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MedKoo Cat#: 597153 | Name: Dichloromethotrexate

Description:

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

Dichloromethotrexate inhibits the enzyme dihydrofolate reductase, thereby preventing the synthesis of purine nucleotides and thymidylates and inhibiting DNA and RNA synthesis. This agent is metabolized and excreted by the liver.

Chemical Structure

Dichloromethotrexate
CAS#528-74-5

Theoretical Analysis

MedKoo Cat#: 597153

Name: Dichloromethotrexate

CAS#: 528-74-5

Chemical Formula: C20H20Cl2N8O5

Exact Mass: 522.0934

Molecular Weight: 523.33

Elemental Analysis: C, 45.90; H, 3.85; Cl, 13.55; N, 21.41; O, 15.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Dichloromethotrexate; 3988-B-129-4; Dichloroamethopterin; NSC-29630; NSC 29630; NSC29630;
IUPAC/Chemical Name
(3,5-dichloro-4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid
InChi Key
MCEHFIXEKNKSRW-LBPRGKRZSA-N
InChi Code
InChI=1S/C20H20Cl2N8O5/c1-30(7-9-6-25-17-14(26-9)16(23)28-20(24)29-17)15-10(21)4-8(5-11(15)22)18(33)27-12(19(34)35)2-3-13(31)32/h4-6,12H,2-3,7H2,1H3,(H,27,33)(H,31,32)(H,34,35)(H4,23,24,25,28,29)/t12-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC(Cl)=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C(Cl)=C1)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 523.33 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
1: Meyers FJ, Blumenstein B, Crawford ED, Hynes HE, Montie JE, Taylor SA, Grossman HB, Natale RB. Combination cisplatin and dichloromethotrexate in patients with advanced bladder cancer. Phase 2. A Southwest Oncology Group study. J Urol. 1992 Jul;148(1):52-4. PubMed PMID: 1613880. 2: Wampler GL, Ahlgren JD, Lokich JJ, Gullo JJ, Phillips JA. Dichloromethotrexate, infusional cisplatin, and infusional 5-fluorouracil for locally advanced or metastatic non-small cell lung cancer. A MAOP study. Am J Clin Oncol. 1991 Oct;14(5):442-5. PubMed PMID: 1659178. 3: Rosowsky A, Wright JE, Holden SA, Waxman DJ. Influence of lipophilicity and carboxyl group content on the rate of hydroxylation of methotrexate derivatives by aldehyde oxidase. Biochem Pharmacol. 1990 Aug 15;40(4):851-7. PubMed PMID: 1696821. 4: Bertino JR. Pharmacology of dichloromethotrexate. J Natl Cancer Inst. 1989 May 10;81(10):815-6. PubMed PMID: 2716075. 5: Golden L, Ahlgren JD, Kattah J, Smith JW, Sisk R, Deeb Z. Cochleovestibular toxicity related to dichloromethotrexate. Cancer Invest. 1989;7(4):345-8. PubMed PMID: 2590860. 6: Romanini A, Chou TC, Bertino JR. Carboxypeptidase G2 enhances trimetrexate cytotoxicity in CCRF-CEM cell lines sensitive and resistant to methotrexate. Adv Enzyme Regul. 1989;28:323-33. PubMed PMID: 2533849. 7: Hantel A, Rowinsky EK, Noe DA, McGuire WP, Grochow LB, Vito BL, Ettinger DS, Donehower RC. Clinical and pharmacologic reappraisal of dichloromethotrexate. J Natl Cancer Inst. 1988 Dec 7;80(19):1547-53. PubMed PMID: 3193470. 8: Klinov SV, Kurganov BI, Sheĭman BM, Gorelik ESh, Birinberg EM. [Inhibition of muscle glycogen phosphorylase b by 5-methyltetrahydrofolic acid, 3'-chloro- and 3',6'-dichloromethotrexates]. Bioorg Khim. 1988 Sep;14(9):1162-5. Russian. PubMed PMID: 3146255. 9: Hammond SJ, Birdsall B, Feeney J, Searle MS, Roberts GC, Cheung HT. Structural comparisons of complexes of methotrexate analogues with Lactobacillus casei dihydrofolate reductase by two-dimensional 1H NMR at 500 MHz. Biochemistry. 1987 Dec 29;26(26):8585-90. PubMed PMID: 3126805. 10: Roberts JA, Blessing JA, McGehee R, Beecham J, Homesley HD. Phase II trial of dichloromethotrexate in patients with advanced squamous cell carcinoma of the cervix: a Gynecologic Oncology Group Study. Cancer Treat Rep. 1987 Dec;71(12):1295-6. PubMed PMID: 3690541. 11: Yagoda A. Chemotherapy of urothelial tract tumors. Cancer. 1987 Aug 1;60(3 Suppl):574-85. Review. PubMed PMID: 3297286. 12: Shepard KV, Levin B, Faintuch J, Doria MI, DuBrow RA, Riddell RH. Hepatitis in patients receiving intraarterial chemotherapy for metastatic colorectal carcinoma. Am J Clin Oncol. 1987 Feb;10(1):36-40. PubMed PMID: 2950752. 13: Natale RB, Wheeler RH, Roberts JA. Cisplatin and dichloromethotrexate: a pharmacologically rational combination. NCI Monogr. 1987;(5):219-23. PubMed PMID: 3431592. 14: Bajorin D, Kelsen D, Heelan R. Phase II trial of dichloromethotrexate in epidermoid carcinoma of the esophagus. Cancer Treat Rep. 1986 Oct;70(10):1245-6. PubMed PMID: 3530454. 15: Johnston MV, Silverstein FS, Greenberg H, Knutsen CA, Chandler W, Phillips T, Ensminger WD. Effects of intraventricular methotrexate on cerebrospinal fluid monoamine metabolites in rhesus monkeys. Cancer Treat Rep. 1986 Oct;70(10):1205-9. PubMed PMID: 2428491. 16: Fabre G, Seither R, Goldman ID. Hydroxylation of 4-amino-antifolates by partially purified aldehyde oxidase from rabbit liver. Biochem Pharmacol. 1986 Apr 15;35(8):1325-30. PubMed PMID: 2421732. 17: O'Dwyer PJ, Leyland-Jones B, Alonso MT, Eisenberger M, Hoth DF. Dichloromethotrexate--a critical reassessment. J Clin Oncol. 1985 Aug;3(8):1148-53. PubMed PMID: 4020413. 18: Sobrero AF, Bertino JR. Sequence-dependent synergism between dichloromethotrexate and cisplatin in a human colon carcinoma cell line. Cancer Treat Rep. 1985 Mar;69(3):279-83. PubMed PMID: 4038918. 19: Ihde DC, Matthews MJ, Makuch RW, McIntire KR, Eddy JL, Seeff LB. Prognostic factors in patients with hepatocellular carcinoma receiving systemic chemotherapy. Identification of two groups of patients with prospects for prolonged survival. Am J Med. 1985 Mar;78(3):399-406. PubMed PMID: 2579551. 20: Shepard KV, Levin B, Karl RC, Faintuch J, DuBrow RA, Hagle M, Cooper RM, Beschorner J, Stablein D. Therapy for metastatic colorectal cancer with hepatic artery infusion chemotherapy using a subcutaneous implanted pump. J Clin Oncol. 1985 Feb;3(2):161-9. PubMed PMID: 3155793.