Heptaplatin | CAS#146665-77-2 | DNA cross-linking agent

MedKoo Cat#: 100422 | Name: Heptaplatin

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Description:

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

Heptaplatin is a third-generation platinum-based anticancer drug structurally related to cisplatin, developed to overcome resistance and reduce toxicity. It exerts its cytotoxic effects by forming DNA crosslinks, leading to inhibition of DNA replication and transcription, and ultimately inducing apoptosis in cancer cells. Heptaplatin shows clinical activity against gastric cancers and has improved tolerability compared to earlier platinum analogs, especially in patients with renal impairment.

Chemical Structure

Heptaplatin

CAS#146665-77-2

Theoretical Analysis

MedKoo Cat#: 100422

Name: Heptaplatin

CAS#: 146665-77-2

Chemical Formula: C11H20N2O6Pt

Exact Mass: 471.0969

Molecular Weight: 471.37

Elemental Analysis: C, 28.03; H, 4.28; N, 5.94; O, 20.37; Pt, 41.39

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Synonym

Heptaplatin Sunpla; Eptaplatin; HTP; NSC644591; NSC 644591; NSC-644591; NSCD644591; NSCD 644591; NSCD-644591; SKI2053R; SKI 2053R; SKI-2053R

IUPAC/Chemical Name

[SP-4-2-[4R-(2a,4a,5b)]]-[2-(1-Methylethyl)-1,3-dioxolane-4,5-dimethanamine-N,N'][propanedioato(2-)-O,O']-platinum

InChi Key

XJXKGUZINMNEDK-GPJOBVNKSA-L

InChi Code

InChI=1S/C8H18N2O2.C3H4O4.Pt/c1-5(2)8-11-6(3-9)7(4-10)12-8;4-2(5)1-3(6)7;/h5-8H,3-4,9-10H2,1-2H3;1H2,(H,4,5)(H,6,7);/q;;+2/p-2/t6-,7-;;/m1../s1

SMILES Code

[O-]C(CC([O-])=O)=O.NC[C@H]1OC(O[C@@H]1CN)C(C)C.[Pt+2]

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

Heptaplatin (HTP), a newly developed platinum analog, has been approved for the treatment of gastric cancers in South Korea. The anti-proliferative activity of HTP was evaluated in FaDu, a human HNSCC cell line. Combinations of HTP with 5-fluorouracil (5-FU) or paclitaxel (PTX) were determined using combination indexes, and were compared with combinations of cisplatin and 5-FU or PTX. In order to evaluate the transport of HTP into tumor tissue, its penetration through multicell layers (MCLs) of cancer cells was measured. Cisplatin+5-FU and HTP+5-FU showed additive to antagonistic interactions. In terms of the HTP+paclitaxel combination, HTP showed antagonism and additivity at the 50 and 80% growth inhibition levels, respectively. An additive interaction was obtained and apoptosis was increased by 2-fold at both inhibition levels when the combinatorial PTX dose was reduced to 1/10. HTP, but not cisplatin or oxaliplatin (L-OHP), maintained its anti-proliferative activity after MCL penetration at clinically relevant concentrations, which can be attributed to lower protein binding of HTP. The results suggest that low-dose PTX may sensitize tumor cells to HTP. HTP also showed greater penetration through multilayers of tumor cells compared to cisplatin and L-OHP, which may be an important characteristic for solid tumor treatment. Overall, the research results support the clinical development of HTP in combination with low-dose PTX against HNSCC. see Anticancer Drugs. 2006 Apr;17(4):377-84.

Instruction

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Preparing Stock Solutions

The following data is based on the product molecular weight 471.37 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

1: Liu W, Chen X, Ye Q, Xu Y, Xie C, Xie M, Chang Q, Lou L. A novel water-soluble heptaplatin analogue with improved antitumor activity and reduced toxicity. Inorg Chem. 2011 Jun 20;50(12):5324-6. doi: 10.1021/ic200436u. Epub 2011 May 20. PubMed PMID: 21598993. 2: Al-Anazi KM, Abou-Tarboush FM, Abdel-Samad MF, Farah MA, Al-Faifi MY, Al-Ahmadi BA. Embryo-feto-toxicity of anticancer drug, heptaplatin in laboratory mice. Pak J Biol Sci. 2010 Sep 15;13(18):896-900. PubMed PMID: 23350163. 3: Lee KH, Hyun MS, Kim HK, Jin HM, Yang J, Song HS, Do YR, Ryoo HM, Chung JS, Zang DY, Lim HY, Jin JY, Yim CY, Park HS, Kim JS, Sohn CH, Lee SN. Randomized, multicenter, phase III trial of heptaplatin 1-hour infusion and 5-fluorouracil combination chemotherapy comparing with cisplatin and 5-fluorouracil combination chemotherapy in patients with advanced gastric cancer. Cancer Res Treat. 2009 Mar;41(1):12-8. doi: 10.4143/crt.2009.41.1.12. Epub 2009 Mar 31. PubMed PMID: 19688066; PubMed Central PMCID: PMC2699097. 4: Lee JW, Park JK, Lee SH, Kim SY, Cho YB, Kuh HJ. Anti-tumor activity of heptaplatin in combination with 5-fluorouracil or paclitaxel against human head and neck cancer cells in vitro. Anticancer Drugs. 2006 Apr;17(4):377-84. PubMed PMID: 16549994. 5: Ryu MR, Paik SY, Chung SM. Combined effect of heptaplatin and ionizing radiation on human squamous carcinoma cell lines. Mol Cells. 2005 Feb 28;19(1):143-8. PubMed PMID: 15750352. 6: Choi CH, Cha YJ, An CS, Kim KJ, Kim KC, Moon SP, Lee ZH, Min YD. Molecular mechanisms of heptaplatin effective against cisplatin-resistant cancer cell lines: less involvement of metallothionein. Cancer Cell Int. 2004 Oct 19;4(1):6. PubMed PMID: 15494073; PubMed Central PMCID: PMC533863. 7: Min YJ, Bang SJ, Shin JW, Kim DH, Park JH, Kim GY, Ko BK, Choi DH, Cho HR. Combination chemotherapy with 5-fluorouracil and heptaplatin as first-line treatment in patients with advanced gastric cancer. J Korean Med Sci. 2004 Jun;19(3):369-73. PubMed PMID: 15201502; PubMed Central PMCID: PMC2816837. 8: Ahn MJ, Oh HS, Choi JH, Lee YY, Kim IS, Choi IY, Lee OY, Choi HS, Kwon SJ. Combination chemotherapy of heptaplatin, paclitaxel and 5-fluorouracil in patients with advanced gastric cancer: a pilot study. Cancer Res Treat. 2004 Jun;36(3):182-6. doi: 10.4143/crt.2004.36.3.182. Epub 2004 Jun 30. PubMed PMID: 20396542; PubMed Central PMCID: PMC2855088. 9: Ahn JH, Kang YK, Kim TW, Bahng H, Chang HM, Kang WC, Kim WK, Lee JS, Park JS. Nephrotoxicity of heptaplatin: a randomized comparison with cisplatin in advanced gastric cancer. Cancer Chemother Pharmacol. 2002 Aug;50(2):104-10. Epub 2002 Jun 25. PubMed PMID: 12172973.

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