1.0 2009-07-05 03:16:06 UTC 2026-08-29 05:25:43 UTC T3D2566 Heparin SmallMolecule Heparin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 1,040 g/mol, Heparin is a heavy molecule. This endogenous compound has the chemical formula C26H41NO34S4 and exists as a solid at room temperature. It is detected in various tissues, including the liver, lung, mast cells, adipose tissue, adrenal cortex, adrenal gland, bladder, epidermis, fibroblasts, intestine, kidney, muscle, nerve cells, neuron, pancreas, placenta, platelet, prostate, skeletal muscle, spleen, stratum corneum, testes, and thyroid gland. Heparin functions biologically as a cofactor (PMC10901620, PMC3923226) and an anticoagulant (PMC10609962, PMC11417148). Its mechanism of action is antithrombin-dependent, acting mainly by accelerating the neutralization of certain activated coagulation factors by antithrombin. It interacts with antithrombin III, prothrombin, and factor X, and its antithrombotic effect correlates to the inhibition of factor Xa. Recorded protein targets include antithrombin-III (SERPINC1), prothrombin (F2), coagulation factor X (F10), P-selectin (SELP), platelet factor 4 (PF4), fibroblast growth factor receptor 2 (FGFR2), fibroblast growth factor 19 (FGF19), and fibroblast growth factor 2 (FGF2). Industrially, it is used as a softener and conditioner. In pharmaceutical and veterinary contexts, heparin is used as an antithrombotic agent, vasoprotective, or ophthalmological, with exposure routes including intraluminal, intraperitoneal, intravenous, irrigation, and subcutaneous administration. It is used to treat thrombosis (PMC11314107, PMC1492602, PMC3952273, PMC4165720, PMC9313999) and COVID-19 (PMC8000639), and it has therapeutic effects on stroke (PMC13479649) and inflammation (PMC10891305). Associated health effects include bleeding (PMC4165720, PMC9487313), thrombocytopenia (PMC1492602, PMC3952273), thrombosis (PMC3952273), osteoporosis (PMC10891305), and acute myeloid leukemia (PMC7500703). Drug Food Toxin Natural Toxin Animal Toxin Organic Compound Ester Drug Food Toxin Anticoagulant Fibrinolytic Agent Heparin Metabolite Animal Toxin Natural Compound alpha-Heparin Arteven Bemiparin Calcilean Calciparine Certoparin Clexane Clivarine Dalteparin Enoxaparin Eparina Fraxiparin Hep-lock Hepalean Heparin LEO Heparin Lock Flush Heparin sodium Heparin sulfate Heparin sulphate Heparinate Heparinic acid Heparinsodiumsalt Liquaemin Liquemin Multiparin Novoheparin Panheprin Thromboliquine C26H41NO34S4 1039.85 1039.039280225 9005-49-6 CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2[C@@H](O)O[C@H](O[C@H]3[C@H](O)[C@@H](OS(O)(=O)=O)C(O)O[C@H]3C(O)=O)[C@H](OS(O)(=O)=O)[C@H]2CS(O)(=O)=O)O[C@@H]1C(O)=O 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 ZFGMDIBRIDKWMY-PASTXAENSA-N Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Disaccharide sulfates Acetals Alkyl sulfates Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives O-glucuronides O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pyrans Secondary alcohols Sulfuric acid monoamides Sulfuric acid monoesters 1-o-glucuronide Acetal Alcohol Aliphatic heteromonocyclic compound Alkyl sulfate Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Disaccharide sulfate Glucuronic acid or derivatives Glycosyl compound Hemiacetal Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives O-glucuronide O-glycosyl compound Organic nitrogen compound Organic oxide Organic sulfuric acid or derivatives Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Pyran Secondary alcohol Sulfate-ester Sulfuric acid ester Sulfuric acid monoamide Sulfuric acid monoester Aliphatic heteromonocyclic compounds Detected and Not Quantified Endogenous Cytoplasm Extracellular Membrane Adipose Tissue Adrenal Cortex Adrenal Gland Bladder Epidermis Fibroblasts Intestine Kidney Liver Lung Mast Cell Muscle Nerve Cells Neuron Pancreas Placenta Platelet Prostate Skeletal Muscle Spleen Stratum Corneum Testes Thyroid Gland Heparin. SMP0000274 Fc Epsilon Receptor I Signaling in Mast Cells SMP0000358 Heparin Action Pathway SMP0123108 Heparin SMP0130950 Heparin Drug Metabolism Action Pathway SMP0143530 Solid White powder. solubility Soluble logp -13.2 logp -2.45 ALOGPS logs -1.96 ALOGPS solubility 6.57e+00 g/l ALOGPS average_mass 1039.85 ChemAxon mono_mass 1039.039280225 ChemAxon smiles CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2[C@@H](O)O[C@H](O[C@H]3[C@H](O)[C@@H](OS(O)(=O)=O)C(O)O[C@H]3C(O)=O)[C@H](OS(O)(=O)=O)[C@H]2CS(O)(=O)=O)O[C@@H]1C(O)=O ChemAxon formula C26H41NO34S4 ChemAxon 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 ChemAxon inchikey ZFGMDIBRIDKWMY-PASTXAENSA-N ChemAxon formal_charge 0 ChemAxon Intravenous, Irrigation, Subcutaneous, Intraperitoneal injection Heparin must be given parenterally as it is not absorbed through the gastrointestinal mucosa. It is usually given by iv infusion or deep sc injection. The onset of action is immediate after iv injection but can be delayed 20 to 60 minutes following sc injection. Plasma heparin concentrations may be increased and activated partial thromboplastin times (aPTTs) may be more prolonged in geriatric adults (older than 60 years of age) compared with younger adults. Heparin-induced thrombocytopenia (HIT) is caused by the formation of abnormal antibodies that activate platelets. Heparin occurs naturally in the human body, but the development of HIT antibodies suggests heparin sulfate may act as a hapten, and thus be targeted by the immune system. In HIT, the immune system forms antibodies against heparin when it is bound to a protein called platelet factor 4 (PF4). These antibodies are usually of the IgG class and their development usually takes about five days. However, those who have been exposed to heparin in the last few months may still have circulating IgG, as IgG-type antibodies generally continue to be produced even when their precipitant has been removed. This is similar to immunity against certain microorganisms, with the difference that the HIT antibody does not persist more than three months. HIT antibodies have been found in individuals with thrombocytopenia and thrombosis who had no prior exposure to heparin sulfate, but the majority are found in people who are receiving heparin. The IgG antibodies form a complex with heparin and PF4 in the bloodstream. The tail of the antibody then binds to the FcγIIa receptor, a protein on the surface of the platelet. This results in platelet activation and the formation of platelet microparticles, which initiate the formation of blood clots; the platelet count falls as a result, leading to thrombocytopenia. (Wikipedia) The cause of the serum aminotransferase elevations during heparin therapy is not known, but it is likely due to a direct hepatotoxic effect on the liver (L2102). Heparin-induced hyperkalemia is the result of heparin-induced aldosterone suppression (Wikipedia). The most important, but probably not the only mechanism of aldosterone inhibition appears to involve reduction in both the number and affinity of the angiotensin-II receptors in the zona glomerulosa (A15335). Alopecia connected to chronic heparin use may be due to the antimitotic effect of heparin on the epithelial cells (A15336). Heparin causes bone loss by decreasing bone formation. The few studies of the mechanism of bone loss have revealed decreased bone formation, increasing bone resorption, or both (L2103). Liver and the reticulo-endothelial system are the sites of biotransformation. The metabolic fate of heparin is not well understood. Route of Elimination: The drug appears to be removed mainly by the reticuloendothelial system. A small fraction of unchanged heparin also appears to be excreted in urine. Heparin cannot be eliminated by hemodialysis. Half Life: 1.5 hours. The plasma half-life of heparin increases from about 60 minutes with a 100 unit/kg dose to about 150 minutes with a 400 unit/kg dose. No indication of carcinogenicity to humans (not listed by IARC). Unfractionated heparin is indicated for prophylaxis and treatment of venous thrombosis and its extension, prevention of post-operative deep venous thrombosis and pulmonary embolism and prevention of clotting in arterial and cardiac surgery. In cardiology, it is used to prevent embolisms in patients with atrial fibrillation and as an adjunct antithrombin therapy in patients with unstable angina and/or non-Q wave myocardial infarctions (i.e. non-ST elevated acute coronary artery syndrome) who are on platelet glycoprotein (IIb/IIIa) receptor inhibitors. Additionally, it is used to prevent clotting during dialysis and surgical procedures, maintain the patency of intravenous injection devices and prevent in vitro coagulation of blood transfusions and in blood samples drawn for laboratory values. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7225ef1048> Heparin sodium - Mouse, median lethal dose greater than 5000 mg/kg. Another side effect is heparin induced thrombocytopenia (HIT syndrome). HIT is caused by an immunological reaction that makes platelets form clots within the blood vessels, thereby using up coagulation factors Protamine sulfate (1 mg per 100 units of heparin that had been given over the past four hours) has been given to counteract the anticoagulant effect of heparin. (Wikipedia) DB01109 HMDB01394 46507594 CHEMBL1909300 751 C00374 107300142360142640176860 28304 HEPARIN D006493 Heparin Heparin 10549711 2331699 8352752 15383472 10201371 11760916 7254945 11576777 12175393 1505142 8294632 8891437 16639677 16044416 16305714 16709700 16928604 845252 16860036 2118944 11007795 9208186 9175766 16382263 7778574 12778433 American Academy of Pediatrics Committee on Fetus and Newborn and Committee on Drugs. Benzyl alcohol: toxic agent in neonatal units. Pediatrics. 1983; 72:356-8. [PubMed] [IDIS 175725] Anon. Benzyl alcohol may be toxic to newborns. FDA Drug Bull. 1982; 12:10-1. [PubMed] Anon. Neonatal deaths associated with use of benzyl alcohol—United States. MMWR Morb Mortal Wkly Rep. 1982; 31:290-1. [PubMed] [IDIS 150868] Abbott Laboratories. Heparin lock flush solution, USP 100 USP units/mL prescribing information. North Chicago, IL; 1998 Jul. Drugs.com: http://www.drugs.com/cons/Heparin.html LiverTox - Heparin: http://livertox.nih.gov/Heparin.htm UpToDate - Drugs that affect bone metabolism: http://www.uptodate.com/contents/drugs-that-affect-bone-metabolism BE0000048 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0000280 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0000216 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0001064 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0001159 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0000364 The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X. BE0005820 BE0001015 BE0000326 BE0002131 BE0000748 BE0001203 BE0001129 BE0000163 BE0000689 BE0001121