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

Stem definitionDrug idCAS RN
angiotensin-converting enzyme inhibitors 484 62571-86-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • captopril
  • (-)-Captopril
  • L-Captopril
  • lopirin
  • S-Captopril
  • SQ14225
  • SQ-14225
  • SQ 14225
A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.
  • Molecular weight: 217.28
  • Formula: C9H15NO3S
  • CLOGP: 0.89
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 57.61
  • ALOGS: -1.68
  • ROTB: 3

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 160 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 38 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.72 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 69 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.75 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 12 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.73 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 6, 1981 FDA PAR PHARM

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
Cardiac failure congestive 69.11 13.80 91 9808 91659 46584504
Segmental diverticular colitis 65.83 13.80 13 9886 130 46676033
Pedal pulse abnormal 64.87 13.80 13 9886 141 46676022
Blood pressure abnormal 64.04 13.80 37 9862 12180 46663983
Toxic epidermal necrolysis 63.51 13.80 46 9853 22232 46653931
Calcium ionised decreased 58.44 13.80 13 9886 240 46675923
Insulin autoimmune syndrome 49.78 13.80 9 9890 53 46676110
Feeding intolerance 49.38 13.80 13 9886 497 46675666
Occupational exposure to product 48.68 13.80 17 9882 1704 46674459
Multiple organ dysfunction syndrome 48.03 13.80 57 9842 51653 46624510
Cardiac failure 40.79 13.80 66 9833 79882 46596281
Labile hypertension 40.00 13.80 11 9888 497 46675666
Left ventricular hypertrophy 37.04 13.80 19 9880 4944 46671219
Hypertension 36.81 13.80 108 9791 196248 46479915
Myocardial infarction 32.55 13.80 67 9832 97461 46578702
Haemodynamic instability 31.70 13.80 20 9879 7705 46668458
Self-injurious ideation 30.18 13.80 13 9886 2287 46673876
Metabolic acidosis 29.98 13.80 39 9860 38741 46637422
Hypotension 29.38 13.80 112 9787 232477 46443686
Dermatitis exfoliative 29.12 13.80 17 9882 5699 46670464
Rheumatoid arthritis 28.22 13.80 8 9891 240207 46435956
Gastrointestinal sounds abnormal 24.95 13.80 13 9886 3493 46672670
Electrolyte imbalance 24.86 13.80 24 9875 17202 46658961
Hyperthyroidism 24.22 13.80 20 9879 11691 46664472
Cardiac failure acute 23.74 13.80 17 9882 8061 46668102
Blood urea increased 23.61 13.80 28 9871 25324 46650839
Hypertensive crisis 23.58 13.80 21 9878 13594 46662569
Skin test positive 23.53 13.80 8 9891 740 46675423
Acute myocardial infarction 22.97 13.80 31 9868 31893 46644270
Vascular stent thrombosis 22.34 13.80 8 9891 863 46675300
Renal failure 20.78 13.80 62 9837 113532 46562631
Renal injury 19.12 13.80 16 9883 9525 46666638
Stevens-Johnson syndrome 18.90 13.80 24 9875 23273 46652890
Respiratory disorder 18.87 13.80 26 9873 27274 46648889
Cholecystitis 18.73 13.80 19 9880 14447 46661716
Hyperkalaemia 18.29 13.80 36 9863 50673 46625490
Progressive supranuclear palsy 18.24 13.80 4 9895 69 46676094
Acute kidney injury 18.06 13.80 98 9801 235757 46440406
Posterior reversible encephalopathy syndrome 18.01 13.80 19 9880 15122 46661041
Artery dissection 17.45 13.80 4 9895 85 46676078
Drug interaction 17.34 13.80 87 9812 203007 46473156
Circulatory collapse 17.10 13.80 22 9877 21602 46654561
Nodal rhythm 17.05 13.80 8 9891 1717 46674446
Renal impairment 16.96 13.80 44 9855 74328 46601835
Extrasystoles 16.06 13.80 11 9888 4858 46671305
Potentiating drug interaction 15.70 13.80 10 9889 3913 46672250
Arthralgia 15.47 13.80 34 9865 364569 46311594
Cyanosis 15.47 13.80 18 9881 15953 46660210
Shock 15.39 13.80 21 9878 21824 46654339
Blister 15.27 13.80 31 9868 44600 46631563
Blood creatinine increased 15.21 13.80 43 9856 76360 46599803
Bradycardia 14.89 13.80 39 9860 66259 46609904
Coronary artery disease 14.72 13.80 26 9873 33726 46642437
Cholelithiasis 14.60 13.80 28 9871 38653 46637510
Product dose omission issue 14.36 13.80 9 9890 168511 46507652
Restlessness 14.28 13.80 22 9877 25502 46650661
Occupational dermatitis 14.13 13.80 3 9896 44 46676119
Dehydration 14.08 13.80 69 9830 159471 46516692
Fatigue 14.06 13.80 74 9825 608623 46067540

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
Blood ketone body increased 36.54 14.49 10 7699 364 29944405
Scleroderma renal crisis 31.93 14.49 7 7702 98 29944671
Cyanosis 28.44 14.49 24 7685 11911 29932858
Cardiac failure congestive 28.08 14.49 65 7644 84342 29860427
Angioedema 27.75 14.49 39 7670 34345 29910424
Hypertensive crisis 24.56 14.49 19 7690 8338 29936431
Kidney small 23.01 14.49 5 7704 67 29944702
Renal failure 21.97 14.49 78 7631 128888 29815881
Long QT syndrome 21.60 14.49 11 7698 2322 29942447
Vitamin B12 deficiency 20.45 14.49 11 7698 2594 29942175
Bladder sphincter atony 19.72 14.49 3 7706 3 29944766
Myocardial infarction 18.89 14.49 73 7636 125552 29819217
Indifference 18.89 14.49 5 7704 160 29944609
Colitis microscopic 18.64 14.49 9 7700 1694 29943075
Hypertension 18.64 14.49 71 7638 121283 29823486
Pulmonary hypertensive crisis 18.62 14.49 5 7704 169 29944600
Reaction to excipient 18.56 14.49 6 7703 390 29944379
Coronary artery disease 18.44 14.49 40 7669 49672 29895097
Cardiac failure 18.28 14.49 55 7654 83363 29861406
Cerebrovascular accident 18.26 14.49 55 7654 83422 29861347
Hypokalaemia 18.18 14.49 40 7669 50152 29894617
Blood creatinine increased 17.95 14.49 58 7651 91317 29853452
Renal failure neonatal 16.81 14.49 4 7705 82 29944687
Haemorrhagic necrotic pancreatitis 16.63 14.49 4 7705 86 29944683
Vascular resistance systemic decreased 16.13 14.49 4 7705 98 29944671
Bronchospasm 15.38 14.49 16 7693 10322 29934447
Orthopnoea 14.84 14.49 11 7698 4529 29940240
Klebsiella infection 14.68 14.49 13 7696 6874 29937895

Pharmacologic Action:

SourceCodeDescription
ATC C09AA01 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, PLAIN
ACE inhibitors, plain
ATC C09BA01 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, COMBINATIONS
ACE inhibitors and diuretics
FDA MoA N0000000181 Angiotensin-converting Enzyme Inhibitors
FDA EPC N0000175562 Angiotensin Converting Enzyme Inhibitor
CHEBI has role CHEBI:35457 ace inhibitor
CHEBI has role CHEBI:35674 antihypertensive
MeSH PA D000806 Angiotensin-Converting Enzyme Inhibitors
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011480 Protease Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Chronic heart failure indication 48447003
Diabetic renal disease indication 127013003
Left ventricular cardiac dysfunction indication 429589006
Atrial fibrillation off-label use 49436004 DOID:0060224
Cystinuria off-label use 85020001 DOID:9266
Diastolic heart failure off-label use 418304008 DOID:9775
Cystine Renal Calculi off-label use
Nondiabetic Proteinuric Nephropathy off-label use
Anuria contraindication 2472002 DOID:2983
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Secondary angle-closure glaucoma contraindication 21571006
Hypovolemia contraindication 28560003
Acute cerebrovascular insufficiency contraindication 29322000
Dehydration contraindication 34095006
Hyperuricemia contraindication 35885006 DOID:1920
Immunosuppression contraindication 38013005
Angioedema contraindication 41291007 DOID:1558
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Cough contraindication 49727002
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Aortic valve stenosis contraindication 60573004 DOID:1712
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hypochloremic alkalosis contraindication 70134007
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Transplantation contraindication 77465005
Hereditary angioneurotic edema contraindication 82966003 DOID:14735
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Disorder of connective tissue contraindication 105969002 DOID:65
Hypomagnesemia contraindication 190855004
Acute pancreatitis contraindication 197456007 DOID:2913
Hypertrophic cardiomyopathy contraindication 233873004 DOID:11984
Disease of liver contraindication 235856003 DOID:409
Neonatal hyperbilirubinemia contraindication 281610001
Pregnancy, function contraindication 289908002
Renal artery stenosis contraindication 302233006
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Azotemia contraindication 445009001
Hemodialysis with High-Flux Membrane contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.85 acidic
pKa2 9.56 acidic

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
Angiotensin-converting enzyme Enzyme INHIBITOR Ki 8.70 WOMBAT-PK CHEMBL
Prothrombin Enzyme Ki 7.32 CHEMBL
Leukotriene A-4 hydrolase Enzyme IC50 7.15 CHEMBL
Prostaglandin G/H synthase 1 Enzyme Ki 4.77 CHEMBL
Renin Enzyme Ki 8.77 CHEMBL
Prostaglandin G/H synthase 2 Enzyme Ki 4.92 CHEMBL
Beta-lactamase Enzyme Ki 5.62 CHEMBL
Angiotensin-converting enzyme Enzyme Ki 8.77 CHEMBL
Angiotensin-converting enzyme Enzyme Ki 8.70 CHEMBL
Succinyl-diaminopimelate desuccinylase Enzyme Ki 5.74 CHEMBL
Beta-lactamase II Unclassified Ki 4.75 CHEMBL
Beta-lactamase class B VIM-2 Unclassified Kd 6.22 CHEMBL

External reference:

IDSource
4017614 VUID
N0000145994 NUI
D00251 KEGG_DRUG
4017614 VANDF
C0006938 UMLSCUI
CHEBI:3380 CHEBI
X8Z PDB_CHEM_ID
2550 PUBCHEM_CID
CHEMBL1560 ChEMBL_ID
DB01197 DRUGBANK_ID
D002216 MESH_DESCRIPTOR_UI
4373 INN_ID
5158 IUPHAR_LIGAND_ID
9G64RSX1XD UNII
1998 RXNORM
4347 MMSL
455 MMSL
d00006 MMSL
000656 NDDF
29439004 SNOMEDCT_US
387160004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0143-1171 TABLET 12.50 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0143-1172 TABLET 25 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0143-1173 TABLET 50 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0143-1174 TABLET 100 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0378-3007 TABLET 12.50 mg ORAL ANDA 25 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0378-3012 TABLET 25 mg ORAL ANDA 25 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0378-3017 TABLET 50 mg ORAL ANDA 25 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0378-3022 TABLET 100 mg ORAL ANDA 25 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0615-4519 TABLET 12.50 mg ORAL ANDA 21 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0615-4520 TABLET 25 mg ORAL ANDA 21 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0615-4521 TABLET 50 mg ORAL ANDA 21 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0781-8052 TABLET 12.50 mg ORAL ANDA 16 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0781-8061 TABLET 25 mg ORAL ANDA 16 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0781-8075 TABLET 50 mg ORAL ANDA 16 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0781-8080 TABLET 100 mg ORAL ANDA 16 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0904-5045 TABLET 12.50 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0904-5046 TABLET 25 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0904-5047 TABLET 50 mg ORAL ANDA 22 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0904-7105 TABLET 12.50 mg ORAL ANDA 12 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 0904-7106 TABLET 25 mg ORAL ANDA 12 sections
CAPTOPRIL HUMAN PRESCRIPTION DRUG LABEL 1 10544-175 TABLET 50 mg ORAL ANDA 19 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 21695-477 TABLET 25 mg ORAL ANDA 24 sections
Captopril HUMAN PRESCRIPTION DRUG LABEL 1 21695-478 TABLET 50 mg ORAL ANDA 24 sections
Captopril Human Prescription Drug Label 1 27241-160 TABLET 12.50 mg ORAL ANDA 12 sections
Captopril Human Prescription Drug Label 1 27241-161 TABLET 25 mg ORAL ANDA 12 sections
Captopril Human Prescription Drug Label 1 27241-162 TABLET 50 mg ORAL ANDA 12 sections
Captopril Human Prescription Drug Label 1 27241-163 TABLET 100 mg ORAL ANDA 12 sections
CAPTOPRIL HUMAN PRESCRIPTION DRUG LABEL 1 33261-182 TABLET 50 mg ORAL ANDA 19 sections
CAPTOPRIL HUMAN PRESCRIPTION DRUG LABEL 1 33261-536 TABLET 100 mg ORAL ANDA 19 sections
CAPTOPRIL HUMAN PRESCRIPTION DRUG LABEL 1 33261-974 TABLET 25 mg ORAL ANDA 19 sections