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

Stem definitionDrug idCAS RN
calcium channel blockers, nifedipine derivatives 1909 55985-32-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nicardipine
  • (+/-)-Nicardipine
  • perpidine
  • nicardipine hydrochloride
  • nicardipine HCl
A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.
  • Molecular weight: 479.53
  • Formula: C26H29N3O6
  • CLOGP: 5.23
  • LIPINSKI: 1
  • HAC: 9
  • HDO: 1
  • TPSA: 111.01
  • ALOGS: -5.29
  • ROTB: 11

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
90 mg O
90 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 7.90 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.17 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 23 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 11 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 21, 1988 FDA CHIESI USA INC

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
Cerebral vasoconstriction 132.80 20.56 31 7128 1002 46677901
Acute pulmonary oedema 130.03 20.56 48 7111 7843 46671060
Hyponatraemia 104.10 20.56 101 7058 101231 46577672
Premature delivery 96.37 20.56 53 7106 22016 46656887
Exposure during pregnancy 93.10 20.56 98 7061 108114 46570789
Posterior reversible encephalopathy syndrome 84.95 20.56 43 7116 15098 46663805
Acute kidney injury 83.70 20.56 138 7021 235717 46443186
Hepatocellular injury 79.63 20.56 52 7107 29470 46649433
Acute motor-sensory axonal neuropathy 74.17 20.56 16 7143 358 46678545
Maternal exposure during pregnancy 64.53 20.56 79 7080 102470 46576433
Cerebral haemorrhage 62.27 20.56 44 7115 28327 46650576
Low birth weight baby 60.91 20.56 25 7134 5409 46673494
Hyperkalaemia 60.53 20.56 55 7104 50654 46628249
Premature labour 54.50 20.56 29 7130 11270 46667633
Bradycardia 53.33 20.56 58 7101 66240 46612663
Haemorrhagic transformation stroke 51.59 20.56 15 7144 1155 46677748
Orthostatic hypotension 51.25 20.56 37 7122 24621 46654282
Cholestasis 50.59 20.56 38 7121 26855 46652048
Eosinophilia 47.33 20.56 32 7127 19185 46659718
Lactic acidosis 46.90 20.56 40 7119 33869 46645034
Fall 45.86 20.56 132 7027 328965 46349938
Haemangioma congenital 43.93 20.56 11 7148 479 46678424
Purpura 43.68 20.56 24 7135 9934 46668969
Acute generalised exanthematous pustulosis 42.17 20.56 23 7136 9382 46669521
Paradoxical drug reaction 41.15 20.56 15 7144 2361 46676542
Hemivertebra 40.30 20.56 8 7151 117 46678786
Thrombocytopenia 39.38 20.56 70 7089 126511 46552392
Caesarean section 39.34 20.56 27 7132 16576 46662327
Drug interaction 39.06 20.56 92 7067 203002 46475901
Fatigue 38.47 20.56 23 7136 608674 46070229
Toxic skin eruption 36.29 20.56 23 7136 12364 46666539
Hypotension 35.98 20.56 97 7062 232492 46446411
Premature baby 34.97 20.56 26 7133 18086 46660817
Hypertension 34.59 20.56 86 7073 196270 46482633
Ischaemic stroke 34.53 20.56 25 7134 16697 46662206
Patent ductus arteriosus 34.09 20.56 15 7144 3847 46675056
Congenital choroid plexus cyst 33.37 20.56 8 7151 290 46678613
Hypokalaemia 33.10 20.56 53 7106 87971 46590932
Haematoma 33.07 20.56 32 7127 31840 46647063
Agranulocytosis 32.37 20.56 27 7132 22158 46656745
Renal failure 31.75 20.56 60 7099 113534 46565369
Pain 31.55 20.56 17 7142 476931 46201972
Gestational hypertension 31.45 20.56 12 7147 2143 46676760
Subarachnoid haemorrhage 30.92 20.56 20 7139 11133 46667770
Arthralgia 30.63 20.56 9 7150 364594 46314309
Foetal growth restriction 29.27 20.56 16 7143 6551 46672352
Tumour rupture 29.05 20.56 6 7153 108 46678795
Anaphylactic shock 28.19 20.56 24 7135 20250 46658653
Foetal arrhythmia 26.80 20.56 6 7153 160 46678743
Metabolic encephalopathy 26.42 20.56 14 7145 5389 46673514
Pre-eclampsia 26.35 20.56 16 7143 7978 46670925
Cutaneous lupus erythematosus 26.19 20.56 11 7148 2518 46676385
Rhabdomyolysis 25.84 20.56 32 7127 41877 46637026
Drug reaction with eosinophilia and systemic symptoms 25.76 20.56 27 7132 29521 46649382
Rash maculo-papular 25.25 20.56 26 7133 27848 46651055
Drug hypersensitivity 24.53 20.56 4 7155 243821 46435082
Acquired haemophilia 24.36 20.56 8 7151 923 46677980
Haemodynamic instability 24.28 20.56 15 7144 7710 46671193
Nausea 24.13 20.56 43 7116 687411 45991492
Cardiogenic shock 24.02 20.56 20 7139 16364 46662539
Mixed liver injury 23.90 20.56 11 7148 3132 46675771
Blood pressure decreased 23.68 20.56 36 7123 57123 46621780
Intra-abdominal haematoma 23.50 20.56 9 7150 1622 46677281
Foetal exposure during pregnancy 23.14 20.56 26 7133 30721 46648182
Wrong patient received product 22.95 20.56 9 7150 1728 46677175
Metabolic acidosis 22.93 20.56 29 7130 38751 46640152
Respiratory distress 22.35 20.56 26 7133 31890 46647013
Rheumatoid arthritis 21.92 20.56 5 7154 240210 46438693
Porphyria acute 21.84 20.56 6 7153 376 46678527
Altered state of consciousness 21.55 20.56 22 7137 23326 46655577
Walking disability 21.29 20.56 8 7151 1370 46677533
Sinus bradycardia 20.57 20.56 17 7142 13765 46665138
Bronchiolitis 20.57 20.56 9 7150 2276 46676627

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
Cerebral vasoconstriction 113.31 19.13 21 4950 191 29947316
Blood lactic acid 78.24 19.13 17 4954 363 29947144
Acute kidney injury 69.69 19.13 145 4826 273697 29673810
Premature baby 64.41 19.13 38 4933 16653 29930854
Foetal disorder 63.93 19.13 16 4955 642 29946865
Cerebral haemorrhage 62.00 19.13 48 4923 32839 29914668
Neutropenia neonatal 56.80 19.13 14 4957 527 29946980
Low birth weight baby 49.98 19.13 23 4948 6053 29941454
Foetal exposure during pregnancy 45.15 19.13 42 4929 36829 29910678
Antiphospholipid antibodies positive 43.25 19.13 10 4961 285 29947222
Cholestasis 33.62 19.13 30 4941 24920 29922587
Haemorrhagic cerebral infarction 33.53 19.13 10 4961 776 29946731
Eosinophilia 32.58 19.13 28 4943 22132 29925375
Phlebitis deep 31.59 19.13 5 4966 15 29947492
Rash maculo-papular 31.19 19.13 29 4942 25389 29922118
Bradycardia 29.90 19.13 45 4926 65481 29882026
Paradoxical drug reaction 28.08 19.13 12 4959 2650 29944857
Brain herniation 27.18 19.13 13 4958 3727 29943780
Extravasation 25.27 19.13 10 4961 1818 29945689
Kidney small 25.20 19.13 5 4966 67 29947440
Cerebral haematoma 24.86 19.13 13 4958 4501 29943006
Hypertension 23.63 19.13 58 4913 121296 29826211
Drug reaction with eosinophilia and systemic symptoms 23.09 19.13 26 4945 28462 29919045
Hyperkalaemia 22.84 19.13 40 4931 65970 29881537
Injection site oedema 22.65 19.13 5 4966 115 29947392
Aortic dissection 22.47 19.13 10 4961 2432 29945075
Renal failure 22.37 19.13 59 4912 128907 29818600
Hypertensive crisis 22.12 19.13 15 4956 8342 29939165
Fatigue 22.06 19.13 13 4958 320660 29626847
Death 21.24 19.13 17 4954 357266 29590241
Phlebitis 21.16 19.13 11 4960 3764 29943743
Respiratory gas exchange disorder 20.78 19.13 6 4965 416 29947091
Cerebral infarction 19.57 19.13 23 4948 26350 29921157
Blood fibrinogen decreased 19.44 19.13 7 4964 982 29946525
Macroglossia 19.44 19.13 5 4966 224 29947283

Pharmacologic Action:

SourceCodeDescription
ATC C08CA04 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
FDA MoA N0000182137 Cytochrome P450 2D6 Inhibitors
FDA MoA N0000182140 Cytochrome P450 2C19 Inhibitors
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000187062 Cytochrome P450 2C8 Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Angina pectoris indication 194828000
Prinzmetal angina off-label use 87343002
Raynaud's phenomenon off-label use 266261006
Portal hypertension contraindication 34742003 DOID:10762
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Chronic idiopathic constipation contraindication 82934008
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Cerebral hemorrhage contraindication 274100004
Cerebral infarction contraindication 432504007 DOID:3526
Severe Aortic Valve Stenosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.02 Basic
pKa2 2.37 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-gated L-type calcium channel Ion channel BLOCKER CHEMBL CHEMBL
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Cytochrome P450 2C9 Enzyme IC50 6.55 WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 6.38 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 5.32 CHEMBL
Malate dehydrogenase cytoplasmic Enzyme IC50 4.30 CHEMBL
Adenosine receptor A3 GPCR Ki 5.49 CHEMBL
ATP-binding cassette sub-family G member 2 Transporter IC50 4.78 CHEMBL
Voltage-dependent T-type calcium channel subunit alpha-1H Ion channel Ki 5.55 WOMBAT-PK
Adrenergic receptor alpha-2 GPCR IC50 5.85 CHEMBL
Equilibrative nucleoside transporter 1 Transporter Ki 5.27 CHEMBL
Beta-lactamase Enzyme IC50 4.70 CHEMBL
Adenosine receptor A3 GPCR Ki 4.96 CHEMBL
Adrenergic receptor alpha-1 GPCR IC50 5.44 CHEMBL
Adenosine receptor A2a GPCR Ki 4.20 CHEMBL
Voltage-gated L-type calcium channel Ion channel Ki 9.08 CHEMBL
Adenosine receptor A1 GPCR Ki 4.71 CHEMBL
Potassium voltage-gated channel subfamily A member 4 Unclassified BLOCKER IC50 6.10 IUPHAR

External reference:

IDSource
4019858 VUID
N0000147944 NUI
D00617 KEGG_DRUG
54527-84-3 SECONDARY_CAS_RN
4019350 VANDF
4019858 VANDF
C0028005 UMLSCUI
CHEBI:7550 CHEBI
CHEMBL1484 ChEMBL_ID
CHEMBL1200326 ChEMBL_ID
D009529 MESH_DESCRIPTOR_UI
DB00622 DRUGBANK_ID
2559 IUPHAR_LIGAND_ID
4745 INN_ID
CZ5312222S UNII
4474 PUBCHEM_CID
235230 RXNORM
2278 MMSL
5171 MMSL
d00315 MMSL
000712 NDDF
004518 NDDF
108526002 SNOMEDCT_US
108527006 SNOMEDCT_US
372502001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9542 INJECTION 2.50 mg INTRAVENOUS NDA 26 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9593 INJECTION 2.50 mg INTRAVENOUS NDA 26 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9633 INJECTION 0.20 mg INTRAVENOUS NDA 27 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9634 INJECTION 0.10 mg INTRAVENOUS NDA 27 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9689 INJECTION 25 mg INTRAVENOUS NDA 27 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1020 CAPSULE 20 mg ORAL ANDA 22 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1430 CAPSULE 30 mg ORAL ANDA 22 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0517-0735 INJECTION, SOLUTION 2.50 mg INTRAVENOUS ANDA 26 sections
Nicardipine Hydrochloride Human Prescription Drug Label 1 0781-3204 INJECTION 2.50 mg INTRAVENOUS ANDA 12 sections
Nicardipine Hydrochloride Human Prescription Drug Label 1 0781-9324 INJECTION 2.50 mg INTRAVENOUS ANDA 12 sections
Cardene IV HUMAN PRESCRIPTION DRUG LABEL 1 10122-313 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 23 sections
Cardene IV HUMAN PRESCRIPTION DRUG LABEL 1 10122-314 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 23 sections
Cardene IV HUMAN PRESCRIPTION DRUG LABEL 1 10122-325 INJECTION, SOLUTION 0.20 mg INTRAVENOUS NDA 23 sections
Nicardipine Hydrochloride Human Prescription Drug Label 1 14593-124 INJECTION 2.50 mg INTRAVENOUS ANDA 12 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24658-750 CAPSULE 20 mg ORAL ANDA 19 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24658-751 CAPSULE 30 mg ORAL ANDA 19 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 40042-047 INJECTION, SOLUTION 2.50 mg INTRAVENOUS ANDA 20 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-501 CAPSULE 20 mg ORAL ANDA 19 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-502 CAPSULE 30 mg ORAL ANDA 19 sections
CARDENE IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-009 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 24 sections
CARDENE IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-016 INJECTION, SOLUTION 0.20 mg INTRAVENOUS NDA 24 sections
Cardene IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-021 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 24 sections
Cardene IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-024 INJECTION, SOLUTION 0.20 mg INTRAVENOUS NDA 24 sections
CARDENE IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-026 INJECTION, SOLUTION 0.10 mg INTRAVENTRICULAR NDA 24 sections
CARDENE IV HUMAN PRESCRIPTION DRUG LABEL 1 43066-028 INJECTION, SOLUTION 0.20 mg INTRAVENOUS NDA 24 sections
nicardipine hydrochloride Human Prescription Drug Label 1 47335-882 INJECTION 2.50 mg INTRAVENOUS NDA 24 sections
NICARDIPINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1428 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 17 sections
NICARDIPINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1482 INJECTION 25 mg INTRAVENOUS NDA 17 sections
NICARDIPINE HYDROCHLORIDE Human Prescription Drug Label 1 55150-183 INJECTION, SOLUTION 25 mg INTRAVENOUS ANDA 24 sections
Nicardipine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55648-631 INJECTION 2.50 mg INTRAVENOUS ANDA 16 sections