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MedKoo Cat#: 592697 | Name: Naftidrofuryl
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Description:

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

Naftidrofuryl is a drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic.

Chemical Structure

Naftidrofuryl
Naftidrofuryl
CAS#31329-57-4

Theoretical Analysis

MedKoo Cat#: 592697

Name: Naftidrofuryl

CAS#: 31329-57-4

Chemical Formula: C24H33NO3

Exact Mass: 383.2460

Molecular Weight: 383.53

Elemental Analysis: C, 75.16; H, 8.67; N, 3.65; O, 12.51

Price and Availability

Size Price Availability Quantity
5mg USD 340.00
50mg USD 1,580.00
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Synonym
Naftidrofuryl
IUPAC/Chemical Name
2-Furanpropanoic acid, tetrahydro-alpha-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester
InChi Key
KBAFPSLPKGSANY-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H33NO3/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3
SMILES Code
O=C(OCCN(CC)CC)C(CC1=C2C=CC=CC2=CC=C1)CC3OCCC3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Naftidrofuryl is a drug used in the management of peripheral and cerebral vascular disorders.
In vitro activity:
Naf (Naftidrofuryl oxalate) inhibited ET-1-mediated detrusor contractions significantly (P<0.04), e.g. at 10(-10) M ET-1, contraction was completely abolished by Naf. Autoradiography indicated that Naf competitively inhibited [(125)I]ET-1 binding in a dose-dependent manner (IC(50)=3x10(-7) M). All radioligand binding was reduced indicating binding of Naf to both ET(A) and ET(B) receptors. Reference: Clin Sci (Lond). 2002 Aug;103 Suppl 48:459S-463S. https://pubmed.ncbi.nlm.nih.gov/12193145/
In vivo activity:
This study aimed to assess the possible protective effects of naftidrofuryl (Naf) against methotrexate (MTX)-induced testicular toxicity in rats. Male rats were randomly distributed into four groups: control, Naf, MTX, and MTX+Naf groups. Naf pretreatment significantly decreased malondialdehyde and interleukin-6 contents, microRNA-29a (miRNA-29a) expression level, and nuclear factor kappa B and p53 immunostaining in the testicular tissues compared to the MTX group. Reference: Environ Toxicol Pharmacol. 2023 Mar;98:104067. https://pubmed.ncbi.nlm.nih.gov/36649853/

Preparing Stock Solutions

The following data is based on the product molecular weight 383.53 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:
1. Calvert RC, Mumtaz FH, Dashwood MR, Khan MA, Morgan RJ, Mikhailidis DP, Thompson CS. Reduction of endothelin-1 binding and inhibition of endothelin-1-mediated detrusor contraction by naftidrofuryl. Clin Sci (Lond). 2002 Aug;103 Suppl 48:459S-463S. doi: 10.1042/CS103S459S. PMID: 12193145. 2. Barradas MA, Jagroop IA, Mikhailidis DP. Naftidrofuryl inhibits the release of 5-hydroxytryptamine and platelet-derived growth factor from human platelets. Clin Chim Acta. 1994 Oct 31;230(2):157-67. doi: 10.1016/0009-8981(94)90268-2. PMID: 7834867. 3. Waly OM, El-Mahdy NA, El-Shitany NAE, Mohammedsaleh ZM, El-Kadem AH. Protective role of naftidrofuryl against methotrexate-induced testicular damage via the amelioration of the p53/miRNA-29a/CDC42 apoptotic pathway, inflammation, and oxidative stress. Environ Toxicol Pharmacol. 2023 Mar;98:104067. doi: 10.1016/j.etap.2023.104067. Epub 2023 Jan 14. PMID: 36649853. 4. García-García L, Gomez F, Delgado M, Fernández de la Rosa R, Pozo MÁ. The vasodilator naftidrofuryl attenuates short-term brain glucose hypometabolism in the lithium-pilocarpine rat model of status epilepticus without providing neuroprotection. Eur J Pharmacol. 2023 Jan 15;939:175453. doi: 10.1016/j.ejphar.2022.175453. Epub 2022 Dec 11. PMID: 36516936.
In vitro protocol:
1. Calvert RC, Mumtaz FH, Dashwood MR, Khan MA, Morgan RJ, Mikhailidis DP, Thompson CS. Reduction of endothelin-1 binding and inhibition of endothelin-1-mediated detrusor contraction by naftidrofuryl. Clin Sci (Lond). 2002 Aug;103 Suppl 48:459S-463S. doi: 10.1042/CS103S459S. PMID: 12193145. 2. Barradas MA, Jagroop IA, Mikhailidis DP. Naftidrofuryl inhibits the release of 5-hydroxytryptamine and platelet-derived growth factor from human platelets. Clin Chim Acta. 1994 Oct 31;230(2):157-67. doi: 10.1016/0009-8981(94)90268-2. PMID: 7834867.
In vivo protocol:
1. Waly OM, El-Mahdy NA, El-Shitany NAE, Mohammedsaleh ZM, El-Kadem AH. Protective role of naftidrofuryl against methotrexate-induced testicular damage via the amelioration of the p53/miRNA-29a/CDC42 apoptotic pathway, inflammation, and oxidative stress. Environ Toxicol Pharmacol. 2023 Mar;98:104067. doi: 10.1016/j.etap.2023.104067. Epub 2023 Jan 14. PMID: 36649853. 2. García-García L, Gomez F, Delgado M, Fernández de la Rosa R, Pozo MÁ. The vasodilator naftidrofuryl attenuates short-term brain glucose hypometabolism in the lithium-pilocarpine rat model of status epilepticus without providing neuroprotection. Eur J Pharmacol. 2023 Jan 15;939:175453. doi: 10.1016/j.ejphar.2022.175453. Epub 2022 Dec 11. PMID: 36516936.
1: de Backer TL, Vander Stichele R, Lehert P, Van Bortel L. Naftidrofuryl for intermittent claudication. Cochrane Database Syst Rev. 2012 Dec 12;12:CD001368. doi: 10.1002/14651858.CD001368.pub4. Review. PubMed PMID: 23235580. 2: Smith FB, Bradbury A, Fowkes G. Intravenous naftidrofuryl for critical limb ischaemia. Cochrane Database Syst Rev. 2012 Jul 11;(7):CD002070. doi: 10.1002/14651858.CD002070.pub2. Review. PubMed PMID: 22786478. 3: Kuznetsov MR, Kosykh IV, Iumin SM, Kunitsyn NV, Kuznetsova VF, Tolstikhin VIu, Magnitskiĭ LA. [Use of naftidrofuryl in angiology]. Angiol Sosud Khir. 2014;20(4):27-35. Review. Russian. PubMed PMID: 25490354. 4: Lu D, Song H, Hao Z, Wu T, McCleery J. Naftidrofuryl for dementia. Cochrane Database Syst Rev. 2011 Dec 7;(12):CD002955. doi: 10.1002/14651858.CD002955.pub4. Review. PubMed PMID: 22161372. 5: Hong H, Mackey WC. The limits of evidence in drug approval and availability: a case study of cilostazol and naftidrofuryl for the treatment of intermittent claudication. Clin Ther. 2014 Aug 1;36(8):1290-301. doi: 10.1016/j.clinthera.2014.06.010. Epub 2014 Jul 8. Review. PubMed PMID: 25012728. 6: Meng Y, Squires H, Stevens JW, Simpson E, Harnan S, Thomas S, Michaels J, Stansby G, O'Donnell ME. Cost-effectiveness of cilostazol, naftidrofuryl oxalate, and pentoxifylline for the treatment of intermittent claudication in people with peripheral arterial disease. Angiology. 2014 Mar;65(3):190-7. doi: 10.1177/0003319712474335. Epub 2013 Jan 31. PubMed PMID: 23378195. 7: Hao J, Chen B, Yao Y, Hossain M, Nagatomo T, Yao H, Kong L, Sun H. Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor. Bioorg Med Chem Lett. 2012 May 15;22(10):3441-4. doi: 10.1016/j.bmcl.2012.03.093. Epub 2012 Apr 1. PubMed PMID: 22516281. 8: Sabry SM, Belal TS, Barary MH, Ibrahim ME. A validated HPLC method for the simultaneous determination of naftidrofuryl oxalate and its degradation product (metabolite), naftidrofuryl acid: applications to pharmaceutical tablets and biological samples. Drug Test Anal. 2013 Jun;5(6):500-8. doi: 10.1002/dta.421. Epub 2012 Feb 28. PubMed PMID: 22374844. 9: Stevens JW, Simpson E, Harnan S, Squires H, Meng Y, Thomas S, Michaels J, Stansby G. Systematic review of the efficacy of cilostazol, naftidrofuryl oxalate and pentoxifylline for the treatment of intermittent claudication. Br J Surg. 2012 Dec;99(12):1630-8. doi: 10.1002/bjs.8895. Epub 2012 Oct 3. Review. PubMed PMID: 23034699. 10: Leonardi-Bee J, Steiner T, Bath-Hextall F. Naftidrofuryl for acute stroke. Cochrane Database Syst Rev. 2007 Apr 18;(2):CD005478. Review. PubMed PMID: 17443593. 11: Roset PN. Systematic review of the efficacy of cilostazol, naftidrofuryl oxalate and pentoxifylline for the treatment of intermittent claudication (Br J Surg 2012; 99: 1630-1638). Br J Surg. 2013 Dec;100(13):1838. doi: 10.1002/bjs.9357. PubMed PMID: 24227374. 12: Stevens JW, Simpson E, Harnan S, Squires H, Meng Y, Thomas S, Michaels J, Stansby G. Authors' reply: systematic review of the efficacy of cilostazol, naftidrofuryl oxalate and pentoxifylline for the treatment of intermittent claudication (Br J Surg 2012; 99: 1630-1638). Br J Surg. 2013 Dec;100(13):1838-9. doi: 10.1002/bjs.9358. PubMed PMID: 24227373. 13: D'Hooge D, Lehert P, Clement DL. Naftidrofuryl in quality of life (NIQOL). A Belgian study. Int Angiol. 2001 Dec;20(4):288-94. PubMed PMID: 11782694. 14: De Backer T, Vander Stichele R, Lehert P, Van Bortel L. Naftidrofuryl for intermittent claudication: meta-analysis based on individual patient data. BMJ. 2009 Mar 10;338:b603. doi: 10.1136/bmj.b603. Review. PubMed PMID: 19276131; PubMed Central PMCID: PMC2659292. 15: Koller MF, Schmid M, Iten PX, Vonlanthen B, Bär W. Fatal intoxication with naftidrofuryl. Leg Med (Tokyo). 2009 Sep;11(5):229-33. doi: 10.1016/j.legalmed.2009.04.003. Epub 2009 Jun 10. PubMed PMID: 19520596. 16: Young JB, Connolly MJ. Naftidrofuryl treatment for rest cramp. Postgrad Med J. 1993 Aug;69(814):624-6. PubMed PMID: 8234106; PubMed Central PMCID: PMC2399689. 17: Praxilene (naftidrofuryl). Drug Ther Bull. 1972 Nov 24;10(24):93-4. PubMed PMID: 4656482. 18: Squires H, Simpson E, Meng Y, Harnan S, Stevens J, Wong R, Thomas S, Michaels J, Stansby G. A systematic review and economic evaluation of cilostazol, naftidrofuryl oxalate, pentoxifylline and inositol nicotinate for the treatment of intermittent claudication in people with peripheral arterial disease. Health Technol Assess. 2011 Dec;15(40):1-210. doi: 10.3310/hta15400. Review. PubMed PMID: 22142554; PubMed Central PMCID: PMC4781353. 19: Le Meur Y, Moesch C, Rincé M, Aldigier JC, Leroux-Robert C. Potential nephrotoxicity of intravenous infusions of naftidrofuryl oxalate. Nephrol Dial Transplant. 1995;10(9):1751-5. PubMed PMID: 8559500. 20: Möller HJ, Hartmann A, Kessler C, Rainer M, Brown T, Gamand S, Lehert P. Naftidrofuryl in the treatment of vascular dementia. Eur Arch Psychiatry Clin Neurosci. 2001 Dec;251(6):247-54. PubMed PMID: 11881837.