Stannsoporfin | Tin Mesoporphyrin | CAS#106344-20-1

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

MedKoo CAT#: 202708

CAS#: 106344-20-1

Description: Stannsoporfin ( SnMP), also known as Tin mesoporphyrin, is a porphyrin-Sn(IV) complex, is also a potent heme oxygenase inhibitor, that inhibits HO-1–mediated heme catabolism with potential medicinal application for the treatment of both neonatal jaundice and inherited hyperbilirubinemia syndromes. It was developed to possess unique structural and photophysical properties that make it a particularly potent and bioavailable in vivo inhibitor suitable for clinical use in newborns and studies to date have revealed a very favorable therapeutic profile with no significant adverse side effects.

Chemical Structure

Stannsoporfin

CAS# 106344-20-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202708
Name: Stannsoporfin
CAS#: 106344-20-1
Chemical Formula: C34H36Cl2N4O4Sn
Exact Mass: 0.00
Molecular Weight: 754.290
Elemental Analysis: C, 54.14; H, 4.81; Cl, 9.40; N, 7.43; O, 8.48; Sn, 15.74

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250
25mg	USD 450
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: Stannsoporfin USAN; Tin mesoporphyrin; SNMPP; SnMP; Sn Mesoporphyrin; Stanate; Stannsoporfin. tin (IV) mesoporphyrin IX dichloride.

IUPAC/Chemical Name: Stannate(2-), dichloro(7,12-diethyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanato(4-)-N21,N22,N23,N24)-, dihydrogen, (OC-6-13)-

InChi Key: LLDZJTIZVZFNCM-UHEVNVKKSA-J

InChi Code: InChI=1S/C34H38N4O4.2ClH.Sn/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;;/h13-16H,7-12H2,1-6H3,(H4,35,36,37,38,39,40,41,42);2*1H;/q;;;+4/p-4/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;;

SMILES Code: O=C(O)CCC1=C2/C=C3C(CCC(O)=O)=C(C)C(/C=C4C(CC)=C(C)/C5=C/C6=N/C(C(C)=C6CC)=C\C(N2[Sn](Cl)(Cl)N/45)=C1C)=N/3

Appearance: Solid powder

Purity: >95% (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: Tin mesoporphyrin (SnMP) has emerged as a potential agent for reducing total bilirubin concentrations in preterm newborns. Adverse effects associated with SnMP use include photosensitization (which complicates its use in conjunction with phototherapy), and potential inhibition of several other enzymes that have essential roles in metabolism. Clinical studies of SnMP have shown that it prevents excessive neonatal hyperbilirubinemia and reduces the need for neonatal phototherapy in term and near-term infants. Because further research, specifically safety investigations, are complicated, use of SnMP should be reserved for neonates who are at especially high risk for developing bilirubin-induced neurologic dysfunction or participating in clinical trials. [source: NeoReviews (2007) 8, 77-84] Tin-mesoporphyrin (SnMP) is a competitive inhibitor of microsomal heme oxygenase (the rate-limiting enzyme in the heme catabolic pathway). It was administered as a single intramuscular dose at 46 hours of life to a very-low-birth-weight infant with severe hemolytic hyperbilirubinemia who had been awaiting an exchange transfusion. This case documents the effective elimination of the need for an exchange transfusion in a very-low-birth-weight infant and is a confirmation of the experience of others for the use of SnMP in reducing bilirubin production. Current developer:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#C9M10C25

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Stannsoporfin is a potent inhibitor of heme oxygenase 1 (HO-1) and heme oxygenase 2 (HO-2).
In vitro activity:	HO activity inhibition has potential as a selective chemotherapy target in lung cancer subtypes. In A549 NSCLC cell lines, stannsoporfin inhibited HO activity, reducing A549 cell proliferation and migration. Stannsoporfin treatment increased oxidative stress. Stannsoporfin had impact on key regulators of the pentose phosphate pathway and glutathione synthesis. However, NCI-H292, a NSCLC subtype, had a minimal response, possibly due to low basal HO-1 levels, suggesting cell-dependent antitumorigenic effects. Reference: Biomolecules. 2021 Jun 21;11(6):917. https://pubmed.ncbi.nlm.nih.gov/34205698/
In vivo activity:	Stannsoporfin could represent a novel immune checkpoint therapy, which may improve the immunological response to chemotherapy. In an aggressive spontaneous murine model of breast cancer, stannsoporfin inhibited immune suppression of chemotherapy-elicited CD8+ T cells by targeting myeloid HO-1 activity in the tumor microenvironment. Reference: Clin Cancer Res. 2018 Apr 1;24(7):1617-1628. https://pubmed.ncbi.nlm.nih.gov/29339440/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	2.0	2.65

Preparing Stock Solutions

The following data is based on the product molecular weight 754.29 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:	1. Sorrenti V, D'Amico AG, Barbagallo I, Consoli V, Grosso S, Vanella L. Tin Mesoporphyrin Selectively Reduces Non-Small-Cell Lung Cancer Cell Line A549 Proliferation by Interfering with Heme Oxygenase and Glutathione Systems. Biomolecules. 2021 Jun 21;11(6):917. doi: 10.3390/biom11060917. PMID: 34205698; PMCID: PMC8235249. 2. Yong SB, Kim J, Chung JY, Ra S, Kim SS, Kim YH. Heme Oxygenase 1-Targeted Hybrid Nanoparticle for Chemo- and Immuno-Combination Therapy in Acute Myelogenous Leukemia. Adv Sci (Weinh). 2020 Jun 3;7(13):2000487. doi: 10.1002/advs.202000487. PMID: 32670766; PMCID: PMC7341080. 3. Rosenfeld WN, Hudak ML, Ruiz N, Gautam S; Jasmine Study Group. Stannsoporfin with phototherapy to treat hyperbilirubinemia in newborn hemolytic disease. J Perinatol. 2022 Jan;42(1):110-115. doi: 10.1038/s41372-021-01223-2. Epub 2021 Oct 11. PMID: 34635771. 4. Muliaditan T, Opzoomer JW, Caron J, Okesola M, Kosti P, Lall S, Van Hemelrijck M, Dazzi F, Tutt A, Grigoriadis A, Gillett CE, Madden SF, Burchell JM, Kordasti S, Diebold SS, Spicer JF, Arnold JN. Repurposing Tin Mesoporphyrin as an Immune Checkpoint Inhibitor Shows Therapeutic Efficacy in Preclinical Models of Cancer. Clin Cancer Res. 2018 Apr 1;24(7):1617-1628. doi: 10.1158/1078-0432.CCR-17-2587. Epub 2018 Jan 16. PMID: 29339440; PMCID: PMC5889101.
In vitro protocol:	1. Sorrenti V, D'Amico AG, Barbagallo I, Consoli V, Grosso S, Vanella L. Tin Mesoporphyrin Selectively Reduces Non-Small-Cell Lung Cancer Cell Line A549 Proliferation by Interfering with Heme Oxygenase and Glutathione Systems. Biomolecules. 2021 Jun 21;11(6):917. doi: 10.3390/biom11060917. PMID: 34205698; PMCID: PMC8235249. 2. Yong SB, Kim J, Chung JY, Ra S, Kim SS, Kim YH. Heme Oxygenase 1-Targeted Hybrid Nanoparticle for Chemo- and Immuno-Combination Therapy in Acute Myelogenous Leukemia. Adv Sci (Weinh). 2020 Jun 3;7(13):2000487. doi: 10.1002/advs.202000487. PMID: 32670766; PMCID: PMC7341080.
In vivo protocol:	1. Rosenfeld WN, Hudak ML, Ruiz N, Gautam S; Jasmine Study Group. Stannsoporfin with phototherapy to treat hyperbilirubinemia in newborn hemolytic disease. J Perinatol. 2022 Jan;42(1):110-115. doi: 10.1038/s41372-021-01223-2. Epub 2021 Oct 11. PMID: 34635771. 2. Muliaditan T, Opzoomer JW, Caron J, Okesola M, Kosti P, Lall S, Van Hemelrijck M, Dazzi F, Tutt A, Grigoriadis A, Gillett CE, Madden SF, Burchell JM, Kordasti S, Diebold SS, Spicer JF, Arnold JN. Repurposing Tin Mesoporphyrin as an Immune Checkpoint Inhibitor Shows Therapeutic Efficacy in Preclinical Models of Cancer. Clin Cancer Res. 2018 Apr 1;24(7):1617-1628. doi: 10.1158/1078-0432.CCR-17-2587. Epub 2018 Jan 16. PMID: 29339440; PMCID: PMC5889101.

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1: Burt TD, Seu L, Mold JE, Kappas A, McCune JM. Naive human T cells are activated and proliferate in response to the heme oxygenase-1 inhibitor tin mesoporphyrin. J Immunol. 2010 Nov 1;185(9):5279-88. Epub 2010 Oct 4. PubMed PMID: 20921523.

2: Tiwari M, Chandra R, Das SK, Prakash S. Tin mesoporphyrin in conjunction with retinoic acid reverses the retinoic acid induced enhancement of phospholipase A(2) activity in vivo in rats. Artif Cells Blood Substit Immobil Biotechnol. 2007;35(3):275-85. PubMed PMID: 17573627.

3: Abate A, Zhao H, Wong RJ, Stevenson DK. The role of Bach1 in the induction of heme oxygenase by tin mesoporphyrin. Biochem Biophys Res Commun. 2007 Mar 16;354(3):757-63. Epub 2007 Jan 18. PubMed PMID: 17257585; PubMed Central PMCID: PMC1805812.

4: DeSandre GH, Wong RJ, Morioka I, Contag CH, Stevenson DK. The effectiveness of oral tin mesoporphyrin prophylaxis in reducing bilirubin production after an oral heme load in a transgenic mouse model. Biol Neonate. 2006;89(3):139-46. Epub 2005 Oct 3. PubMed PMID: 16205054.

5: Koeppen AH, Dickson AC, Smith J. Heme oxygenase in experimental intracerebral hemorrhage: the benefit of tin-mesoporphyrin. J Neuropathol Exp Neurol. 2004 Jun;63(6):587-97. PubMed PMID: 15217087.

6: Reddy P, Najundaswamy S, Mehta R, Petrova A, Hegyi T. Tin-mesoporphyrin in the treatment of severe hyperbilirubinemia in a very-low-birth-weight infant. J Perinatol. 2003 Sep;23(6):507-8. PubMed PMID: 13679941.

7: Laftah AH, Raja K, Simpson RJ, Peters TJ. Effect of Tin-mesoporphyrin, an inhibitor of haem catabolism, on intestinal iron absorption. Br J Haematol. 2003 Jul;122(2):298-304. PubMed PMID: 12846900.

8: Nalos M, Vassilev D, Pittner A, Asfar P, BrÃ¼ckner UB, Schneider EM, Georgieff M, Radermacher P, Froeba G. Tin-mesoporphyrin for inhibition of heme oxygenase during long-term hyperdynamic porcine endotoxemia. Shock. 2003 Jun;19(6):526-32. PubMed PMID: 12785007.

9: MartÃnez JC, GarcÃa HO, Otheguy LE, Drummond GS, Kappas A. Treatment of hyperbilirubinemia pharmacologic approach SnMP(tin-mesoporphyrin). J Perinatol. 2001 Dec;21 Suppl 1:S101-3; discussion S104-7. PubMed PMID: 11803428.

10: Chen Y, Zhang B, Chen JG, Huang DY. Solvent effects on the absorption and fluorescence characteristics of tin(IV) mesoporphyrin. Spectrochim Acta A Mol Biomol Spectrosc. 2001 Oct;57(12):2451-6. PubMed PMID: 11767838.

11: Wagner KR, Hua Y, de Courten-Myers GM, Broderick JP, Nishimura RN, Lu SY, Dwyer BE. Tin-mesoporphyrin, a potent heme oxygenase inhibitor, for treatment of intracerebral hemorrhage: in vivo and in vitro studies. Cell Mol Biol (Noisy-le-grand). 2000 May;46(3):597-608. PubMed PMID: 10872746.

12: Lutton JD, Jiang S, Drummond GS, Abraham NG, Kappas A. Comparative pharmacology of zinc mesoporphyrin and tin mesoporphyrin: toxic actions of zinc mesoporphyrin on hematopoiesis and progenitor cell mobilization. Pharmacology. 1999 Jan;58(1):44-50. PubMed PMID: 9831830.

13: Rubaltelli FF, Dario C, Zancan L. Congenital nonobstructive, nonhemolytic jaundice: effect of tin-mesoporphyrin. Pediatrics. 1995 Jun;95(6):942-4. PubMed PMID: 7761229.

14: Valaes T, Petmezaki S, Henschke C, Drummond GS, Kappas A. Control of jaundice in preterm newborns by an inhibitor of bilirubin production: studies with tin-mesoporphyrin. Pediatrics. 1994 Jan;93(1):1-11. PubMed PMID: 8265301.

15: BÃ¶ni RE, Huch BÃ¶ni RA, Galbraith RA, Drummond GS, Kappas A. Tin-mesoporphyrin inhibits heme oxygenase activity and heme-iron absorption in the intestine. Pharmacology. 1993 Nov;47(5):318-29. PubMed PMID: 8265722.

16: Cannon JB, Martin C, Drummond GS, Kappas A. Targeted delivery of a heme oxygenase inhibitor with a lyophilized liposomal tin mesoporphyrin formulation. Pharm Res. 1993 May;10(5):715-21. PubMed PMID: 8321837.

17: Galbraith RA, Drummond GS, Kappas A. Suppression of bilirubin production in the Crigler-Najjar type I syndrome: studies with the heme oxygenase inhibitor tin-mesoporphyrin. Pediatrics. 1992 Feb;89(2):175-82. PubMed PMID: 1734381.

18: Fort FL, Gold J. Phototoxicity of tin protoporphyrin, tin mesoporphyrin, and tin diiododeuteroporphyrin under neonatal phototherapy conditions. Pediatrics. 1989 Dec;84(6):1031-7. PubMed PMID: 2531365.

19: Galbraith RA, Kappas A. Pharmacokinetics of tin-mesoporphyrin in man and the effects of tin-chelated porphyrins on hyperexcretion of heme pathway precursors in patients with acute inducible porphyria. Hepatology. 1989 Jun;9(6):882-8. PubMed PMID: 2714739.

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