aminocaproic acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
163 60-32-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • aminocaproic acid
  • 6-Aminocaproic acid
  • 6-Aminohexanoic acid
  • acepramin
  • epsilon-aminocaproic acid
An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.
  • Molecular weight: 131.18
  • Formula: C6H13NO2
  • CLOGP: -2.24
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 63.32
  • ALOGS: -0.46
  • ROTB: 5

Drug dosage:

DoseUnitRoute
16 g O
16 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 333 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 65 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1524.67 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.39 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.92 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 3, 1964 FDA CLOVER PHARMS

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
Fear 51.24 37.67 17 894 16155 46668996
Renal injury 51.14 37.67 15 896 9526 46675625
Injury 50.45 37.67 22 889 44005 46641146
Unevaluable event 43.10 37.67 20 891 46155 46638996
Anhedonia 41.45 37.67 13 898 10322 46674829

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
Fear 143.86 32.99 42 1387 10783 29940266
Injury 137.90 32.99 48 1381 21683 29929366
Renal injury 127.60 32.99 39 1390 11690 29939359
Unevaluable event 116.64 32.99 47 1382 31738 29919311
Anhedonia 104.64 32.99 31 1398 8338 29942711
Emotional distress 104.45 32.99 36 1393 15729 29935320
Factor VIII inhibition 72.33 32.99 14 1415 606 29950443
Renal failure 68.06 32.99 53 1376 128913 29822136
Anxiety 68.06 32.99 46 1383 89825 29861224
Stress 67.51 32.99 28 1401 20207 29930842
Multiple organ dysfunction syndrome 51.59 32.99 34 1395 63453 29887596
Pain 50.87 32.99 51 1378 172590 29778459
Renal impairment 34.58 32.99 30 1399 84154 29866895

Pharmacologic Action:

SourceCodeDescription
ATC B02AA01 BLOOD AND BLOOD FORMING ORGANS
ANTIHEMORRHAGICS
ANTIFIBRINOLYTICS
Amino acids
FDA PE N0000175632 Decreased Fibrinolysis
FDA EPC N0000175634 Antifibrinolytic Agent
MeSH PA D000933 Antifibrinolytic Agents
MeSH PA D003029 Coagulants
MeSH PA D006401 Hematologic Agents
MeSH PA D006490 Hemostatics
CHEBI has role CHEBI:25212 metabolites
CHEBI has role CHEBI:48675 antifibrinolytic agents
CHEBI has role CHEBI:50248 hematologic agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postsurgical Hemorrhage indication
Hyperfibrinolysis Induced Hemorrhage indication
Prevention of Peri-Operative Hemorrhage off-label use
Hemorrhaging in Hemophilia off-label use
Prevention of Hemorrhage with Cardiovascular Instability from Cardiopulmonary Bypass - CABG off-label use
Blood in urine contraindication 34436003
Disseminated intravascular coagulation contraindication 67406007 DOID:11247
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Thrombosis contraindication 439127006
Increased Creatine Phosphokinase contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.22 acidic
pKa2 10.69 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
Plasminogen Enzyme INHIBITOR IC50 4.40 CHEMBL CHEMBL
Tissue-type plasminogen activator Enzyme INHIBITOR DRUGBANK CHEMBL

External reference:

IDSource
U6F3787206 UNII
4017911 VUID
N0000170207 NUI
D00160 KEGG_DRUG
C0000608 UMLSCUI
CHEBI:16586 CHEBI
ACA PDB_CHEM_ID
CHEMBL1046 ChEMBL_ID
564 PUBCHEM_CID
DB00513 DRUGBANK_ID
D015119 MESH_DESCRIPTOR_UI
1189 INN_ID
6574 IUPHAR_LIGAND_ID
99 RXNORM
4169 MMSL
4207 MMSL
d00528 MMSL
002072 NDDF
360246003 SNOMEDCT_US
59882007 SNOMEDCT_US
4017911 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 0409-4346 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 20 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 0517-9120 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 0517-9191 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 20 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 17478-447 SYRUP 0.25 g ORAL NDA authorized generic 18 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 17478-768 TABLET 500 mg ORAL NDA authorized generic 18 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 17478-769 TABLET 1000 mg ORAL NDA authorized generic 18 sections
Solmeet denti doctor HUMAN OTC DRUG LABEL 4 42352-2001 PASTE, DENTIFRICE 0.05 g DENTAL unapproved drug other 8 sections
Solmeet HUMAN OTC DRUG LABEL 4 42352-3001 PASTE, DENTIFRICE 0.05 g DENTAL unapproved drug other 8 sections
Solmeet HUMAN OTC DRUG LABEL 4 42352-7001 PASTE, DENTIFRICE 0.05 g DENTAL unapproved drug other 8 sections
Solmeet denti doctor HUMAN OTC DRUG LABEL 4 42352-8001 PASTE, DENTIFRICE 0.05 g DENTAL unapproved drug other 8 sections
Aminocaproic Acid Human Prescription Drug Label 1 42799-054 TABLET 500 mg ORAL ANDA 18 sections
AMICAR HUMAN PRESCRIPTION DRUG LABEL 1 49411-050 TABLET 500 mg ORAL NDA 19 sections
AMICAR HUMAN PRESCRIPTION DRUG LABEL 1 49411-051 TABLET 1000 mg ORAL NDA 19 sections
AMICAR HUMAN PRESCRIPTION DRUG LABEL 1 49411-052 SOLUTION 0.25 g ORAL NDA 19 sections
AMINOCAPROIC ACID HUMAN PRESCRIPTION DRUG LABEL 1 52584-346 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 11 sections
Aminocaproic acid HUMAN PRESCRIPTION DRUG LABEL 1 52817-815 SOLUTION 0.25 g ORAL ANDA 19 sections
BAMBOO SALT Eunganggo Jook Yeom Toothpaste HUMAN OTC DRUG LABEL 7 53208-459 PASTE 0.05 g DENTAL OTC monograph not final 4 sections
BAMBOO SALT Eunganggo Jook Yeom HUMAN OTC DRUG LABEL 7 53208-505 PASTE 0.05 g DENTAL OTC monograph not final 8 sections
Aminocaproic acid HUMAN PRESCRIPTION DRUG LABEL 1 60219-1637 TABLET 500 mg ORAL ANDA 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 60687-505 TABLET 500 mg ORAL ANDA 21 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 61748-044 SYRUP 0.25 g ORAL ANDA 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 61748-045 TABLET 500 mg ORAL ANDA 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 61748-046 TABLET 1000 mg ORAL NDA authorized generic 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 62559-225 TABLET 500 mg ORAL ANDA 19 sections
Aminocaproic Acid HUMAN PRESCRIPTION DRUG LABEL 1 66689-330 SOLUTION 0.25 g ORAL ANDA 19 sections
AMICAR HUMAN PRESCRIPTION DRUG LABEL 1 68151-3023 TABLET 500 mg ORAL NDA 19 sections
Aminocaproic acid HUMAN PRESCRIPTION DRUG LABEL 1 69238-1596 SOLUTION 0.25 g ORAL ANDA 19 sections
Aminocaproic acid HUMAN PRESCRIPTION DRUG LABEL 1 69238-1637 TABLET 500 mg ORAL ANDA 19 sections
AMINOCAPROIC ACID HUMAN PRESCRIPTION DRUG LABEL 1 69315-231 TABLET 500 mg ORAL ANDA 13 sections
AMINOCAPROIC ACID HUMAN PRESCRIPTION DRUG LABEL 1 69315-232 TABLET 1000 mg ORAL ANDA 13 sections