Page last updated: 2024-09-24

cellulose sulfate

Description

cellulose sulfate: RN given refers to cpd with unknown MF; vaginal gel being developed as both a contraceptive and blockage to STD somewhat like nonoxynol-9 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID98941
CHEMBL ID154126
CHEBI ID135742
SCHEMBL ID6394045
MeSH IDM0073824

Synonyms (17)

Synonym
brn 6075091
pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)-, cis-
nsc 147956
cellulose sulfate
51423-20-2
nsc147956
nsc-147956
CHEBI:135742
CHEMBL154126
1-[2-[4-(7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl)phenoxy]ethyl]pyrrolidine
FT-0664458
SCHEMBL6394045
1-[2-[4-(2,2-dimethyl-7-methoxy-3-phenylchroman-4-yl)phenoxy]ethyl]pyrrolidine
levormeloxifene;centchroman;78994-24-8
BCP15758
DTXSID60860460
1-{2-[4-(7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydro-2h-1-benzopyran-4-yl)phenoxy]ethyl}pyrrolidine

Research Excerpts

Overview

ExcerptReference
"Cellulose sulfate (CelS), which is a GAG mimetic, was evaluated for its use in promoting neurite extension."( Arinzeh, TL; Collins, G; Foston, M; Hashemi, S; Menezes, R; Meyer, J; Vincent, R, 2019)
"Cellulose sulfate is a semi-synthesized polysaccharide sulfate with a relatively simple chain structure and unique biological properties and its biological applications have been explored in research and clinical trials."( Lin, D; Yao, S; Zhang, Q, 2015)
"Cellulose sulfate (CS) is a noncytotoxic antifertility agent that exhibits in vitro antimicrobial activity against sexually transmitted pathogens, including HIV."( Ballagh, SA; Brache, V; Callahan, M; Creinin, MD; Fichorova, RN; Hillier, SL; Lai, JJ; Mauck, C; Schwartz, JL; Weiner, DH, 2006)
"Cellulose sulfate (CS) is a promising vaginal microbicide. "( Buvé, A; Jespers, V; Van Damme, L, 2007)
"Cellulose sulfate (CS) is an antimicrobial and contraceptive agent. "( Cheng, H; Chipato, T; Depineres, T; Dhlakama, P; Hammond, N; Mauck, C; Napierala, S; Padian, N; Thompson, M; van der Straten, A, 2007)
"Cellulose sulfate (CS) is a non-cytotoxic antifertility agent that also exhibits in vitro antimicrobial activity against sexually transmitted pathogens, including HIV."( Archer, DF; Ballagh, S; Callahan, M; Creinin, M; Lai, JJ; Mauck, C; Pymar, H; Schwartz, J; Weiner, DH, 2001)

Drug Classes (2)

ClassDescription
flavonoidsAny organic molecular entity whose stucture is based on derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 or C16 skeleton, or such a structure which is condensed with a C6-C3 lignan precursors. The term is a 'superclass' comprising all members of the classes of flavonoid, isoflavonoid, neoflavonoid, chalcones, dihydrochalcones, aurones, pterocarpan, coumestans, rotenoid, flavonolignan, homoflavonoid and flavonoid oligomers. Originally restricted to natural products, the term is also applied to synthetic compounds related to them.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[compound class information is derived from 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]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency50.11870.141337.9142100.0000AID1490
USP1 protein, partialHomo sapiens (human)Potency50.11870.031637.5844354.8130AID504865
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.99530.035520.977089.1251AID504332
huntingtin isoform 2Homo sapiens (human)Potency35.48130.000618.41981,122.0200AID1688
gemininHomo sapiens (human)Potency22.69190.004611.374133.4983AID624296; AID624297
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency28.69540.005612.367736.1254AID624032
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID451833Displacement of [3H]estradiol from rat estrogen receptor by radiometric assay relative to estradiol2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer.
AID173474Estrogenic activity as percent of control at 100 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID184492Antiimplantation activity in sperm-positive female albino rats mated to coeval males of proven fertility1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID194107Anti-uterotrophic activity in immature rats at 5 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID196351Antiuterotrophic activity in immature rats at 5 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197051Estrogenic activity in immature rats and assayed as uterine weight gain at 50 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197049Estrogenic activity in immature rats and assayed as uterine weight gain at 100 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID194105Anti-uterotrophic activity in immature rats at 100 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID173605Effective dose for antiimplantation activity in male albino rats1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans.
AID451834Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer.
AID173477Estrogenic activity as percent of control at 500 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID195685Uterotrophic activity in rats relative to estradiol (E2 = 100%)1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID189169Relative binding affinity for uterine cytosolic estrogen receptors of immature rats1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197043Estrogenic activity in immature rats and assayed as uterine weight gain at 0.05 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID196350Antiuterotrophic activity in immature rats at 50 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197040Anti-uterotrophic activity in immature rats at 50 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197041Anti-uterotrophic activity in immature rats at 5 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID173472Estrogenic activity as percent of control at 0.5 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID173475Estrogenic activity as percent of control at 5 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID69538Relative binding affinity for uterine cytosol 17-beta-estradiol receptor obtained from immature Charles Foster rats1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans.
AID197050Estrogenic activity in immature rats and assayed as uterine weight gain at 5 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID173476Estrogenic activity as percent of control at 50 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID196349Antiuterotrophic activity in immature rats at 100 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID197047Estrogenic activity in immature rats and assayed as uterine weight gain at 0.05 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID343883Antiimplantation activity against Sprague-Dawley albino rat at 1 mg/kg, po administered for 1-5 days measured on day 10 of pregnancy relative to control2008Bioorganic & medicinal chemistry letters, Jul-15, Volume: 18, Issue:14
Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents.
AID197039Anti-uterotrophic activity in immature rats at 100 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID194106Anti-uterotrophic activity in immature rats at 50 ug1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID173469Estrogenic activity as percent of control at 0.05 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID451832Estrogenic antagonistic activity in bilaterally ovariectomized Sprague-Dawley rat assessed as inhibition of ethynylesterol-induced uterine weight at 10 mg/kg, po once daily for 3 days measured on day 31 of age2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer.
AID343882Antiimplantation activity against Sprague-Dawley albino rat at 10 mg/kg, po administered for 1-5 days measured on day 10 of pregnancy relative to control2008Bioorganic & medicinal chemistry letters, Jul-15, Volume: 18, Issue:14
Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents.
AID180231Effect on uterine weight gain in immature rats by subcutaneous dose; N-Nil1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans.
AID451835Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer.
AID197052Estrogenic activity in immature rats and assayed as uterine weight gain at 500 ug subcutaneous dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity.
AID180230Compound was evaluated in immature rats as assessed by uterine weight gain (subcutaneously)1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans.
AID451831Estrogenic agonistic activity in bilaterally ovariectomized Sprague-Dawley rat assessed as uterine weight gain at 10 mg/kg, po once daily for three days measured on day 31 of age2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Synthesis and biological evaluation of 2,3,4-triarylbenzopyran derivatives as SERM and therapeutic agent for breast cancer.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (152)

TimeframeStudies, This Drug (%)All Drugs %
pre-199023 (15.13)18.7374
1990's12 (7.89)18.2507
2000's59 (38.82)29.6817
2010's47 (30.92)24.3611
2020's11 (7.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials16 (9.70%)5.53%
Reviews5 (3.03%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other144 (87.27%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (14)

ArticleYear
New candidate biomarkers in the female genital tract to evaluate microbicide toxicity.
PloS one, Volume: 9, Issue: 10
2014
Toward early safety alert endpoints: exploring biomarkers suggestive of microbicide failure.
AIDS research and human retroviruses, Volume: 29, Issue: 11
2013
Bridging the gap between preclinical and clinical microbicide trials: blind evaluation of candidate gels in murine models of efficacy and safety.
PloS one, Volume: 6, Issue: 11
2011
Disruption of tight junctions by cellulose sulfate facilitates HIV infection: model of microbicide safety.
The Journal of infectious diseases, Aug-15, Volume: 200, Issue: 4
2009
A randomized controlled safety trial of the diaphragm and cellulose sulfate microbicide gel in sexually active women in Zimbabwe.
Contraception, Volume: 76, Issue: 5
2007
Safety and acceptability of 6% cellulose sulfate vaginal gel applied four times per day for 14 days.
Contraception, Volume: 76, Issue: 3
2007
Safety trial of the vaginal microbicide cellulose sulfate gel in HIV-positive men.
Sexually transmitted diseases, Volume: 34, Issue: 7
2007
Fourteen-day safety and acceptability study of 6% cellulose sulfate gel: a randomized double-blind Phase I safety study.
Contraception, Volume: 74, Issue: 2
2006
Safety and acceptability of cellulose sulfate as a vaginal microbicide in HIV-infected women.
AIDS (London, England), May-12, Volume: 20, Issue: 8
2006
Expanded Phase I safety and acceptability study of 6% cellulose sulfate vaginal gel.
AIDS (London, England), Dec-02, Volume: 19, Issue: 18
2005
Single and multiple exposure tolerance study of cellulose sulfate gel: a Phase I safety and colposcopy study.
Contraception, Volume: 64, Issue: 6
2001
Prevention of complement-mediated cytotoxicity against rat islets by encapsulation in a cellulose sulphate membrane.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme, Volume: 19, Issue: 8
1987
Effectiveness of sodium sugar sulfates on acute toxicity of paraquat in mice.
Journal of pharmacobio-dynamics, Volume: 12, Issue: 8
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Vaginal distribution of two volumes of the novel microbicide gel cellulose sulfate (2.5 and 3.5 mL).
Contraception, Volume: 72, Issue: 1
2005
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Gellan gum macrobeads loaded with naproxen: The impact of various naturally derived polymers on pH-dependent behavior.
Journal of biomaterials applications, Volume: 33, Issue: 1
2018
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Natural Sources (1)

ArticleYear
Gellan gum macrobeads loaded with naproxen: The impact of various naturally derived polymers on pH-dependent behavior.
Journal of biomaterials applications, Volume: 33, Issue: 1
2018
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]