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Tranexamic Acid, Cyclo Capron, Transamin, Trans AMCHA, AMCA, 1197-18-8

Tranexamic Acid, Cyclo Capron, Transamin, Trans AMCHA, AMCA, 1197-18-8

TRANEXAMIC ACID

SECTION 1: PRODUCT IDENTITY AND CHEMICAL IDENTIFICATION

Parameter Information
Product Name Tranexamic Acid
Chemical Name (IUPAC) trans-4-(Aminomethyl)cyclohexanecarboxylic acid
Synonyms (Turkish) Traneksamik Asit, AMCA, trans-AMCHA
Synonyms (English) Tranexamic Acid, AMCA, trans-AMCHA, Cyclocapron, Transamin
CAS Number 1197-18-8
EC Number (EINECS) 214-818-2
Molecular Formula C₈H₁₅NO₂
Molecular Weight 157.21 g/mol
Chemical Class Amino acid derivative; Antifibrinolytic agent
Pharmacological Class Antifibrinolytic; Plasminogen inhibitor
Physical State (20°C) Solid (crystalline powder)
Color White to off-white
Odor Odorless
Taste Slightly bitter

SECTION 2: CHEMICAL STRUCTURE

         COOH
           |
           C
          / \
         /   \
        /     \
       /       \
      /         \
     /           \
    C             C
    |             |
    C——CH₂——NH₂   C
    |             |
    C             C
     \           /
      \         /
       \       /
        \     /
         \   /
          \ /
           C

    Tranexamic Acid
    trans-4-(Aminomethyl)cyclohexanecarboxylic acid
    C₈H₁₅NO₂

Simplified Structure:

    HOOC — (C₆H₁₀) — CH₂NH₂

    Tranexamic Acid
    (trans-isomer)
Parameter Description
Molecular Formula C₈H₁₅NO₂
Molecular Weight 157.21 g/mol
Chemical Class Amino acid derivative (cyclohexane carboxylic acid)
Functional Groups Carboxylic acid (-COOH), primary amine (-CH₂NH₂)
Isomerism trans-isomer (active form); cis-isomer (inactive)
SMILES C1CC(CCC1CN)C(=O)O
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-
InChI Key GYDJEQRTZSCIOI-LJGSYFOKSA-N
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
Rotatable Bond Count 2
Polar Surface Area (PSA) 63.3 Ų
Optical Activity Optically active (trans-isomer)
Chirality 2 stereocenters

SECTION 3: PHYSICAL AND CHEMICAL PROPERTIES

Property Value Test Method / Note
Appearance White to off-white crystalline powder Visual
Odor Odorless Olfactometric
Molecular Weight 157.21 g/mol Calculated
Melting Point ~300°C (decomposes) DSC / Capillary
Density (20°C) ~1.2 g/cm³ (estimated) -
Water Solubility (20°C) High (>100 g/L) General Method
Hot Water Solubility Very high General Method
Ethanol Solubility Slightly soluble (~5-10 g/L) General Method
Methanol Solubility Soluble General Method
Acetone Solubility Practically insoluble General Method
Chloroform Solubility Insoluble General Method
Ether Solubility Insoluble General Method
Log P (Octanol/Water) < -1.0 (very hydrophilic) Calculated / Experimental
pKa ~4.3 (carboxylic acid); ~10.6 (amine) Potentiometric
pH (1% Solution) ~5.0 – 7.0 pH Meter
Vapor Pressure (25°C) Very low -
Flash Point >150°C -
Thermal Stability Stable up to 200°C; decomposes at higher temperatures -
Hygroscopicity Low (not hygroscopic) -
Optical Rotation [α]D²⁰ +14° to +16° (c=1, H₂O) Polarimetry
UV Maximum (λmax) None (no UV absorption) UV-VIS Spectrophotometer
Heat of Solution Exothermic (when dissolved in water) -
Surface Activity Low -

SECTION 4: PHARMACOLOGICAL PROPERTIES AND MECHANISM OF ACTION

Property Description
Pharmacological Class Antifibrinolytic agent
Mechanism of Action Competitively inhibits plasminogen activators (tissue plasminogen activator - tPA, urokinase) that convert plasminogen to plasmin; Reduces plasmin formation; Inhibits fibrin breakdown (fibrinolysis); Maintains blood clot stability.
Lysine Binding Site Binds to lysine binding sites (kringle domains) on plasminogen; Blocks interaction of plasminogen with activators.
Antifibrinolytic Potency Approximately 6-10 times more potent than aminocaproic acid (EACA)
Oral Bioavailability ~30-50% (with first-pass metabolism)
Peak Plasma Concentration (Cmax) 10-20 µg/mL (after 25 mg/kg oral dose)
Peak Time (Tmax) ~2-3 hours (oral)
Plasma Half-Life (t½) ~2-3 hours
Protein Binding Low (~3-5%)
Volume of Distribution (Vd) ~0.3 L/kg
Metabolism Minimal (<5%); Mainly excreted unchanged
Elimination • Urine: ~90-95% (unchanged)
• Feces: ~5-10%
Renal Clearance Equivalent to plasma clearance (~90-110 mL/minute)
Elimination Half-Life Prolonged in renal failure
Pregnancy Category FDA Category B
Maximum Daily Dose 3-4 g/day (IV); 2-6 g/day (oral)

SECTION 5: CLINICAL USE AND INDICATIONS

Indication Formulation Dose Route Duration
Surgical Bleeding Control IV Injection 10-15 mg/kg (bolus); 1-2 mg/kg/hour (infusion) Intravenous Throughout surgery
Cardiopulmonary Bypass (CABG) IV 10-30 mg/kg bolus; 1-10 mg/kg/hour infusion Intravenous During bypass
Heavy Menstrual Bleeding Tablet 500-1000 mg, 3 times daily (days 1-5) Oral 3-5 days
Postpartum Hemorrhage IV / Oral 1 g (IV); 500 mg (oral), 2-3 times daily IV / Oral 3-5 days
Dental Surgery (Hemophilia) Tablet / IV 10-25 mg/kg, 2-3 times daily Oral / IV 2-7 days
Trauma (Injury) IV 1-2 g bolus; 1-2 mg/kg/hour infusion Intravenous 8-24 hours
Melasma (Hyperpigmentation) Topical 2-3% cream / lotion Topical 8-12 weeks
Systemic Allergic Reactions Topical / Oral Variable Topical / Oral Symptomatic
Menorrhagia Tablet 500-1000 mg, 3 times daily Oral 3-5 days/cycle
Subarachnoid Hemorrhage IV 1-2 g/day Intravenous Variable

SECTION 6: COMMERCIAL GRADES AND VARIANTS

Grade / Type Purity Particle Size Primary Application
Pharmaceutical Grade (USP/EP) ≥99.0% Standard Tablet, injectable solution production
Research Grade (R&D) ≥99.5% Standard Analytical standards, formulation development
GMP Grade ≥99.0% Standard / Micronized Pharmaceutical manufacturing
Analytical Standard ≥99.8% Standard HPLC reference standards
Topical Grade ≥99.0% Micronized (optional) Cream, lotion formulations
Veterinary Grade ≥98.0% Standard Animal bleeding control

SECTION 7: FORMULATION GUIDELINES

Parameter Recommendation
Oral Tablet Formulation • Lactose, MCC, sodium starch glycolate, povidone, magnesium stearate
• Strength: 500 mg, 750 mg, 1000 mg
Injectable Solution • 100 mg/mL (10 mL ampoule)
• pH: 6.5-7.5
• Isotonic adjustment (NaCl)
• Light-protected ampoule
Topical Cream (2-3%) • O/W emulsion
• Transdermal penetration enhancers
• pH: 5.0-6.0
Solubility Enhancement High water solubility; additional solvents not required
pH Range Optimum pH 5.0-7.0; Stable in acidic or basic conditions
Compatibility Compatible with most excipients; Avoid strong oxidizing agents
Temperature Processing Dissolve at 60-70°C; avoid high temperatures (>100°C) causing degradation
Sterilization Autoclaving possible (121°C, 15 minutes); Aseptic filtration (0.2 µm)
Color Colorless solution (injection); White tablet
Preservatives Injectable formulations do not require preservatives; Can be added for multi-dose formulations

SECTION 8: QUALITY SPECIFICATIONS (USP/EP)

Parameter USP / EP Specification Test Method
Appearance White to off-white crystalline powder Visual
Assay (on dried basis) ≥99.0% - ≤101.0% HPLC / Titrimetric
Melting Point ~300°C (decomposes) Capillary
pH (1:100 Solution) 5.0 – 7.0 pH Meter
Water Content ≤0.5% Karl Fischer
Residue on Ignition ≤0.1% Gravimetric
Heavy Metals (Pb) ≤10 ppm ICP-MS / USP <231>
Arsenic (As) ≤2 ppm ICP-MS
Lead (Pb) ≤3 ppm ICP-MS
Cadmium (Cd) ≤1 ppm ICP-MS
Mercury (Hg) ≤1 ppm ICP-MS
Related Substances (Single) ≤0.2% HPLC
Related Substances (Total) ≤0.5% HPLC
Chloride (Cl) ≤0.02% Titrimetric
Sulfate (SO₄) ≤0.05% Turbidimetric
Particle Size As per customer specification Laser Diffraction
Microbiological Purity TAMC ≤10² CFU/g; TYMC ≤10¹ CFU/g USP <61>
E. coli Negative in 1g USP <62>
Salmonella spp. Negative in 25g USP <62>
S. aureus Negative in 1g USP <62>
P. aeruginosa Negative in 1g USP <62>
Optical Rotation +14° to +16° (c=1, H₂O) Polarimetry

SECTION 9: TOXICOLOGICAL PROFILE

Parameter Value
Acute Oral Toxicity (LD50, Rat) >5000 mg/kg (very low toxicity)
Acute Dermal Toxicity (LD50, Rabbit) >2000 mg/kg (low toxicity)
Skin Irritation May cause mild irritation
Eye Irritation May cause mild irritation
Skin Sensitization Does not cause sensitization
Carcinogenicity Not classified as carcinogenic
Mutagenicity Not mutagenic (AMES test negative)
Reproductive Toxicity Fetotoxic potential at high doses; Pregnancy Category B
Target Organs Kidneys, liver, gastrointestinal system
Common Side Effects • Nausea (5-10%)
• Vomiting (2-5%)
• Diarrhea (2-5%)
• Headache (2-5%)
Serious Side Effects • Thromboembolic complications (rare)
• Anaphylactic reactions (very rare)
• Color vision disturbances (long-term high dose)
Thromboembolic Risk Use with caution in patients with history of active thromboembolic disease
NOAEL (Rat, 90 days) ~500 mg/kg/day
Therapeutic Window Wide; low toxicity

SECTION 10: GHS CLASSIFICATION AND LABELING

GHS Classification (in accordance with 1272/2008/EC):

Hazard Class Category H-Statement
Generally not classified as hazardous substance
Skin Irritation Category 2 (optional) H315
Eye Irritation Category 2 (optional) H319

Signal Word: None (Not classified as hazardous) or Warning (optional)

Hazard Pictograms: None (generally) or GHS07 (Exclamation mark)

NFPA 704 Hazard Classification:

Health Flammability Reactivity Special
1 0 0 -
(Minimal health hazard) (Non-combustible) (Stable) (None)

SECTION 11: PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P261 Avoid breathing dust/fume/gas
P264 Wash hands thoroughly after handling
P270 Do not eat, drink or smoke when using this product
P271 Use only outdoors or in a well-ventilated area
P280 Wear protective gloves/protective clothing/eye protection/face protection
P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell
P302+P352 IF ON SKIN: Wash with plenty of soap and water
P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and continue rinsing
P332+P313 If skin irritation occurs: Get medical advice/attention
P337+P313 If eye irritation persists: Get medical advice/attention
P362+P364 Take off contaminated clothing and wash it before reuse
P403+P233 Store in a well-ventilated place. Keep container tightly closed
P405 Store locked up
P501 Dispose of contents/container in accordance with local/regional/national/international regulations

SECTION 12: FIRST AID MEASURES

Route of Exposure Action
Inhalation If inhaled as powder, move to fresh air. Seek medical attention if respiratory symptoms persist.
Skin Contact Remove contaminated clothing. Wash with plenty of soap and water. Seek medical attention if irritation develops.
Eye Contact Rinse thoroughly with plenty of water for at least 15 minutes. Keep eyelids open. Remove contact lenses if present. Seek medical attention if irritation persists.
Ingestion Rinse mouth with water. Do NOT induce vomiting. Drink 1-2 glasses of water. Seek medical attention.
Note Symptomatic treatment is administered. No specific antidote available.

SECTION 13: ADVERSE EFFECTS AND MANAGEMENT

Adverse Effect Frequency Severity Management
Nausea Common (5-10%) Mild Take with meals; dose reduction
Vomiting Common (2-5%) Mild Take with meals; antiemetics
Diarrhea Common (2-5%) Mild Increase fluid intake; probiotics
Headache Common (2-5%) Mild Analgesics; rest
Dizziness Less common (1-2%) Mild Rest; move slowly
Thromboembolic Events Rare (<0.5%) Serious Discontinue treatment; emergency medical attention
Anaphylactic Reaction Very rare (<0.1%) Serious Discontinue treatment; emergency medical attention
Color Vision Disturbance Rare (long-term high dose) Moderate Dose reduction; ophthalmologic examination

SECTION 14: CONTRAINDICATIONS AND WARNINGS

Condition Description
Active Thromboembolic Disease Use with caution; History of deep vein thrombosis, pulmonary embolism, cerebrovascular event
Color Vision Disturbance Risk of retinal damage with long-term high-dose therapy; Regular eye examinations
Renal Failure Dose adjustment required (GFR <30 mL/minute)
Hematuria (Upper Urinary) Risk of urinary tract obstruction; Evaluation of urinary system
Pregnancy FDA Category B; No teratogenic effects in animal studies; Use only if clearly necessary
Lactation Excreted in breast milk (low concentration); Use with caution
Drug Interactions • Concomitant use with anticoagulants (warfarin, heparin)
• Interaction with thrombolytic agents (streptokinase, tPA)
Pediatric Use Safety data limited; Dose adjustment required
Elderly Patients Dose adjustment based on renal function

SECTION 15: DRUG INTERACTIONS

Drug / Substance Interaction Type Severity Management
Anticoagulants (Warfarin, Heparin) Anticoagulant effect potentially increased Moderate INR monitoring; dose adjustment
Thrombolytic Agents (Streptokinase, tPA, Urokinase) Antifibrinolytic effect; Thrombolytic effect reduced Moderate-Serious Concomitant use not recommended
Factor IX Complex Concentrates Thrombotic risk increased Moderate Use with caution
Oral Contraceptives Thromboembolic risk increased (theoretical) Low Monitoring
Desmopressin Hemostatic effect increased (synergy) Positive Combination may be beneficial
Estrogens Thromboembolic risk increased (theoretical) Low Monitoring

SECTION 16: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Store in a cool (<25°C), dry, well-ventilated area; protect from direct sunlight and moisture.
Temperature Limits 15-25°C (ideal); do not exceed 30°C
Humidity Low humidity environment (not hygroscopic)
Light Protect from UV light and direct sunlight
Oxygen Protect against oxidation; keep containers tightly closed
Incompatible Materials Strong oxidizing agents, strong acids, strong bases
Container Requirements Light-proof, moisture-proof containers: Amber glass, aluminum foil, HDPE
Shelf Life 36-60 months (unopened original packaging, under proper storage conditions)
Shelf Life (After Opening) 12-24 months (under proper storage conditions)
Signs of Degradation Color change (yellowing), caking, decreased solubility, HPLC impurity increase
Stability Warning Stable under normal conditions; May degrade under high temperature and humidity

SECTION 17: PACKAGING OPTIONS

Packaging Type Quantity / Capacity Material Application Area
Fiber Drum (PE Lined) 25 kg Fiber / PE liner Pharmaceutical manufacturing, industrial supply
HDPE Drum 25 kg, 50 kg HDPE (opaque, moisture barrier) Pharmaceutical, industrial supply
Aluminum Foil Bag 1 kg, 5 kg, 10 kg Aluminum / PE (light and moisture proof) High purity, pharmaceutical
Amber Glass Bottle 100 g, 500 g, 1 kg Amber glass (UV protected) Laboratory, analytical standards
Kraft Bag (PE Lined) 10 kg, 25 kg Kraft paper / PE liner Economical packaging
IBC Container 500 kg, 1000 kg UV-protected HDPE Large-scale industrial supply

SECTION 18: TRANSPORTATION INFORMATION

Parameter Information
UN Number Not applicable (not classified as dangerous substance)
Hazard Class Not applicable
Packing Group Not applicable
ADR/RID Not classified as dangerous goods
IMDG Code Not marine pollutant; not classified as dangerous goods
IATA (Air) Not classified as dangerous goods; can be transported by air
Transport Temperature Ambient temperature; protect from heat, moisture, and light
Transport Precautions Light-proof packaging; keep away from strong oxidizing agents
Spill Cleanup Collect mechanically; clean with absorbent material; avoid dust generation
Marine Pollutant No

SECTION 19: REGULATORY STATUS

Region / Authority Status
USA (USP/NF) Official monograph (Tranexamic Acid)
European Pharmacopoeia Official monograph (Tranexamic Acid)
USA (FDA) Prescription drug; Approved (IV, oral, topical forms)
WHO Essential Medicines List Essential medicine (antifibrinolytic)
Turkey Licensed pharmaceutical active ingredient; Prescription drug; KKDIK registered
ECHA (REACH) Registered substance
TSCA (USA) Listed
DEA / Controlled Substance Not a controlled substance
IARC Not classified (not carcinogenic)
NTP Not listed
California (Prop 65) Not listed

SECTION 20: OTHER NAMES AND SYNONYMS

Type Name
Chemical Name (IUPAC) trans-4-(Aminomethyl)cyclohexanecarboxylic acid
Common Names (Turkish) Traneksamik Asit, AMCA
Common Names (English) Tranexamic Acid, AMCA, trans-AMCHA, Cyclocapron, Transamin
Trade Marks Cyklokapron®, Transamin®, Tranex®, Exacyl®, Lysteda®
CAS Number 1197-18-8
EC Number 214-818-2
PubChem CID 5526
DrugBank ID DB00302
FDA UNII 6T84R30KC1
ATC Code B02AA02

SECTION 21: SUMMARY TABLE

Parameter Value
CAS Number 1197-18-8
Molecular Formula C₈H₁₅NO₂
Molecular Weight 157.21 g/mol
Appearance White to off-white crystalline powder
Melting Point ~300°C (decomposes)
Water Solubility High (>100 g/L)
pKa ~4.3 (carboxylic); ~10.6 (amine)
Primary Function Antifibrinolytic agent
Main Indications Surgical bleeding, menorrhagia, trauma, dental surgery, melasma
Maximum Daily Dose 3-4 g/day (IV); 2-6 g/day (oral)
Plasma Half-Life ~2-3 hours
Bioavailability ~30-50% (oral)
Shelf Life 36-60 months
Storage Cool (<25°C), dry, light-protected
GHS Classification Generally not hazardous
FDA Pregnancy Category B
UN Number Not applicable

SECTION 22: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

  1. Thromboembolic Risk: Use with caution in patients with history of active thromboembolic disease. Risk of deep vein thrombosis, pulmonary embolism, or cerebrovascular events.

  2. Renal Failure: Dose adjustment required (GFR <30 mL/minute). Risk of accumulation at high doses.

  3. Color Vision Disturbance: Risk of retinal damage with long-term high-dose therapy; Regular eye examinations.

  4. Hematuria (Upper Urinary): Risk of urinary tract obstruction; Urinary system should be evaluated.

  5. Pregnancy: FDA Category B; Use only if clearly necessary.

  6. Lactation: Excreted in breast milk (low concentration); Use with caution.

  7. Drug Interactions: Avoid concomitant use with anticoagulants and thrombolytic agents.

  8. Pediatric Use: Safety data limited; Dose adjustment required.

  9. Elderly Patients: Dose adjustment based on renal function.

BEST PRACTICE RECOMMENDATIONS:

  1. Dosage: For surgical bleeding control: 10-15 mg/kg IV bolus, followed by 1-2 mg/kg/hour infusion. For menorrhagia: 500-1000 mg oral, 3 times daily.

  2. Dose in Renal Failure: GFR 30-60 mL/minute: 50% dose; GFR <30 mL/minute: 25% dose.

  3. Administration: Oral forms should be taken with meals (GI tolerance). IV form should be administered as slow injection (>1 minute).

  4. Monitoring: Periodic eye examinations (color vision, visual acuity) should be performed during long-term therapy.

  5. Stability: Stable under normal conditions; 60 months shelf life. Protect from high temperature and humidity.

  6. Quality Control: Assay (HPLC), melting point, pH, water content, heavy metals, microbiological purity tests should be performed regularly.

  7. Formulation: Injectable solutions: pH 6.5-7.5; Isotonic adjustment; Light-protected ampoules.

  8. Patient Education: Inform patients about side effects (nausea, vomiting, headache) and thromboembolic symptoms (leg pain, swelling, shortness of breath).

  9. Microbiological Control: Powder form should be tested for microbiological contamination (TAMC, TYMC, pathogens).

  10. Spill Cleanup: Avoid dust generation; use HEPA-filtered vacuum or wet cleaning. Prevent entry into water and sewers.

LEGAL DISCLAIMER:

The information provided in this document is based on our current knowledge and experience and is presented in good faith. However, as all conditions of use are beyond our control, it does not constitute a binding specification or guarantee. This Technical Data Sheet is for informational purposes only and does not constitute medical advice. Users are responsible for testing suitability for their own applications and for complying with all local, regional, and national regulations. For complete safety, storage, use, handling, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Tranexamic Acid is a prescription medication; its use must be under the supervision of a healthcare professional.

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