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Heparin Sodium
Also known as: (2s,3s,4r,5r,6r)-6-{[(2s,3s,4s,5r,6s)-6-{[(2r,3s,4s,5r)-2-carboxy-4,6-dihydroxy-5-(sulfooxy)oxan-3-yl]oxy}-2-hydroxy-4-(sulfomethyl)-5-(sulfooxy)oxan-3-yl]oxy}-3-{[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid, Hepflush, Chembl526514, Gtpl4214, S01xa14, Bdbm50480251
Molecular Formula
C26H41NO34S4
Molecular Weight
1039.9  g/mol
InChI Key
ZFGMDIBRIDKWMY-PASTXAENSA-N

A highly acidic mucopolysaccharide formed of equal parts of sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from six to twenty thousand. Heparin occurs in and is obtained from liver, lung, mast cells, etc., of vertebrates. Its function is unknown, but it is used to prevent blood clotting in vivo and vitro, in the form of many different salts.
1 2D Structure

Heparin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3S,4R,5R,6R)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(sulfooxymethyl)oxan-2-yl]oxy-6-[(2S,3S,4S,5R,6S)-6-[(2R,3S,4S,5R)-2-carboxy-4,6-dihydroxy-5-sulfooxyoxan-3-yl]oxy-2-hydroxy-4-(sulfomethyl)-5-sulfooxyoxan-3-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C26H41NO34S4/c1-4(28)27-7-9(30)8(29)6(2-52-63(43,44)45)53-24(7)56-15-10(31)11(32)25(58-19(15)21(36)37)55-13-5(3-62(40,41)42)14(60-64(46,47)48)26(59-22(13)38)57-16-12(33)17(61-65(49,50)51)23(39)54-18(16)20(34)35/h5-19,22-26,29-33,38-39H,2-3H2,1H3,(H,27,28)(H,34,35)(H,36,37)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t5-,6+,7+,8+,9+,10+,11+,12-,13-,14+,15-,16-,17+,18+,19-,22-,23?,24+,25+,26-/m0/s1
2.1.3 InChI Key
ZFGMDIBRIDKWMY-PASTXAENSA-N
2.1.4 Canonical SMILES
CC(=O)NC1C(C(C(OC1OC2C(C(C(OC2C(=O)O)OC3C(C(C(OC3O)OC4C(C(C(OC4C(=O)O)O)OS(=O)(=O)O)O)OS(=O)(=O)O)CS(=O)(=O)O)O)O)COS(=O)(=O)O)O)O
2.1.5 Isomeric SMILES
CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2C(=O)O)O[C@H]3[C@@H]([C@H]([C@H](O[C@@H]3O)O[C@H]4[C@@H]([C@H](C(O[C@H]4C(=O)O)O)OS(=O)(=O)O)O)OS(=O)(=O)O)CS(=O)(=O)O)O)O)COS(=O)(=O)O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Alpha Heparin

2. Alpha-heparin

3. Heparin

4. Heparin Sodium

5. Heparin, Sodium

6. Heparin, Unfractionated

7. Heparinic Acid

8. Liquaemin

9. Unfractionated Heparin

2.2.2 Depositor-Supplied Synonyms

1. (2s,3s,4r,5r,6r)-6-{[(2s,3s,4s,5r,6s)-6-{[(2r,3s,4s,5r)-2-carboxy-4,6-dihydroxy-5-(sulfooxy)oxan-3-yl]oxy}-2-hydroxy-4-(sulfomethyl)-5-(sulfooxy)oxan-3-yl]oxy}-3-{[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic Acid

2. Hepflush

3. Chembl526514

4. Gtpl4214

5. S01xa14

6. Bdbm50480251

7. (2s,3s,4r,5r,6r)-3-[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-(sulfooxymethyl)oxan-2-yl]oxy-6-[(2s,3s,4s,5r,6s)-6-[(2r,3s,4s,5r)-2-carboxy-4,6-dihydroxy-5-sulfooxyoxan-3-yl]oxy-2-hydroxy-4-(sulfomethyl)-5-sulfooxyoxan-3-yl]oxy-4,5-dihydroxyoxane-2-carboxylic Acid

2.2.3 Other Synonyms

1. 9005-49-6

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 1039.9 g/mol
Molecular Formula C26H41NO34S4
XLogP3-10.4
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count34
Rotatable Bond Count18
Exact Mass1039.0392821 g/mol
Monoisotopic Mass1039.0392821 g/mol
Topological Polar Surface Area589 Ų
Heavy Atom Count65
Formal Charge0
Complexity2140
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameHeparin sodium
Drug LabelIntravenous solutions with heparin sodium (derived from porcine intestinal mucosa) are sterile, nonpyrogenic fluids for intravenous administration. They contain no bacteriostat or antimicrobial agent or added buffer. Edetate disodium, anhydrous is ad...
Active IngredientHeparin sodium
Dosage FormInjectable
RouteInjection
Strength5,000 units/ml; 10,000 units/ml; 20,000 units/ml; 1,000 units/ml
Market StatusPrescription
CompanyHospira; Shenzhen Techdow; Sandoz; Pfizer; Fresenius Kabi Usa; Hikma Maple; Sagent Pharms

2 of 2  
Drug NameHeparin sodium
Drug LabelIntravenous solutions with heparin sodium (derived from porcine intestinal mucosa) are sterile, nonpyrogenic fluids for intravenous administration. They contain no bacteriostat or antimicrobial agent or added buffer. Edetate disodium, anhydrous is ad...
Active IngredientHeparin sodium
Dosage FormInjectable
RouteInjection
Strength5,000 units/ml; 10,000 units/ml; 20,000 units/ml; 1,000 units/ml
Market StatusPrescription
CompanyHospira; Shenzhen Techdow; Sandoz; Pfizer; Fresenius Kabi Usa; Hikma Maple; Sagent Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


Fibrinolytic Agents

Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN. (See all compounds classified as Fibrinolytic Agents.)


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  • INJECTABLE;INJECTION - 1,000 UNITS/ML
  • INJECTABLE;INJECTION - 10,000 UNITS/ML
  • INJECTABLE;INJECTION - 20,000 UNITS/ML
  • INJECTABLE;INJECTION - 5,000 UNITS/ML
  • INJECTABLE;INJECTION - 1,000 UNITS/ML
  • INJECTABLE;INJECTION - 10,000 UNITS/ML
  • INJECTABLE;INJECTION - 5,000 UNITS/ML
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