Prinomastat

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

MedKoo CAT#: 202332

CAS#: 192329-42-3

Description: Prinomastat, also known as AG3340 amd KBR-9896, is a synthetic hydroxamic acid derivative with potential antineoplastic activity. Prinomastat inhibits matrix metalloproteinases (MMPs) (specifically, MMP-2, 9, 13, and 14), thereby inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. As a lipophilic agent, prinomastat crosses the blood-brain barrier.


Price and Availability

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10mg
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100mg
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1g
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25mg
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200mg
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2g
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50mg
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500mg
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5g
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Prinomastat is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202332
Name: Prinomastat
CAS#: 192329-42-3
Chemical Formula: C18H21N3O5S2
Exact Mass: 423.09226
Molecular Weight: 423.51
Elemental Analysis: C, 51.05; H, 5.00; N, 9.92; O, 18.89; S, 15.14


Synonym: AG3340; AG-3340; AG 3340; KBR-9896; KBR 9896; KBR9896; Prinomastat.

IUPAC/Chemical Name: (S)-N-hydroxy-2,2-dimethyl-4-((4-(pyridin-4-yloxy)phenyl)sulfonyl)thiomorpholine-3-carboxamide


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, 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).

Harmonized System Code:
293490


References

1: Wang A, Savas U, Hsu MH, Stout CD, Johnson EF. Crystal Structure of Human Cytochrome P450 2D6 with Prinomastat Bound. J Biol Chem. 2012 Mar 30;287(14):10834-43. Epub 2012 Feb 3. PubMed PMID: 22308038; PubMed Central PMCID: PMC3322812.

2: Younis HS, Jessen BA, Wu EY, Stevens GJ. Inhibiting matrix metalloproteinases with prinomastat produces abnormalities in fetal growth and development in rats. Birth Defects Res B Dev Reprod Toxicol. 2006 Apr;77(2):95-103. PubMed PMID: 16607633.

3: Heath EI, Burtness BA, Kleinberg L, Salem RR, Yang SC, Heitmiller RF, Canto MI, Knisely JP, Topazian M, Montgomery E, Tsottles N, Pithavala Y, Rohmiller B, Collier M, Forastiere AA. Phase II, parallel-design study of preoperative combined modality therapy and the matrix metalloprotease (mmp) inhibitor prinomastat in patients with esophageal adenocarcinoma. Invest New Drugs. 2006 Mar;24(2):135-40. PubMed PMID: 16502351.

4: Bissett D, O'Byrne KJ, von Pawel J, Gatzemeier U, Price A, Nicolson M, Mercier R, Mazabel E, Penning C, Zhang MH, Collier MA, Shepherd FA. Phase III study of matrix metalloproteinase inhibitor prinomastat in non-small-cell lung cancer. J Clin Oncol. 2005 Feb 1;23(4):842-9. PubMed PMID: 15681529.

5: El-Bradey MH, Cheng L, Bartsch DU, Niessman M, El-Musharaf A, Freeman WR. The effect of prinomastat (AG3340), a potent inhibitor of matrix metalloproteinase, on a new animal model of epiretinal membrane. Retina. 2004 Oct;24(5):783-9. PubMed PMID: 15492635.

6: Wiart M, Fournier LS, Novikov VY, Shames DM, Roberts TP, Fu Y, Shalinsky DR, Brasch RC. Magnetic resonance imaging detects early changes in microvascular permeability in xenograft tumors after treatment with the matrix metalloprotease inhibitor Prinomastat. Technol Cancer Res Treat. 2004 Aug;3(4):377-82. PubMed PMID: 15270589.

7: Ferrario A, Chantrain CF, von Tiehl K, Buckley S, Rucker N, Shalinsky DR, Shimada H, DeClerck YA, Gomer CJ. The matrix metalloproteinase inhibitor prinomastat enhances photodynamic therapy responsiveness in a mouse tumor model. Cancer Res. 2004 Apr 1;64(7):2328-32. PubMed PMID: 15059880.

8: Hande KR, Collier M, Paradiso L, Stuart-Smith J, Dixon M, Clendeninn N, Yeun G, Alberti D, Binger K, Wilding G. Phase I and pharmacokinetic study of prinomastat, a matrix metalloprotease inhibitor. Clin Cancer Res. 2004 Feb 1;10(3):909-15. PubMed PMID: 14871966.

9: Liu J, Tsao MS, Pagura M, Shalinsky DR, Khoka R, Fata J, Johnston MR. Early combined treatment with carboplatin and the MMP inhibitor, prinomastat, prolongs survival and reduces systemic metastasis in an aggressive orthotopic lung cancer model. Lung Cancer. 2003 Dec;42(3):335-44. PubMed PMID: 14644522.

10: Behrendt CE, Ruiz RB. Venous thromboembolism among patients with advanced lung cancer randomized to prinomastat or placebo, plus chemotherapy. Thromb Haemost. 2003 Oct;90(4):734-7. PubMed PMID: 14515196.

11: Deryugina EI, Ratnikov BI, Strongin AY. Prinomastat, a hydroxamate inhibitor of matrix metalloproteinases, has a complex effect on migration of breast carcinoma cells. Int J Cancer. 2003 May 1;104(5):533-41. PubMed PMID: 12594807.

12: Garcia C, Bartsch DU, Rivero ME, Hagedorn M, McDermott CD, Bergeron-Lynn G, Cheng L, Appelt K, Freeman WR. Efficacy of Prinomastat) (AG3340), a matrix metalloprotease inhibitor, in treatment of retinal neovascularization. Curr Eye Res. 2002 Jan;24(1):33-8. PubMed PMID: 12187492.

13: Ozerdem U, Mach-Hofacre B, Varki N, Folberg R, Mueller AJ, Ochabski R, Pham T, Appelt K, Freeman WR. The effect of prinomastat (AG3340), a synthetic inhibitor of matrix metalloproteinases, on uveal melanoma rabbit model. Curr Eye Res. 2002 Feb;24(2):86-91. PubMed PMID: 12187478.

14: Foda HD, Rollo EE, Drews M, Conner C, Appelt K, Shalinsky DR, Zucker S. Ventilator-induced lung injury upregulates and activates gelatinases and EMMPRIN: attenuation by the synthetic matrix metalloproteinase inhibitor, Prinomastat (AG3340). Am J Respir Cell Mol Biol. 2001 Dec;25(6):717-24. PubMed PMID: 11726397.

15: Cheng L, Rivero ME, Garcia CR, McDermott CD, Keefe KS, Wiley CA, Soules KA, Bergeron-Lynn G, Vekich S, Zhang K, Appelt K, Freeman WR. Evaluation of intraocular pharmacokinetics and toxicity of prinomastat (AG3340) in the rabbit. J Ocul Pharmacol Ther. 2001 Jun;17(3):295-304. PubMed PMID: 11436949.

16: Ozerdem U, Mach-Hofacre B, Keefe K, Pham T, Soules K, Appelt K, Freeman WR. The effect of prinomastat (AG3340), a synthetic inhibitor of matrix metalloproteinases, on posttraumatic proliferative vitreoretinopathy. Ophthalmic Res. 2001 Jan-Feb;33(1):20-3. PubMed PMID: 11114600.

17: Scatena R. Prinomastat, a hydroxamate-based matrix metalloproteinase inhibitor. A novel pharmacological approach for tissue remodelling-related diseases. Expert Opin Investig Drugs. 2000 Sep;9(9):2159-65. Review. PubMed PMID: 11060800.

18: Ozerdem U, Mach-Hofacre B, Cheng L, Chaidhawangul S, Keefe K, McDermott CD, Bergeron-Lynn G, Appelt K, Freeman WR. The effect of prinomastat (AG3340), a potent inhibitor of matrix metalloproteinases, on a subacute model of proliferative vitreoretinopathy. Curr Eye Res. 2000 Jun;20(6):447-53. PubMed PMID: 10980656.