N-Trifluoroacetyladriamycin
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MedKoo CAT#: 597592

CAS#: 26295-56-7

Description: N-Trifluoroacetyladriamycin is a metabolite of valrubicin. Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. It was originally launched as Valstar in the U.S.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 510 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-08-08. Prices are subject to change without notice.

N-Trifluoroacetyladriamycin purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597592
Name: N-Trifluoroacetyladriamycin
CAS#: 26295-56-7
Chemical Formula: C29H28F3NO12
Exact Mass: 639.1564
Molecular Weight: 639.53
Elemental Analysis: C, 54.46; H, 4.41; F, 8.91; N, 2.19; O, 30.02


Synonym: N-Trifluoroacetyladriamycin; NSC 283464; NSC-283464; NSC283464; AD 41; AD-41; AD41;

IUPAC/Chemical Name: 2,2,2-trifluoro-N-((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)acetamide

InChi Key: RQIOYWADAKTIJC-QFVZNODKSA-N

InChi Code: InChI=1S/C29H28F3NO12/c1-10-22(36)13(33-27(41)29(30,31)32)6-17(44-10)45-15-8-28(42,16(35)9-34)7-12-19(15)26(40)21-20(24(12)38)23(37)11-4-3-5-14(43-2)18(11)25(21)39/h3-5,10,13,15,17,22,34,36,38,40,42H,6-9H2,1-2H3,(H,33,41)/t10-,13-,15?,17-,22+,28-/m0/s1

SMILES Code: C[C@H]1[C@@H](O)[C@@H](NC(C(F)(F)F)=O)C[C@H](OC2C[C@@](C(CO)=O)(O)Cc3c(O)c(C(c4c(C5=O)c(OC)ccc4)=O)c5c(O)c32)O1


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

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


References

1: Krishan A, Dutt K, Israel M, Ganapathi R. Comparative effects of adriamycin and N-trifluoroacetyladriamycin-14-valerate on cell kinetics, chromosomal damage, and macromolecular synthesis in vitro. Cancer Res. 1981 Jul;41(7):2745-50. PubMed PMID: 6972801.

2: Chuang RY, Chuang LF, Kawahata RT, Israel M. Effect of N-trifluoroacetyladriamycin-14-valerate on [3H]thymidine uptake and DNA synthesis of human lymphoma cells. J Biol Chem. 1983 Jan 25;258(2):1062-5. PubMed PMID: 6822492.

3: Israel M, Modest EJ, Frei E 3rd. N-trifluoroacetyladriamycin-14-valerate, an analog with greater experimental antitumor activity and less toxicity than adriamycin. Cancer Res. 1975 May;35(5):1365-8. PubMed PMID: 1054622.

4: Sweatman TW, Parker RF, Israel M. Pharmacologic rationale for intravesical N-trifluoroacetyladriamycin-14-valerate (AD 32): a preclinical study. Cancer Chemother Pharmacol. 1991;28(1):1-6. PubMed PMID: 2040028.

5: Zirvi KA, Gilani SH, Hill GJ. Embryotoxic effects of doxorubicin and N-trifluoroacetyladriamycin-14-valerate (AD-32). Teratology. 1985 Apr;31(2):247-52. PubMed PMID: 3992493.

6: Niell HB, Hunter RF, Herrod HG, Israel M. Effects of N-trifluoroacetyladriamycin-14-valerate (AD-32) on human bladder tumor cell lines. Cancer Chemother Pharmacol. 1987;19(1):47-52. PubMed PMID: 3815726.

7: Brox L, Gowans B, Belch A. N-trifluoroacetyladriamycin-14-valerate and adriamycin induced DNA damage in the RPMI-6410 human lymphoblastoid cell line. Can J Biochem. 1980 Sep;58(9):720-5. PubMed PMID: 7006761.

8: Israel M, Wilkinson PM, Pegg WJ, Frei E 3rd. Hepatobiliary metabolism and excretion of adriamycin and N-trifluoroacetyladriamycin-14-valerate in the rat. Cancer Res. 1978 Feb;38(2):365-70. PubMed PMID: 620407.

9: Facchinetti T, Raz A, Goldman R. A differential interaction of daunomycin, adriamycin, and N-trifluoroacetyladriamycin 14-valerate with mouse peritoneal macrophages. Cancer Res. 1978 Nov;38(11 Pt 1):3944-9. PubMed PMID: 212183.

10: Marsh JC. Comparison of the sensitivities of human, canine, and murine hematopoietic precursor cells to adriamycin and N-trifluoroacetyladriamycin-14-valerate. Cancer Res. 1979 Feb;39(2 Pt 1):360-4. PubMed PMID: 761207.

11: Chuang LF, Kung HF, Israel M, Chuang RY. Activation of human leukemia protein kinase C by tumor promoters and its inhibition by N-trifluoroacetyladriamycin-14-valerate (AD 32). Biochem Pharmacol. 1992 Feb 18;43(4):865-72. PubMed PMID: 1540240.

12: Kanter PM, Schwartz HS. Effects of N-trifluoroacetyladriamycin-14-valerate and related agents on DNA strand damage and thymidine incorporation in CCRF-CEM cells. Cancer Res. 1979 Feb;39(2 Pt 1):448-51. PubMed PMID: 761217.

13: Parker LM, Hirst M, Israel M. N-trifluoroacetyladriamycin-14-valerate: additional mouse antitumor and toxicity studies. Cancer Treat Rep. 1978 Jan;62(1):119-27. PubMed PMID: 272230.

14: Chuang LF, Kawahata RT, Chuang RY. Inhibition of chicken myeloblastosis RNA polymerase II activity in vitro by N-trifluoroacetyladriamycin-14-valerate. FEBS Lett. 1980 Aug 11;117(1):247-51. PubMed PMID: 7409170.

15: Potmesil M, Israel M, Kirschenbaum S, Bowen J, Silber R. Effects of N-trifluoroacetyladriamycin-14-O-hemiadipate and radiation on L1210 cells. Radiat Res. 1986 Feb;105(2):147-57. PubMed PMID: 3754052.

16: Vecchi A, Cairo M, Mantovani A, Sironi M, Spreafico F. Comparative antineoplastic activity of adriamycin and N-trifluoroacetyladriamycin-14-valerate. Cancer Treat Rep. 1978 Jan;62(1):111-7. PubMed PMID: 626989.

17: Abbruzzi R, Rizzardini M, Benigni A, Barbieri B, Donelli MG, Salmona M. Possible relevance of N-trifluoroacetyladriamycin (AD 41) in the antitumoral activity of N-trifluoroacetyladriamycin-14-valerate (AD 32) in tumor-bearing mice. I. Pharmacokinetic evidence. Cancer Treat Rep. 1980 Aug-Sep;64(8-9):873-8. PubMed PMID: 7448825.

18: Blum RH, Garnick MB, Israel M, Canellos GP, Henderson IC, Frei E 3rd. Initial clinical evaluation of N-trifluoroacetyladriamycin-14-valerate (AD-32), an adriamycin analog. Cancer Treat Rep. 1979 May;63(5):919-23. PubMed PMID: 455334.

19: Lameh J, Chuang RY, Israel M, Chuang LF. Nucleoside uptake and membrane fluidity studies on N-trifluoroacetyladriamycin-14-O-hemiadipate-treated human leukemia and lymphoma cells. Cancer Res. 1989 Jun 1;49(11):2905-8. PubMed PMID: 2541896.

20: Chuang LF, Israel M, Chuang RY. Inhibition of the initiation of leukemic transcription by N-trifluoroacetyladriamycin-14-O-hemiadipate in vitro. Impaired formation of RNA polymerase-DNA complex. J Biol Chem. 1984 Sep 25;259(18):11391-5. PubMed PMID: 6206068.