argatroban Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
thromboxane A2-receptor antagonists; antithrombotic agents 239 74863-84-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • argatroban
  • argatroban sodium
  • argatroban hydrate
  • novastan
  • argatroban monohydrate
  • Molecular weight: 508.64
  • Formula: C23H36N6O5S
  • CLOGP: -0.57
  • LIPINSKI: 3
  • HAC: 11
  • HDO: 6
  • TPSA: 177.71
  • ALOGS: -3.48
  • ROTB: 8

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 16 % Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution) 0.17 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.46 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 30, 2000 FDA PFIZER

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Heparin-induced thrombocytopenia 259.61 50.87 48 905 4501 53343612
Coagulation time prolonged 192.06 50.87 31 922 1293 53346820
Activated partial thromboplastin time prolonged 134.76 50.87 30 923 7029 53341084
International normalised ratio increased 111.70 50.87 39 914 47722 53300391
Oesophageal intramural haematoma 51.60 50.87 7 946 84 53348029

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Heparin-induced thrombocytopenia 306.94 40.59 66 1292 5648 32506520
Activated partial thromboplastin time prolonged 117.48 40.59 33 1325 8422 32503746
Coagulation time prolonged 114.87 40.59 23 1335 1365 32510803
International normalised ratio increased 84.48 40.59 41 1317 48994 32463174
Cerebral infarction 65.96 40.59 29 1329 27585 32484583
Haemorrhage 55.35 40.59 31 1327 49417 32462751
Coagulopathy 51.42 40.59 22 1336 19555 32492613
Disseminated intravascular coagulation 51.01 40.59 23 1335 23153 32489015

Pharmacologic Action:

SourceCodeDescription
ATC B01AE03 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Direct thrombin inhibitors
FDA MoA N0000009963 Thrombin Inhibitors
FDA EPC N0000175518 Direct Thrombin Inhibitor
MeSH PA D000925 Anticoagulants
MeSH PA D000991 Antithrombins
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006401 Hematologic Agents
MeSH PA D010975 Platelet Aggregation Inhibitors
MeSH PA D011480 Protease Inhibitors
MeSH PA D015842 Serine Proteinase Inhibitors
FDA EPC N0000175980 Anti-coagulant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Percutaneous coronary intervention indication 415070008
Thrombosis Prevention in Heparin-Induced Thrombocytopenia indication
Thrombosis in Heparin Induced Thrombocytopenia indication
Peptic ulcer contraindication 13200003 DOID:750
Duodenal ulcer disease contraindication 51868009 DOID:1724
Blood coagulation disorder contraindication 64779008 DOID:1247
Procedure on central nervous system contraindication 118679007
Bleeding contraindication 131148009
Disease of liver contraindication 235856003 DOID:409
Lumbar puncture contraindication 277762005
Surgical procedure on eye proper contraindication 373353005
Surgical procedure contraindication 387713003
Gastric ulcer contraindication 397825006 DOID:10808
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.3 acidic
pKa2 9.73 acidic
pKa3 9.18 Basic
pKa4 3.93 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
50MG/50ML (1MG/ML) ARGATROBAN IN SODIUM CHLORIDE EAGLE PHARMS N022434 June 29, 2011 DISCN INJECTABLE INTRAVENOUS 7589106 Sept. 26, 2027 METHOD OF TREATING THROMBOSIS
50MG/50ML (1MG/ML) ARGATROBAN IN SODIUM CHLORIDE EAGLE PHARMS N022434 June 29, 2011 DISCN INJECTABLE INTRAVENOUS 7687516 Sept. 26, 2027 METHOD OF TREATING AN ARGATROBAN TREATABLE CONDITION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prothrombin Enzyme INHIBITOR Ki 7.40 WOMBAT-PK CHEMBL
Coagulation factor X Enzyme Ki 4.28 CHEMBL
Tissue-type plasminogen activator Enzyme Ki 4.06 CHEMBL
Cationic trypsin Enzyme Ki 5.54 CHEMBL
Prothrombin Enzyme Ki 8.02 CHEMBL

External reference:

IDSource
4021239 VUID
N0000148682 NUI
D00181 KEGG_DRUG
15202 RXNORM
C0048470 UMLSCUI
CHEBI:94385 CHEBI
CHEMBL1166 ChEMBL_ID
DB00278 DRUGBANK_ID
C031942 MESH_SUPPLEMENTAL_RECORD_UI
6385 IUPHAR_LIGAND_ID
141396-28-3 SECONDARY_CAS_RN
IY90U61Z3S UNII
92722 PUBCHEM_CID
15642 MMSL
63931 MMSL
d04698 MMSL
008966 NDDF
116508003 SNOMEDCT_US
398738008 SNOMEDCT_US
725736007 SNOMEDCT_US
4021239 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ARGATROBAN HUMAN PRESCRIPTION DRUG LABEL 1 0078-0930 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 27 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 0143-9288 INJECTION 250 mg INTRAVENOUS NDA 25 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 0143-9377 INJECTION 50 mg INTRAVENOUS NDA 25 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 0143-9559 INJECTION 50 mg INTRAVENOUS NDA 25 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 0143-9674 INJECTION 250 mg INTRAVENOUS NDA 25 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 0409-1140 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 26 sections
ARGATROBAN HUMAN PRESCRIPTION DRUG LABEL 1 16729-430 INJECTION 1 mg INTRAVENOUS NDA 27 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 25021-414 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 27 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 42023-182 INJECTION 250 mg INTRAVENOUS ANDA 29 sections
Argatroban Human Prescription Drug Label 1 55150-241 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 25 sections
Argatroban Human Prescription Drug Label 1 63323-526 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 26 sections
ARGATROBAN Human Prescription Drug Label 1 65145-126 INJECTION 50 mg INTRAVENOUS ANDA 25 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 65219-429 INJECTION 50 mg INTRAVENOUS ANDA 28 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 67457-212 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 26 sections
Argatroban Human Prescription Drug Label 1 68083-141 SOLUTION 125 mg INTRAVENOUS ANDA 26 sections
Argatroban HUMAN PRESCRIPTION DRUG LABEL 1 70121-1037 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 25 sections