MENOGARIL

Investigational

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=CC3=C(C(=O)C4=C(C3=O)C5=C(C=C4O)[C@@]6(C)O[C@@H](O5)[C@@H](O)[C@@H]([C@H]6O)N(C)C)C(O)=C12

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

Molecular Formula	C28H31NO10
Molecular Weight	541.5464
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Phase II evaluation of menogaril in advanced prostate cancer: Eastern Cooperative Oncology Group EST P-A885.	2001-04	11319290
Phase II trial of menogaril in patients with previously treated multiple myeloma or chronic lymphocytic leukemia.	2000-08	10955868
Differential poisoning of topoisomerases by menogaril and nogalamycin dictated by the minor groove-binding nogalose sugar.	1997-10-28	9341219
Menogaril, an anthracycline derivative, inhibits DNA topoisomerase II by stabilizing cleavable complexes.	1992-09	1331004
Menogaril: a new anthracycline agent entering clinical trials.	1984	6239835

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

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:53:51 GMT 2025` Edited by `admin` on `Wed Apr 02 07:53:51 GMT 2025`
Record UNII	8JSV4O30HQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-269,148

Preferred Name

English

MENOGARIL

Official Name

English

MENOGARIL [MART.]

Common Name

English

7-O-METHYLNOGAROL

Common Name

English

Menogaril [WHO-DD]

Common Name

English

U-52047

Code

English

U-52,047

Code

English

TUT-7

Common Name

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