MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318482 | Name: Phenprocoumon
Featured

Description:

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

Phenprocoumon is a long-acting oral anticoagulant drug, a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders.

Chemical Structure

Phenprocoumon
Phenprocoumon
CAS#435-97-2

Theoretical Analysis

MedKoo Cat#: 318482

Name: Phenprocoumon

CAS#: 435-97-2

Chemical Formula: C18H16O3

Exact Mass: 280.1099

Molecular Weight: 280.32

Elemental Analysis: C, 77.12; H, 5.75; O, 17.12

Price and Availability

Size Price Availability Quantity
100mg USD 385.00 2 Weeks
250mg USD 650.00 2 Weeks
500mg USD 1,050.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Phenprocoumon; Phenprocoumarol; Marcumar; Phenprocoumarole; Falithrom; Marcoumar; Roche Brand of Phenprocoumon; Wörwag Brand of Phenprocoumon; Phenprogramma; Phenylpropylhydroxycumarinum; Roche Brand of Phenprocoumon;
IUPAC/Chemical Name
4-hydroxy-3-(1-phenylpropyl)chromen-2-one
InChi Key
DQDAYGNAKTZFIW-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
SMILES Code
CCC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=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, 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenprocoumon is a coumarin derivative that acts as a long acting oral anticoagulant and an antagonist of vitamin K.
In vitro activity:
Surprisingly, however, increasing concentrations of phenprocoumon resulted in a significant enhancement of cell death under different ferroptosis conditions when induced with relatively weak stimuli. This effect was detectable in both RSL3- and erastin-induced ferroptosis and was consistent with observations in murine and human cells (Fig. 4a–c). Notably, the cell death additionally triggered by supplementation of phenprocoumon was completely reversed by both vitamin K1 and ferrostatin-1 (Fig. 4a–c). These results indicate that phenprocoumon aggravates ferroptosis induced by other stimuli, which is counteracted by vitamin K1 as well as the canonical ferroptosis inhibitor ferrostatin-1, whereas inhibition of VKOR alone does not induce ferroptosis. Reference: Cell Mol Life Sci. 2022 Jun 28;79(7):387. https://pubmed.ncbi.nlm.nih.gov/35763128/
In vivo activity:
Indeed, animals pretreated with phenprocoumon showed marked AKI and tubular necrosis in IRI, whereas phenprocoumon without IRI did not cause notable kidney function impairment in mice (Fig. 5a and b and Supplemental Fig. 4). Renal expression of ACSL4 as a marker of ferroptosis was further increased in the IR + phenprocoumon group compared to the other groups (Fig. 5c and d). Simultaneous additional treatment with vitamin K1 significantly preserved renal function parameters compared with the IR + phenprocoumon group (Fig. 5a and b). Renal ACSL4 expression was again reduced by concomitant vitamin K1 application in phenprocoumon-treated IR animals (Fig. 5c and d). Reference: Cell Mol Life Sci. 2022 Jun 28;79(7):387. https://pubmed.ncbi.nlm.nih.gov/35763128/
Solvent mg/mL mM comments
Solubility
DMF 30.0 107.02
DMSO 70.3 250.90
DMSO:PBS (pH 7.2) (1:4) 0.2 0.71
Ethanol 30.5 108.80
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 280.32 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.

Recalculate based on batch purity %
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:
Kolbrink B, von Samson-Himmelstjerna FA, Messtorff ML, Riebeling T, Nische R, Schmitz J, Bräsen JH, Kunzendorf U, Krautwald S. Vitamin K1 inhibits ferroptosis and counteracts a detrimental effect of phenprocoumon in experimental acute kidney injury. Cell Mol Life Sci. 2022 Jun 28;79(7):387. doi: 10.1007/s00018-022-04416-w. PMID: 35763128; PMCID: PMC9239973.
In vitro protocol:
Kolbrink B, von Samson-Himmelstjerna FA, Messtorff ML, Riebeling T, Nische R, Schmitz J, Bräsen JH, Kunzendorf U, Krautwald S. Vitamin K1 inhibits ferroptosis and counteracts a detrimental effect of phenprocoumon in experimental acute kidney injury. Cell Mol Life Sci. 2022 Jun 28;79(7):387. doi: 10.1007/s00018-022-04416-w. PMID: 35763128; PMCID: PMC9239973.
In vivo protocol:
Kolbrink B, von Samson-Himmelstjerna FA, Messtorff ML, Riebeling T, Nische R, Schmitz J, Bräsen JH, Kunzendorf U, Krautwald S. Vitamin K1 inhibits ferroptosis and counteracts a detrimental effect of phenprocoumon in experimental acute kidney injury. Cell Mol Life Sci. 2022 Jun 28;79(7):387. doi: 10.1007/s00018-022-04416-w. PMID: 35763128; PMCID: PMC9239973.
1: Riedel F, Hahn M, Bader W, Schäfgen B, Fastner S, Hennigs A, Gomez C, Stieber A, Fastner C, Wallwiener M, Golatta M, Heil J, Fallenberg EM. Management of Patients with Breast Biopsy under Anti-Coagulation or Anti-Platelet Therapy: Results of a Survey of German Experts. Breast Care (Basel). 2024 Apr;19(2):87-94. doi: 10.1159/000536079. Epub 2024 Jan 10. PMID: 38765898; PMCID: PMC11096796. 2: Camilleri E, Ghobreyal M, Bos MHA, Reitsma PH, Van Der Meer FJM, Swen JJ, Cannegieter SC, van Rein N. Genetic polymorphisms and major bleeding risk during vitamin K antagonists treatment: The BLEEDS case-cohort. Pharmacotherapy. 2024 Jun;44(6):416-424. doi: 10.1002/phar.2923. Epub 2024 Apr 30. PMID: 38686648. 3: Doldi F, Geßler N, Anwar O, Kahle AK, Scherschel K, Rath B, Köbe J, Lange PS, Frommeyer G, Metzner A, Meyer C, Willems S, Kuck KH, Eckardt L. In-Hospital Pulmonary Arterial Embolism after Catheter Ablation of Over 45,000 Cardiac Arrhythmias: Individualized Case Analysis of Multicentric Data. Thromb Haemost. 2024 Mar 31. doi: 10.1055/s-0044-1785519. Epub ahead of print. PMID: 38555641. 4: Kreutz R, Kloss S, Enders D, Abdelgawwad K, Häckl D, Schmedt N, Bonnemeier H. Comparative effectiveness of factor Xa non-vitamin K antagonist oral anticoagulants versus phenprocoumon in patients with non-valvular atrial fibrillation. Int J Cardiol. 2024 Jun 1;404:131894. doi: 10.1016/j.ijcard.2024.131894. Epub 2024 Mar 2. PMID: 38437952. 5: de Lucena LA, Freitas MAA, Souza AKC, Silva CHA, Watanabe JMF, Guedes FL, Almeida JB, de Oliveira RA. Direct oral anticoagulants versus vitamin K antagonists in patients with atrial fibrillation and stage 5 chronic kidney disease under dialysis: A systematic review and meta-analysis of randomized controlled trials. J Thromb Thrombolysis. 2024 Mar;57(3):381-389. doi: 10.1007/s11239-023-02945-0. Epub 2024 Jan 28. PMID: 38281231. 6: Erhard N, Bahlke F, Spitzauer L, Englert F, Popa M, Bourier F, Reents T, Lennerz C, Kraft H, Maurer S, Tunsch-Martinez A, Syväri J, Tydecks M, Telishevska M, Lengauer S, Hessling G, Deisenhofer I, Kottmaier M. Renal function and periprocedural complications in patients undergoing left atrial catheter ablation: A comparison between uninterrupted direct oral anticoagulants and phenprocoumon administration. Clin Res Cardiol. 2024 Jan 23. doi: 10.1007/s00392-024-02374-w. Epub ahead of print. PMID: 38261026. 7: Haußmann R, Homeyer P, Haußmann M, Sauer C, Linn J, Donix M, Brandt M, Puetz V. Analyse zur Häufigkeit einer gerinnungshemmenden Medikation bei Patientinnen mit kognitiven Störungen und zerebraler Amyloidangiopathie (CAA) [Analysis of the prevalence of anticoagulant therapy in patients with cognitive disorders and cerebral amyloid angiopathy (CAA)]. Nervenarzt. 2024 Feb;95(2):146-151. German. doi: 10.1007/s00115-023-01547-8. Epub 2023 Sep 25. PMID: 37747503; PMCID: PMC10850242. 8: Atakanova A, Heiligers A, Kirschner M, Bollheimer C, Fleig S. Geriatrischer Patient mit neurologischer Symptomatik und verlängerter aPTT [Geriatric patient with neurological symptoms and prolonged aPTT]. Inn Med (Heidelb). 2024 Apr;65(4):402-406. German. doi: 10.1007/s00108-023-01581-3. Epub 2023 Sep 20. PMID: 37728737; PMCID: PMC10959806. 9: Voss A, Kollhorst B, Platzbecker K, Amann U, Haug U. Risk Profiles of New Users of Oral Anticoagulants Between 2011 and 2019 in Germany. Clin Epidemiol. 2023 Jul 18;15:827-837. doi: 10.2147/CLEP.S405585. PMID: 37483262; PMCID: PMC10362862. 10: Gjermeni D, Saglam NP, Olivier CB, Kühlkamp V. Comparison of phenprocoumon with direct oral anticoagulants in catheter ablation of atrial fibrillation. Eur Heart J Open. 2023 Jun 20;3(4):oead065. doi: 10.1093/ehjopen/oead065. PMID: 37427356; PMCID: PMC10329261. 11: Visser C, Yousefi A, Nierman MC, Huisman MV, Gulpen AJW, van Ommen CH, Kruip MJHA; Dutch COVID and Thrombosis Coalition. The effect of COVID-19 vaccination on anticoagulation stability in adolescents and young adults using vitamin K antagonists. Thromb Res. 2023 Aug;228:121-127. doi: 10.1016/j.thromres.2023.06.005. Epub 2023 Jun 12. PMID: 37321159; PMCID: PMC10258126. 12: Platzbecker K, Müller-Fielitz H, Foraita R, Koepp MJ, Voss A, Pflock R, Linder R, Pigeot I, Schink T, Schwaninger M. In atrial fibrillation epilepsy risk differs between oral anticoagulants: active comparator, nested case-control study. Europace. 2023 May 19;25(5):euad087. doi: 10.1093/europace/euad087. PMID: 37013704; PMCID: PMC10228540. 13: Lechner R, Hanke K, Schmid A, Mayer B, Helm M, Kulla M, Hossfeld B. Hemostatics in patients with inhibited coagulation-A viscoelastic in-vitro analysis. Transfusion. 2023 May;63 Suppl 3:S159-S167. doi: 10.1111/trf.17333. Epub 2023 Apr 26. PMID: 36971054. 14: Wieringa A, Fiebrich HB, Gelder FV, Valkenburg AJ, Maring JG, Smolders EJ. Bleeding Complications in a Patient After the Unexpected Interaction between Valproic Acid and Phenprocoumon. Curr Drug Saf. 2024;19(1):142-144. doi: 10.2174/1574886318666230310104322. PMID: 36896908. 15: Finsterer J. Hereditary Protein S Deficiency and Activated Protein C Resistance Manifesting With Recurrent Thrombosis and Stroke. Cureus. 2023 Jan 20;15(1):e34012. doi: 10.7759/cureus.34012. PMID: 36824536; PMCID: PMC9941041. 16: Schlöglhofer T, Marschütz A, Combs P, Stonebraker C, Lupo S, Jeevanandam V, Riebandt J, Schima H, Zimpfer D, Meehan K. Quality of Anticoagulation With Phenprocoumon and Warfarin in Left Ventricular Assist Device Patients: A Multicenter Study. ASAIO J. 2023 Jun 1;69(6):595-601. doi: 10.1097/MAT.0000000000001895. Epub 2023 Feb 23. PMID: 36821448. 17: Treyer A, Reinhardt JK, Eigenmann DE, Oufir M, Hamburger M. Phytochemical Comparison of Medicinal Cannabis Extracts and Study of Their CYP-Mediated Interactions with Coumarinic Oral Anticoagulants. Med Cannabis Cannabinoids. 2023 Feb 8;6(1):21-31. doi: 10.1159/000528465. PMID: 36814687; PMCID: PMC9940649. 18: Meinel K, Korak F, Dusleag M, Strini T, Baumgartner D, Burmas A, Sallmon H, Zieger B, Schlagenhauf A, Koestenberger M. Mild Acquired von Willebrand Syndrome and Cholestasis in Pediatric and Adult Patients with Fontan Circulation. J Clin Med. 2023 Feb 3;12(3):1240. doi: 10.3390/jcm12031240. PMID: 36769887; PMCID: PMC9917608. 19: Hermann SA, Mikus G, Chobanyan-Jürgens K, Gorenflo M, Ziesenitz VC. Pharmacokinetics of a microdosed cocktail of three direct oral anticoagulants in children with congenital heart defects: study protocol for a single-centre clinical trial (DOAC-Child). BMJ Paediatr Open. 2023 Jan;7(1):e001662. doi: 10.1136/bmjpo-2022-001662. PMID: 36720501; PMCID: PMC9890763. 20: Warkentin L, Klohn F, Deiters B, Kühlein T, Hueber S. Vitamin-K-antagonist phenprocoumon versus direct oral anticoagulants in patients with atrial fibrillation: a real-world analysis of German claims data. BMJ Open. 2023 Jan 2;13(1):e063490. doi: 10.1136/bmjopen-2022-063490. PMID: 36593002; PMCID: PMC9809214.