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74863-84-6 molecular structure
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(2R,4R)-1-[(2S)-5-[(diaminomethylidene)amino]-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl]-4-methylpiperidine-2-carboxylic acid

ChemBase ID: 163
Molecular Formular: C23H36N6O5S
Molecular Mass: 508.63414
Monoisotopic Mass: 508.24678928
SMILES and InChIs

SMILES:
S(=O)(=O)(N[C@H](C(=O)N1[C@H](C[C@@H](CC1)C)C(=O)O)CCCN=C(N)N)c1c2NC[C@@H](Cc2ccc1)C
Canonical SMILES:
NC(=NCCC[C@@H](C(=O)N1CC[C@H](C[C@@H]1C(=O)O)C)NS(=O)(=O)c1cccc2c1NC[C@@H](C2)C)N
InChI:
InChI=1S/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
InChIKey:
KXNPVXPOPUZYGB-XYVMCAHJSA-N

Cite this record

CBID:163 http://www.chembase.cn/molecule-163.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,4R)-1-[(2S)-5-[(diaminomethylidene)amino]-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl]-4-methylpiperidine-2-carboxylic acid
IUPAC Traditional name
(2R,4R)-1-[(2S)-5-[(diaminomethylidene)amino]-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl]-4-methylpiperidine-2-carboxylic acid
Synonyms
argatroban
Argatroban
CAS Number
74863-84-6
PubChem SID
46507650
160963626
PubChem CID
152951

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.0738177  H Acceptors
H Donor LogD (pH = 5.5) -0.9708456 
LogD (pH = 7.4) -0.9700008  Log P -0.96971005 
Molar Refractivity 133.5362 cm3 Polarizability 51.34015 Å3
Polar Surface Area 180.21 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.19  LOG S -3.36 
Solubility (Water) 2.21e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00278 external link
Item Information
Drug Groups approved; investigational
Description Argatroban is a direct, selective thrombin inhibitor. The American College of Cardiologists (ACC) recommend using bivalirudin or argatroban in patients who have had, or at risk for, heparin induced thrombocytopenia (HIT) and are undergoing percutaneous coronary intervention. Argatroban is a non-heparin anticoagulant shown to both normalize platelet count in patients with HIT and prevent the formation of thrombi. Parental anticoagulants must be stopped and a baseline activated partial thromboplastin time must be obtained prior to administering argatroban.
Indication Argatroban is indicated for prevention and treatment of thrombosis caused by heparin induced thrombocytopenia (HIT). It is also indicated for use in patients with, or at risk for, HIT who are undergoing percutaneous coronary intervention.
Pharmacology Argatroban is a synthetic direct thrombin inhibitor derived from L-arginine indicated as an anticoagulant for prophylaxis or treatment of thrombosis in patients with heparin-induced thrombocytopenia. Argatroban is a direct thrombin inhibitor that reversibly binds to the thrombin active site. Argatroban does not require the co-factor antithrombin III for antithrombotic activity. Argatroban exerts its anticoagulant effects by inhibiting thrombin-catalyzed or -induced reactions, including fibrin formation; activation of coagulation factors V, VIII, and XIII; protein C; and platelet aggregation. Argatroban is highly selective for thrombin with an inhibitory constant (Ki) of 0.04 µM. At therapeutic concentrations, Argatroban has little or no effect on related serine proteases (trypsin, factor Xa, plasmin, and kallikrein).
Argatroban is capable of inhibiting the action of both free and clot-associated thrombin.
Toxicity Excessive bleeding
Affected Organisms
Humans and other mammals
Biotransformation Liver via hydroxylation and aromatization of the 3-methyltetrahydroquinoline ring. Age and gender do not substantially affect the pharmacodynamic or pharmacokinetic profile of argatroban.
Absorption Bioavailability is 100% (intravenous).
Half Life 39 and 51 minutes
Protein Binding 54%
Elimination Argatroban is excreted primarily in the feces (65%), presumably through biliary secretion; 22% is eliminated via urine.
Distribution * 174 mL/kg
* 12.18 L [70-kg adult]
Clearance * 5.1 L/kg/hr [infusion doses up to 40?mcg/kg/min]
References
Di Nisio M, Middeldorp S, Buller HR: Direct thrombin inhibitors. N Engl J Med. 2005 Sep 8;353(10):1028-40. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Di Nisio M, Middeldorp S, Buller HR: Direct thrombin inhibitors. N Engl J Med. 2005 Sep 8;353(10):1028-40. Pubmed
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PATENTS

PATENTS

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