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1197-18-8

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1197-18-8 Usage

Properties

Amstat is an antifibrinolytic drug, commonly called Tranexamic acid. Tranexamic acid is a white crystalline powder. It is freely soluble in water and in glacial acetic acid and is very slightly soluble in ethanol and practically insoluble in ether.

Coagulation and hemostasis drugs

Tranexamic acid is a derivative of aminomethylbenzoic acid, and a kind of antifibrinolytic drugs to stop bleeding. The hemostasis mechanism of tranexamic acid is similar to aminocaproic acid and aminomethylbenzoic acid, but the effect is stronger. The strength is 7 to 10 times of aminocaproic acid, 2 times of aminomethylbenzoic acid, but toxicity is similar. The chemical structure of tranexamic acid is similar to lysine, competitive inhibition of plasmin original in fibrin adsorption, to prevent their activation, protection fiber protein not to degrade by plasmin and dissolve, eventually achieve hemostasis. Applicable in the treatment of acute or chronic, localized or systemic primary fiber fibrinolytic hyperthyroidism caused by bleeding, such as obstetric hemorrhage, renal hemorrhage, hemorrhage of hypertrophy of the prostate, hemophilia, pulmonary tuberculosis hemoptysis, stomach bleeding, after operation of liver, lung, spleen and other viscera hemorrhage; also can be used in surgery when abnormal bleeding etc.. Clinical tranexamic acid has effect significantly to insect bites disease, dermatitis and eczema, simple purpura, chronic urticaria, artificial sex urticaria, toxic eruption and eruption. And also has a certain effect on erythroderma, scleroderma, systemic lupus erythematosus (SLE), Erythema multiforme, shingles and alopecia areata. Treatment of hereditary angioedema effect is also good. In the treatment of Chloasma, general medicine is effective about 3 weeks, markedly effective 5 weeks, a course of 60 days. Given orally in doses of 0.25 ~ 0.5 g, a day 3 ~ 4 times. A few patients can nausea, fatigue, pruritus, abdominal discomfort, and diarrhea side effects after withdrawal symptoms disappear.

Indications

Various bleedings caused by acute or chronic, localized or systemic primary hyperfibrinolysis; secondary hyperfibrinolytic state caused by disseminated intravascular coagulation. Generally do not use this product before heparinization. Trauma or surgical bleeding in tissue and organs with abundant plasminogen activators such as prostate, urethra, lung, brain, uterus, adrenal glands, and thyroid. An antagonist of tissue plasminogen activator (t-PA), streptokinase, and urokinase. Fibrinolytic hemorrhage caused by artificial abortion, early placental detachment, stillbirth and amniotic fluid embolism; and increased menorrhagia caused by pathological intrauterine fibrinolysis. Cerebral neuropathy mild bleeding, such as subarachnoid hemorrhage and intracranial aneurysm hemorrhage, the effect of Amstat in this condition is better than that of other anti-fibrinolytic agents. Special attention must be paid to the risk of cerebral edema or cerebral infarction. ?For severe patients with surgical indications, this product can only be used as an adjuvant drug. For the treatment of hereditary angioneurotic edema, it can reduce the number and severity of episodes. Used in patients with hemophilia for their active hemorrhage in combination with others drug. Hemophilia patients with factor VIII or factor IX deficiency in their tooth extraction or oral surgery in case of operating bleeding.

Mechanism of action

Different sources of media describe the Mechanism of action of 1197-18-8 differently. You can refer to the following data:
1. Tranexamic acid is a synthetic lysine amino acid derivative, which diminishes the dissolution of hemostatic fibrin by plasmin. In the presence of tranexamic acid, the lysine receptor binding sites of plasmin for fibrin are occupied, preventing binding to fibrin monomers, thus preserving and stabilizing fibrin’s matrix structure.
2. Tranexamic acid can also be viewed as a structural analog of lysine. It is presumed that it works by the same mechanism as aminocaproic acid; however, it is 6–10 times more active. It inhibits action of a plasmin and plasminogen inhibitor, and has a hemostatic effect.

Pharmacokinetics

After a single oral administration of two 650 mg tablets of LYSTEDA, the peak plasma concentration (Cmax ) occurred at approximately 3 hours (Tmax ). The absolute bioavailability of LYSTEDA in women aged 18-49 is approximately 45%. Following multiple oral doses (two 650 mg tablets three times daily). administration of LYSTEDA for 5 days, the mean C max increased by approximately 19% and the mean area under the plasma concentration-time curve (AUC) remained unchanged, compared to a single oral dose administration (two 650 mg tablets). Plasma concentrations reached steady state at the 5th dose of LYSTEDA on Day 2.

Side effects

The table below contains some of the side-effects associated with tranexamic acid, although these occur only rarely. ▼▲ Tranexamic acid side-effects What can I do if I experience this? Feeling or being sick Stick to simple meals avoid rich and spicy food. If you are not already doing so, try taking the tablets after meals Diarrhoea Drink plenty of water to replace the lost fluids Eyesight problems (such as problems with your colour vision) Let your doctor know about this as soon as possible as your treatment will need to be reviewed

Chemical Properties

White or almost white, crystalline powder.

Originator

Anvitoff,Knoll,W. Germany,1967

Uses

Different sources of media describe the Uses of 1197-18-8 differently. You can refer to the following data:
1. Used as lysine analogue to characterize binding sites in plasminogen
2. Fibrinolysis, the cleavage of fibrin by plasmin, is a normal step in the dissolution of fibrin clots after wound repair. Tranexamic acid is an inhibitor of fibrinolysis that blocks the interaction of plasmin with fibrin (IC50 = 3.1 μM). It is a lysine mimetic that binds the lysine binding site in plasmin. Antifibrinolytic agents have value when fibrinolytic activity is abnormally high or when coagulation is impaired.

Manufacturing Process

In an autoclave, 2 grams of a mixture of cis- and trans-4- aminomethylcyclohexane-1-carboxylic acid, which is obtained by catalytic reduction of p-aminomethylbenzoic acid in the presence of platinum catalyst and contains 60% by weight of cis-isomer was reacted at 200°C, for 8 hours with 20 ml of ethyl alcohol in which 0.44 gram of sodium metal had been dissolved. After cooling, the reaction solution was concentrated under a reduced pressure to give a white residue. This residue was dissolved in 40 ml of water and passed through a column of a strongly acidic cation ion_x0002_exchanger resin (NH4+). The eluate was concentrated under reduced pressure to form a white mass. An adequate amount of acetone was added thereto and 1.95 grams of white powder was obtained. This powder was recrystallized from water-acetone to give 1.85 grams (yield, 92.5%) of white crystalline powder having a melting point of 380° to 390°C (decomposition). This product was identified as trans-4-aminomethylcyclohexane-1-carboxylic acid by means of infrared spectrum.

Therapeutic Function

Coagulant

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Flammability and Explosibility

Notclassified

Clinical Use

Haemostatic agent

Synthesis

Tranexamic acid, trans-4-(aminomethyl)cyclohexane carboxylic acid (24.4.5), is synthesized from 4-methylbenzonitrile. Oxidation of the methyl group gives the mononitrile of terephthalic acid 24.4.2. The cyano group in this compound is reduced by hydrogen using Raney nickel as a catalyst. The benzene ring of the resulting 4- aminomethylbenzoic acid (24.4.3) is reduced to a cyclohexane moiety by hydrogen and a platinum catalyst, which forms an isomeric mixture of 4-aminomethylcyclohexane carboxylic acids (24.4.4), and the desired trans-isomer 24.4.5 is isolated by crystallization of the mixture of its sodium salts.

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Tranexamic acid is excreted as unchanged drug mainly by urinary excretion via glomerular filtration.

Check Digit Verification of cas no

The CAS Registry Mumber 1197-18-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 7 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1197-18:
(6*1)+(5*1)+(4*9)+(3*7)+(2*1)+(1*8)=78
78 % 10 = 8
So 1197-18-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-

1197-18-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A0236)  trans-4-(Aminomethyl)cyclohexanecarboxylic Acid  >98.0%(GC)(T)

  • 1197-18-8

  • 5g

  • 90.00CNY

  • Detail
  • TCI America

  • (A0236)  trans-4-(Aminomethyl)cyclohexanecarboxylic Acid  >98.0%(GC)(T)

  • 1197-18-8

  • 25g

  • 350.00CNY

  • Detail
  • TCI America

  • (A0236)  trans-4-(Aminomethyl)cyclohexanecarboxylic Acid  >98.0%(GC)(T)

  • 1197-18-8

  • 100g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (B21742)  trans-4-(Aminomethyl)cyclohexanecarboxylic acid, 97%   

  • 1197-18-8

  • 10g

  • 840.0CNY

  • Detail
  • Alfa Aesar

  • (B21742)  trans-4-(Aminomethyl)cyclohexanecarboxylic acid, 97%   

  • 1197-18-8

  • 50g

  • 1566.0CNY

  • Detail
  • Alfa Aesar

  • (B21742)  trans-4-(Aminomethyl)cyclohexanecarboxylic acid, 97%   

  • 1197-18-8

  • 250g

  • 4797.0CNY

  • Detail
  • Sigma-Aldrich

  • (T1810000)  Tranexamicacid  European Pharmacopoeia (EP) Reference Standard

  • 1197-18-8

  • T1810000

  • 1,880.19CNY

  • Detail
  • USP

  • (1672745)  Tranexamicacid  United States Pharmacopeia (USP) Reference Standard

  • 1197-18-8

  • 1672745-200MG

  • 4,662.45CNY

  • Detail

1197-18-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name tranexamic acid

1.2 Other means of identification

Product number -
Other names Amstat

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1197-18-8 SDS

1197-18-8Synthetic route

concentrated ammonia water

concentrated ammonia water

trans-4-cyanocyclohexane-1-ylcarboxylic acid
15177-68-1

trans-4-cyanocyclohexane-1-ylcarboxylic acid

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Conditions
ConditionsYield
aluminum nickel In methanol; water; acetone92%
methyl 4-(acetamidomethyl)cyclohexane-1-carboxylate
51782-10-6

methyl 4-(acetamidomethyl)cyclohexane-1-carboxylate

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Conditions
ConditionsYield
With barium hydroxide octahydrate; hydrogen In ethanol; water at 250℃; under 7500.75 - 30003 Torr; for 7.5h; Pressure; Temperature;85.11%
methyl trans-4-cyanocyclohexane-1-carboxylate
19145-95-0

methyl trans-4-cyanocyclohexane-1-carboxylate

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Conditions
ConditionsYield
With triethylamine In hydrous methanol
C12H17NO5
953817-12-4

C12H17NO5

A

maleic anhydride
108-31-6

maleic anhydride

B

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 1h; Kinetics;
4-cyanobenzoic acid methyl ester
1129-35-7

4-cyanobenzoic acid methyl ester

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; hydrogen; ruthenium-carbon composite / 7 h / 40 °C / 6750.68 - 7500.75 Torr
2: hydrogen; potassium acetate / toluene / 13 h / 150 °C / 7500.75 - 75007.5 Torr
3: hydrogen; barium hydroxide octahydrate / ethanol; water / 7.5 h / 250 °C / 7500.75 - 30003 Torr
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-4-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid

trans-4-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; sodium hydroxide100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans 4-(tert-butyloxycarbonylamino)methylcyclohexanecarboxylic acid
27687-14-5

trans 4-(tert-butyloxycarbonylamino)methylcyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 20℃; for 18h; Industrial scale;97%
With sodium hydrogencarbonate In 1,4-dioxane95%
With sodium hydroxide In water; tert-butyl alcohol for 18h; Ambient temperature;94%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

(1r,4r)-4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexane-1-carboxylic acid
27687-12-3

(1r,4r)-4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexane-1-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h;97%
With sodium hydroxide
With sodium hydroxide for 1h;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

Allyl chloroformate
2937-50-0

Allyl chloroformate

trans-4-allyloxycarbonylaminomethylcyclohexanecarboxylic acid
177583-51-6

trans-4-allyloxycarbonylaminomethylcyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane97%
ethanol
64-17-5

ethanol

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

ethyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride
19878-18-3

ethyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 70℃; for 1.16667h;96%
5-Phenylpentanoic acid
2270-20-4

5-Phenylpentanoic acid

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans--4-aminomethyl>-cyclohexanecarboxylic acid

trans--4-aminomethyl>-cyclohexanecarboxylic acid

Conditions
ConditionsYield
95%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(1R,4R)-4-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]cyclohexane-1-carboxylic acid
167690-53-1

(1R,4R)-4-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]cyclohexane-1-carboxylic acid

Conditions
ConditionsYield
Stage #1: trans-4-aminomethyl-cyclohexyl-carboxylic acid With triethylamine In water at 20℃;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In water; acetonitrile at 20℃;
95%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
With sodium carbonate In N,N-dimethyl-formamide
Stage #1: trans-4-aminomethyl-cyclohexyl-carboxylic acid With potassium carbonate In acetonitrile for 0.333333h;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In acetonitrile for 2h; Cooling with ice;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

2,5-dichlorobenzenesulphonyl chloride
5402-73-3

2,5-dichlorobenzenesulphonyl chloride

4-({[(2,5-dichlorophenyl)sulfonyl]amino}methyl)cyclohexanecarboxylic acid

4-({[(2,5-dichlorophenyl)sulfonyl]amino}methyl)cyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=8 - 9;94%
methanolic hydrochloric acid

methanolic hydrochloric acid

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-4-(aminomethyl)cyclohexanemethanol hydrochloride
178972-33-3

trans-4-(aminomethyl)cyclohexanemethanol hydrochloride

Conditions
ConditionsYield
With borane In tetrahydrofuran; methanol93%
icewater-cooled methanol

icewater-cooled methanol

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-(4-aminomethyl)cyclohexane-1-carboxylic acid methyl ester hydrochloride

trans-(4-aminomethyl)cyclohexane-1-carboxylic acid methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride92.1%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

ethylene glycol
107-21-1

ethylene glycol

2-hydroxyethyl-trans-4-(aminomethyl)cyclohexylcarboxylate hydrochloride
1034250-62-8

2-hydroxyethyl-trans-4-(aminomethyl)cyclohexylcarboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 75℃; for 1h;92%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

4-bromobenzenesulfonyl chloride
98-58-8

4-bromobenzenesulfonyl chloride

trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid
674819-27-3

trans-4-[(4-bromobenzenesulfonyl)aminomethyl]cyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=8 - 9;91%
With sodium hydroxide In water at 20℃; for 24h;21%
With sodium hydroxide at 20℃; for 48h;
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

2-methoxyethyl-trans-4-(aminomethyl)cyclohexylcarboxylate hydrochloride
1034250-63-9

2-methoxyethyl-trans-4-(aminomethyl)cyclohexylcarboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 75℃; for 1h;90%
p-fluorobenzoic acid succinimidyl ester
66134-67-6

p-fluorobenzoic acid succinimidyl ester

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-4-(4-fluorobenzamidomethyl)cyclohexanecarboxylic acid

trans-4-(4-fluorobenzamidomethyl)cyclohexanecarboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;89%
maleic anhydride
108-31-6

maleic anhydride

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

C12H17NO5
953817-12-4

C12H17NO5

Conditions
ConditionsYield
Stage #1: trans-4-aminomethyl-cyclohexyl-carboxylic acid With sodium hydroxide In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: maleic anhydride In tetrahydrofuran for 12h; Inert atmosphere; Reflux;
87%
In 1,4-dioxane at 20℃; for 48h;
Stage #1: maleic anhydride; trans-4-aminomethyl-cyclohexyl-carboxylic acid In N,N-dimethyl-formamide at 15 - 25℃;
Stage #2: With 2,4,6-trimethyl-pyridine In N,N-dimethyl-formamide at -5 - 5℃; for 0.333333h;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

4-[(4-acetylaminobenzenesulfonylamino)methyl]cyclohexane carboxylic acid

4-[(4-acetylaminobenzenesulfonylamino)methyl]cyclohexane carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=8 - 9;87%
maleic anhydride
108-31-6

maleic anhydride

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid
69907-68-2

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; for 6h; Inert atmosphere;86%
With acetic acid at 20℃;
With acetic acid at 20℃;
phthalic anhydride
85-44-9

phthalic anhydride

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

(1R*,4R*)-4-((1,3-dioxoisoindolin-2-yl)methyl)cyclohexane-1-carboxylic acid
80191-01-1

(1R*,4R*)-4-((1,3-dioxoisoindolin-2-yl)methyl)cyclohexane-1-carboxylic acid

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;85%
In acetic acid for 16h; Heating;80%
at 150℃; for 0.75h; Yield given;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-[(toluene-4-sulfonylamino)methyl]cyclohexanecarboxylic acid
38697-79-9

4-[(toluene-4-sulfonylamino)methyl]cyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=8 - 9;84%
With sodium hydroxide at 20℃; for 48h;
With sodium hydroxide In chloroform; water at 20℃; for 48h;
With sodium hydroxide In chloroform; water at 20℃; for 72h;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

methyl carbamimidothioate bis(sulfate)
867-44-7, 2260-00-6, 14527-26-5

methyl carbamimidothioate bis(sulfate)

4-guanidinomethylcyclohexanecarboxylic acid
38697-86-8

4-guanidinomethylcyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water Ambient temperature;83%
L-arginine
74-79-3

L-arginine

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

trifluoroacetic acid
76-05-1

trifluoroacetic acid

6-((S)-1-{[(E)-Allyloxycarbonylimino]-amino-methyl}-3-tert-butoxycarbonylamino-piperidin-2-yloxy)-hexanoic acid
241146-47-4

6-((S)-1-{[(E)-Allyloxycarbonylimino]-amino-methyl}-3-tert-butoxycarbonylamino-piperidin-2-yloxy)-hexanoic acid

4-[((S)-2-Amino-5-guanidino-pentanoylamino)-methyl]-cyclohexanecarboxylic acid ((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-amide; compound with trifluoro-acetic acid

4-[((S)-2-Amino-5-guanidino-pentanoylamino)-methyl]-cyclohexanecarboxylic acid ((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-amide; compound with trifluoro-acetic acid

Conditions
ConditionsYield
With aminomethylated polystyrene resin Solid phase reaction;83%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

trans-4-[N-(3',4'-dihydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylic acid
81519-03-1

trans-4-[N-(3',4'-dihydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylic acid

Conditions
ConditionsYield
In methanol82.7%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

allyl alcohol
107-18-6

allyl alcohol

allyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride

allyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 75℃; for 1h;82%
With thionyl chloride at 0 - 75℃; for 1.16667h;82%
1-Naphthalenesulfonyl chloride
85-46-1

1-Naphthalenesulfonyl chloride

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

4-[(naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid
192322-99-9

4-[(naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃; sulfonylation;80%
With sodium hydroxide In chloroform at 20℃; for 48h;
With sodium hydroxide In chloroform; water at 20℃; for 72h;
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

{[2-methyl-4-oxo-3-(4-chlorophenyl)-4H-chromen-7-yl]oxy}acetic acid

{[2-methyl-4-oxo-3-(4-chlorophenyl)-4H-chromen-7-yl]oxy}acetic acid

trans-4-{[({[2-methyl-4-oxo-3-(4-chlorophenyl)-4H-chromen-7-yl]oxy}acetyl)amino]methyl}cyclohexanecarboxylic acid

trans-4-{[({[2-methyl-4-oxo-3-(4-chlorophenyl)-4H-chromen-7-yl]oxy}acetyl)amino]methyl}cyclohexanecarboxylic acid

Conditions
ConditionsYield
Stage #1: {[2-methyl-4-oxo-3-(4-chlorophenyl)-4H-chromen-7-yl]oxy}acetic acid With 1-hydroxy-pyrrolidine-2,5-dione; diisopropyl-carbodiimide In 1,4-dioxane at 20℃; for 2h;
Stage #2: trans-4-aminomethyl-cyclohexyl-carboxylic acid With sodium hydrogencarbonate In 1,4-dioxane; water
79%
1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-ylmethyl)cyclohexanecarboxylic acid
1361130-80-4

4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-ylmethyl)cyclohexanecarboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Reflux;78%
trans-4-aminomethyl-cyclohexyl-carboxylic acid
1197-18-8

trans-4-aminomethyl-cyclohexyl-carboxylic acid

2-[(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]pyran-3-yl)oxy]acetic acid
325737-63-1

2-[(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]pyran-3-yl)oxy]acetic acid

N-[2-[(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]pyran-3-yl)oxy]acetyl]-trans-4-aminomethylcyclohexanecarboxylic acid

N-[2-[(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]pyran-3-yl)oxy]acetyl]-trans-4-aminomethylcyclohexanecarboxylic acid

Conditions
ConditionsYield
Stage #1: 2-[(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]pyran-3-yl)oxy]acetic acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In 1,4-dioxane for 2h;
Stage #2: trans-4-aminomethyl-cyclohexyl-carboxylic acid With sodium hydroxide In 1,4-dioxane; water
71%

1197-18-8Relevant articles and documents

Lundstroem et al.

, p. 307,309 (1976)

READY-TO-USE TRANEXAMIC ACID INTRAVENOUS SOLUTION

-

, (2020/04/09)

Ready-to-use, stable aqueous intravenous tranexamic acid compositions are provided.

Design, synthesis and in vitro kinetic study of tranexamic acid prodrugs for the treatment of bleeding conditions

Karaman, Rafik,Ghareeb, Hiba,Dajani, Khuloud Kamal,Scrano, Laura,Hallak, Hussein,Abu-Lafi, Saleh,Mecca, Gennaro,Bufo, Sabino A.

, p. 615 - 635 (2013/09/02)

Based on density functional theory (DFT) calculations for the acid-catalyzed hydrolysis of several maleamic acid amide derivatives four tranexamic acid prodrugs were designed. The DFT results on the acid catalyzed hydrolysis revealed that the reaction rate-limiting step is determined on the nature of the amine leaving group. When the amine leaving group was a primary amine or tranexamic acid moiety, the tetrahedral intermediate collapse was the rate-limiting step, whereas in the cases by which the amine leaving group was aciclovir or cefuroxime the rate-limiting step was the tetrahedral intermediate formation. The linear correlation between the calculated DFT and experimental rates for N-methylmaleamic acids 1-7 provided a credible basis for designing tranexamic acid prodrugs that have the potential to release the parent drug in a sustained release fashion. For example, based on the calculated B3LYP/6-31G(d,p) rates the predicted t1/2 (a time needed for 50 % of the prodrug to be converted into drug) values for tranexamic acid prodrugs ProD 1-ProD 4 at pH 2 were 556 h [50.5 h as calculated by B3LYP/311+G(d,p)] and 6.2 h as calculated by GGA: MPW1K), 253 h, 70 s and 1.7 h, respectively. Kinetic study on the interconversion of the newly synthesized tranexamic acid prodrug ProD 1 revealed that the t1/2 for its conversion to the parent drug was largely affected by the pH of the medium. The experimental t1/2 values in 1 N HCl, buffer pH 2 and buffer pH 5 were 54 min, 23.9 and 270 h, respectively. Graphical Abstract: [Figure not available: see fulltext.]

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