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Details

Stereochemistry ACHIRAL
Molecular Formula C29H31NO2.ClH
Molecular Weight 462.023
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFOXIDINE HYDROCHLORIDE

SMILES

Cl.COC1=CC2=C(C=C1)C(C3=CC=C(OCCN4CCCC4)C=C3)=C(CC2)C5=CC=CC=C5

InChI

InChIKey=HJOOGTROABIIIU-UHFFFAOYSA-N
InChI=1S/C29H31NO2.ClH/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30;/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C29H31NO2
Molecular Weight 425.5619
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Nafoxidine is a nonsteroidal antiestrogen available as an investigational agent from the Investigational Drug Branch of the National Cancer Institute. It has been used effectively in the treatment of breast cancer patients. Nafoxidine competes with endogenous estrogen for binding to specific estrogen receptors. This agent also inhibits angiogenesis in some tissues by blocking the effects of fibroblast growth factor (FGF) and vascular endothelial growth factor (VEGF); paradoxically, it may enhance angiogenesis in uterine tissue. Nafoxidine also induces oxidative stress, protein kinase C and calcium signaling.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 40.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Disc. AE: Ichthyosis...
Other AEs: Serum transaminase increased, Nausea...
AEs leading to
discontinuation/dose reduction:
Ichthyosis
Other AEs:
Serum transaminase increased (2%)
Nausea (grade 3, 2%)
Vomiting (grade 3, 2%)
Hypercalcaemia (2%)
Thrombophlebitis leg (2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4561336
Page: p.388
unhealthy, ADULT
n = 23
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/4561336
Page: p.388
Disc. AE: Hypercalcemia...
AEs leading to
discontinuation/dose reduction:
Hypercalcemia (4.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4561336
Page: p.388
AEs

AEs

AESignificanceDosePopulation
Hypercalcaemia 2%
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Serum transaminase increased 2%
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Thrombophlebitis leg 2%
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Ichthyosis Disc. AE
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Nausea grade 3, 2%
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Vomiting grade 3, 2%
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/1095121
Page: p.713
Hypercalcemia 4.3%
Disc. AE
60 mg 3 times / day multiple, oral
Studied dose
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4561336
Page: p.388
unhealthy, ADULT
n = 23
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/4561336
Page: p.388
Sourcing

Sourcing

Vendor/AggregatorIDURL
AChemBlock
10755
http://www.achemblock.com/catalogsearch/result/?q=10755
AK Scientific
3697AL
https://aksci.com/item_detail.php?cat=3697AL
Angene
AGN-PC-0QDKPN
http://www.angenechemical.com/productshow/AGN-PC-0QDKPN.html
AstaTech
42119
http://astatechinc.com/CPSResult.php?CRNO=42119
BOC Sciences
1845-11-0
http://www.bocsci.com/description.asp?cas=1845-11-0
BOC Sciences
1847-63-8
http://www.bocsci.com/description.asp?cas=1847-63-8
Combi-Blocks
QJ-8061
http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-8061
MuseChem
M120421
https://www.musechem.com/product/M120421.html
MuseChem
R056483
https://www.musechem.com/product/R056483.html
ShangHai Biochempartner
BCP07493
http://www.biochempartner.com/search_BCP07493
Toronto Research Chemicals
A613195
https://www.trc-canada.com/product-detail/?CatNum=A613195
Toronto Research Chemicals
N212800
https://www.trc-canada.com/product-detail/?CatNum=N212800
eMolecules
300557368
https://orderbb.emolecules.com/search/#?query=300557368
eMolecules
36772485
https://orderbb.emolecules.com/search/#?query=36772485
eMolecules
48542635
https://orderbb.emolecules.com/search/#?query=48542635
PubMed

PubMed

TitleDatePubMed
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
1997 Mar
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
The differential effects of bisphosphonates, SERMS (selective estrogen receptor modulators), and parathyroid hormone on bone remodeling in osteoporosis.
2007
Granulosa cell tumor of the ovary and antecedent of adjuvant tamoxifen use for breast cancer.
2010 Aug 12
Patents

Patents

US3692895
2
US8268352
6
WO2012159981A2
2

Sample Use Guides

In Vivo Use Guide
Most breast cancer patients have been treated with a dose of 60 mg three times a day.
Route of Administration: Oral
In Vitro Use Guide
In vitro nafoxidine competitively inhibits binding of [3H]oestradiol in nuclear extracts. The Ki for the inhibition is 43 nM, which indicates an affinity of nafoxidine for the binding protein about 4% of that of oestradiol.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:03 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:03 GMT 2023
Record UNII
SU8WBD61G1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAFOXIDINE HYDROCHLORIDE
USAN  
USAN  
Official Name English
NAFOXIDINE HYDROCHLORIDE [USAN]
Common Name English
U-11100A
Code English
1-(2-(P-(3,4-DIHYDRO-6-METHOXY-2-PHENYL-1-NAPHTHYL)PHENOXY)ETHYL)PYRROLIDINE HYDROCHLORIDE
Common Name English
11100A
Code English
NAFOXIDINE HCL
Common Name English
PYRROLIDINE 1-(2-(4-(3,4-DIHYDRO-6-METHOXY-2-PHENYL-1-NAPHTHALENYL)PHENOXY)ETHYL)-, HYDROCHLORIDE
Common Name English
NSC-70735
Code English
U-11100
Code English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
NCI_THESAURUS C1971
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL28211
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID30171651
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
PUBCHEM
15805
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
FDA UNII
SU8WBD61G1
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
NCI_THESAURUS
C1448
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
NSC
70735
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
CAS
1847-63-8
Created by admin on Fri Dec 15 15:12:03 GMT 2023 , Edited by admin on Fri Dec 15 15:12:03 GMT 2023
PRIMARY
Related Record Type Details
Structure of NAFOXIDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of NAFOXIDINE
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