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{{chembox {{chembox
| Verifiedfields = changed
|ImageFile=Menogaril.png
| Watchedfields = changed
|ImageSize=200px
| verifiedrevid = 300995705
|IUPACName=
| ImageFile=Menogaril.png
|OtherNames=7-''O''-Methylnogarol
| ImageSize=200px
| IUPACName=
| OtherNames=7-''O''-Methylnogarol
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|changed|FDA}}
| CASNo=71628-96-1
| UNII = 8JSV4O30HQ
| PubChem=320697
| CASNo_Ref = {{cascite|correct|??}}
| SMILES=C1(C(C2=C(C1)C=C3C(=C2O)C(=O)C4=C(C=C5C(=C4C3=O)OC6(((C5(O6)C)O)N(C)C)O)O)OC)
| CASNo=71628-96-1
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1234391
| PubChem = 5288818
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4450900
| SMILES = CO1C(C)(O)Cc2cc3c(c(O)c21)C(=O)c1c(O)cc2c(c1C3=O)O1O2(C)(O)(N(C)C)1O
| InChI = 1/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
| InChIKey = LWYJUZBXGAFFLP-OCNCTQISBR
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LWYJUZBXGAFFLP-OCNCTQISSA-N
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>28</sub>H<sub>31</sub>NO<sub>10</sub> | Formula=C<sub>28</sub>H<sub>31</sub>NO<sub>10</sub>
| MolarMass=541.55 g/mol | MolarMass=541.55 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Menogaril''' is an ] analog of ] 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 (43-44% in ] patients).<ref name="Moore 1999">{{cite journal | title=Phase II trial of menogaril in non-Hodgkin's lymphomas: a Southwest Oncology Group trial. |author1=Moore DF Jr |author2=Brown TD |author3=LeBlanc M |author4=Dahlberg S |author5=Miller TP |author6=McClure S |author7=Fisher RI. | journal=Invest New Drugs | year=1999 | volume=17 | issue=2 | pages=169–72 | doi=10.1023/A:1006375301205}}</ref>
'''Menogaril''' is a ] analog.


== References ==
<references/>


{{Chemotherapeutic agents}}
{{pharma-stub}}


] ]


{{antineoplastic-drug-stub}}

Latest revision as of 23:41, 22 June 2023

Menogaril
Names
Other names 7-O-Methylnogarol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: LWYJUZBXGAFFLP-OCNCTQISSA-N
  • InChI=1/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/s1Key: LWYJUZBXGAFFLP-OCNCTQISBR
SMILES
  • CO1C(C)(O)Cc2cc3c(c(O)c21)C(=O)c1c(O)cc2c(c1C3=O)O1O2(C)(O)(N(C)C)1O
Properties
Chemical formula C28H31NO10
Molar mass 541.55 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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 (43-44% in non-Hodgkin's lymphoma patients).

References

  1. Moore DF Jr; Brown TD; LeBlanc M; Dahlberg S; Miller TP; McClure S; Fisher RI. (1999). "Phase II trial of menogaril in non-Hodgkin's lymphomas: a Southwest Oncology Group trial". Invest New Drugs. 17 (2): 169–72. doi:10.1023/A:1006375301205.
Intracellular chemotherapeutic agents / antineoplastic agents (L01)
SPs/MIs
(M phase)
Block microtubule assembly
Block microtubule disassembly
DNA replication
inhibitor
DNA precursors/
antimetabolites
(S phase)
Folic acid
Purine
Pyrimidine
Deoxyribonucleotide
Topoisomerase inhibitors
(S phase)
I
II
II+Intercalation
Crosslinking of DNA
(CCNS)
Alkylating
Platinum-based
Nonclassical
Intercalation
Photosensitizers/PDT
Other
Enzyme inhibitors
Receptor antagonists
Other/ungrouped


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