NSC77674
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555535

CAS#: 737-86-0

Description: NSC77674, also known as Pyridoxal isonicotinoyl hydrazone and PIH is is a lipophilic, nontoxic, iron-chelating agent that shows high iron chelation efficacy both in vitro in cell culture models and in vivo in rats and mice.


Price and Availability

Size
Price

100mg
USD 550
1g
USD 2750
Size
Price

200mg
USD 950
2g
USD 3950
Size
Price

500mg
USD 1950
5g
USD 4950

NSC 77674, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 555535
Name: NSC77674
CAS#: 737-86-0
Chemical Formula: C14H14N4O3
Exact Mass: 286.1066
Molecular Weight: 286.291
Elemental Analysis: C, 58.74; H, 4.93; N, 19.57; O, 16.77


Synonym: NSC 77674; NSC-77674; NSC77674; PIH; Pyridoxal isonicotinoyl hydrazone;

IUPAC/Chemical Name: 4-pyridinecarboxylic acid, 2-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]methylene]hydrazide

InChi Key: BQYIXOPJPLGCRZ-REZTVBANSA-N

InChi Code: InChI=1S/C14H14N4O3/c1-9-13(20)12(11(8-19)6-16-9)7-17-18-14(21)10-2-4-15-5-3-10/h2-7,19-20H,8H2,1H3,(H,18,21)/b17-7+

SMILES Code: O=C(C1=CC=NC=C1)N/N=C/C2=C(O)C(C)=NC=C2CO


Technical Data

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).

Harmonized System Code:
2934990300


References

1: Brewer CT, Yang L, Edwards A, Lu Y, Low J, Wu J, Lee RE, Chen T. The Isoniazid Metabolites Hydrazine and Pyridoxal Isonicotinoyl Hydrazone Modulate Heme Biosynthesis. Toxicol Sci. 2019 Mar 1;168(1):209-224. doi: 10.1093/toxsci/kfy294. PubMed PMID: 30517741; PubMed Central PMCID: PMC6390808.

2: Sarno F, Papulino C, Franci G, Andersen JH, Cautain B, Melardo C, Altucci L, Nebbioso A. 3-Chloro-N'-(2-hydroxybenzylidene) benzohydrazide: An LSD1-Selective Inhibitor and Iron-Chelating Agent for Anticancer Therapy. Front Pharmacol. 2018 Sep 7;9:1006. doi: 10.3389/fphar.2018.01006. eCollection 2018. PubMed PMID: 30245629; PubMed Central PMCID: PMC6137965.

3: Chen YL, Kong X, Xie Y, Hider RC. The interaction of pyridoxal isonicotinoyl hydrazone (PIH) and salicylaldehyde isonicotinoyl hydrazone (SIH) with iron. J Inorg Biochem. 2018 Mar;180:194-203. doi: 10.1016/j.jinorgbio.2017.12.007. Epub 2017 Dec 21. PubMed PMID: 29329026.

4: Fratz-Berilla EJ, Breydo L, Gouya L, Puy H, Uversky VN, Ferreira GC. Isoniazid inhibits human erythroid 5-aminolevulinate synthase: Molecular mechanism and tolerance study with four X-linked protoporphyria patients. Biochim Biophys Acta Mol Basis Dis. 2017 Feb;1863(2):428-439. doi: 10.1016/j.bbadis.2016.11.011. Epub 2016 Nov 10. PubMed PMID: 27838491.

5: Merlot AM, Sahni S, Lane DJ, Fordham AM, Pantarat N, Hibbs DE, Richardson V, Doddareddy MR, Ong JA, Huang ML, Richardson DR, Kalinowski DS. Potentiating the cellular targeting and anti-tumor activity of Dp44mT via binding to human serum albumin: two saturable mechanisms of Dp44mT uptake by cells. Oncotarget. 2015 Apr 30;6(12):10374-98. PubMed PMID: 25848850; PubMed Central PMCID: PMC4496362.

6: Ellis S, Kalinowski DS, Leotta L, Huang ML, Jelfs P, Sintchenko V, Richardson DR, Triccas JA. Potent antimycobacterial activity of the pyridoxal isonicotinoyl hydrazone analog 2-pyridylcarboxaldehyde isonicotinoyl hydrazone: a lipophilic transport vehicle for isonicotinic acid hydrazide. Mol Pharmacol. 2014 Feb;85(2):269-78. doi: 10.1124/mol.113.090357. Epub 2013 Nov 15. PubMed PMID: 24243647; PubMed Central PMCID: PMC6067633.

7: Merlot AM, Pantarat N, Menezes SV, Sahni S, Richardson DR, Kalinowski DS. Cellular uptake of the antitumor agent Dp44mT occurs via a carrier/receptor-mediated mechanism. Mol Pharmacol. 2013 Dec;84(6):911-24. doi: 10.1124/mol.113.088393. Epub 2013 Oct 1. PubMed PMID: 24085840.

8: DeRuisseau KC, Park YM, DeRuisseau LR, Cowley PM, Fazen CH, Doyle RP. Aging-related changes in the iron status of skeletal muscle. Exp Gerontol. 2013 Nov;48(11):1294-302. doi: 10.1016/j.exger.2013.08.011. Epub 2013 Aug 29. PubMed PMID: 23994517; PubMed Central PMCID: PMC3812819.

9: Pelle E, Jian J, Declercq L, Dong K, Yang Q, Pourzand C, Maes D, Pernodet N, Yarosh DB, Huang X. Protection against ultraviolet A-induced oxidative damage in normal human epidermal keratinocytes under post-menopausal conditions by an ultraviolet A-activated caged-iron chelator: a pilot study. Photodermatol Photoimmunol Photomed. 2011 Oct;27(5):231-5. doi: 10.1111/j.1600-0781.2011.00604.x. PubMed PMID: 21950626.

10: Pasáková I, Gladziszová M, Charvátová J, Stariat J, Klimeš J, Kovaříková P. Use of different stationary phases for separation of isoniazid, its metabolites and vitamin B6 forms. J Sep Sci. 2011 Jun;34(12):1357-65. doi: 10.1002/jssc.201100081. Epub 2011 May 13. PubMed PMID: 21567949.

11: Kovacevic Z, Yu Y, Richardson DR. Chelators to the rescue: different horses for different courses! Chem Res Toxicol. 2011 Mar 21;24(3):279-82. doi: 10.1021/tx100435c. Epub 2011 Jan 7. PubMed PMID: 21214214.

12: Merlot AM, Pantarat N, Lovejoy DB, Kalinowski DS, Richardson DR. Membrane transport and intracellular sequestration of novel thiosemicarbazone chelators for the treatment of cancer. Mol Pharmacol. 2010 Oct;78(4):675-84. doi: 10.1124/mol.110.066126. Epub 2010 Jul 6. PubMed PMID: 20605952.

13: Bendova P, Mackova E, Haskova P, Vavrova A, Jirkovsky E, Sterba M, Popelova O, Kalinowski DS, Kovarikova P, Vavrova K, Richardson DR, Simunek T. Comparison of clinically used and experimental iron chelators for protection against oxidative stress-induced cellular injury. Chem Res Toxicol. 2010 Jun 21;23(6):1105-14. doi: 10.1021/tx100125t. PubMed PMID: 20521781.

14: Stariat J, Kovaríková P, Klimes J, Lovejoy DB, Kalinowski DS, Richardson DR. HPLC methods for determination of two novel thiosemicarbazone anti-cancer drugs (N4mT and Dp44mT) in plasma and their application to in vitro plasma stability of these agents. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):316-22. doi: 10.1016/j.jchromb.2008.11.044. Epub 2008 Dec 6. PubMed PMID: 19097949.

15: Whitnall M, Suryo Rahmanto Y, Sutak R, Xu X, Becker EM, Mikhael MR, Ponka P, Richardson DR. The MCK mouse heart model of Friedreich's ataxia: Alterations in iron-regulated proteins and cardiac hypertrophy are limited by iron chelation. Proc Natl Acad Sci U S A. 2008 Jul 15;105(28):9757-62. doi: 10.1073/pnas.0804261105. Epub 2008 Jul 9. PubMed PMID: 18621680; PubMed Central PMCID: PMC2474513.

16: Szuber N, Buss JL, Soe-Lin S, Felfly H, Trudel M, Ponka P. Alternative treatment paradigm for thalassemia using iron chelators. Exp Hematol. 2008 Jul;36(7):773-85. doi: 10.1016/j.exphem.2008.01.006. Epub 2008 May 5. PubMed PMID: 18456387.

17: Hershko C, Abrahamov A, Konijn AM, Breuer W, Cabantchik IZ, Pootrakul P, Link G. Objectives and methods of iron chelation therapy. Bioinorg Chem Appl. 2003:151-68. doi: 10.1155/S1565363303000128. PubMed PMID: 18365050; PubMed Central PMCID: PMC2267048.

18: Kovaríková P, Mrkvicková Z, Klimes J. Investigation of the stability of aromatic hydrazones in plasma and related biological material. J Pharm Biomed Anal. 2008 Jun 9;47(2):360-70. doi: 10.1016/j.jpba.2008.01.011. Epub 2008 Jan 16. PubMed PMID: 18294799.

19: Simunek T, Sterba M, Popelova O, Kaiserova H, Potacova A, Adamcova M, Mazurova Y, Ponka P, Gersl V. Pyridoxal isonicotinoyl hydrazone (PIH) and its analogs as protectants against anthracycline-induced cardiotoxicity. Hemoglobin. 2008;32(1-2):207-15. doi: 10.1080/03630260701680276. PubMed PMID: 18274998.

20: Kalinowski DS, Richardson DR. Future of toxicology--iron chelators and differing modes of action and toxicity: the changing face of iron chelation therapy. Chem Res Toxicol. 2007 May;20(5):715-20. Epub 2007 Apr 3. PubMed PMID: 17402750.