Acenocoumarol | Anticoagulant | Vitamin K Antagonist | CAS#152-72-7

Acenocoumarol
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317152

CAS#: 152-72-7

Description: Acenocoumarol is a coumarin that is used as an anticoagulant. Its actions and uses are similar to those of Warfarin. As a vitamin K antagonist, acenocoumarol inhibits vitamin K epoxide reductase, thereby inhibiting the reduction of vitamin K and the availability of vitamin KH2. This prevents gamma carboxylation of glutamic acid residues near the N-terminals of the vitamin K-dependent clotting factors, including factor II, VII, IX, and X and anticoagulant proteins C and S. This prevents their activity, preventing thrombin formation.

Chemical Structure

Acenocoumarol

CAS# 152-72-7

Instruction

Theoretical Analysis

MedKoo Cat#: 317152
Name: Acenocoumarol
CAS#: 152-72-7
Chemical Formula: C19H15NO6
Exact Mass: 353.09
Molecular Weight: 353.330
Elemental Analysis: C, 64.59; H, 4.28; N, 3.96; O, 27.17

Price and Availability

Size	Price	Availability
10mg	USD 250	2 Weeks
25mg	USD 450	2 Weeks
50mg	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Sintrom, Acenocoumarin, Nicoumalone, G-23350, Sinthrome

IUPAC/Chemical Name: 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one

InChi Key: VABCILAOYCMVPS-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

SMILES Code: CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=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, not in water

Shelf Life: >2 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: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 353.33 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:

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1: Trailokya A, Hiremath JS, Sawhney J, Mishra YK, Kanhere V, Srinivasa R, Tiwaskar M. Acenocoumarol: A Review of Anticoagulant Efficacy and Safety. J Assoc Physicians India. 2016 Feb;64(2):88-93. PMID: 27730796.

2: ACENOCOUMAROL. J Am Med Assoc. 1958 May 3;167(1):62. PMID: 13538672.

3: Fragomeno M, Assad S, Mobili P, Peruzzo PJ, Minnaard J, Pérez PF. Biomodification of acenocoumarol by bifidobacteria. FEMS Microbiol Lett. 2021 Oct 4;368(18):fnab125. doi: 10.1093/femsle/fnab125. PMID: 34529059.

4: Mondillo S, Ballo P, Galderisi M. Rosuvastatin-acenocoumarol interaction. Clin Ther. 2005 Jun;27(6):782-4. doi: 10.1016/j.clinthera.2005.06.007. PMID: 16117985.

5: Soto J, Sacristan JA, Alsar MJ, Fernandez-Viadero C, Verduga R. Probable acenocoumarol-amoxycillin interaction. Acta Haematol. 1993;90(4):195-7. doi: 10.1159/000204457. PMID: 8140860.

6: Valdivielso M, Longo I, Lecona M, Lázaro P. Cutaneous necrosis induced by acenocoumarol. J Eur Acad Dermatol Venereol. 2004 Mar;18(2):211-5. doi: 10.1111/j.1468-3083.2004.00735.x. PMID: 15009309.

7: van Miert JHA, Piersma-Wichers M, Meijer K. Overstappen van acenocoumarol naar fenprocoumon [Switching from acenocoumarol to phenprocoumon: step in personalised anticoagulation?]. Ned Tijdschr Geneeskd. 2021 Sep 9;165:D5533. Dutch. PMID: 34523845.

8: Lanas F, Castro C, Vallejos C, Bustos L, de La Puente C, Velasquez M, Zaror C. Latin American Clinical Epidemiology Network Series - Paper 2: Apixaban was cost-effective vs. acenocoumarol in patients with nonvalvular atrial fibrillation with moderate to severe risk of embolism in Chile. J Clin Epidemiol. 2017 Jun;86:75-83. doi: 10.1016/j.jclinepi.2016.05.018. Epub 2016 Oct 15. PMID: 27756577.

9: Takahashi H, Wilkinson GR, Padrini R, Echizen H. CYP2C9 and oral anticoagulation therapy with acenocoumarol and warfarin: similarities yet differences. Clin Pharmacol Ther. 2004 May;75(5):376-80. doi: 10.1016/j.clpt.2004.01.007. PMID: 15116049.

10: Becker ML, van Uden RCAE, Giezen TJ, Meijer K, Houtenbos I, van den Bemt PMLA. Drug-drug interactions with metronidazole and itraconazole in patients using acenocoumarol. Eur J Clin Pharmacol. 2020 Oct;76(10):1457-1464. doi: 10.1007/s00228-020-02930-z. Epub 2020 Jun 10. PMID: 32524154.

11: Suárez-Peñaranda JM, Minasyan A, Sainz-Gaspar L, Sánchez-Aguilar MD. Resolution of acenocoumarol-associated calciphylaxis with drug withdrawal. Australas J Dermatol. 2019 Aug;60(3):e223-e226. doi: 10.1111/ajd.13006. Epub 2019 Feb 20. PMID: 30790279.

12: Das S, Behera SK, Ramakrishnan K, Ganesapandian M, Munuswamy H, Selvarajan S. A complex interaction between antitubercular treatment and acenocoumarol. Eur J Clin Pharmacol. 2020 Jan;76(1):133-135. doi: 10.1007/s00228-019-02776-0. Epub 2019 Oct 29. PMID: 31664473.

13: Morin S, Bodin L, Loriot MA, Thijssen HH, Robert A, Strabach S, Verstuyft C, Tregouet DA, Dubert L, Laurent-Puig P, Funck-Brentano C, Jaillon P, Beaune PH, Becquemont L. Pharmacogenetics of acenocoumarol pharmacodynamics. Clin Pharmacol Ther. 2004 May;75(5):403-14. doi: 10.1016/j.clpt.2004.01.008. PMID: 15116053.

14: Sychev DA, Rozhkov AV, Ananichuk AV, Kazakov RE. Evaluation of genotype- guided acenocoumarol dosing algorithms in Russian patients. Drug Metab Pers Ther. 2017 May 24;32(2):109-114. doi: 10.1515/dmpt-2016-0043. PMID: 28525318.

15: Barcellona D, Vannini ML, Fenu L, Balestrieri C, Marongiu F. Warfarin or acenocoumarol: which is better in the management of oral anticoagulants? Thromb Haemost. 1998 Dec;80(6):899-902. PMID: 9869157.

16: Brands MR, Sytema J, van Hulst M, Kamps AW. Unintentional ingestion of a high dose of acenocoumarol in a young child. BMJ Case Rep. 2021 Apr 1;14(4):e240365. doi: 10.1136/bcr-2020-240365. PMID: 33795273; PMCID: PMC8023619.

17: Lokhorst B, Rolfes L, Jessurun NT. Interaction of OTC drug noscapine and acenocoumarol and phenprocoumon. Br J Clin Pharmacol. 2019 May;85(5):1041-1043. doi: 10.1111/bcp.13887. Epub 2019 Feb 26. PMID: 30809820; PMCID: PMC6475677.

18: Jiménez-Varo E, Cañadas-Garre M, Garcés-Robles V, Gutiérrez-Pimentel MJ, Calleja-Hernández MÁ. Extrapolation of acenocoumarol pharmacogenetic algorithms. Vascul Pharmacol. 2015 Nov;74:151-157. doi: 10.1016/j.vph.2015.06.010. Epub 2015 Jun 27. PMID: 26122664.

19: Vázquez C, Orlova M, Scibona P, Ferreyro BL, Otero V, Jáuregui EG, Arbelbide J, Belloso WH. Clinical and genetic factors influencing acenocoumarol dosing: a cross-sectional study. Blood Coagul Fibrinolysis. 2018 Sep;29(6):496-500. doi: 10.1097/MBC.0000000000000746. PMID: 29916837.

20: Lozano R. Drug-drug interactions between acenocoumarol and proton pump inhibitors in hospitalized patients: Overanticoagulation associated with intravenous omeprazole. Int J Clin Pharmacol Ther. 2021 Oct;59(10):671-673. doi: 10.5414/CP203997. PMID: 34423773.

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