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

Stem definitionDrug idCAS RN
calcium channel blockers, nifedipine derivatives 1922 21829-25-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • BAY A1040
  • nifedipine
  • nedipin
  • fedipin
A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.
  • Molecular weight: 346.34
  • Formula: C17H18N2O6
  • CLOGP: 3.12
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 1
  • TPSA: 110.45
  • ALOGS: -4.29
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
30 mg O
30 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.01 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.71 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.79 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1981 FDA PFIZER

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
Exposure during pregnancy 647.01 41.08 196 1728 25023 2331138
Drug hypersensitivity 569.97 41.08 207 1717 46436 2309725
Premature delivery 540.37 41.08 113 1811 3087 2353074
Maternal exposure during pregnancy 527.46 41.08 149 1775 14714 2341447
Completed suicide 405.67 41.08 132 1792 20902 2335259
Premature baby 387.12 41.08 86 1838 3118 2353043
Hypotension 375.50 41.08 139 1785 32297 2323864
Toxicity to various agents 333.92 41.08 128 1796 32626 2323535
Low birth weight baby 258.66 41.08 49 1875 780 2355381
Foetal exposure during pregnancy 256.49 41.08 68 1856 5184 2350977
Drug ineffective 203.72 41.08 131 1793 101493 2254668
Caesarean section 199.87 41.08 53 1871 4028 2352133
Hypertension 198.55 41.08 84 1840 27277 2328884
Blood pressure inadequately controlled 175.89 41.08 36 1888 864 2355297
Bradycardia 164.84 41.08 56 1868 9925 2346236
Blood pressure increased 163.65 41.08 64 1860 16922 2339239
Pre-eclampsia 162.87 41.08 37 1887 1467 2354694
Premature labour 135.39 41.08 34 1890 2072 2354089
Oedema peripheral 120.85 41.08 57 1867 23706 2332455
Medication error 115.40 41.08 38 1886 6093 2350068
Acute pulmonary oedema 109.76 41.08 26 1898 1237 2354924
Foetal growth restriction 107.11 41.08 25 1899 1115 2355046
Pulmonary oedema 97.16 41.08 35 1889 7328 2348833
Acute kidney injury 94.55 41.08 51 1873 28071 2328090
Drug interaction 92.81 41.08 51 1873 29112 2327049
Dizziness 91.18 41.08 65 1859 58600 2297561
Metabolic acidosis 88.56 41.08 31 1893 5967 2350194
Headache 87.63 41.08 72 1852 80107 2276054
Foetal death 84.81 41.08 23 1901 1889 2354272
Off label use 84.41 41.08 68 1856 73530 2282631
Shock 84.15 41.08 27 1897 3977 2352184
Overdose 83.77 41.08 42 1882 19865 2336296
Tachycardia 79.12 41.08 38 1886 16371 2339790
Cardiac arrest 76.33 41.08 36 1888 14894 2341267
Product complaint 72.95 41.08 25 1899 4513 2351648
Neonatal respiratory distress syndrome 72.50 41.08 16 1908 552 2355609
Blood pressure decreased 72.15 41.08 30 1894 9206 2346955
Porphyria acute 70.57 41.08 12 1912 98 2356063
Hypoxia 68.83 41.08 26 1898 6201 2349960
Palpitations 64.17 41.08 33 1891 16423 2339738
Renal impairment 63.07 41.08 28 1896 10064 2346097
Respiratory arrest 61.84 41.08 24 1900 6154 2350007
Intentional overdose 59.99 41.08 28 1896 11293 2344868
Hypoglycaemia 57.96 41.08 25 1899 8382 2347779
Haemolysis 57.72 41.08 15 1909 1043 2355118
Product use in unapproved indication 57.18 41.08 27 1897 11173 2344988
Multiple organ dysfunction syndrome 56.90 41.08 24 1900 7617 2348544
Product residue present 51.93 41.08 14 1910 1122 2355039
Dyspnoea 51.19 41.08 53 1871 78680 2277481
Suicide attempt 50.93 41.08 25 1899 11257 2344904
Proteinuria 50.90 41.08 17 1907 2833 2353328
CD30 expression 50.45 41.08 7 1917 10 2356151
Drug intolerance 49.13 41.08 26 1898 13691 2342470
Stillbirth 48.63 41.08 14 1910 1427 2354734
Live birth 45.61 41.08 13 1911 1278 2354883
Cardio-respiratory arrest 43.47 41.08 21 1903 9125 2347036
HELLP syndrome 43.00 41.08 9 1915 240 2355921
Heart rate decreased 42.97 41.08 16 1908 3660 2352501
Death 42.73 41.08 49 1875 81419 2274742
Pseudolymphoma 41.54 41.08 8 1916 138 2356023

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
Hypotension 467.07 41.29 161 1078 29493 1716049
Completed suicide 348.45 41.29 112 1127 16200 1729342
Toxicity to various agents 313.65 41.29 120 1119 29021 1716521
Foetal exposure during pregnancy 290.98 41.29 79 1160 6280 1739262
Premature baby 276.20 41.29 65 1174 2877 1742665
Bradycardia 264.24 41.29 82 1157 10452 1735090
Shock 210.17 41.29 56 1183 4105 1741437
Drug hypersensitivity 208.21 41.29 75 1164 15060 1730482
Low birth weight baby 203.97 41.29 41 1198 846 1744696
Cardiac arrest 182.33 41.29 69 1170 15861 1729681
Intentional overdose 168.05 41.29 54 1185 7616 1737926
Acute kidney injury 150.64 41.29 76 1163 34868 1710674
Drug interaction 132.69 41.29 65 1174 27893 1717649
Suicide attempt 129.57 41.29 44 1195 7337 1738205
Overdose 120.43 41.29 52 1187 16649 1728893
Bezoar 120.35 41.29 20 1219 131 1745411
Orthostatic hypotension 117 41.29 34 1205 3397 1742145
Metabolic acidosis 113.90 41.29 37 1202 5365 1740177
Gingival hypertrophy 101.55 41.29 20 1219 367 1745175
Oesophageal obstruction 91.36 41.29 15 1224 90 1745452
Hypertension 85.37 41.29 43 1196 19405 1726137
Foetal growth restriction 79.27 41.29 18 1221 666 1744876
Depressed level of consciousness 73.01 41.29 28 1211 6564 1738978
Dizziness 72.33 41.29 47 1192 34314 1711228
Loss of consciousness 71.45 41.29 35 1204 14840 1730702
Blood pressure increased 69.25 41.29 31 1208 10722 1734820
Polydactyly 67.30 41.29 13 1226 214 1745328
Oedema peripheral 67.03 41.29 34 1205 15516 1730026
Lactic acidosis 64.80 41.29 24 1215 5105 1740437
Renal failure 61.66 41.29 35 1204 19982 1725560
Hyperkalaemia 59.38 41.29 26 1213 8521 1737021
Blood pressure decreased 58.82 41.29 25 1214 7621 1737921
General physical health deterioration 57.42 41.29 29 1210 13089 1732453
Acute lung injury 56.66 41.29 11 1228 186 1745356
Pulmonary oedema 55.56 41.29 23 1216 6563 1738979
Dyspnoea 50.79 41.29 45 1194 52014 1693528
Syncope 46.89 41.29 26 1213 14143 1731399
Left ventricular dysfunction 45.65 41.29 13 1226 1198 1744344
Blood pressure inadequately controlled 44.22 41.29 11 1228 602 1744940
Oesophageal haemorrhage 42.56 41.29 9 1230 237 1745305
Multiple organ dysfunction syndrome 42.07 41.29 21 1218 9221 1736321

Pharmacologic Action:

SourceCodeDescription
ATC C07FB03 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS, OTHER COMBINATIONS
Beta blocking agents and calcium channel blockers
ATC C08CA05 CARDIOVASCULAR SYSTEM
CALCIUM CHANNEL BLOCKERS
SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS
Dihydropyridine derivatives
ATC C08CA55 CARDIOVASCULAR SYSTEM
CALCIUM CHANNEL BLOCKERS
SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS
Dihydropyridine derivatives
ATC C08GA01 CARDIOVASCULAR SYSTEM
CALCIUM CHANNEL BLOCKERS
CALCIUM CHANNEL BLOCKERS AND DIURETICS
Calcium channel blockers and diuretics
FDA MoA N0000000069 Calcium Channel Antagonists
FDA EPC N0000175421 Dihydropyridine Calcium Channel Blocker
FDA CS M0006414 Dihydropyridines
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 D012102 Reproductive Control Agents
CHEBI has role CHEBI:35620 vasodilator agent
CHEBI has role CHEBI:66993 tocolytic agent
MeSH PA D015149 Tocolytic Agents
MeSH PA D014665 Vasodilator Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Prinzmetal angina indication 87343002
Angina pectoris indication 194828000
Premature labor off-label use 6383007
Raynaud's phenomenon off-label use 266261006
Cirrhosis of liver contraindication 19943007 DOID:5082
Myocardial infarction contraindication 22298006 DOID:5844
Stenosis of intestine contraindication 23065003
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Chronic idiopathic constipation contraindication 82934008
Left heart failure contraindication 85232009
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Gastrointestinal obstruction contraindication 126765001
Disease of liver contraindication 235856003 DOID:409
Pyloric obstruction contraindication 244815007
Peripheral edema contraindication 271809000
Continent ileostomy - stoma contraindication 311414006
Non-Q wave myocardial infarction contraindication 314207007
Acute coronary syndrome contraindication 394659003
Porphyria contraindication 418470004
Severe Aortic Valve Stenosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.5 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-1C Ion channel BLOCKER Kd 9.40 CHEMBL SCIENTIFIC LITERATURE
Voltage-dependent L-type calcium channel subunit alpha-1D Ion channel GATING INHIBITOR IC50 7.70 IUPHAR CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1F Ion channel GATING INHIBITOR IC50 6 IUPHAR
5-hydroxytryptamine receptor 2C GPCR Ki 5.02 DRUG MATRIX
Adenosine receptor A1 GPCR Ki 5.35 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 6.52 DRUG MATRIX
cAMP-specific 3',5'-cyclic phosphodiesterase 4A Enzyme IC50 4.35 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 4.73 DRUG MATRIX
C-C chemokine receptor type 2 GPCR Ki 6.07 DRUG MATRIX
Sodium/nucleoside cotransporter 1 Transporter Ki 5.09 DRUG MATRIX
Potassium voltage-gated channel subfamily A member 2 Ion channel Kd 4.70 WOMBAT-PK
Voltage-dependent T-type calcium channel subunit alpha-1H Ion channel Ki 4.67 WOMBAT-PK
Transthyretin Secreted IC50 5.66 WOMBAT-PK
Glycine receptor subunit alpha-1 Ion channel IC50 5.48 CHEMBL
Adenosine receptor A3 GPCR Ki 5.08 CHEMBL
Glutathione reductase, mitochondrial Enzyme Ki 4.76 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 4.43 CHEMBL
Potassium voltage-gated channel subfamily A member 5 Ion channel IC50 5.21 CHEMBL
Adenosine receptor A2a GPCR Ki 4.65 CHEMBL
Cytochrome P450 3A4 Enzyme IC50 5.26 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 4.30 WOMBAT-PK
Glycine receptor subunit alpha-3 Ion channel ANTAGONIST IC50 4.50 IUPHAR
Glycine receptor subunit beta Ion channel ANTAGONIST IC50 5.90 IUPHAR
Bile salt export pump Transporter IC50 4.51 CHEMBL
Myosin light chain kinase, smooth muscle Kinase IC50 5.69 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1S Ion channel INHIBITOR IC50 6.30 IUPHAR
5-hydroxytryptamine receptor 2A GPCR Ki 6.49 PDSP
Arachidonate 15-lipoxygenase Enzyme IC50 4.82 DRUG MATRIX
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel IC50 9 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel IC50 8.59 CHEMBL
Adenosine receptor A2a GPCR Ki 4.74 CHEMBL
Cholinesterase Enzyme Ki 5.92 CHEMBL
Voltage-gated L-type calcium channel Ion channel Ki 8.33 CHEMBL
Adenosine receptor A1 GPCR Ki 5.54 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.34 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1D Ion channel Ki 8.92 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel Ki 8.46 CHEMBL
Acetylcholinesterase Enzyme Ki 5.40 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.82 CHEMBL
Bile salt export pump Unclassified IC50 4.34 CHEMBL
Potassium voltage-gated channel subfamily A member 1 Unclassified BLOCKER IC50 4 IUPHAR
Potassium voltage-gated channel subfamily A member 2 Unclassified BLOCKER Kd 4.70 IUPHAR
Potassium voltage-gated channel subfamily A member 7 Unclassified BLOCKER IC50 4.90 IUPHAR

External reference:

IDSource
4018390 VUID
N0000146717 NUI
C0028066 UMLSCUI
D00437 KEGG_DRUG
017700 NDDF
85272000 SNOMEDCT_US
4018390 VANDF
2302 MMSL
7417 RXNORM
387490003 SNOMEDCT_US
5175 MMSL
d00051 MMSL
000710 NDDF
CHEMBL193 ChEMBL_ID
DB01115 DRUGBANK_ID
I9ZF7L6G2L UNII
3222 INN_ID
CHEBI:7565 CHEBI
D009543 MESH_DESCRIPTOR_UI
4485 PUBCHEM_CID
2514 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Procardia HUMAN PRESCRIPTION DRUG LABEL 1 0069-2600 CAPSULE 10 mg ORAL NDA 12 sections
Procardia HUMAN PRESCRIPTION DRUG LABEL 1 0069-2650 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL NDA 12 sections
Procardia HUMAN PRESCRIPTION DRUG LABEL 1 0069-2660 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL NDA 12 sections
Procardia HUMAN PRESCRIPTION DRUG LABEL 1 0069-2670 TABLET, FILM COATED, EXTENDED RELEASE 90 mg ORAL NDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 0228-2497 CAPSULE, LIQUID FILLED 10 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 0228-2530 CAPSULE, LIQUID FILLED 20 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0353 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0360 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0390 TABLET, FILM COATED, EXTENDED RELEASE 90 mg ORAL ANDA 11 sections
NIFEDIPINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-319 CAPSULE, LIQUID FILLED 10 mg ORAL ANDA 11 sections
NIFEDIPINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-948 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL ANDA 11 sections
nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 21695-807 TABLET, FILM COATED, EXTENDED RELEASE 90 mg ORAL ANDA 13 sections
nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 21695-908 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 21695-909 TABLET, EXTENDED RELEASE 60 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 23155-194 CAPSULE 10 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 23155-195 CAPSULE 20 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 24979-009 TABLET, EXTENDED RELEASE 90 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 24979-010 TABLET, EXTENDED RELEASE 60 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 24979-011 TABLET, EXTENDED RELEASE 30 mg ORAL ANDA 11 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 33261-840 TABLET, FILM COATED, EXTENDED RELEASE 90 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 42254-095 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 43353-209 TABLET, EXTENDED RELEASE 60 mg ORAL ANDA 17 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 43353-750 TABLET, FILM COATED, EXTENDED RELEASE 90 mg ORAL ANDA 12 sections
Afeditab HUMAN PRESCRIPTION DRUG LABEL 1 43353-782 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL ANDA 12 sections
Afeditab HUMAN PRESCRIPTION DRUG LABEL 1 43353-792 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 43353-836 TABLET, FILM COATED, EXTENDED RELEASE 60 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 43353-929 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL ANDA 12 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 43386-440 CAPSULE 10 mg ORAL ANDA 10 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 45963-152 TABLET, EXTENDED RELEASE 90 mg ORAL ANDA 13 sections
Nifedipine HUMAN PRESCRIPTION DRUG LABEL 1 50090-0695 TABLET, FILM COATED, EXTENDED RELEASE 30 mg ORAL NDA authorized generic 11 sections