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MedKoo Cat#: 462681 | Name: Menogaril

Description:

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

Menogaril is an anthracycline analog of nogalamycin which was developed in late 1970s. It has even stronger anticancer activity than nogalamycin and has less toxicity than nogalamycin. However, its development for clinical use was cancelled due to only moderate success with relatively high incidence of serious toxicity.

Chemical Structure

Menogaril
Menogaril
CAS#71628-96-1

Theoretical Analysis

MedKoo Cat#: 462681

Name: Menogaril

CAS#: 71628-96-1

Chemical Formula: C28H31NO10

Exact Mass: 541.1948

Molecular Weight: 541.55

Elemental Analysis: C, 62.10; H, 5.77; N, 2.59; O, 29.54

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 #
No Data
Synonym
NSC 269148; NSC269148; NSC-269148; NSC-269,148; NSC269,148; NSC 269,148;
IUPAC/Chemical Name
(2R,3S,4R,5R,6R,11R,13R)-4-(dimethylamino)-3,5,8,10,13-pentahydroxy-11-methoxy-6,13-dimethyl-3,4,5,6,11,12,13,14-octahydro-2H-2,6-epoxytetraceno[1,2-b]oxocine-9,16-dione
InChi Key
LWYJUZBXGAFFLP-OCNCTQISSA-N
InChi Code
InChI=1S/C28H31NO10/c1-27(36)8-10-6-11-16(21(32)15(10)14(9-27)37-5)22(33)17-13(30)7-12-24(18(17)20(11)31)38-26-23(34)19(29(3)4)25(35)28(12,2)39-26/h6-7,14,19,23,25-26,30,32,34-36H,8-9H2,1-5H3/t14-,19+,23+,25-,26-,27-,28-/m1/s1
SMILES Code
CO[C@@H]1C[C@](O)(Cc2c1c(O)c3c(C(c4c(C3=O)c(O)cc5c4O[C@@H]6O[C@@]([C@@H]([C@@H](N(C)C)[C@@H]6O)O)5C)=O)c2)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 541.55 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: Peng R, VanNieuwenhze MS. Construction of the DEF-Benzoxocin Ring System of Nogalamycin and Menogaril via a Reductive Heck Cyclization. J Org Chem. 2019 Jan 4;84(1):173-180. doi: 10.1021/acs.joc.8b02575. Epub 2018 Dec 24. PMID: 30525623. 2: Yoshida M, Fujioka A, Nakano K, Yuasa C, Toko T, Takeda S, Unemi N. Activity of menogaril against various malignant lymphoma cell lines and a human lymphoma xenograft in mice. Anticancer Res. 1996 Sep-Oct;16(5A):2875-9. PMID: 8917401. 3: McGovren JP, Nelson KG, Lassus M, Cradock JC, Plowman J, Christopher JP. Menogaril: a new anthracycline agent entering clinical trials. Invest New Drugs. 1984;2(4):359-67. doi: 10.1007/BF00171586. PMID: 6239835. 4: Inaba M, Sato S, Yamori T, Tashiro T, Ohnishi Y, Maruo K, Ueyama Y, Tsuruo T. Anticancer activities of orally administered menogaril against human stomach and breast cancers implanted in nude mice. Anticancer Res. 1992 Nov- Dec;12(6B):1953-6. PMID: 1295442. 5: Badiner GJ, Moy BC, Smith KS, Tarpley WG, Groppi VE, Bhuyan BK. P388 leukaemia cells resistant to the anthracycline menogaril lack multidrug resistant phenotype. Br J Cancer. 1990 Sep;62(3):378-84. doi: 10.1038/bjc.1990.302. PMID: 2145026; PMCID: PMC1971454. 6: Taguchi T, Ohta K, Hotta T, Shirakawa S, Masaoka T, Kimura I. [Menogaril (TUT-7) late phase II study for malignant lymphoma, adult T-cell leukemia and lymphoma (ATLL)]. Gan To Kagaku Ryoho. 1997 Aug;24(10):1263-71. Japanese. PMID: 9279345. 7: Stewart DJ, Grewaal D, Green RM, Goel R, Mikhael N, Montpetit VA, Redmond D, Earhart R. Human autopsy-tissue distribution of menogaril and its metabolites. Cancer Chemother Pharmacol. 1993;32(5):373-8. doi: 10.1007/BF00735922. PMID: 8339388. 8: Moore DF Jr, Brown TD, LeBlanc M, Dahlberg S, Miller TP, McClure S, Fisher RI. Phase II trial of menogaril in non-Hodgkin's lymphomas: a Southwest Oncology Group trial. Invest New Drugs. 1999;17(2):169-72. doi: 10.1023/a:1006375301205. PMID: 10638487. 9: Piergies AA, Benson AB 3rd. Pharmacokinetics and acute cardiovascular effects of menogaril in patients with metastatic tumors. Int J Clin Pharmacol Ther. 1995 Feb;33(2):63-9. PMID: 7757312. 10: Weiss GR, Brown TD, Kuhn JG, Von Hoff DD, Earhart RH, Adams WJ, Brewer JE, Hosley JD, Kasunic DA. A phase I clinical and pharmacokinetic study of the oral and the oral/intravenous administration of menogaril. Invest New Drugs. 1993 Feb;11(1):17-27. doi: 10.1007/BF00873906. PMID: 8349432. 11: Falkson G, Lipsitz S, Borden E, Simson I, Haller D. Hepatocellular carcinoma. An ECOG randomized phase II study of beta-interferon and menogaril. Am J Clin Oncol. 1995 Aug;18(4):287-92. PMID: 7625367. 12: Long HJ, Powis G, Schutt AJ, Moertel CG. Phase I and pharmacokinetic study of menogaril administered as a 72-hour continuous i.v. infusion. Cancer Treat Rep. 1987 Jun;71(6):593-8. PMID: 2953414. 13: Adams EG, Bhuyan BK. Effects of 7-R-O-methylnogarol (menogaril) on L1210 cell progression in vitro and in vivo. Cancer Res. 1986 Dec;46(12 Pt 1):6125-30. PMID: 2946401. 14: LONG HJ 3rd, Wieand HS, Foley JF, Niedringhaus RD, Laurie JA, Morton RF, Goldberg RM, Mailliard JA, Malkasian GD, Edmonson JH. Phase II evaluation of menogaril in patients with advanced cervical carcinoma. A collaborative trial of the North Central Cancer Treatment Group and Mayo Clinic. Invest New Drugs. 1991 Nov;9(4):349-51. doi: 10.1007/BF00183579. PMID: 1839536. 15: Obasaju C, Manola J, Hudes GR, Khandekar JD, Citrin DL, Carbone P, Trump DL. Phase II evaluation of menogaril in advanced prostate cancer: Eastern Cooperative Oncology Group EST P-A885. Am J Clin Oncol. 2001 Apr;24(2):150-4. doi: 10.1097/00000421-200104000-00011. PMID: 11319290. 16: Adams WJ, McGovren JP, Dalm EA, Brewer JE, Hosley JD. Pharmacokinetics and systemic bioavailability of menogaril, an anthracycline antitumor agent, in the mouse, dog, and monkey. Cancer Res. 1989 Nov 15;49(22):6328-36. PMID: 2529962. 17: Dodion P, de Valeriola D, Crespeigne N, Peeters B, Wery F, van Berchem C, Piccart M, Tueni E, Joggi J, Kenis Y. Phase I clinical and pharmacokinetic trial of oral menogaril administered on three consecutive days. Eur J Cancer Clin Oncol. 1988 Jun;24(6):1019-26. doi: 10.1016/0277-5379(88)90152-6. PMID: 2970391. 18: Egorin MJ, Conley BA, Forrest A, Zuhowski EG, Sinibaldi V, Van Echo DA. Phase I study and pharmacokinetics of menogaril (NSC 269148) in patients with hepatic dysfunction. Cancer Res. 1987 Nov 15;47(22):6104-10. PMID: 2959359. 19: Sinha BK, Atwell J, Politi PM. Role of oxygen free radical formation in the mechanism of menogaril resistance in multidrug resistant tumor cells. Chem Biol Interact. 1990;76(1):89-99. doi: 10.1016/0009-2797(90)90036-m. PMID: 2168296. 20: Yoshida M, Fujioka A, Nakano K, Kobunai T, Saito H, Toko T, Takeda S, Unemi N. Antitumor activity of menogaril alone, and in combination against human mammary cancer models in mice and rats. Anticancer Res. 1996 May- Jun;16(3A):1155-9. PMID: 8702227.