Identification

Name
Tranexamic Acid
Accession Number
DB00302  (APRD01270, EXPT00508)
Type
Small Molecule
Groups
Approved
Description

Antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]

Structure
Thumb
Synonyms
  • Acide tranexamique
  • Acido tranexamico
  • Acidum tranexamicum
  • Tranexamsaeure
  • Tranexmic acid
  • Tranhexamic acid
  • Trans AMCHA
  • trans-4-(Aminomethyl)cyclohexanecarboxylic acid
  • trans-4-aminomethylcyclohexane-1-carboxylic acid
  • trans-Amcha
  • trans-Tranexamic acid
External IDs
CL 65336 / CL-65336 / RP-18429
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CyklokapronTablet500 mg/1OralPharmacia and Upjohn Company2006-01-042006-01-04Us
CyklokapronInjection, solution100 mg/1mLIntravenousPharmacia & 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 Inc2017-07-31Not applicableCanada
LystedaTablet650 mg/1OralFerring Pharmaceuticals2010-05-172015-12-31Us
LystedaTablet650 mg/1OralXanodyne Pharmaceuticals2010-05-172010-05-17Us
LystedaTablet650 mg/1OralFerring Pharmaceuticals2010-05-17Not applicableUs
LystedaTablet650.0 mgOralFerring PharmaceuticalsNot applicableNot applicableCanada
Tranexamic Acid InjectionSolution100 mgIntravenousAuro Pharma IncNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
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
Tranexamic AcidInjection100 mg/1mLIntravenousMicro Labs Limited2017-08-01Not applicableUs
Tranexamic AcidTablet650 mg/1OralPrasco, Laboratories2010-05-17Not applicableUs
Tranexamic AcidInjection100 mg/1mLIntravenousCadila Pharnmaceuticals2017-10-04Not applicableUs
Tranexamic AcidInjection, solution100 mg/1mLIntravenousAkorn2017-09-28Not applicableUs
Tranexamic AcidInjection, solution100 mg/1mLIntravenousAmerican Regent2011-11-15Not applicableUs
Tranexamic AcidInjection, solution1 g/10mLIntravenousHeritage2014-08-13Not applicableUs
Tranexamic AcidInjection, solution100 mg/1mLIntravenousFresenius Kabi2012-05-24Not applicableUs
Tranexamic AcidTablet, film coated650 mg/1OralAmerincan Health Packaging2015-12-18Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pure Whitenol SerumCream0.05 mg/50mLTopicalSkin M.D. Korea2015-02-01Not applicableUs
Skinmd Laboratories Pure Whitenol SerumCream0.05 g/50mLTopicalReviresco Co., Ltd.2017-12-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Skinmd Laboratories Pure Whitenol IntensiveTranexamic Acid (0.02 g/10mL) + Adenosine (0.004 g/10mL)CreamTopicalReviresco Co., Ltd.2017-12-01Not applicableUs
SKINMD LABORATORIES ReviTox blueTranexamic Acid (0.001 g/10mL) + Adenosine (0.004 g/10mL)LiquidTopicalReviresco Co., Ltd.2017-12-01Not applicableUs
International/Other Brands
Cyclo-F / Cyklokapron / Espercil / Femstrual / Rikavarin / Transamin / Transcam / Traxyl
Categories
UNII
6T84R30KC1
CAS number
1197-18-8
Weight
Average: 157.2102
Monoisotopic: 157.110278729
Chemical Formula
C8H15NO2
InChI Key
GYDJEQRTZSCIOI-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[C@H]1CC[C@@H](CC1)C(O)=O

Pharmacology

Indication

For 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.

Associated Conditions
Pharmacodynamics

Tranexamic 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 action

Tranexamic 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.

TargetActionsOrganism
APlasminogen
inhibitor
Human
Absorption

Absorption 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 binding

The 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 elimination

Urinary excretion is the main route of elimination via glomerular filtration.

Half life

Biological half-life in the joint fluid is about 3 hours.

Clearance
  • 110 - 116 mL/min
Toxicity

Oral 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
PathwayCategory
Tranexamic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Alpha-1-proteinase inhibitorTranexamic Acid may increase the thrombogenic activities of Alpha-1-proteinase inhibitor.
Aminocaproic AcidTranexamic Acid may increase the thrombogenic activities of Aminocaproic Acid.
Aminomethylbenzoic acidTranexamic Acid may increase the thrombogenic activities of Aminomethylbenzoic acid.
Andexanet alfaTranexamic Acid may increase the thrombogenic activities of Andexanet alfa.
Anti-inhibitor coagulant complexTranexamic Acid may increase the thrombogenic activities of Anti-inhibitor coagulant complex.
Antihemophilic Factor (Recombinant), PEGylatedTranexamic Acid may increase the thrombogenic activities of Antihemophilic Factor (Recombinant), PEGylated.
Antihemophilic factor humanTranexamic Acid may increase the thrombogenic activities of Antihemophilic factor human.
Antihemophilic factor, human recombinantTranexamic Acid may increase the thrombogenic activities of Antihemophilic factor, human recombinant.
AprotininTranexamic Acid may increase the thrombogenic activities of Aprotinin.
Beroctocog alfaTranexamic Acid may increase the thrombogenic activities of Beroctocog alfa.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0014447
KEGG Drug
D01136
PubChem Compound
5526
PubChem Substance
46508089
ChemSpider
10482000
BindingDB
50428067
ChEBI
48669
ChEMBL
CHEMBL877
Therapeutic Targets Database
DAP000199
PharmGKB
PA164750514
HET
AMH
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
ATC Codes
B02AA02 — Tranexamic acid
AHFS Codes
  • 20:28.16 — Hemostatics
PDB Entries
1b2i / 1ceb / 5v3c
MSDS
Download (63.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedOtherKnee Prosthesis1
0Not Yet RecruitingPreventionInduction of intra-operative hypotension1
0RecruitingPreventionBlood Loss,Surgical / Hysterectomy1
0RecruitingTreatmentMalignant Neoplasms of Bone and Articular Cartilage / Pelvic Neoplasms1
1Active Not RecruitingTreatmentHemorrhage/Blood Loss During Myomectomies / Leiomyomas1
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingTreatmentHeavy Menstrual Bleeding1
1Unknown StatusPreventionDegenerative Arthritis1
1Unknown StatusTreatmentAcute Blood Loss Anemia / Osteoarthritis, Hip1
1, 2CompletedPreventionAdolescent Idiopathic Scoliosis (AIS)1
1, 2CompletedPreventionHemorrhage1
1, 2CompletedPreventionPostpartum Haemorrage Sever Bleeding After Delivery1
1, 2Not Yet RecruitingPreventionPostpartum Haemorrhage (PPH)1
1, 2RecruitingTreatmentChronic Subdural Hematomas1
1, 2RecruitingTreatmentHypermenorrhea1
1, 2Unknown StatusPreventionHemorrhage of Cesarean Section and/or Perineal Wound1
2Active Not RecruitingPreventionOsteoarthritis (OA)1
2Active Not RecruitingPreventionPostpartum Haemorrhage (PPH)1
2Active Not RecruitingTreatmentBrain Injury / Hemorrhage / Wounds and Injuries1
2Active Not RecruitingTreatmentHemorrhage / Shock / Wounds and Injuries1
2CompletedPreventionBloodloss / Surgical Procedures, Operative1
2CompletedPreventionDegenerative Joint Disease1
2CompletedPreventionJoint Dysfunction1
2CompletedPreventionPostoperative Hemorrhages1
2CompletedPreventionPostpartum Haemorrhage (PPH)1
2CompletedSupportive CareHaemorrhage1
2CompletedTreatmentAcute Blood Loss Anemia / Knee Osteoarthritis (Knee OA)1
2CompletedTreatmentCurvature of Spine1
2CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Nasal Bleeding1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentTraumatic Brain Injury (TBI)1
2Not Yet RecruitingTreatmentAnterior Cruciate Ligament Reconstruction1
2RecruitingPreventionBlood Clots / Blood Loss / Knee Osteoarthritis (Knee OA) / Transfusion Related Complications1
2RecruitingPreventionBronchoscopy Biopsy1
2RecruitingTreatmentHip Fractures1
2RecruitingTreatmentIntracerebral Hemorrhage1
2RecruitingTreatmentIntracerebral Hemorrhage / Strokes2
2RecruitingTreatmentIntraoperative Bleeding1
2SuspendedTreatmentNon-idiopathic Scoliosis1
2TerminatedTreatmentArterial Hypotension / Critical Illness / Sepsis / Shock1
2TerminatedTreatmentHaemorrhage1
2TerminatedTreatmentPost Operative Blood Loss1
2TerminatedTreatmentShock, Septic1
2TerminatedTreatmentTotal Knee Arthroplasty (TKA)1
2, 3CompletedPreventionPostpartum Haemorrhage (PPH)1
2, 3CompletedTreatmentBlood Loss,Surgical / Complications; Arthroplasty / Intraoperative Complications / Shoulder Joint Disease1
2, 3CompletedTreatmentIntraoperative Bleeding / Osteoarthritis (OA)1
2, 3Not Yet RecruitingTreatmentSpinal Deformities / Spinal Injuries1
2, 3RecruitingPreventionBladder Cancers1
2, 3RecruitingPreventionPostpartum Haemorrhage (PPH)1
2, 3RecruitingTreatmentAdult Spinal Deformity1
2, 3RecruitingTreatmentChronic Subdural Hematomas1
2, 3RecruitingTreatmentIntracerebral Hemorrhage1
2, 3RecruitingTreatmentPostinflammatory Hyperpigmentation1
2, 3RecruitingTreatmentSubarachnoid Hemorrhage1
2, 3Unknown StatusTreatmentHepatocellular Cancer / Malignant Neoplasm of Colon / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach1
3Active Not RecruitingPreventionBlood Loss, Postoperative / Blood Loss,Surgical / Osteoarthritis (OA)1
3Active Not RecruitingTreatmentAcetabular Fractures1
3Active Not RecruitingTreatmentPostpartum Haemorrhage (PPH)1
3CompletedDiagnosticBlood Loss1
3CompletedPreventionAtherosclerotic Disease / Postoperative Hemorrhages1
3CompletedPreventionCoronary Artery Disease1
3CompletedPreventionImmediate Postpartum Hemorrhage1
3CompletedPreventionKnee Arthropathy1
3CompletedPreventionObstetrical Hemorrhage1
3CompletedPreventionPlacenta Previa1
3CompletedTreatmentBlood Loss2
3CompletedTreatmentBlood Loss After a Total Hip Replacement1
3CompletedTreatmentBlood Loss / Hip Fractures1
3CompletedTreatmentBrain Injury1
3CompletedTreatmentCancers / General Surgery / Tumour1
3CompletedTreatmentHeavy Menstrual Bleeding / Hypermenorrhea3
3CompletedTreatmentHemoptysis1
3CompletedTreatmentHemorrhage1
3CompletedTreatmentHereditary Angioedema1
3CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Osler-Rendu Disease1
3CompletedTreatmentHip Fractures1
3CompletedTreatmentHypermenorrhea1
3CompletedTreatmentNeoplasms, Head and Neck1
3CompletedTreatmentPostpartum Haemorrhage (PPH)1
3CompletedTreatmentShock, Hemorrhagic / Trauma Injury1
3CompletedTreatmentSpine Surgery1
3CompletedTreatmentSurgery, Cardiac1
3Enrolling by InvitationTreatmentOther Fusion of Spine, Lumbar Region / Scoliosis1
3Not Yet RecruitingBasic ScienceHaemorrhage / Transfusion Related Complications1
3Not Yet RecruitingPreventionIntrapartum - Moderate and Severe Anaemia1
3Not Yet RecruitingPreventionPost Partum Hemorrhage1
3Not Yet RecruitingPreventionUterine Hemorrhage1
3Not Yet RecruitingTreatmentArterial thrombosis / Postoperative Hemorrhages / Thrombosis, Venous1
3Not Yet RecruitingTreatmentBrain Injuries,Traumatic1
3Not Yet RecruitingTreatmentChloasma / Melanosis / Melasma1
3Not Yet RecruitingTreatmentFusion of Spine (Disease)1
3Not Yet RecruitingTreatmentIntracerebral Hemorrhage / Stroke Hemorrhagic1
3Not Yet RecruitingTreatmentType 1 Von Willebrand Disease1
3RecruitingOtherNeoplasms, Hematologic1
3RecruitingPreventionAnemias / Hip Fractures1
3RecruitingPreventionGeneral Surgery / Peri-operative Hemorrhage or Hematoma / Retrognathism1
3RecruitingPreventionHemorrhage / Labor and Delivery / Obstetrical Complications1
3RecruitingPreventionPelvic Organ Prolapse (POP)1
3RecruitingPreventionPost Operative Hemorrhage1
3RecruitingPreventionPost Partum Hemorrhage1
3RecruitingPreventionPostpartum Haemorrhage (PPH)2
3RecruitingPreventionThrombocytopenias1
3RecruitingSupportive CareHematopoietic Stem Cell Transplantation (HSCT) / Hemorrhage / Neoplasms, Hematologic1
3RecruitingTreatmentAbdominal Aortic Aneurysms (AAA) / Blood Transfusion Requirements1
3RecruitingTreatmentAcute Coagulopathy / Wounds and Injuries1
3RecruitingTreatmentAnemias / Hip Fracture Pathologic / Hip Fractures Pathologic1
3RecruitingTreatmentBlood Loss,Surgical / Degenerative Lumbar Spinal Stenosis / Spinal Deformities1
3RecruitingTreatmentCancers / General Surgery / Tumour1
3RecruitingTreatmentChronic Subdural Hematomas1
3RecruitingTreatmentGastrointestinal Bleedings1
3RecruitingTreatmentHypermenorrhea1
3RecruitingTreatmentIntra-Operative Injury - Other / Post Operative Hemorrhage / Tranexamic Acid1
3RecruitingTreatmentTotal Blood Loss1
3RecruitingTreatmentTraumatic Brain Injury (TBI)1
3RecruitingTreatmentTraumatic haemorrhage1
3SuspendedTreatmentPostpartum Haemorrhage (PPH)1
3TerminatedTreatmentBlood Loss / Bone Tumour1
3Unknown StatusTreatmentAcute Upper Gastrointestinal Hemorrhage1
3Unknown StatusTreatmentAstrocytomas / Gliomas / Meningiomas / Neoplasms / Neoplasms, Brain1
3Unknown StatusTreatmentCraniosynostoses1
3Unknown StatusTreatmentFracture of Neck of Femur1
3Unknown StatusTreatmentHemoptisis1
3Unknown StatusTreatmentNeoplasms, Head and Neck1
3WithdrawnPreventionPlacenta Accreta1
4Active Not RecruitingTreatmentHeavy Menstrual Bleeding1
4Active Not RecruitingTreatmentLeiomyomas1
4Active Not RecruitingTreatmentOsteoarthritis (OA)1
4Active Not RecruitingTreatmentPrimary Total Hip Arthroplasty / Primary Total Knee Arthroplasty1
4CompletedNot AvailableHypermenorrhea1
4CompletedNot AvailableRevision Total Hip Arthroplasty (RTHA)1
4CompletedOtherComplication of Extracorporeal Circulation / Pediatric Cardiac Surgery1
4CompletedPreventionAdenoidectomy / Tonsillectomy / Tranexamic Acid1
4CompletedPreventionGynecologic Surgical Procedures / Hysterectomy / Tranexamic Acid1
4CompletedPreventionHaemorrhage / Prostatectomy1
4CompletedPreventionHaemorrhage / Surgical Blood Loss1
4CompletedPreventionHemorrhage1
4CompletedPreventionHemorrhage of Cesarean Section and/or Perineal Wound / Postpartum Haemorrhage (PPH)1
4CompletedPreventionHemorrhage of Cesarean Section and/or Perineal Wound / Postpartum Haemorrhage (PPH) / Uterine Atony1
4CompletedPreventionHip Fractures1
4CompletedPreventionIntraoperative Bleeding / Postoperative Edema1
4CompletedPreventionPostoperative Hemorrhages / Postoperative pain1
4CompletedPreventionSurgical Blood Loss / Total Knee Arthroplasty (TKA)1
4CompletedSupportive CareSpinal Stenosis of Lumbar Region / Thoracic Spinal Stenosis1
4CompletedTreatmentAntifibrinolytic Agents / Blood Transfusions / Fusion of Spine (Disease) / Hemorrhage1
4CompletedTreatmentAntifibrinolytic Agents / Emergency Department / Hemorrhage, Gastrointestinal / Tranexamic Acid1
4CompletedTreatmentArthropathy of Hip / Arthropathy of Knee1
4CompletedTreatmentBlood Loss3
4CompletedTreatmentBlood Loss,Surgical1
4CompletedTreatmentBlood Loss,Surgical / Hip Replacement Surgery / Tranexamic Acid Adverse Reaction1
4CompletedTreatmentBlood Loss / Hip Arthritis / Knee Arthritis1
4CompletedTreatmentBlood Loss / Postoperative Blood Loss / Thromboembolic Complications1
4CompletedTreatmentC.Surgical Procedure; Cardiac1
4CompletedTreatmentCancer of the Ovary1
4CompletedTreatmentCardiopulmonary Bypass / Hemorrhage1
4CompletedTreatmentCleft Palates / Hemorrhage1
4CompletedTreatmentCoronary Artery Occlusive Disease1
4CompletedTreatmentHaemorrhage1
4CompletedTreatmentHip Arthroplasty1
4CompletedTreatmentHypermenorrhea1
4CompletedTreatmentNasal Bleeding / Nasal Packing / Tranexamic Acid1
4CompletedTreatmentOsteoarthritis (OA)1
4CompletedTreatmentPost Partum Hemorrhage1
4CompletedTreatmentPostpartum Haemorrhage (PPH)1
4CompletedTreatmentScoliosis1
4CompletedTreatmentUterine Hemorrhage1
4Not Yet RecruitingPreventionBlood Loss Anemia / Blood Loss,Surgical1
4Not Yet RecruitingPreventionHematoma / Seroma1
4Not Yet RecruitingPreventionInjuries and Wounds / Postoperative Hemorrhages1
4Not Yet RecruitingPreventionKnee Osteoarthritis (Knee OA)2
4Not Yet RecruitingPreventionPostpartum Hemorrhage, Cesarean Section1
4Not Yet RecruitingPreventionTotal Blood Loss1
4Not Yet RecruitingTreatmentBlood Loss Following Open Femur Fracture Surgery1
4Not Yet RecruitingTreatmentDeep Vein Thrombosis (DVT) / Myocardial Infarction / Pulmonary Embolism (PE) / Safety / Strokes1
4RecruitingPreventionArthroplasty, Replacement, Hip / Blood Loss,Surgical / Tranexamic Acid1
4RecruitingPreventionBlood Loss / Hip Fractures1
4RecruitingPreventionHip Fractures / Surgical Blood Loss1
4RecruitingPreventionNeoplasms, Breast / Postoperative Hemorrhages / Seroma1
4RecruitingPreventionPostpartum Haemorrhage (PPH)1
4RecruitingPreventionTranexamic Acid Adverse Reaction1
4RecruitingSupportive CareBleeding Reduction1
4RecruitingTreatmentAnemias / Hip Fractures1
4RecruitingTreatmentBunions / Foot and Ankle Surgeries1
4RecruitingTreatmentCalcium Nephrolithiasis / Staghorn Calculus1
4RecruitingTreatmentCesarean Section / Placenta Accreta / Postpartum Haemorrhage (PPH) / Tranexamic Acid1
4RecruitingTreatmentComplications, Pregnancy / Hemorrhage1
4RecruitingTreatmentFracture of Neck of Femur1
4RecruitingTreatmentGeneral Surgery / Minor burns / Tranexamic Acid / Wounds and Injuries1
4RecruitingTreatmentHeavy Menstrual Bleeding / Hypermenorrhea / Uterine Leiomyomas1
4RecruitingTreatmentHigh Tibial Osteotomy (HTO) / Osteotomy / Patello-femoral Ligament1
4RecruitingTreatmentHip Arthropathy / Osteoarthritis (OA) / Shoulder Arthropathy1
4RecruitingTreatmentHip Fractures1
4RecruitingTreatmentKnee Osteoarthritis (Knee OA)2
4RecruitingTreatmentLiver Cirrhosis / Portal Hypertension / Upper Digestive Bleeding1
4RecruitingTreatmentMelasma1
4RecruitingTreatmentOsteotomy1
4RecruitingTreatmentSubdural haematoma1
4RecruitingTreatmentSurgery, Colorectal1
4RecruitingTreatmentTooth Extractions1
4TerminatedTreatmentAnemias / Arthritis / Total Hip Arthroplasty (THA) / Total Knee Arthroplasty (TKA)1
4TerminatedTreatmentCranial Vault Surgery for Craniosynostosis / Craniosynostosis / Haemorrhage1
4Unknown StatusDiagnosticHaemorrhage1
4Unknown StatusPreventionPostoperative Blood Loss / Total Hip Arthroplasty (THA)1
4Unknown StatusSupportive CareHaemorrhage1
4Unknown StatusTreatmentHemorrhage1
4Unknown StatusTreatmentKnee Osteoarthritis (Knee OA)1
4Unknown StatusTreatmentNative Arteriovenous Fistula1
4Unknown StatusTreatmentOsteoarthritis (OA)1
4WithdrawnPreventionFemur Surgery / Proximal Femur Surgery 1
4WithdrawnTreatmentBlood Loss / Hip Fractures1
4WithdrawnTreatmentHeart Defect, Congenital / Whole Blood Platelet Aggregation Following Tranexamic Acid Administration or Placebo Administration1
Not AvailableActive Not RecruitingTreatmentCancers / Major Surgery / Tranexamic Acid1
Not AvailableActive Not RecruitingTreatmentOsteoarthritis (OA)1
Not AvailableCompletedPreventionAvascular Necrosis of Femoral Head / Degenerative Arthritis of Hip1
Not AvailableCompletedPreventionBlood Loss After Primary Total Joint Arthroplasty / Need for Blood Transfusion After Total Joint Arthroplasty1
Not AvailableCompletedPreventionBlood Platelet Disorders / Disorders, Blood Coagulation / Hematologic Diseases / Hypermenorrhea / Von Willebrand 's disease Type 11
Not AvailableCompletedPreventionCraniosynostosis Patients Undergoing Distraction Osteotomy1
Not AvailableCompletedPreventionKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedSupportive CareHaemorrhage1
Not AvailableCompletedTreatmentAcetabulum Fractures / Pelvic Ring Injury1
Not AvailableCompletedTreatmentAnatomic Total Shoulder Arthroplasty / Blood Loss / Reverse Total Shoulder Arthroplasty / Tranexamic Acid / Transfusions1
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 AvailableCompletedTreatmentHypermenorrhea1
Not AvailableCompletedTreatmentKnee Arthroplasty, Total1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedTreatmentNeurosurgery / Orthopedic Procedures / Red Blood Cells Transfusion1
Not AvailableCompletedTreatmentOff Pump Coronary Artery Bypass Surgery1
Not AvailableCompletedTreatmentOsteoarthritis (OA)1
Not AvailableCompletedTreatmentPost CABG Bleeding1
Not AvailableCompletedTreatmentPrimary Osteoarthritis of Knee Nos1
Not AvailableEnrolling by InvitationPreventionBlood Loss / Fracture Bone / General Surgery / Traumas1
Not AvailableEnrolling by InvitationTreatmentDysplasia, Congenital Hip1
Not AvailableNot Yet RecruitingNot AvailableAnkle Osteoarthritis / Haemorrhage / Knee Osteoarthritis (Knee OA) / Tranexamic Acid1
Not AvailableNot Yet RecruitingPreventionAnemias / Hip Fractures1
Not AvailableNot Yet RecruitingPreventionCytoreductive Surgery1
Not AvailableNot Yet RecruitingPreventionPosterior Lumbar Spinal Fusion Surgery1
Not AvailableRecruitingNot AvailableHip Fractures1
Not AvailableRecruitingNot AvailableMAPCA - Major Aortopulmonary Collateral Artery / Pulmonary Haemorrhage1
Not AvailableRecruitingNot AvailableThrombosis, Venous1
Not AvailableRecruitingPreventionCesarean Section Complications2
Not AvailableRecruitingTreatmentAcute Hip Fractures1
Not AvailableRecruitingTreatmentAnterior Shoulder Instability1
Not AvailableRecruitingTreatmentBlood Loss2
Not AvailableRecruitingTreatmentGastrointestinal Bleedings1
Not AvailableRecruitingTreatmentHemostasis1
Not AvailableRecruitingTreatmentMajor Surgery / Minor burns / Tranexamic Acid1
Not AvailableRecruitingTreatmentNasal Bleeding1
Not AvailableRecruitingTreatmentVaginal Bleeding During Pregnancy1
Not AvailableTerminatedTreatmentAnemias / Hip Fractures1
Not AvailableUnknown StatusPreventionAcute Aortic Dissection1
Not AvailableUnknown StatusPreventionClosed Fracture of Hip1
Not AvailableUnknown StatusPreventionNasolacrimal Tract Obstruction1
Not AvailableUnknown StatusTreatmentCardiopulmonary Bypass1
Not AvailableUnknown StatusTreatmentHemostasis / Hexacapron / Mortality / Rebleeding / Upper Gastrointestinal Hemorrhage1
Not AvailableUnknown StatusTreatmentHip Replacement Surgery / Postoperative Hemorrhages1
Not AvailableUnknown StatusTreatmentIdiopathic Scoliosis1
Not AvailableUnknown StatusTreatmentMenstrual Cycle and Uterine Bleeding Disorders1
Not AvailableWithdrawnNot AvailableCongenital Heart Disease (CHD)1
Not AvailableWithdrawnTreatmentArthroplasty, Replacement, Hip1
Not AvailableWithdrawnTreatmentChronic Rhinosinusitis1
Not AvailableWithdrawnTreatmentHemorrhage, Gastrointestinal1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
  • Gallipot
  • Pfizer Inc.
  • Pharmacia Inc.
  • Professional Compounding Centers America LLC
  • Xanodyne Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
TabletOral500 mg/1
SolutionIntravenous100 mg
TabletOral500 mg
TabletOral650 mg/1
TabletOral650.0 mg
CreamTopical0.05 mg/50mL
CreamTopical
CreamTopical0.05 g/50mL
LiquidTopical
InjectionIntravenous100 mg/1mL
Injection, solutionIntravenous1 g/10mL
Injection, solutionIntravenous100 mg/1mL
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)
US8022106No2005-03-042025-03-04Us
US8273795No2005-03-042025-03-04Us
US8487005No2005-03-042025-03-04Us
US8791160No2005-03-042025-03-04Us
US8809394No2005-03-042025-03-04Us
US8957113No2005-03-042025-03-04Us
US9060939No2005-03-042025-03-04Us
US7947739No2005-03-042025-03-04Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Amino acids
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:48669)

Targets

Details
1. Plasminogen
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...
Gene Name
PLG
Uniprot ID
P00747
Uniprot Name
Plasminogen
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
Uniprot Name
Solute carrier family 15 member 2
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]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:25