4-(aminomethyl)cyclohexane-1-carboxylic acid

• ChemBase ID: 187
• Molecular Formular: C8H15NO2
• Molecular Mass: 157.2102
• Monoisotopic Mass: 157.11027873
• SMILES: OC(=O)C1CCC(CC1)CN
• Canonical SMILES: NCC1CCC(CC1)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)
• InChIKey: GYDJEQRTZSCIOI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(aminomethyl)cyclohexane-1-carboxylic acid
• IUPAC Traditional name: tranexamic acid
• Brand Name: Amcha; Amikapron; Amstat; Anvitoff; Carxamin; Cyclocapron; Cyklokapron; Emorhalt; Frenolyse; Mastop; Rikavarin; Rikavarin-S; Tamcha; Tranexan; Transamin; Trasamlon; Ugurol
• Synonyms: trans-4-(Aminomethyl)cyclohexanecarboxylic acid; 4-(aminomethyl)cyclohexane-1-carboxylic acid; 4-(Aminomethyl)cyclohexanecarboxylic acid; Tranexamsaeure; tranexmic acid; Tranhexamic acid; Trans AMCHA; trans-Amcha; trans-Tranexamic acid; trans-4-aminomethylcyclohexane-1-carboxylic acid; Tranexamic Acid; 反-4-氨甲基环己羧酸

Database IDs

• CAS Number: 1197-18-8
• EC Number: 214-818-2
• MDL Number: MFCD00001466; MFCD00064951
• Beilstein Number: 2207452
• Merck Index: 149569
• PubChem SID: 160963650
• PubChem CID: 5526

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.5582533
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5895343
• LogD (pH = 7.4): -1.5519825
• Log P: -1.5523915
• Molar Refractivity: 41.9037 cm^3
• Polarizability: 16.785397 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.42
• LOG S: -0.94
• Solubility (Water): 1.82e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.67E+005 mg/L
• Melting Point: >300°C; 300 - 302°C
• Hydrophobicity(logP): 0.3; -1.801

Safety Information

• Storage Warning: IRRITANT
• RTECS: GU8400000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 95%; 95+%; 97%

DETAILS

DrugBank - DB00302

• Drug Groups: approved
• Description: Antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]
• 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.
• Pharmacology: 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).
• 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
• Biotransformation: Only a small fraction of the drug is metabolized (less than 5%).
• 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.
• Half Life: Biological half-life in the joint fluid is about 3 hours.
• 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).
• Elimination: Urinary excretion is the main route of elimination via glomerular filtration.
• Distribution: * 9 to 12 L
• Clearance: * 110 - 116 mL/min
• External Links: Wikipedia; RxList; Drugs.com