4-(Aminomethyl)cyclohexanecarboxylic acid
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4-(Aminomethyl)cyclohexanecarboxylic acid
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CAS No:
701-54-2
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Formula:
C8H15NO2
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Chemical Name:
4-(Aminomethyl)cyclohexanecarboxylic acid
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Synonyms:
Cyclohexanecarboxylic acid,4-(aminomethyl)-;4-(Aminomethyl)cyclohexanecarboxylic acid;AMCA;4-(Aminomethyl)-1-cyclohexanecarboxylic acid;1-(Aminomethyl)cyclohexane-4-carboxylic acid;p-(Aminomethyl)cyclohexanecarboxylic acid;1510-00-5;21573-60-4
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CAS No:
Description
White Solid
Tranexamic acid is a monocarboxylic acid. It has a role as an antifibrinolytic drug and a hematologic agent. It derives from a cyclohexanecarboxylic acid.|Antifibrinolytic hemostatic used in severe hemorrhage.|Tranexamic acid is an Antifibrinolytic Agent. The physiologic effect of tranexamic acid is by means of Decreased Fibrinolysis.|Tranexamic Acid is a synthetic derivative of the amino acid lysine with antifibrinolytic activity. With strong affinity for the five lysine-binding sites of plasminogen, tranexamic acid competitively inhibits the activation of plasminogen to plasmin, resulting in inhibition of fibrinolysis; at higher concentrations, this agent noncompetitively inhibits plasmin. This agent has a longer half-life, is approximately ten times more potent, and is less toxic than aminocaproic acid, which possesses similar mechanisms of action.
4-(Aminomethyl)cyclohexanecarboxylic acid Basic Attributes
157.21
157.21
214-818-2
6T84R30KC1|37YD696II6
758176|291305
DTXSID3045350
C47765
B02AA02|B - Blood and blood forming organs
2922499990
Characteristics
63.32000
0.31
1.1±0.1 g/cm3
237-240 °C
300.2±15.0 °C at 760 mmHg
135.4±20.4 °C
1.497
167000 mg/L
Refrigerator
Safety Information
GU8399950
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (99.17%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 150 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.
Toxicity
Oral LD50 in mice is >10 gm/kg. Symptoms of overdosage may be nausea, vomiting, orthostatic symptoms and/or hypotension.
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).
Drug Information
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.
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).
Agents that prevent fibrinolysis or lysis of a blood clot or thrombus. Several endogenous antiplasmins are known. The drugs are used to control massive hemorrhage and in other coagulation disorders. (See all compounds classified as Antifibrinolytic Agents.)
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.|Urinary excretion is the main route of elimination via glomerular filtration.|9 to 12 L|110 - 116 mL/min
Only a small fraction of the drug is metabolized (less than 5%).
Biological half-life in the joint fluid is about 3 hours.
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.
AMCA
4-(Aminomethyl)cyclohexanecarboxylic acid Use and Manufacturing
Tranexamic acid (T714505) impurity.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan|Cosmetics -> Astringent
Computed Properties
Molecular Weight:157.21
XLogP3:-2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:157.110278721
Monoisotopic Mass:157.110278721
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Competitively inhibit the adsorption of plasminogen on fibrin, prevent its activation, protect fibrin from being degraded and dissolved by plasmin, and achieve hemostatic effect; at the same time, directly inhibit the activity of plasmin, reduce the effect of plasmin in activating complement, and prevent the occurrence of hereditary angioedema.
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4-(Aminomethyl)cyclohexanecarboxylic acid
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