Product Name

  • Name

    Argatroban

  • EINECS 638-764-8
  • CAS No. 74863-84-6
  • Article Data7
  • CAS DataBase
  • Density 1.47 g/cm3
  • Solubility
  • Melting Point 188-189 °C
  • Formula C23H36N6O5S
  • Boiling Point 801.3 °C at 760 mmHg
  • Molecular Weight 508.642
  • Flash Point 438.4 °C
  • Transport Information
  • Appearance white to off-white crystalline solid
  • Safety
  • Risk Codes R20/21/22; R51/53
  • Molecular Structure Molecular Structure of 74863-84-6 (Argatroban)
  • Hazard Symbols Xn,N
  • Synonyms 2-Piperidinecarboxylicacid,1-[5-[(aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-,[2R-[1(2S*),2a,4b]]-[partial]-;Acova;Argatra;Argipidin;Argipidine;DK 7419;GN 1600;MCI 9038;MD 805;MQPA;Novastan;OM 805;Slonnon;
  • PSA 186.09000
  • LogP 3.65110

Synthetic route

(2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulphonyl)-L-arginyl]-4-methyl-2-piperidine carboxylic acid
74874-10-5

(2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulphonyl)-L-arginyl]-4-methyl-2-piperidine carboxylic acid

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In methanol; acetic acid at 85℃; under 6375.64 Torr; for 8h; Product distribution / selectivity;93%
With palladium on activated charcoal; hydrogen; acetic acid In ethanol under 760.051 Torr;
C30H37N7O7S
367952-84-9

C30H37N7O7S

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol; acetic acid at 20℃; under 760 Torr; for 20h;90%
(2R,4R)-1-(Nω′-((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-4-methylpiperidine-2-carboxylic acid

(2R,4R)-1-(Nω′-((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-4-methylpiperidine-2-carboxylic acid

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 20℃; under 760.051 Torr; for 16h;88%
4-methylpiperidin
626-58-4

4-methylpiperidin

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C
2.1: s-BuLi; TMEDA / diethyl ether / -90 °C
2.2: 35 percent / diethyl ether / -90 - 20 °C
3.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C
4.1: 100 percent / HCl / ethyl acetate / 20 °C
5.1: 86 percent / Et3N / CH2Cl2 / 0 °C
6.1: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
4-methylpiperidine-1-carboxylic acid tert-butyl ester
123387-50-8

4-methylpiperidine-1-carboxylic acid tert-butyl ester

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: s-BuLi; TMEDA / diethyl ether / -90 °C
1.2: 35 percent / diethyl ether / -90 - 20 °C
2.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C
3.1: 100 percent / HCl / ethyl acetate / 20 °C
4.1: 86 percent / Et3N / CH2Cl2 / 0 °C
5.1: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
Nα-(tert-butoxycarbonyl)-Nω-nitro-arginine

Nα-(tert-butoxycarbonyl)-Nω-nitro-arginine

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / -35 °C
2: 100 percent / HCl / ethyl acetate / 20 °C
3: 86 percent / Et3N / CH2Cl2 / 0 °C
4: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
8-(chlorosulphonyl)-3-methylquinoline
74863-82-4

8-(chlorosulphonyl)-3-methylquinoline

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / Et3N / CH2Cl2 / 0 °C
2: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
trans-benzyl 4-methylpipecolic acid ester

trans-benzyl 4-methylpipecolic acid ester

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / HCl / ethyl acetate / 20 °C
2: 86 percent / Et3N / CH2Cl2 / 0 °C
3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
benzyl trans-N-Boc-4-methylpipecolic acid ester

benzyl trans-N-Boc-4-methylpipecolic acid ester

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / HCl / ethyl acetate / 0 - 20 °C
2: 100 percent / HCl / ethyl acetate / 20 °C
3: 86 percent / Et3N / CH2Cl2 / 0 °C
4: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
C16H29N5O8

C16H29N5O8

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / HCl / ethyl acetate / 20 °C
2: 86 percent / Et3N / CH2Cl2 / 0 °C
3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
C25H38N6O7
367952-82-7

C25H38N6O7

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / HCl / ethyl acetate / 20 °C
2: 86 percent / Et3N / CH2Cl2 / 0 °C
3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
C20H30N6O5*ClH

C20H30N6O5*ClH

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / Et3N / CH2Cl2 / 0 °C
2: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
View Scheme
Nω,Nω'-bis((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfon-yl)-L-arginine

Nω,Nω'-bis((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfon-yl)-L-arginine

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,2,2-trifluoroethanol / 20 °C
2: sodium hydroxide / water; ethanol / 1 h / Reflux
3: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
View Scheme
1-(Nω,Nω'-bis(1-(benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-N-(6-bromopyridin-2-yl)-4-methylpiperidine-2-carboxamide

1-(Nω,Nω'-bis(1-(benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-N-(6-bromopyridin-2-yl)-4-methylpiperidine-2-carboxamide

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; ethanol / 1 h / Reflux
2: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
View Scheme
Boc-Arg(Z)2-OH
120267-95-0

Boc-Arg(Z)2-OH

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: trifluoroacetic acid / dichloromethane / 0 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 16 h / 0 - 20 °C
3: 2,2,2-trifluoroethanol / 20 °C
4: sodium hydroxide / water; ethanol / 1 h / Reflux
5: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
View Scheme
H-L-Arg(Cbz)2-OH

H-L-Arg(Cbz)2-OH

argatroban
74863-84-6

argatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 16 h / 0 - 20 °C
2: 2,2,2-trifluoroethanol / 20 °C
3: sodium hydroxide / water; ethanol / 1 h / Reflux
4: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
View Scheme

Argatroban History

In 2000, argatroban(74863-84-6) was licensed by the Food and Drug Administration (FDA) for prophylaxis or treatment of thrombosis in patients with heparin-induced thrombocytopenia (HIT). In 2002, it was approved for use during percutaneous coronary interventions in patients who have HIT or are at risk for developing it.

Argatroban Specification

The IUPAC name of Argatroban is (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid. With the CAS registry number 74863-84-6, it is also named as 2-Piperidinecarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. It is white to off-white crystalline solid.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.56; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.43; (4)ACD/LogD (pH 7.4): -0.45; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.02; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 11; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.674; (13)Molar Refractivity: 129.78 cm3; (14)Molar Volume: 345.7 cm3; (15)Polarizability: 51.45×10-24 cm3; (16)Surface Tension: 61.6 dyne/cm; (17)Enthalpy of Vaporization: 122.18 kJ/mol; (18)Vapour Pressure: 4.23E-27 mmHg at 25°C; (19)Rotatable Bond Count: 9; (20)Tautomer Count: 2; (21)Exact Mass: 508.246789; (22)MonoIsotopic Mass: 508.246789; (23)Topological Polar Surface Area: 189; (24)Heavy Atom Count: 35; (25)Complexity: 887.

Preparation of Argatroban: It can be obtained by the following reaction.


this product

Uses of Argatroban: It is used as an anticoagulant in individuals with thrombosis and heparin induced thrombocytopenia. The combination of argatroban and warfarin may raise the INR to greater than 5.0 without a significant increased risk of bleeding complications.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@@H]3N(C(=O)C(NS(=O)(=O)c1cccc2c1NCC(C2)C)CCC/N=C(\N)N)CC[C@@H](C)C3
2. InChI:InChI=1/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15,17,18-/m1/s1

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