Nafoxidine

Nafoxidine: Nafoxidine

Systematic (IUPAC) name

1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine

Clinical data

Pregnancy cat. ?

Legal status ?

Identifiers

CAS number 1845-11-0

ATC code None

PubChem CID 4416

ChemSpider 4263

UNII 4RIY10WM82^Y

ChEMBL CHEMBL28211

Chemical data

Formula C₂₈H₃₁N O₂

Mol. mass 425.562 g/mol

SMILES eMolecules & PubChem

Nafoxidine (U-11,000A) is a non-steroidal antiestrogenic drug that has been investigated to treat advanced breast cancer.^[1] It is structurally related to tamoxifen.

The drug is one of a series of similar structures invented by Dan Lednicer at Upjohn.

An earlier compound known as "U-11,555" is related to Nafoxidine was found to cause photosensitivity in human volunteers(as for example does psoralen).

See: D. Lednicer, J.C. Babcock, P.E. Marlatt, S.C. Lyster, G.W. Duncan, J.Med.Chem., 8, 52(1965). for details.^[2]

Synthesis

The synthesis depicted is more modern, but also see Lasofoxifene for an earlier synthesis.

Cameron, C. O.; Dasilva Jardine, P. A.; Rosati, R. L.; 1996, U.S. Patent 5,552,412.

References

^ Steinbaum, F. L.; De Jager, R.; Krakoff, I. (1978). "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology 4 (2): 123–126. doi:10.1002/mpo.2950040207. PMID 661750. edit

^ http://dx.doi.org/10.1021%2Fjm00325a013

v · d · eIntracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid

dihydrofolate reductase inhibitor (Aminopterin, Methotrexate, Pemetrexed, Pralatrexate) • thymidylate synthase inhibitor (Raltitrexed, Pemetrexed)

Purine

adenosine deaminase inhibitor (Pentostatin)

halogenated/ribonucleotide reductase inhibitors (Cladribine, Clofarabine, Fludarabine)
thiopurine (Thioguanine, Mercaptopurine)

Pyrimidine

thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine)

DNA polymerase inhibitor (Cytarabine)

ribonucleotide reductase inhibitor (Gemcitabine)
hypomethylating agent (Azacitidine, Decitabine)

Deoxyribonucleotide

ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I

Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II

Podophyllum (Etoposide, Teniposide)

II+Intercalation

Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating

Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine

Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin

Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan)
Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine

Alkylating-like

Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical

Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation

Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT
Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors

FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

Receptor antagonists

ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)

Other/ungrouped

Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

v · d · eEstrogens and progestogens (G03C-D, L02)

Progestogens/
progestins
(progesterone)

Agonist

1st

Norpregnene (Norethisterone^#/Norethisterone acetate • Ethynodiol diacetate)

2nd

Norpregnene (Levonorgestrel^#/Norgestrel/Norelgestromin)

3rd

19-nortestosterone (Desogestrel/Etonogestrel • Gestodene • Norgestimate)

4th

Androstene (Drospirenone) • 19-norprogesterone (Nomegestrol • Promegestone • Trimegestone) • 19-nortestosterone (Dienogest)

17-OH

Chlormadinone • Cyproterone • Medroxyprogesterone/Medroxyprogesterone 17-acetate^# • Megestrol

Other/
ungrouped

Pregnenedione (Gestonorone) • Pregnene (Ethisterone) • Pregnadiene (Medrogestone • Melengestrol) • Norpregnane (Norgestrienone) • Lynestrenol • Norethynodrel • Tibolone • Dydrogesterone • Quingestanol

Antiprogestin/
SPRM

antagonist: Mifepristone

Asoprisnil • CDB-4124 • Ulipristal acetate

Estrogens

Agonist

Steroidal

Diosgenin • Estradiol (Ethinylestradiol^#/Mestranol • Estradiol 17 beta-cypionate^# • Polyestradiol phosphate) • Estrone (Estrone sulfate) • Estriol • Promestriene • Equilenin • Equilin

Nonsteroidal

Chlorotrianisene • Dienestrol • Fosfestrol • Diethylstilbestrol • Zeranol

Antiestrogen/
SERM

Afimoxifene • Arzoxifene • Bazedoxifene • Cyclofenil • Lasofoxifene • Ormeloxifene • Raloxifene • Tamoxifen • Toremifene

Clomifene^# • Mepitiostane • Nafoxidine

pure antagonist: Fulvestrant

Aromatase inhibitors

nonselective: Aminoglutethimide • Testolactone
selective: Anastrozole • Atamestane • Exemestane • Fadrozole • Formestane • Letrozole • Vorozole

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: ♀ FRS

anat/phys/devp

noco/cong/npls, sysi/epon

proc/asst, drug (G1/G2B/G3CD)

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Academic Dictionaries and Encyclopedias

Nafoxidine

Synthesis

References

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Systematic (IUPAC) name
1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	1845-11-0
ATC code	None
PubChem	CID 4416
ChemSpider	4263
UNII	4RIY10WM82^Y
ChEMBL	CHEMBL28211
Chemical data
Formula	C₂₈H₃₁N O₂
Mol. mass	425.562 g/mol
SMILES	eMolecules & PubChem

Academic Dictionaries and Encyclopedias

Wikipedia

Nafoxidine

Synthesis

References

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