enoxaparin   Click here for help

GtoPdb Ligand ID: 6811

Synonyms: Clexane® | enoxaparin sodium | Lovenox® | PK-10169 | RP-54563
Approved drug
enoxaparin is an approved drug (FDA (1993), FDA (2016))
Compound class: Synthetic organic
Comment: A Low-Molecular-Weight Heparin antithrombin-III activator. It consists of fractionated material from pig mucosa but the PubChem structure represents the major form.

Biosimilar drugs: The EMA approved enoxaparin biosimilars named Inhixa and Thorinane in 2016.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: enoxaparin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 39
Hydrogen bond donors 15
Rotatable bonds 22
Topological polar surface area 652.39
Molecular weight 1134.01
XLogP -13.27
No. Lipinski's rules broken 3
Click here for help
Canonical SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
Isomeric SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
InChI InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1993), FDA (2016))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
6-[5-acetamido-4,6-dihydroxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3-[5-(6-carboxy-4,5-dihydroxy-3-sulfooxyoxan-2-yl)oxy-6-(hydroxymethyl)-3-(sulfoamino)-4-sulfooxyoxan-2-yl]oxy-4-hydroxy-5-sulfooxyoxane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5452 enoxaparin sodium
Synonyms Click here for help
Clexane® | enoxaparin sodium | Lovenox® | PK-10169 | RP-54563
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9693050
Reactome Reaction Reactome logo R-HSA-140870, R-HSA-140872, R-HSA-140806, R-HSA-140791
Other databases
CAS Registry No. 679809-58-6
ChEMBL Ligand CHEMBL1201476
DrugBank Ligand DB01225
GtoPdb PubChem SID 178103417
Immunopaedia Search enoxaparin
PubChem CID 772
Search Google for chemical match using the InChIKey HTTJABKRGRZYRN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HTTJABKRGRZYRN
Search PubMed clinical trials enoxaparin sodium
Search PubMed titles enoxaparin sodium
Search PubMed titles/abstracts enoxaparin sodium
UniChem Compound Search for chemical match using the InChIKey HTTJABKRGRZYRN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HTTJABKRGRZYRN-UHFFFAOYSA-N
Wikipedia Enoxaparin