Page last updated: 2024-12-06

mdl 27695

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

MDL 27695: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	72453
CHEMBL ID	40258
SCHEMBL ID	7015048
MeSH ID	M0162620

Synonyms (10)

Synonym
1,7-heptanediamine, n,n'-bis(3-((phenylmethyl)amino)propyl)-
n,n'-bis[3-(benzylamino)propyl]heptane-1,7-diamine
n,n'-bis(3-((phenylmethyl)amino)propyl)-1,7-diaminoheptane
117654-71-4
mdl-27695
mdl 27695
CHEMBL40258
SCHEMBL7015048
DTXSID50151859
n,n'-bis{3-[(phenylmethyl)amino]propyl}-1,7-diaminoheptane

Research Excerpts

Effects

Excerpt	Reference	Relevance
"MDL 27695 has also been shown to possess significant antimalarial effects both in vitro and in vivo, and it is possible that the marked suppression of polyamine biosynthesis described herein may contribute to its anti-malarial effects as well as its antiproliferative effects in mammalian cells."	( Regulation of polyamine biosynthesis in rat hepatoma (HTC) cells by a bisbenzyl polyamine analogue. Bitonti, AJ; Bush, TL; McCann, PP, 1989)	1

Compound-Compound Interactions

Excerpt	Reference	Relevance
" three times per day for 3 days in combination with 2% alpha-difluoromethylornithine (DFMO; eflornithine) in drinking water effected cures of 47/54 mice infected with Plasmodium berghei."	( Bis(benzyl)polyamine analogs inhibit the growth of chloroquine-resistant human malaria parasites (Plasmodium falciparum) in vitro and in combination with alpha-difluoromethylornithine cure murine malaria. Bitonti, AJ; Bush, TL; Dumont, JA; Edwards, ML; McCann, PP; Sjoerdsma, A; Stemerick, DM, 1989)	0.28

Dosage Studied

Excerpt	Relevance	Reference
" donovani infections in BALB/c mice were suppressed greater than 99% after intraperitoneal dosing for 20 days with a total dose of 150 mg of MDL 27,695 per kg of body weight or 560 mg of Sbv per kg."	( Suppression of Leishmania donovani by oral administration of a bis(benzyl)polyamine analog. Baumann, RJ; Bitonti, AJ; McCann, PP, 1991)	0.28

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay ID	Title	Year	Journal	Article
AID215498	In vitro growth Inhibitory activity against LAB 110 Strain of Trypanosoma brucei	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID215363	In vitro growth Inhibitory activity against K269 Strain of Trypanosoma brucei.	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID81368	Anti-proliferative activity against HeLa cells	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID87901	Ability to cause aggregation of purified HeLa cell DNA	1991	Journal of medicinal chemistry, Aug, Volume: 34, Issue:8	Synthesis and DNA-binding properties of polyamine analogues.
AID215500	In vitro growth inhibitory activity against Trypanosoma brucei strain K243 (As-10-3)	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Novel alkylpolyamine analogues that possess both antitrypanosomal and antimicrosporidial activity.
AID421189	Antiparasitic activity against Plasmodium falciparum	2009	Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15	Recent advances in the development of polyamine analogues as antitumor agents.
AID556064	Activity of Encephalitozoon cuniculi polyamine oxidase assessed as hydrogen peroxide release per mg protein by spectrophotometry	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Metabolism of an alkyl polyamine analog by a polyamine oxidase from the microsporidian Encephalitozoon cuniculi.
AID86842	Ability to inhibit 50% growth of HeLa cells	1991	Journal of medicinal chemistry, Aug, Volume: 34, Issue:8	Synthesis and DNA-binding properties of polyamine analogues.
AID54444	Ability to displace ethidium bromide from calf thymus DNA	1991	Journal of medicinal chemistry, Aug, Volume: 34, Issue:8	Synthesis and DNA-binding properties of polyamine analogues.
AID162553	Ability to displace ethidium bromide from double stranded synthetic poly (dG-dC)	1991	Journal of medicinal chemistry, Aug, Volume: 34, Issue:8	Synthesis and DNA-binding properties of polyamine analogues.
AID215502	In vitro growth inhibitory activity against Trypanosoma brucei strain LAB110	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Novel alkylpolyamine analogues that possess both antitrypanosomal and antimicrosporidial activity.
AID80472	Antitumor activity was determined against H157 cell line	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID215499	In vitro growth inhibitory activity against Trypanosoma brucei strain K243	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Novel alkylpolyamine analogues that possess both antitrypanosomal and antimicrosporidial activity.
AID215362	In vitro growth Inhibitory activity against K243 Strain of Trypanosoma brucei.	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID80492	In vitro activity against H157 non-small-cell lung tumor line (non-SCLC) cultures.	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID221123	Antimalarial activity was determined against Leishmania donovani in hamsters	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID215501	In vitro growth inhibitory activity against Trypanosoma brucei strain K269	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Novel alkylpolyamine analogues that possess both antitrypanosomal and antimicrosporidial activity.
AID86980	Compound was evaluated for its ability to inhibit proliferation of HeLa cells	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID556065	Activity of Encephalitozoon cuniculi polyamine oxidase assessed as hydrogen peroxide release per mg protein by spectrophotometry relative to 0.1 mM N'-acetylspermine	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Metabolism of an alkyl polyamine analog by a polyamine oxidase from the microsporidian Encephalitozoon cuniculi.
AID162413	Ability to displace ethidium bromide from double stranded synthetic Poly (dA-dT)	1991	Journal of medicinal chemistry, Aug, Volume: 34, Issue:8	Synthesis and DNA-binding properties of polyamine analogues.
AID129292	Antimalarial activity was determined against Leishmania donovani in mice (Mus musculus)	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID215361	In vitro growth Inhibitory activity against K243 As-10-3 Strain of Trypanosoma brucei	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID78586	In vitro activity against H82 small-cell lung tumor line (SCLC) cultures.	2001	Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1	Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID556066	Activity of Encephalitozoon cuniculi polyamine oxidase assessed as hydrogen peroxide release per mg protein by spectrophotometry relative to 1 mM N'-acetylspermine	2009	Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6	Metabolism of an alkyl polyamine analog by a polyamine oxidase from the microsporidian Encephalitozoon cuniculi.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (18.75)	18.7374
1990's	8 (50.00)	18.2507
2000's	5 (31.25)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.72

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 weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	11.72 (24.57)
Research Supply Index	2.89 (2.92)
Research Growth Index	4.61 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.72)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (11.76%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	15 (88.24%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
benzaldehyde [no description available]	1.97	1	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
n'-acetylspermine N(1)-acetylspermine : An acetylspermine carrying an acetyl group at position N(1).	2.05	1	acetamides; acetylspermine	human metabolite
putrescine [no description available]	2.38	2	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
spermidine [no description available]	2.38	2	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	2.67	3	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	1.97	1	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2.67	3	alpha-amino acid; fluoroamino acid	trypanocidal drug
hexamethylene bisacetamide N,N'-diacetyl-1,6-diaminohexane: chemical name obtained from Acta Biol Hung 1990;41(1-3):199-208	1.98	1	acetamides
entinostat [no description available]	3.14	1	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
n(1),n(11)-diethylnorspermine N(1),N(11)-diethylnorspermine: structure given in first source	4.32	3
n(1), n(12)-diethylspermine N(1), N(12)-diethylspermine: structure in first source. N(1),N(12)-diethylspermine : A substituted spermine that is spermine in which a hydrogen attached to each of the primary amino groups has been replaced by an ethyl group.	4.04	2	polyazaalkane; secondary amino compound; substituted spermine; tetramine	antineoplastic agent
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	3.14	1	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
dipropylenetriame N-(3-aminopropyl)-1,3-propanediamine: structure in first source	1.97	1	polyazaalkane	algal metabolite; plant metabolite
melarsen oxide melarsen oxide: inhibits glutathione reductase	3.1	1
n(1),n(14)-bis(ethyl)homospermine N(1),N(14)-bis(ethyl)homospermine: structure given in first source; depletes polyamines and inhibits the growth of tumor cells in tissue culture	4.04	2
s-adenosyl-3-thio-1,8-diaminooctane S-adenosyl-3-thio-1,8-diaminooctane: structure given in first source	3.1	1
n(1),n(8)-diethylspermidine N(1),N(8)-diethylspermidine: regulator of ornithine decarboxylase	3.1	1
be 4-4-4-4 BE 4-4-4-4: structure given in first source	3.14	1
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	3.14	1	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
s-adenosyl-1,12-diamino-3-thio-9-azadodecane S-adenosyl-1,12-diamino-3-thio-9-azadodecane: structure given in first source	3.1	1
mitoguazone Mitoguazone: Antineoplastic agent effective against myelogenous leukemia in experimental animals. Also acts as an inhibitor of animal S-adenosylmethionine decarboxylase.. mitoguazone : A hydrazone obtained by formal condensation of the two carbonyl groups of methylglyoxal with the primary amino groups of two molecules of aminoguanidine.	3.1	1	guanidines; hydrazone	antineoplastic agent; apoptosis inducer; EC 4.1.1.50 (adenosylmethionine decarboxylase) inhibitor
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	1.97	1	metalloid atom; pnictogen
cgc 11047 CGC 11047: may prove useful in promoting regression of choroidal neovascularization	3.14	1
antimony sodium gluconate Antimony Sodium Gluconate: Antimony complex where the metal may exist in either the pentavalent or trivalent states. The pentavalent gluconate is used in leishmaniasis. The trivalent gluconate is most frequently used in schistosomiasis.	1.98	1

Condition	Relationship Strength	Studies
Opportunistic Infections An infection caused by an organism which becomes pathogenic under certain conditions, e.g., during immunosuppression.	2.92	1
Breast Cancer [description not available]	2.96	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.96	1
Black Fever [description not available]	2.67	3
Leishmaniasis, Visceral A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.	2.67	3
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2	1
P carinii Pneumonia [description not available]	2	1
AIDS-Related Opportunistic Infections Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.	2	1
Pneumonia, Pneumocystis A pulmonary disease in humans occurring in immunodeficient or malnourished patients or infants, characterized by DYSPNEA, tachypnea, and HYPOXEMIA. Pneumocystis pneumonia is a frequently seen opportunistic infection in AIDS. It is caused by the fungus PNEUMOCYSTIS JIROVECII. The disease is also found in other MAMMALS where it is caused by related species of Pneumocystis.	2	1
Infections, Plasmodium [description not available]	2.38	2
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.38	2
Experimental Hepatoma [description not available]	1.97	1

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