nimodipine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
calcium channel blockers, nifedipine derivatives 1937 66085-59-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nimodipine
  • nemotan
  • nymalize
A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.
  • Molecular weight: 418.45
  • Formula: C21H26N2O7
  • CLOGP: 4
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 1
  • TPSA: 117
  • ALOGS: -4.54
  • ROTB: 10

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
50 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 14.34 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 11 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 28, 1988 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Patent ductus arteriosus 81.51 38.01 17 619 3845 46681581
Subarachnoid haemorrhage 49.63 38.01 14 622 11139 46674287
Cerebral vasoconstriction 49.23 38.01 9 627 1024 46684402
Foetal exposure during pregnancy 46.60 38.01 17 619 30730 46654696
Premature baby 42.94 38.01 14 622 18098 46667328

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Brain injury 81.74 70.26 19 504 5529 29946426
Cerebral ischaemia 74.46 70.26 18 505 6182 29945773

Pharmacologic Action:

SourceCodeDescription
ATC C08CA06 CARDIOVASCULAR SYSTEM
CALCIUM CHANNEL BLOCKERS
SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS
Dihydropyridine derivatives
FDA CS M0006414 Dihydropyridines
FDA MoA N0000000069 Calcium Channel Antagonists
FDA EPC N0000175421 Dihydropyridine Calcium Channel Blocker
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002121 Calcium Channel Blockers
MeSH PA D000077264 Calcium-Regulating Hormones and Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D014665 Vasodilator Agents
CHEBI has role CHEBI:35554 cardiovascular drugs
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:35674 antihypertensive
CHEBI has role CHEBI:38215 calcium channel blockers

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Subarachnoid intracranial hemorrhage indication 21454007
nerve regeneration after iatrogenic nerve injury off-label use 57182000
Essential tremor off-label use 609558009 DOID:4990
Low blood pressure contraindication 45007003
Chronic idiopathic constipation contraindication 82934008
Disease of liver contraindication 235856003 DOID:409

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.09 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Voltage-dependent L-type calcium channel subunit alpha-1D Ion channel BLOCKER UNKNOWN CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel BLOCKER UNKNOWN CHEMBL
Cytochrome P450 2C9 Enzyme IC50 6 DRUG MATRIX
Cytochrome P450 2C19 Enzyme IC50 5.40 DRUG MATRIX
Sodium/nucleoside cotransporter 1 Transporter Ki 6.36 DRUG MATRIX
Voltage-dependent T-type calcium channel subunit alpha-1H Ion channel Ki 5.25 WOMBAT-PK
Adenosine receptor A3 GPCR Ki 5.07 WOMBAT-PK
Cytochrome P450 3A4 Enzyme Ki 6.12 WOMBAT-PK
Mineralocorticoid receptor Nuclear hormone receptor ANTAGONIST IC50 6.80 IUPHAR
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor EC50 6.41 CHEMBL
Bile acid receptor Nuclear hormone receptor IC50 5.05 CHEMBL
Voltage-dependent calcium channel gamma-1 subunit Ion channel WOMBAT-PK
Voltage-dependent L-type calcium channel subunit alpha-1F Ion channel GATING INHIBITOR IC50 6 IUPHAR
Voltage-dependent L-type calcium channel subunit alpha-1S Ion channel GATING INHIBITOR IC50 6 IUPHAR
Cannabinoid receptor 1 GPCR Ki 5.86 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 4.35 CHEMBL
Adenosine receptor A1 GPCR Ki 4.70 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel GATING INHIBITOR IC50 6.80 IUPHAR
Voltage-dependent L-type calcium channel subunit alpha-1D Ion channel GATING INHIBITOR IC50 6.60 IUPHAR

External reference:

IDSource
4019390 VUID
N0000147543 NUI
D00438 KEGG_DRUG
4019390 VANDF
C0028094 UMLSCUI
CHEBI:7575 CHEBI
6U9 PDB_CHEM_ID
CHEMBL1428 ChEMBL_ID
CHEMBL255033 ChEMBL_ID
D009553 MESH_DESCRIPTOR_UI
DB00393 DRUGBANK_ID
2523 IUPHAR_LIGAND_ID
4528 INN_ID
57WA9QZ5WH UNII
4497 PUBCHEM_CID
1423768 RXNORM
109672 MMSL
203915 MMSL
5177 MMSL
d00318 MMSL
000713 NDDF
387502003 SNOMEDCT_US
87285001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 23155-512 CAPSULE, LIQUID FILLED 30 mg ORAL ANDA 13 sections
Nymalize HUMAN PRESCRIPTION DRUG LABEL 1 24338-200 SOLUTION 60 mg ORAL NDA 25 sections
Nymalize HUMAN PRESCRIPTION DRUG LABEL 1 24338-205 SOLUTION 30 mg ORAL NDA 25 sections
Nymalize HUMAN PRESCRIPTION DRUG LABEL 1 24338-230 SOLUTION 30 mg ORAL NDA 26 sections
Nymalize HUMAN PRESCRIPTION DRUG LABEL 1 24338-260 SOLUTION 60 mg ORAL NDA 26 sections
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 62559-210 CAPSULE 30 mg ORAL ANDA 23 sections
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 63739-797 CAPSULE, LIQUID FILLED 30 mg ORAL ANDA 25 sections
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 67877-297 CAPSULE, LIQUID FILLED 30 mg ORAL ANDA 26 sections
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 68084-912 CAPSULE, LIQUID FILLED 30 mg ORAL ANDA 26 sections
Nimodipine HUMAN PRESCRIPTION DRUG LABEL 1 69452-209 CAPSULE, LIQUID FILLED 30 mg ORAL ANDA 23 sections