515067 Pubchem
47515068 Pubchem
47515069 Pubchem
47588741 Pubchem
47885149 Pubchem
48258944 Pubchem
48416329 Pubchem
49635687 Pubchem
49699210 Pubchem
50104485 Pubchem
50104486 Pubchem
50104487 Pubchem
53777997 Pubchem
53788670 Pubchem
56310702 Pubchem
56422227 Pubchem
56463276 Pubchem
56463546 Pubchem
57322299 Pubchem
596563 Pubchem
6951262 Pubchem
7404101 Pubchem
77150490 Pubchem
7847504 Pubchem
7980128 Pubchem
81041039 Pubchem
8152770 Pubchem
85088151 Pubchem
85231145 Pubchem
85360301 Pubchem
855566 Pubchem
85654728 Pubchem
85788239 Pubchem
88883173 Pubchem
90340912 Pubchem
92124648 Pubchem
92125762 Pubchem
92304294 Pubchem
92307961 Pubchem
92308650 Pubchem
92308829 Pubchem
92309813 Pubchem
92711037 Pubchem
94491343 Pubchem
94569202 Pubchem
9476 Kegg
OMIM ID
Not Available Not Applicable
ChEBI
Not Available Not Applicable
BioCyc
Not Available Not Applicable
PharmGKB
PA450633 DrugBank
HET ID
Not Available Not Applicable
DPD ID
02155923 DPD
Rxlist Link
http://www.rxlist.com/cgi/generic2/nimodip.htm DrugBank
Wikipedia
nimodipine Wikipedia
Pdr Health Link
http://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=qui1368.html&contentName=Quinidine+sulfate&contentId=639 PDRHealth
Melting Point
7 °C (45 °F) Wikipedia
State
Liquid BioSpider
MSDS Link
1278005614.pdf www.sciencelab.com
FDA Label
1278005616.pdf FDA
Experimental Water Solubility
Not Available Not Applicable
Predicted Water Solubility
0.012 mg/mL [Predicted by ALOGPS] Alogps
0.0243 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] PhysProp
Experimental LogP
3.05 [MASUMOTO,K ET AL. (1995)] PhysProp
Predicted LogP
3.41 [Predicted by ALOGPS] Alogps
pKa
Not Available Not Applicable
SDF File
1278005562.sdf Pubchem
Mol File
1278005548.mol Molconvert
Pdb File
1278005618.pdb Molconvert
Mass Spec File
Not Available Not Applicable
Associated Disorder
Not Available Not Applicable
Pathway
Not Available Not Applicable
Category
Not Available Not Applicable
ATC Code
C08CA06 DPD
AHFS Code
24:12.92 DPD
Schedule
SCHEDULE F (Canada) DPD
Indication
For the treatment of subarachnoid bleeding. DrugBank
Nimodipine is associated with low blood pressure, flushing and sweating, edema, nausea and other gastrointestinal problems, most of which are known characteristics of calcium channel blockers. It is contraindicated in unstable angina or an episode of myocardial infarction more recently than one month. Wikipedia
Pharmacology
Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured congenital aneurysms who are in good neurological condition post-ictus (e.g., Hunt and Hess Grades I-III). The contractile processes of smooth muscle cells are dependent upon calcium ions, which enter these cells during depolarization as slow ionic transmembrane currents. Nimodipine inhibits calcium ion transfer into these cells and thus inhibits contractions of vascular smooth muscle. In animal experiments, nimodipine had a greater effect on cerebral arteries than on arteries elsewhere in the body perhaps because it is highly lipophilic, allowing it to cross the blood brain barrier. DrugBank
Mechanism Of Action
Although the precise mechanism of action is not known, nimodipine blocks intracellular influx of calcium that is thought to be a central to ischaemic neuronal damage. Nimodipine binds specifically to L-type voltage-gated calcium channels. DrugBank
Nimodipine binds specifically to L-type voltage-gated calcium channels. There are numerous theories about its mechanism in preventing vasospasm, but none are conclusive. Contraindications Wikipedia
Absorption
100% (Intravenous) 13% (Oral) Wikipedia
Bioavailability is 100% following intravenous administration and 13% following oral administration. DrugBank
Protein Binding
95% DrugBank
Half Life
8-9 hours DrugBank
8–9 hours Wikipedia
Biotransformation
Hepatic. DrugBank
Nimodipine is metabolized in the first pass metabolism Wikipedia
Toxicity
Symptoms of overdosage would be expected to be related to cardiovascular effects such as excessive peripheral vasodilation with marked systemic hypotension. DrugBank
Dosage
Capsule (Oral) DPD
Patient Information
1278005642.html RxList
Interactions
Not Available Not Applicable
Contraindications
Not Available Not Applicable
Targets 
Q06432
[ UniProt | Analyze ]		 DrugBank