MENOGARIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H31NO10
Molecular Weight	541.5464
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]1C[C@](C)(O)CC2=C1C(O)=C3C(=O)C4=C(O)C=C5C(O[C@@H]6O[C@@]5(C)[C@H](O)[C@H]([C@@H]6O)N(C)C)=C4C(=O)C3=C2

InChI

InChIKey=LWYJUZBXGAFFLP-AOZXJLOUSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/menogaril | https://www.ncbi.nlm.nih.gov/pubmed/1331004 | https://www.ncbi.nlm.nih.gov/pubmed/6239835 | https://adisinsight.springer.com/drugs/800000892

Menogaril is a semisynthetic derivative of the anthracycline antineoplastic antibiotic nogalamycin. Biochemical studies indicated that, in comparison to doxorubicin, menogaril is bound weakly to DNA, inhibits RNA synthesis less, and has different cell cycle phase-specific cytotoxicity. Menogaril acts as a cleavable complex-stabilizing topoisomerase II inhibitor. Menogaril has been studied in the treatment of various cancers.

Originator

Approval Year

PubMed

Title	Date	PubMed
Menogaril: a new anthracycline agent entering clinical trials.	1984	6239835
Menogaril, an anthracycline derivative, inhibits DNA topoisomerase II by stabilizing cleavable complexes.	1992 Sep	1331004
Differential poisoning of topoisomerases by menogaril and nogalamycin dictated by the minor groove-binding nogalose sugar.	1997 Oct 28	9341219
Phase II trial of menogaril in patients with previously treated multiple myeloma or chronic lymphocytic leukemia.	2000 Aug	10955868
Phase II evaluation of menogaril in advanced prostate cancer: Eastern Cooperative Oncology Group EST P-A885.	2001 Apr	11319290

Patents

Sample Use Guides

In Vivo Use Guide

Phase II trial of menogaril in non-Hodgkin's lymphomas. Menogaril was administered at 160 mg/m2 intravenously over 1 hour, once every 28 days.

Route of Administration: Intravenous

Name

Type

Language

MENOGARIL

Official Name

English

MENOGARIL [MART.]

Common Name

English

7-O-METHYLNOGAROL

Common Name

English

U-52047

Code

English

U-52,047

Code

English

TUT-7

Common Name

English

NSC-269,148

Code

English

MENOGARIL [USAN]

Common Name

English

2,6-EPOXY-2H-NAPHTHACENO(1,2-B)OXOCIN-9,16-DIONE, 4-(DIMETHYLAMINO)-3,4,5,6,11,12,13,14-OCTAHYDRO-3,5,8,10,13-PENTAHYDROXY-11-METHOXY-6,13-DIMETHYL-, (2R-(2.ALPHA.,3.BETA.,4.ALPHA.,5.BETA.,6.ALPHA.,11.ALPHA.,13.ALPHA.))-

Systematic Name

English

MENOGARIL [JAN]

Common Name

English

7-OMEN

Common Name

English

menogaril [INN]

Common Name

English

MENOGARIL [MI]

Common Name

English

2,6-EPOXY-2H-NAPHTHACENO(1,2-B)OXOCIN-9,16-DIONE, 4-(DIMETHYLAMINO)-3,4,5,6,11,12,13,14-OCTAHYDRO-3,5,8,10,13-PENTAHYDROXY-11-METHOXY-6,13-DIMETHYL-, (2R,3S,4R,5R,6R,11R,13R)-

Systematic Name

English

7-CON-O-METHYLNOGAROL

Common Name

English

7(R)-O-METHYLNOGAROL

Common Name

English

NSC-269148

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1594