Details of the Drug

General Information of Drug (ID: DMFGND4)

Drug Name
Aminocaproic acid
Synonyms
6-Aminohexanoic acid; 6-aminohexanoic acid; 6-Aminocaproic acid; aminocaproic acid; 60-32-2; amicar; Epsikapron; Caprocid; Capramol; Epsamon; EACA; Caprolisin; Acepramin; Hemocaprol; Epsicapron; Respramin; Amikar; EPSILON-AMINOCAPROIC ACID; Hexanoic acid, 6-amino-; Epsilcapramin; Aminokapron; Caplamin; Acepramine; Capracid; Hemopar; Ipsilon; Afibrin; Atsemin; Hepin; Epsilon S; Aminocaproic; Capralense; epsilon-Leucine; EACS; epsilon-Norleucine; epsilcapramine; 6-Amino-n-hexanoic acid; omega-Aminocaproic acid; epsilon-Aminohexanoic acid; 6-amino-hexanoic acid; ACS; Amicar; Aminocaproate; Capranol; Caproamin; Epsicaprom; Epsilcapramine; Hemopar;Hepin; Acide aminocaproique; Acide aminocaproique [French]; Acide aminocaproque; Acido aminocaproico; Acidum aminocaproicum; Acidum aminocaproicum [Latin]; Aminocaproic Acid In Plastic Container; Aminocaproic Acids; Aminohexanoic acid; Eaca kabi; Epsilon Aminocaproic Acid; A 7824; CL 10304; CY 116; CY116; JD 177; Acide aminocaproique [INN-French]; Acido aminocaproico [DCIT,Spanish]; Acido aminocaproico [INN-Spanish]; Acidum aminocaproicum [INN-Latin]; Amicar (TN); Aminocaproic acid (USP); CL-10304; CY-116; Epsilon-Ahx; Epsilon-Aminocaproic acid; Epsilon-Aminocapronsaeure; Epsilon-Aminohexanoic acid; Epsilon-Leucine; Epsilon-Norleucine; Epsilon-aminocaproate; Epsilon-aminocapronzuur; Fullevir (TN); Kyselina omega-aminokapronova; Kyselina omega-aminokapronova [Czech]; Omega-Aminocaproic acid; Omega-Aminohexanoic acid; S04-0132; Acid, 6-Aminocaproic; Acid, 6-Aminohexanoic; Acid, epsilon-Aminocaproic; Aminocaproic acid (USP/INN); Aminocaproic acid [USAN:BAN:INN]; Aminocaproic acid [USAN:INN:BAN]; Epsilon-Aminocaproic acid (JAN); HEXANOIC ACID,6-AMINO; Epsilon-Amino-n-caproic acid; Epsilon-Amino-n-hexanoic acid; Amicar, A-amino caproic acid, A-Ahx, 6-aminohexanoic acid, Aminocaproic acid; 6 Aminocaproic Acid; 6 Aminohexanoic Acid; 6-amino-n-caproate; 6-amino-n-caproic acid; 6-aminohexanoate; 6-Amino Hexanoic Acid
Indication
Disease Entry ICD 11 Status REF
Bleeding disorder GA20-GA21 Approved [1]
Postoperative hemorrhage NE81.0Z Approved [2], [3]
Therapeutic Class
Antifibrinolytic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 131.17
Topological Polar Surface Area (xlogp) -3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Clearance
The clearance of drug is 169 mL/min [5]
Elimination
65% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 2 hours [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1524.66907 micromolar/kg/day [7]
Unbound Fraction
The unbound fraction of drug in plasma is 0.92% [6]
Vd
The volume of distribution (Vd) of drug is 23.1 +/- 6.6 L [5]
Water Solubility
The ability of drug to dissolve in water is measured as 333 mg/mL [4]
Chemical Identifiers
Formula
C6H13NO2
IUPAC Name
6-aminohexanoic acid
Canonical SMILES
C(CCC(=O)O)CCN
InChI
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
InChIKey
SLXKOJJOQWFEFD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
564
ChEBI ID
CHEBI:16586
CAS Number
60-32-2
DrugBank ID
DB00513
TTD ID
D0FD0H
VARIDT ID
DR01014
ACDINA ID
D00030

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Plasminogen (PLG) TTP86E2 PLMN_HUMAN Inhibitor [8], [9]
Tissue-type plasminogen activator (PLAT) TTXAGYU TPA_HUMAN Inhibitor [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Bleeding disorder
ICD Disease Classification GA20-GA21
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Plasminogen (PLG) DTT PLG 8.61E-01 -0.01 -0.09
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Aminocaproic acid (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Carfilzomib DM48K0X Major Additive thrombogenic effects by the combination of Aminocaproic acid and Carfilzomib. Multiple myeloma [2A83] [26]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Crospovidone E00626 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Aminocaproic acid 500 mg tablet 500 mg Oral Tablet Oral
Aminocaproic acid 1000 mg tablet 1000 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6574).
3 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 071192.
4 BDDCS applied to over 900 drugs
5 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 The blockage of the high-affinity lysine binding sites of plasminogen by EACA significantly inhibits prourokinase-induced plasminogen activation. Biochim Biophys Acta. 2002 Apr 29;1596(2):182-92.
9 Analysis of plasmin binding and urokinase activation of plasminogen bound to the Heymann nephritis autoantigen, gp330. Arch Biochem Biophys. 1992 Dec;299(2):255-60.
10 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
11 Development of serine protease inhibitors displaying a multicentered short (<2.3 A) hydrogen bond binding mode: inhibitors of urokinase-type plasmi... J Med Chem. 2001 Aug 16;44(17):2753-71.
12 Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-sulfonamidoisoquinolinyl)guanidines. J Med Chem. 2007 May 17;50(10):2341-51.
13 Aroylguanidine-based factor Xa inhibitors: the discovery of BMS-344577. Bioorg Med Chem Lett. 2009 Dec 15;19(24):6882-9.
14 Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 3: 1-isoquinolinylguanidines. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3227-30.
15 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
16 Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 1: 2-Pyridinylguanidines. Bioorg Med Chem Lett. 2002 Jan 21;12(2):181-4.
17 Tranexamic acid in trauma: how should we use it. J Trauma Acute Care Surg. 2013 Jun;74(6):1575-86.
18 Acute anuric renal failure with streptokinase therapy in a patient with acute venous thromboembolic disease and the review of renal side effects of streptokinase. Tuberk Toraks. 2008;56(4):456-61.
19 Evaluation of aprotinin and tranexamic acid in different in vitro and in vivo models of fibrinolysis, coagulation and thrombus formation. J Thromb Haemost. 2007 Oct;5(10):2113-8.
20 Thrombolytic therapies: the current state of affairs. J Endovasc Ther. 2005 Apr;12(2):224-32.
21 Evaluation of thrombolytic agents. Drugs. 1997;54 Suppl 3:11-6; discussion 16-7.
22 Fibrin binding and the regulation of plasminogen activators during thrombolytic therapy. Cardiovasc Hematol Agents Med Chem. 2008 Jul;6(3):212-23.
23 Orally active thrombin inhibitors. Part 1: optimization of the P1-moiety. Bioorg Med Chem Lett. 2006 May 15;16(10):2641-7.
24 Vampire bat salivary plasminogen activator (desmoteplase): a unique fibrinolytic enzyme that does not promote neurodegeneration. Stroke. 2003 Feb;34(2):537-43.
25 Structure and function of the plasminogen/plasmin system. Thromb Haemost. 2005 Apr;93(4):647-54.
26 Cerner Multum, Inc. "Australian Product Information.".