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Identification
NameTranexamic Acid
Accession NumberDB00302  (APRD01270, EXPT00508)
TypeSmall Molecule
GroupsApproved
DescriptionAntifibrinolytic hemostatic used in severe hemorrhage. [PubChem]
Structure
Thumb
Synonyms
Acide tranexamique
Acido tranexamico
Acidum tranexamicum
Cyklokapron
Tranexamsaeure
Tranexmic acid
Tranhexamic acid
Trans AMCHA
trans-4-(Aminomethyl)cyclohexanecarboxylic acid
trans-4-aminomethylcyclohexane-1-carboxylic acid
trans-Amcha
trans-Tranexamic acid
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CyklokapronInjection, solution100 mg/mLIntravenousPharmacia & Upjohn Inc1986-12-30Not applicableUs
Cyklokapron 100 mg/mlSolution100 mgIntravenousPfizer1995-12-31Not applicableCanada
Cyklokapron 500 mgTablet500 mgOralPfizer1995-12-31Not applicableCanada
Erfa-tranexamicSolution100 mgIntravenousErfa Canada 2012 IncNot applicableNot applicableCanada
Gd-tranexamic AcidTablet500 mgOralGenmed A Division Of Pfizer Canada Inc2014-03-07Not applicableCanada
Gd-tranexamic AcidSolution100 mgIntravenousGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
LystedaTablet650 mg/1OralFerring Pharmaceuticals2010-05-172016-10-13Us
LystedaTablet650.0 mgOralFerring PharmaceuticalsNot applicableNot applicableCanada
LystedaTablet650 mg/1OralFerring Pharmaceuticals2010-05-17Not applicableUs
Tranexamic AcidTablet650 mg/1OralPrasco, Laboratories2010-05-17Not applicableUs
Tranexamic AcidTablet650 mg/1OralPrasco, Laboratories2010-05-17Not applicableUs
Tranexamic AcidTablet650 mg/1OralAmring Pharmaceuticals, Inc.2016-03-01Not applicableUs
Tranexamic Acid InjectionSolution100 mgIntravenousOmega Laboratories Ltd2013-03-27Not applicableCanada
Tranexamic Acid InjectionSolution100 mgIntravenousMethapharm, Inc.Not applicableNot applicableCanada
Tranexamic Acid Injection BPSolution100 mgIntravenousSandoz Canada Incorporated2002-10-29Not applicableCanada
Tranexamic Acid Injection BPSolution100 mgIntravenousSterimax Inc2012-11-15Not applicableCanada
Tranexamic Acid Injection BPSolution100 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Tranexamic Acid TabletsTablet500 mgOralSterimax Inc2013-02-13Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tranexamic AcidTablet650 1/1OralApotex Corporation2014-01-27Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAkorn2016-06-09Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousNexus Pharmaceuticals Inc2012-03-15Not applicableUs
Tranexamic AcidTablet, film coated650 mg/1OralAmerincan Health Packaging2015-03-31Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAmneal Biosciences2017-02-28Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousX Gen Pharmaceuticals, Inc.2012-05-18Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousFresenius Kabi2012-04-20Not applicableUs
Tranexamic AcidTablet, film coated650 mg/1OralActavis Pharma Company2013-01-03Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAkorn2015-03-09Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAuro Medics Pharma Llc2016-01-14Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAcella Pharmaceuticals, LLC2014-02-11Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousMylan Institutional2011-11-29Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousVirtus Pharmaceuticals2017-02-13Not applicableUs
Tranexamic AcidInjection, solution1 g/10mLIntravenousHeritage2014-08-13Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousAmerican Regent2011-11-15Not applicableUs
Tranexamic AcidTablet650 1/1OralGolden State Medical Supply2014-08-20Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousMylan Institutional2011-11-29Not applicableUs
Tranexamic AcidInjection, solution100 mg/mLIntravenousX Gen Pharmaceuticals, Inc.2012-05-18Not applicableUs
Tranexamic AcidInjection, solution1 g/10mLIntravenousHeritage2012-02-20Not applicableUs
Tranexamic Acid Tranexamic AcidInjection, solution100 mg/mLIntravenousGland Pharma Limited2017-02-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pure Whitenol SerumCream.05 mg/50mLTopicalSkin M.D. Korea2015-02-01Not applicableUs
International Brands
NameCompany
Cyclo-FNot Available
EspercilNot Available
FemstrualNot Available
RikavarinNot Available
TransaminNot Available
TranscamNot Available
TraxylNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6T84R30KC1
CAS number1197-18-8
WeightAverage: 157.2102
Monoisotopic: 157.110278729
Chemical FormulaC8H15NO2
InChI KeyGYDJEQRTZSCIOI-LJGSYFOKSA-N
InChI
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-
IUPAC Name
(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES
NC[[email protected]]1CC[C@@H](CC1)C(O)=O
Pharmacology
IndicationFor use in patients with hemophilia for short term use (two to eight days) to reduce or prevent hemorrhage and reduce the need for replacement therapy during and following tooth extraction. It can also be used for excessive bleeding in menstruation, surgery, or trauma cases.
Structured Indications
PharmacodynamicsTranexamic acid is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin. Tranexamic acid is a competitive inhibitor of plasminogen activation, and at much higher concentrations, a noncompetitive inhibitor of plasmin, i.e., actions similar to aminocaproic acid. Tranexamic acid is about 10 times more potent in vitro than aminocaproic acid. Tranexamic acid binds more strongly than aminocaproic acid to both the strong and weak receptor sites of the plasminogen molecule in a ratio corresponding to the difference in potency between the compounds. Tranexamic acid in a concentration of 1 mg per mL does not aggregate platelets in vitro. In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by tranexamic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1).
Mechanism of actionTranexamic acid competitively inhibits activation of plasminogen (via binding to the kringle domain), thereby reducing conversion of plasminogen to plasmin (fibrinolysin), an enzyme that degrades fibrin clots, fibrinogen, and other plasma proteins, including the procoagulant factors V and VIII. Tranexamic acid also directly inhibits plasmin activity, but higher doses are required than are needed to reduce plasmin formation.
TargetKindPharmacological actionActionsOrganismUniProt ID
PlasminogenProteinyes
inhibitor
HumanP00747 details
Related Articles
AbsorptionAbsorption of tranexamic acid after oral administration in humans represents approximately 30 to 50% of the ingested dose and bioavailability is not affected by food intake.
Volume of distribution
  • 9 to 12 L
Protein bindingThe plasma protein binding of tranexamic acid is about 3% at therapeutic plasma levels and seems to be fully accounted for by its binding to plasminogen (does not bind serum albumin).
Metabolism

Only a small fraction of the drug is metabolized (less than 5%).

Route of eliminationUrinary excretion is the main route of elimination via glomerular filtration.
Half lifeBiological half-life in the joint fluid is about 3 hours.
Clearance
  • 110 – 116 mL/min
ToxicityOral LD50 in mice is >10 gm/kg. Symptoms of overdosage may be nausea, vomiting, orthostatic symptoms and/or hypotension.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Tranexamic Acid Action PathwayDrug actionSMP00287
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
ChlorotrianiseneChlorotrianisene may increase the thrombogenic activities of Tranexamic Acid.Withdrawn
Conjugated Equine EstrogensConjugated Equine Estrogens may increase the thrombogenic activities of Tranexamic Acid.Approved
DesogestrelDesogestrel may increase the thrombogenic activities of Tranexamic Acid.Approved
DienestrolDienestrol may increase the thrombogenic activities of Tranexamic Acid.Approved
DienogestDienogest may increase the thrombogenic activities of Tranexamic Acid.Approved
DiethylstilbestrolDiethylstilbestrol may increase the thrombogenic activities of Tranexamic Acid.Approved
DrospirenoneDrospirenone may increase the thrombogenic activities of Tranexamic Acid.Approved
EstradiolEstradiol may increase the thrombogenic activities of Tranexamic Acid.Approved, Investigational, Vet Approved
EstramustineEstramustine may increase the thrombogenic activities of Tranexamic Acid.Approved
Estrogens, esterifiedEstrogens, esterified may increase the thrombogenic activities of Tranexamic Acid.Approved
Estrone sulfateEstrone sulfate may increase the thrombogenic activities of Tranexamic Acid.Approved
Ethinyl EstradiolEthinyl Estradiol may increase the thrombogenic activities of Tranexamic Acid.Approved
Ethynodiol diacetateEthynodiol diacetate may increase the thrombogenic activities of Tranexamic Acid.Approved
EtonogestrelEtonogestrel may increase the thrombogenic activities of Tranexamic Acid.Approved, Investigational
Fibrinogen Concentrate (Human)The risk or severity of adverse effects can be increased when Tranexamic Acid is combined with Fibrinogen Concentrate (Human).Approved
GestodeneGestodene may increase the thrombogenic activities of Tranexamic Acid.Approved
HexestrolHexestrol may increase the thrombogenic activities of Tranexamic Acid.Withdrawn
LevonorgestrelLevonorgestrel may increase the thrombogenic activities of Tranexamic Acid.Approved, Investigational
LynestrenolLynestrenol may increase the thrombogenic activities of Tranexamic Acid.Investigational
Medroxyprogesterone acetateMedroxyprogesterone acetate may increase the thrombogenic activities of Tranexamic Acid.Approved, Investigational
MestranolMestranol may increase the thrombogenic activities of Tranexamic Acid.Approved
MethallenestrilMethallenestril may increase the thrombogenic activities of Tranexamic Acid.Experimental
NorelgestrominNorelgestromin may increase the thrombogenic activities of Tranexamic Acid.Approved
NorgestimateNorgestimate may increase the thrombogenic activities of Tranexamic Acid.Approved
NorgestrelNorgestrel may increase the thrombogenic activities of Tranexamic Acid.Approved
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinTretinoin may increase the thrombogenic activities of Tranexamic Acid.Approved, Investigational, Nutraceutical
Food InteractionsNot Available
References
Synthesis Reference

Noa Zerangue, Bernd Jandeleit, Yunxiao Li, “Acyloxyalkyl carbamate prodrugs of tranexamic acid, methods of synthesis and use.” U.S. Patent US20070027210, issued February 01, 2007.

US20070027210
General ReferencesNot Available
External Links
ATC CodesB02AA02
AHFS Codes
  • 20:28.16
PDB Entries
FDA labelNot Available
MSDSDownload (63.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingNot AvailableKnee Prosthesis1
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingPreventionDegenerative Arthritis1
1RecruitingTreatmentFibroids / Hemorrhage/Blood Loss During Myomectomies1
1, 2CompletedPreventionHemorrhage1
1, 2CompletedPreventionPostpartum Haemorrage Sever Bleeding After Delivery1
1, 2Not Yet RecruitingPreventionPostpartum Hemorrhage1
1, 2RecruitingPreventionAdolescent Idiopathic Scoliosis (AIS)1
1, 2RecruitingPreventionHemorrhage of Cesarean Section and/or Perineal Wound1
1, 2RecruitingTreatmentMenorrhagia1
2Active Not RecruitingTreatmentPost Operative Blood Loss1
2Active Not RecruitingTreatmentTraumatic Brain Injury (TBI)1
2CompletedPreventionArthrosis1
2CompletedPreventionBloodloss / Surgical Procedures, Operative1
2CompletedPreventionPostpartum Hemorrhage1
2CompletedSupportive CareBleeding1
2CompletedTreatmentAcute Blood Loss Anemia / Osteoarthritis,Knee1
2CompletedTreatmentEpistaxis / Hereditary Haemorrhagic Telangiectasia (HHT)1
2Enrolling by InvitationTreatmentCurvature of Spine1
2Not Yet RecruitingPreventionBronchoscopy Biopsy1
2RecruitingPreventionPostpartum Hemorrhage1
2RecruitingPreventionSynovitis of osteoarthritis1
2RecruitingTreatmentCancers / General Surgery / Tumour1
2RecruitingTreatmentHemorrhage / Shock / Wounds and Injuries1
2RecruitingTreatmentIntracerebral Haemorrhage / Stroke1
2RecruitingTreatmentIntracerebral Hemorrhage / Stroke1
2RecruitingTreatmentShock, Septic1
2TerminatedTreatmentBleeding1
2TerminatedTreatmentCritical Illness / Hypotension / Sepsis / Shock1
2, 3Active Not RecruitingTreatmentColon Cancer / Gastric Cancers / Hepatocellular Cancer / Pancreatic Cancers1
2, 3CompletedTreatmentIntraoperative Bleeding / Synovitis of osteoarthritis1
2, 3Not Yet RecruitingTreatmentSpinal Deformities / Spinal Injuries1
2, 3RecruitingPreventionBladder Cancers1
2, 3RecruitingTreatmentAdult Spinal Deformity1
2, 3RecruitingTreatmentBlood Loss,Surgical / Complications; Arthroplasty / Intraoperative Complications / Shoulder Joint Disease1
2, 3RecruitingTreatmentChronic Subdural Hematomas1
2, 3RecruitingTreatmentSubarachnoid Hemorrhage1
3Active Not RecruitingPreventionBlood Loss, Postoperative / Blood Loss,Surgical / Synovitis of osteoarthritis1
3Active Not RecruitingPreventionPlacenta Accreta1
3CompletedDiagnosticBlood Loss1
3CompletedPreventionCoronary Artery Disease1
3CompletedPreventionKnee Arthropathy1
3CompletedPreventionObstetrical Hemorrhage1
3CompletedTreatmentBlood Loss2
3CompletedTreatmentBrain Injury1
3CompletedTreatmentCancers / General Surgery / Tumour1
3CompletedTreatmentHeavy Menstrual Bleeding / Menorrhagia3
3CompletedTreatmentHemorrhage1
3CompletedTreatmentHereditary Angioedema1
3CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Osler-Rendu Disease1
3CompletedTreatmentHip Fractures1
3CompletedTreatmentMenorrhagia1
3CompletedTreatmentNeoplasms, Head and Neck1
3CompletedTreatmentSpine Surgery1
3CompletedTreatmentSurgery, Cardiac1
3Enrolling by InvitationTreatmentOther Fusion of Spine, Lumbar Region / Scoliosis1
3Not Yet RecruitingNot AvailableNeoplasms, Hematologic1
3Not Yet RecruitingBasic ScienceBleeding / Transfusion Related Complications1
3Not Yet RecruitingPreventionThrombocytopenias1
3Not Yet RecruitingPreventionUterine Hemorrhage1
3Not Yet RecruitingTreatmentBrain Injuries,Traumatic1
3Not Yet RecruitingTreatmentPostpartum Hemorrhage1
3Not Yet RecruitingTreatmentType 1 Von Willebrand Disease1
3RecruitingPreventionAtherosclerotic Disease / Postoperative Bleeding1
3RecruitingPreventionGeneral Surgery / Peri-operative Hemorrhage or Hematoma / Retrognathism1
3RecruitingPreventionImmediate Postpartum Hemorrhage1
3RecruitingTreatmentAcetabular Fractures1
3RecruitingTreatmentAcute Coagulopathy / Wounds and Injuries1
3RecruitingTreatmentAstrocytomas / Gliomas / Meningiomas / Neoplasms / Tumor, Brain1
3RecruitingTreatmentBlood Loss After a Total Hip Replacement1
3RecruitingTreatmentBlood Loss / Bone Tumour1
3RecruitingTreatmentBlood Loss / Hip Fractures1
3RecruitingTreatmentCraniosynostoses1
3RecruitingTreatmentFemoral Neck Fractures1
3RecruitingTreatmentGastrointestinal Bleedings1
3RecruitingTreatmentHemoptisis1
3RecruitingTreatmentNeoplasms, Head and Neck1
3RecruitingTreatmentPostpartum Haemorrhage1
3RecruitingTreatmentTotal Blood Loss1
3RecruitingTreatmentTraumatic Brain Injury (TBI)1
3RecruitingTreatmentTraumatic Hemorrhage1
4Active Not RecruitingPreventionHip Fractures1
4CompletedNot AvailableMenorrhagia1
4CompletedPreventionAdenoidectomy / Tonsillectomy / Tranexamic Acid1
4CompletedPreventionBleeding / Prostatectomy1
4CompletedPreventionGynecologic Surgical Procedures / Hysterectomy / Tranexamic Acid1
4CompletedPreventionIntraoperative Bleeding / Postoperative Edema1
4CompletedPreventionPostoperative Hemorrhages / Postoperative Pain1
4CompletedPreventionSurgical Blood Loss / Total Knee Arthroplasty (TKA)1
4CompletedSupportive CareLumbar Spinal Stenosis / Thoracic Spinal Stenosis1
4CompletedTreatmentAntifibrinolytic Agents / Blood Transfusions / Hemorrhage / Spinal Fusions1
4CompletedTreatmentArthropathy of Hip / Arthropathy of Knee1
4CompletedTreatmentBleeding1
4CompletedTreatmentBlood Loss3
4CompletedTreatmentBlood Loss,Surgical / Hip Replacement Surgery / Tranexamic Acid Adverse Reaction1
4CompletedTreatmentBlood Loss / Postoperative Blood Loss / Thromboembolic Complications1
4CompletedTreatmentC.Surgical Procedure; Cardiac1
4CompletedTreatmentCancer, Ovarian1
4CompletedTreatmentCardiopulmonary Bypass / Hemorrhage1
4CompletedTreatmentCleft Palates / Hemorrhage1
4CompletedTreatmentCoronary Artery Occlusive Disease1
4CompletedTreatmentMenorrhagia1
4CompletedTreatmentPost Partum Hemorrhage1
4CompletedTreatmentUterine Hemorrhage1
4CompletedTreatmentSynovitis of osteoarthritis1
4Not Yet RecruitingPreventionHematoma / Seroma1
4Not Yet RecruitingPreventionInjuries and Wounds / Postoperative Hemorrhages1
4Not Yet RecruitingTreatmentDeep Vein Thrombosis (DVT) / Myocardial Infarction (MI) / Prophylaxis of Pulmonary embolism / Safety / Stroke1
4Not Yet RecruitingTreatmentNative Arteriovenous Fistula1
4RecruitingNot AvailableComplication of Extracorporeal Circulation / Pediatric Cardiac Surgery1
4RecruitingDiagnosticBleeding1
4RecruitingPreventionHemorrhage1
4RecruitingPreventionHip Fractures / Surgical Blood Loss1
4RecruitingPreventionNeoplasms, Breast / Postoperative Hemorrhages / Seroma1
4RecruitingPreventionPostoperative Blood Loss / Total Hip Arthroplasty (THA)1
4RecruitingSupportive CareBleeding1
4RecruitingSupportive CareBleeding Reduction1
4RecruitingTreatmentAcetabulum Fractures / Pelvic Ring Injury1
4RecruitingTreatmentBlood Loss / Hip Arthritis / Knee Arthritis1
4RecruitingTreatmentBlood Loss / Hip Fractures1
4RecruitingTreatmentFemoral Neck Fractures1
4RecruitingTreatmentFibroids1
4RecruitingTreatmentHeavy Menstrual Bleeding1
4RecruitingTreatmentHemorrhage1
4RecruitingTreatmentOsteoarthritis,Knee1
4RecruitingTreatmentScoliosis1
4RecruitingTreatmentSubdural haematoma1
4RecruitingTreatmentSynovitis of osteoarthritis1
4TerminatedTreatmentCranial Vault Surgery for Craniosynostosis1
4WithdrawnTreatmentHeart Defect, Congenital / Whole Blood Platelet Aggregation Following Tranexamic Acid Administration or Placebo Administration1
Not AvailableActive Not RecruitingPreventionAcute Aortic Dissection1
Not AvailableActive Not RecruitingTreatmentCardiopulmonary Bypass1
Not AvailableActive Not RecruitingTreatmentIdiopathic Scoliosis1
Not AvailableCompletedPreventionAvascular Necrosis of Femoral Head / Degenerative Arthritis of Hip1
Not AvailableCompletedPreventionBlood Platelet Disorders / Disorders, Blood Coagulation / Hematologic Diseases / Menorrhagia / Von Willebrand 's disease Type 11
Not AvailableCompletedPreventionOsteoarthritis Of Knee1
Not AvailableCompletedTreatmentBlood Loss / Congenital Heart Disease (CHD)1
Not AvailableCompletedTreatmentCervical Myelopathy1
Not AvailableCompletedTreatmentChronic Hyperplastic Sinusitis / Chronic Rhinosinusitis With Polyposis1
Not AvailableCompletedTreatmentCoronary Artery Bypass Graft / Coronary Artery Disease1
Not AvailableCompletedTreatmentCoronary Artery Disease1
Not AvailableCompletedTreatmentHemophilia A1
Not AvailableCompletedTreatmentHemophilia / Platelet Coagulation Disorders / VonWillebrand's Disease1
Not AvailableCompletedTreatmentHemorrhage1
Not AvailableCompletedTreatmentHemorrhage / Valvular Heart Surgery1
Not AvailableCompletedTreatmentNeurosurgery / Orthopedic Surgery / Red Blood Cells Transfusion1
Not AvailableCompletedTreatmentOff Pump Coronary Artery Bypass Surgery1
Not AvailableCompletedTreatmentPost CABG Bleeding1
Not AvailableCompletedTreatmentPrimary Osteoarthritis of Knee Nos1
Not AvailableCompletedTreatmentSynovitis of osteoarthritis2
Not AvailableEnrolling by InvitationPreventionBlood Loss / Fractures / General Surgery / Traumas1
Not AvailableEnrolling by InvitationTreatmentDysplasia, Congenital Hip1
Not AvailableNot Yet RecruitingPreventionAnemias / Hip Fractures1
Not AvailableNot Yet RecruitingPreventionClosed Fracture of Hip1
Not AvailableNot Yet RecruitingPreventionNasolacrimal Tract Obstruction1
Not AvailableNot Yet RecruitingTreatmentHemostasis / Hexacapron / Mortality / Rebleeding / Upper Gastrointestinal Bleeding1
Not AvailableRecruitingPreventionCraniosynostosis Patients Undergoing Distraction Osteotomy1
Not AvailableRecruitingTreatmentAnatomic Total Shoulder Arthroplasty / Blood Loss / Reverse Total Shoulder Arthroplasty / Tranexamic Acid / Transfusions1
Not AvailableRecruitingTreatmentCancers / Major Surgery / Tranexamic Acid1
Not AvailableRecruitingTreatmentHemostasis1
Not AvailableRecruitingTreatmentHip Replacement Surgery / Postoperative Hemorrhages1
Not AvailableRecruitingTreatmentKnee Arthroplasty, Total1
Not AvailableRecruitingTreatmentMenstrual Cycle and Uterine Bleeding Disorders1
Not AvailableTerminatedTreatmentAnemias / Hip Fractures1
Not AvailableWithdrawnNot AvailableCongenital Heart Disease (CHD)1
Not AvailableWithdrawnTreatmentArthroplasty, Replacement, Hip1
Not AvailableWithdrawnTreatmentChronic Rhinosinusitis1
Not AvailableWithdrawnTreatmentGastrointestinal Hemorrhage1
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous100 mg
TabletOral500 mg
TabletOral650 mg/1
TabletOral650.0 mg
CreamTopical.05 mg/50mL
Injection, solutionIntravenous1 g/10mL
Injection, solutionIntravenous100 mg/mL
TabletOral650 1/1
Tablet, film coatedOral650 mg/1
Prices
Unit descriptionCostUnit
Cyklokapron 100 mg/ml ampul8.8USD ml
Tranexamic acid powder1.97USD g
Cyklokapron 500 mg Tablet1.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7947739 No2005-03-042025-03-04Us
US8022106 No2005-03-042025-03-04Us
US8273795 No2005-03-042025-03-04Us
US8487005 No2005-03-042025-03-04Us
US8791160 No2005-03-042025-03-04Us
US8809394 No2005-03-042025-03-04Us
US8957113 No2005-03-042025-03-04Us
US9060939 No2005-03-042025-03-04Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point>300 °CPhysProp
water solubility1.67E+005 mg/LMERCK INDEX (1996)
logP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.2 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.9 m3·mol-1ChemAxon
Polarizability17.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9538
Blood Brain Barrier+0.8672
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7572
P-glycoprotein inhibitor INon-inhibitor0.9915
P-glycoprotein inhibitor IINon-inhibitor0.8475
Renal organic cation transporterNon-inhibitor0.7446
CYP450 2C9 substrateNon-substrate0.8862
CYP450 2D6 substrateNon-substrate0.7898
CYP450 3A4 substrateNon-substrate0.829
CYP450 1A2 substrateNon-inhibitor0.9504
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9577
CYP450 2C19 inhibitorNon-inhibitor0.9452
CYP450 3A4 inhibitorNon-inhibitor0.9313
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9698
Ames testNon AMES toxic0.8916
CarcinogenicityNon-carcinogens0.8495
BiodegradationReady biodegradable0.6921
Rat acute toxicity1.0517 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8797
hERG inhibition (predictor II)Non-inhibitor0.9156
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAmino acids
Alternative Parents
Substituents
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type peptidase activity
Specific Function:
Plasmin dissolves the fibrin of blood clots and acts as a proteolytic factor in a variety of other processes including embryonic development, tissue remodeling, tumor invasion, and inflammation. In ovulation, weakens the walls of the Graafian follicle. It activates the urokinase-type plasminogen activator, collagenases and several complement zymogens, such as C1 and C5. Cleavage of fibronectin ...
Gene Name:
PLG
Uniprot ID:
P00747
Molecular Weight:
90568.415 Da
References
  1. Dunn CJ, Goa KL: Tranexamic acid: a review of its use in surgery and other indications. Drugs. 1999 Jun;57(6):1005-32. [PubMed:10400410 ]
  2. Marti DN, Schaller J, Llinas M: Solution structure and dynamics of the plasminogen kringle 2-AMCHA complex: 3(1)-helix in homologous domains. Biochemistry. 1999 Nov 30;38(48):15741-55. [PubMed:10625440 ]
  3. Jansen AJ, Andreica S, Claeys M, D'Haese J, Camu F, Jochmans K: Use of tranexamic acid for an effective blood conservation strategy after total knee arthroplasty. Br J Anaesth. 1999 Oct;83(4):596-601. [PubMed:10673876 ]
  4. Bangert K, Thorsen S: Assay of functional plasminogen in rat plasma applicable to experimental studies of thrombolysis. Thromb Haemost. 2000 Aug;84(2):299-306. [PubMed:10959704 ]
  5. Hanson AJ, Quinn MT: Effect of fibrin sealant composition on human neutrophil chemotaxis. J Biomed Mater Res. 2002 Sep 5;61(3):474-81. [PubMed:12115473 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
References
  1. Dieck ST, Heuer H, Ehrchen J, Otto C, Bauer K: The peptide transporter PepT2 is expressed in rat brain and mediates the accumulation of the fluorescent dipeptide derivative beta-Ala-Lys-Nepsilon-AMCA in astrocytes. Glia. 1999 Jan;25(1):10-20. [PubMed:9888294 ]
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Drug created on June 13, 2005 07:24 / Updated on March 24, 2017 02:27