WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H461259
CAS#: 9005-49-6
Description: Heparin is a sulfated polysaccharide that has been used as a life-saving anticoagulant in clinics well before its detailed structure was known.
Hodoodo Cat#: H461259
Name: Heparin
CAS#: 9005-49-6
Chemical Formula: C26H42N2O37S5
Exact Mass: 1,134.01
Molecular Weight: 1,134.890
Elemental Analysis: C, 27.52; H, 3.73; N, 2.47; O, 52.16; S, 14.12
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 9005-49-6 (free) 37270-89-6 (Ca)
Synonym: Heparin; Adomiparin; Bemiparin; Certoparin; Dalteparin; Eparina; Fraxiparin; M118; M-118; M 118; Nadroparine; Parvoparin; Thromboliquine;
IUPAC/Chemical Name: 6-((5-acetamido-4,6-dihydroxy-2-((sulfooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-3-((5-((6-carboxy-4,5-dihydroxy-3-(sulfooxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)-3-(sulfoamino)-4-(sulfooxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-5-(sulfooxy)tetrahydro-2H-pyran-2-carboxylic acid
InChi Key: HTTJABKRGRZYRN-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: CC(NC1C(OC(C(C1O)OC2OC(C(O)=O)C(C(C2OS(=O)(O)=O)O)OC3OC(C(C(C3NS(=O)(O)=O)OS(=O)(O)=O)OC4OC(C(O)=O)C(C(C4OS(=O)(O)=O)O)O)CO)COS(=O)(O)=O)O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,134.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Erickson M, Hiebert LM, Carr AP, Stickney JD. Effect of oral administration of unfractionated heparin (UFH) on coagulation parameters in plasma and levels of urine and fecal heparin in dogs. Can J Vet Res. 2014 Jul;78(3):193-201. PubMed PMID: 24982550; PubMed Central PMCID: PMC4068410.
2: Barrowcliffe TW. History of heparin. Handb Exp Pharmacol. 2012;(207):3-22. doi: 10.1007/978-3-642-23056-1_1. PubMed PMID: 22566218.
3: Hemker HC. A century of heparin: past, present and future. J Thromb Haemost. 2016 Dec;14(12):2329-2338. doi: 10.1111/jth.13555. Epub 2016 Dec 16. PubMed PMID: 27862941.
4: Casu B, Naggi A, Torri G. Re-visiting the structure of heparin. Carbohydr Res. 2015 Feb 11;403:60-8. doi: 10.1016/j.carres.2014.06.023. Epub 2014 Jul 3. Review. PubMed PMID: 25088334.
5: Chan KE, Thadhani RI, Maddux FW. No difference in bleeding risk between subcutaneous enoxaparin and heparin for thromboprophylaxis in end-stage renal disease. Kidney Int. 2013 Sep;84(3):555-61. doi: 10.1038/ki.2013.152. Epub 2013 May 15. PubMed PMID: 23677243.
6: Deep venous thrombosis and pulmonary embolism. Part 1. Initial treatment: usually a low-molecular-weight heparin. Prescrire Int. 2013 Apr;22(137):99-101, 103-4. Review. PubMed PMID: 23662321.
7: Alyahya R, Sudha T, Racz M, Stain SC, Mousa SA. Anti-metastasis efficacy and safety of non-anticoagulant heparin derivative versus low molecular weight heparin in surgical pancreatic cancer models. Int J Oncol. 2015 Mar;46(3):1225-31. doi: 10.3892/ijo.2014.2803. Epub 2014 Dec 19. PubMed PMID: 25530018.
8: Ang E. Unfractionated heparin versus low-molecular-weight heparin for avoiding heparin-induced thrombocytopenia in postoperative patients. Clin Nurse Spec. 2013 Sep-Oct;27(5):229-30. doi: 10.1097/NUR.0b013e3182a0ba2b. Review. PubMed PMID: 23942101.
9: Walenga JM, Lyman GH. Evolution of heparin anticoagulants to ultra-low-molecular-weight heparins: a review of pharmacologic and clinical differences and applications in patients with cancer. Crit Rev Oncol Hematol. 2013 Oct;88(1):1-18. doi: 10.1016/j.critrevonc.2013.06.007. Epub 2013 Jul 12. Review. PubMed PMID: 23849978.
10: Pasquale LD, Ferneini EM. Heparin and Lovenox: What the Oral and Maxillofacial Surgeon Needs to Know. Oral Maxillofac Surg Clin North Am. 2016 Nov;28(4):507-513. doi: 10.1016/j.coms.2016.06.008. Epub 2016 Sep 10. Review. PubMed PMID: 27624773.
11: Hirsh J, Warkentin TE, Shaughnessy SG, Anand SS, Halperin JL, Raschke R, Granger C, Ohman EM, Dalen JE. Heparin and low-molecular-weight heparin: mechanisms of action, pharmacokinetics, dosing, monitoring, efficacy, and safety. Chest. 2001 Jan;119(1 Suppl):64S-94S. Review. PubMed PMID: 11157643.
12: Ye H, Toby TK, Sommers CD, Ghasriani H, Trehy ML, Ye W, Kolinski RE, Buhse LF, Al-Hakim A, Keire DA. Characterization of currently marketed heparin products: key tests for LMWH quality assurance. J Pharm Biomed Anal. 2013 Nov;85:99-107. doi: 10.1016/j.jpba.2013.06.033. Epub 2013 Jul 16. PubMed PMID: 23917037.
13: Riaz IB, Asawaeer M, Riaz H, Gabriel WM, Tabash IK, Bilal J, Alpert JS. Optimal anticoagulation duration of unfractionated and low molecular weight heparin in non-ST elevation acute coronary syndrome: a systematic review of the literature. Int J Cardiol. 2014 Dec 15;177(2):461-6. doi: 10.1016/j.ijcard.2014.09.105. Epub 2014 Sep 30. Review. PubMed PMID: 25443247.
14: Zhao D, Sang Q, Cui H. Preparation and evaluation a new generation of low molecular weight heparin. Biomed Pharmacother. 2016 Apr;79:194-200. doi: 10.1016/j.biopha.2016.02.021. Epub 2016 Mar 9. PubMed PMID: 27044828.
15: Warkentin TE, Levine MN, Hirsh J, Horsewood P, Roberts RS, Gent M, Kelton JG. Heparin-induced thrombocytopenia in patients treated with low-molecular-weight heparin or unfractionated heparin. N Engl J Med. 1995 May 18;332(20):1330-5. PubMed PMID: 7715641.
16: Dluha J, Sivak S, Kurca E, Dusenka R, Kalmarova K, Turcanova Koprusakova M, Kantorova E, Nosal V. The safety and efficacy of Heparin and Nadroparin compared to placebo in acute ischemic stroke - pilot study. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2016 Dec;160(4):543-548. doi: 10.5507/bp.2016.042. Epub 2016 Sep 19. PubMed PMID: 27646496.
17: Masuko S, Linhardt RJ. Chemoenzymatic synthesis of the next generation of ultralow MW heparin therapeutics. Future Med Chem. 2012 Mar;4(3):289-96. doi: 10.4155/fmc.11.185. Review. PubMed PMID: 22393937; PubMed Central PMCID: PMC3320513.
18: Phung OJ, Kahn SR, Cook DJ, Murad MH. Dosing frequency of unfractionated heparin thromboprophylaxis: a meta-analysis. Chest. 2011 Aug;140(2):374-381. doi: 10.1378/chest.10-3084. Epub 2011 Feb 24. Erratum in: Chest. 2015 Nov;148(5):1363. PubMed PMID: 21349929.
19: Cassinelli G, Naggi A. Old and new applications of non-anticoagulant heparin. Int J Cardiol. 2016 Jun;212 Suppl 1:S14-21. doi: 10.1016/S0167-5273(16)12004-2. Review. PubMed PMID: 27264866.
20: Guler T, Polat ZA, Yayci E, Atacag T, Cetin A. Effects of low molecular weight heparins and unfractionated heparin on viability of human umbilical vein endothelial cells. Arch Gynecol Obstet. 2013 Feb;287(2):217-22. doi: 10.1007/s00404-012-2558-1. Epub 2012 Sep 18. PubMed PMID: 22987257.
