Page last updated: 2024-12-08

nogalamycin

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Description

Nogalamycin: An anthrocycline from a Streptomyces nogalater variant. It is a cytolytic antineoplastic that inhibits DNA-dependent RNA synthesis by binding to DNA. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nogalamycin : An anthracycline antibiotic isolated from Streptomyces nogalater. It is a DNA intercalator and exhibits anticancer properties. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID250876
CHEMBL ID1991217
SCHEMBL ID1649692
MeSH IDM0014939

Synonyms (17)

Synonym
NCI60_038415
nsc 70845
2,2-b]oxocin-14-carboxylic acid, 11-[(6-deoxy-3-c-methyl-2,3,4-tri-o-methyl-.alpha.-l-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9.11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-
antibiotic from streptomyces nogalater
antibiotic 205t3
2,2-b]oxocin-14-carboxylic acid, 11-[(6-deoxy-3-c-methyl-2,3,4-tri-o-methyl-.alpha.-l-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-, methyl ester, (2.alpha.,3.beta.,4.alpha.,5.b
NSC70845 ,
nogalamycin
u 15167
1404-15-5
2,6-epoxy-2h-naphthaceno[1,2-b]oxocin-14-carboxylic acid, 11-[(6-deoxy-3-c-methyl-2,3,4-tri-o-methylhexopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-, methyl ester, (2s,3s,4r,5r,...
methyl dimethylamino-pentahydroxy-dimethyl-dioxo-(3,4,5-trimethoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-[?]carboxylate
SCHEMBL1649692
CHEMBL1991217
methyl (1s,10s,12s,13r,21s,22s,23r,24r)-23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-(3,4,5-trimethoxy-4,6-dimethyloxan-2-yl)oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxy
methyl 23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(2r,3r,4r,5s,6s)-3,4,5-trimethoxy-4,6-dimethyloxan-2-yl]oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate
PD011266

Research Excerpts

Overview

Nogalamycin is an anthracycline antibiotic that intercalates into the DNA double helix. It was markedly cytotoxic in vitro and was active against several tumor systems in vivo.

ExcerptReferenceRelevance
"Nogalamycin is an anthracycline anti-cancer agent that intercalates into the DNA double helix. "( The Rieske Oxygenase SnoT Catalyzes 2''-Hydroxylation of l-Rhodosamine in Nogalamycin Biosynthesis.
Metsä-Ketelä, M; Nji Wandi, B; Palmu, K; Siitonen, V, 2020
)
2.23
"Nogalamycin is an anthracycline antitumor antibiotic, consisting of the aromatic aglycone attached with a nogalose and a nogalamine. "( Inactivation and identification of three genes encoding glycosyltransferase required for biosynthesis of nogalamycin.
Gao, X; Liu, W; Ma, B; Pu, T; Shao, L; Shi, X; Wang, S,
)
1.79
"Nogalamycin is an anthracycline antibiotic that has been shown to exhibit significant cytotoxicity. "( Identification of late-stage glycosylation steps in the biosynthetic pathway of the anthracycline nogalamycin.
Aromaa, M; Claesson, M; Mäntsälä, P; Metsä-Ketelä, M; Patrikainen, P; Schneider, G; Siitonen, V, 2012
)
2.04
"Nogalamycin is an anthracycline polyketide antibiotic that contains two deoxysugars, at positions C-1 and C-7. "( Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis.
Blauenburg, B; Kallio, P; Mäntsälä, P; Metsä-Ketelä, M; Siitonen, V, 2012
)
2.06
"Nogalamycin is an anthracycline antibiotic which was markedly cytotoxic in vitro and was active against several tumor systems in vivo. "( Cell kill kinetics of several nogalamycin analogs and adriamycin for Chinese hamster ovary, L1210 leukemia, and B16 melanoma cells in culture.
Bhuyan, BK; Blowers, CL; Crampton, SL; Shugars, KD, 1981
)
1.99
"Nogalamycin is an anthracycline antibiotic produced by Streptomyces nogalater. "( Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater.
Hakala, J; Kunnari, T; Mäntsälä, P; Palmu, K; Torkkell, S; Ylihonko, K, 2000
)
1.75

Effects

Nogalamycin has bulky sugar groups at either end of a planar aglycon chromophore. In order for intercalation to occur, the DNA must either transiently open or flex along the helix axis.

ExcerptReferenceRelevance
"Nogalamycin (1) has been modified by changes at C-10 and C-7 and in the dimethylamino group to prepare an extensive series of analogues. "( Structure--activity relationships of nogalamycin analogues.
Elrod, DW; Houser, DJ; Richard, FA; Wiley, PF, 1982
)
1.98
"Nogalamycin has bulky sugar groups at either end of a planar aglycon chromophore; therefore, in order for intercalation to occur, the DNA must either transiently open or flex along the helix axis to allow insertion of the chromophore between the base pairs."( DNA-nogalamycin interactions: the crystal structure of d(TGATCA) complexed with nogalamycin.
Davies, GJ; Dodson, EJ; Moore, MH; Smith, CK, 1995
)
1.57

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic parameters derived from plasma concentration-time profiles after repeated (for 14 days) or single oral administration of TUT-7 to rats were found to be not significantly different by either administration schedule."( [Pharmacokinetic studies of menogaril (TUT-7) with rats].
Akimoto, T; Aso, R; Hara, H; Nakama, K; Ohashi, K; Takahashi, F, 1992
)
0.28
" We report here the results of pharmacokinetic and systemic bioavailability studies of menogaril in three species (mouse, dog, and monkey)."( Pharmacokinetics and systemic bioavailability of menogaril, an anthracycline antitumor agent, in the mouse, dog, and monkey.
Adams, WJ; Brewer, JE; Dalm, EA; Hosley, JD; McGovren, JP, 1989
)
0.28
" Pharmacokinetic studies showed that the rise in plasma concentration during infusion was first-order, with a half-life of 11."( Phase I and pharmacokinetic study of menogaril administered as a 72-hour continuous i.v. infusion.
Long, HJ; Moertel, CG; Powis, G; Schutt, AJ, 1987
)
0.27
" The drug disappeared from plasma biexponentially with a mean elimination half-life of 38 +/- 3 h; the mean apparent volume of distribution and the plasma clearance were 805 +/- 91 1/m2 and 14 +/- 2 1/h per m2."( Pharmacokinetics of 7-con-O-methylnogarol in patients with solid tumors.
D'Incalci, M; Figoli, F; Monfardini, S; Sorio, R; Tirelli, U; Zadro, D; Zanette, ML, 1987
)
0.27
" The mean harmonic half-life was 11."( Phase I clinical and pharmacokinetic trial of oral menogaril administered on three consecutive days.
Crespeigne, N; de Valeriola, D; Dodion, P; Joggi, J; Kenis, Y; Peeters, B; Piccart, M; Tueni, E; van Berchem, C; Wery, F, 1988
)
0.27

Compound-Compound Interactions

ExcerptReferenceRelevance
" This reversal was inhibited when menogarol was combined with melphalan."( Synergistic combination of menogarol and melphalan and other two drug combinations.
Adams, EG; Bhuyan, BK; Crampton, SL; Johnson, M, 1985
)
0.27

Bioavailability

ExcerptReferenceRelevance
" We report here the results of pharmacokinetic and systemic bioavailability studies of menogaril in three species (mouse, dog, and monkey)."( Pharmacokinetics and systemic bioavailability of menogaril, an anthracycline antitumor agent, in the mouse, dog, and monkey.
Adams, WJ; Brewer, JE; Dalm, EA; Hosley, JD; McGovren, JP, 1989
)
0.28
" A comparison of the data from the present trial and our previous study with intravenous menogaril indicates a bioavailability of 32 +/- 12%."( Phase I clinical and pharmacokinetic trial of oral menogaril administered on three consecutive days.
Crespeigne, N; de Valeriola, D; Dodion, P; Joggi, J; Kenis, Y; Peeters, B; Piccart, M; Tueni, E; van Berchem, C; Wery, F, 1988
)
0.27
" Oral bioavailability studies in the mouse showed significant absorption of menogaril from the gastrointestinal tract followed by first-pass metabolism."( Menogaril: a new anthracycline agent entering clinical trials.
Christopher, JP; Cradock, JC; Lassus, M; McGovren, JP; Nelson, KG; Plowman, J, 1984
)
0.27

Dosage Studied

ExcerptRelevanceReference
" At that those, 20 of 37 patients developed grade 3 or 4 granulocytopenia and 22 required dosage delays."( Phase II study of oral menogaril as first line chemotherapy for advanced breast cancer: a National Cancer Institute of Canada Clinical Trials Group study.
Aitken, S; Buckman, R; Eisenhauer, EA; Norris, B; Pritchard, KI; Skillings, J; Stewart, DJ; VAndenberg, T; Verma, S, 1992
)
0.28
" Menogaril as administered in this protocol is ineffective in treating previously irradiated advanced/recurrent squamous cell carcinoma of the uterine cervix and warrants no further investigation in this disease at the dosage and administration schedule used in this protocol."( Phase II evaluation of menogaril in patients with advanced cervical carcinoma. A collaborative trial of the North Central Cancer Treatment Group and Mayo Clinic.
Edmonson, JH; Foley, JF; Goldberg, RM; Laurie, JA; LONG, HJ; Mailliard, JA; Malkasian, GD; Morton, RF; Niedringhaus, RD; Wieand, HS, 1991
)
0.28
" At this dosage and schedule, menogaril has no substantial anti-tumor activity for patients with non-small cell lung cancer."( Phase II evaluation of menogaril (NSC-269148) in non-small cell lung carcinoma. A Southwest Oncology Group study.
Ahmann, FR; Crowley, JJ; Macdonald, JS; Vance, RB, 1991
)
0.28
" These latter findings should be useful in developing more precise and intelligent dosing schemes for 7-OMEN."( Human pharmacokinetics, excretion, and metabolism of the anthracycline antibiotic menogaril (7-OMEN, NSC 269148) and their correlation with clinical toxicities.
Aisner, J; Egorin, MJ; Engisch, KL; Forrest, A; Sigman, LM; Van Echo, DA; Whitacre, MY, 1986
)
0.27
"We performed a phase I study of menogaril to determine if dosage reduction was required in patients with hepatic dysfunction and if the relationship between pharmacokinetics and leukopenia, previously defined in patients with normal hepatic and renal function, was altered."( Phase I study and pharmacokinetics of menogaril (NSC 269148) in patients with hepatic dysfunction.
Conley, BA; Egorin, MJ; Forrest, A; Sinibaldi, V; Van Echo, DA; Zuhowski, EG, 1987
)
0.27
" This regimen and dosage schedule are well tolerated, with minimal toxicity that included myelosupression; median white blood cell (WBC) count nadir of 2,700 cells/mm3 (range 1,400-7,100 cells/mm3) and median platelet nadir of 162,000 cells/mm3 (range 53,000-390,000 cells/mm3)."( Phase II trial of menogarol in the treatment of advanced adenocarcinoma of the pancreas.
Cheng, EW; Hollander, P; Magill, GB; Sternberg, CN, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (215)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990100 (46.51)18.7374
1990's66 (30.70)18.2507
2000's30 (13.95)29.6817
2010's16 (7.44)24.3611
2020's3 (1.40)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.36

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.36 (24.57)
Research Supply Index5.53 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials20 (8.66%)5.53%
Reviews11 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other200 (86.58%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]