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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O2
Molecular Weight 316.4776
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALUSTERONE

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])[C@@H](C)CC4=CC(=O)CC[C@]34C

InChI

InChIKey=IVFYLRMMHVYGJH-PVPPCFLZSA-N
InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16-,17-,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H32O2
Molecular Weight 316.4776
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

CALUSTERONE is a 17-alkylated androgenic steroid. It may alter the metabolism of estradiol and reduce estrogen production. As an androgen, CALUSTERONE was used as a therapeutic agent in postmenopausal women with metastatic breast cancer.

Originator

Approval Year

1973
98
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Methosarb

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/161435/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CALUSTERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/5457511
unhealthy
n = 22
Health Status: unhealthy
Condition: Breast Cancer
Sex: F
Population Size: 22
Sources:
https://pubmed.ncbi.nlm.nih.gov/5457511
Other AEs: Acne...
Other AEs:
Acne (severe, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/5457511
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
unhealthy
n = 45
Health Status: unhealthy
Condition: Advanced Breast Cancer
Sex: F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (25%)
Vomiting (25%)
Fluid retention (25%)
SGOT increased (25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
AEs

AEs

AESignificanceDosePopulation
Acne severe, 1 patient
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/5457511
unhealthy
n = 22
Health Status: unhealthy
Condition: Breast Cancer
Sex: F
Population Size: 22
Sources:
https://pubmed.ncbi.nlm.nih.gov/5457511
Fluid retention 25%
Disc. AE
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
unhealthy
n = 45
Health Status: unhealthy
Condition: Advanced Breast Cancer
Sex: F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
Nausea 25%
Disc. AE
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
unhealthy
n = 45
Health Status: unhealthy
Condition: Advanced Breast Cancer
Sex: F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
SGOT increased 25%
Disc. AE
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
unhealthy
n = 45
Health Status: unhealthy
Condition: Advanced Breast Cancer
Sex: F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
Vomiting 25%
Disc. AE
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
unhealthy
n = 45
Health Status: unhealthy
Condition: Advanced Breast Cancer
Sex: F
Population Size: 45
Sources:
https://pubmed.ncbi.nlm.nih.gov/141327
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L1EU7
AHH Chemical co.,ltd
MT-41423
http://www.ahhchemical.com/product/MT-41423.html
Alfa Chemistry
ACM17021260
https://www.alfa-chemistry.com/4-androsten-7-17-dimethyl-17-ol-3-one-cas-17021-26-0-item-26736.htm
Chemieliva Pharmaceutical Co., Ltd
PBCM1211696
Compound Cloud
28204
NCI Plated 2007
66233
NCI Plated 2007
88536
NovoSeek
28204
Smolecule
S522531
http://www.smolecule.com/products/s522531
THE BioTek
bt-262562
https://www.thebiotek.com/product/inhibitors/bt-262562
Tetrahedron
TS76858
ZINC
ZINC000004215173
http://zinc15.docking.org/substances/ZINC000004215173
PubMed

PubMed

TitleDatePubMed
Calusterone (7beta,17alpha-dimethyltestosterone) as primary and secondary therapy of advanced breast cancer.
1973
Calusterone therapy for advanced breast cancer.
1977 May-Jun
MR appearance of intra-abdominal metastatic melanoma.
1992
Patents

Patents

JP2011525180A
180
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:16 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:16 GMT 2023
Record UNII
0678G6Q58A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALUSTERONE
HSDB   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
ANDROST-4-EN-3-ONE, 17-HYDROXY-7,17-DIMETHYL-, (7.BETA.,17.BETA.)-
Common Name English
U-22550
Code English
calusterone [INN]
Common Name English
CALUSTERONE [MI]
Common Name English
7.BETA.,17.ALPHA.-DIMETHYLTESTOSTERONE
Common Name English
Calusterone [WHO-DD]
Common Name English
NSC-88536
Code English
17β-Hydroxy-7β,17-dimethylandrost-4-en-3-one
Systematic Name English
7.BETA.,17.ALPHA.-DIMETHYL-17.BETA.-HYDROXYANDROST-4-EN-3-ONE
Systematic Name English
METHOSARB
Brand Name English
CALUSTERONE [HSDB]
Common Name English
U-22,550
Code English
DIMETHYLTESTOSTERONE
Common Name English
CALUSTERONE [MART.]
Common Name English
CALUSTERONE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C243
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
DEA NO. 4000
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C337
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL455706
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
INN
2873
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
WIKIPEDIA
Calusterone
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
SMS_ID
100000081615
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
DRUG CENTRAL
468
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
EVMPD
SUB06060MIG
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
NSC
88536
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
CAS
17021-26-0
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
PUBCHEM
28204
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
DRUG BANK
DB01564
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
MERCK INDEX
m2994
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY Merck Index
MESH
C073055
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
HSDB
3210
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022723
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
FDA UNII
0678G6Q58A
Created by admin on Fri Dec 15 16:10:16 GMT 2023 , Edited by admin on Fri Dec 15 16:10:16 GMT 2023
PRIMARY
Related Record Type Details
Structure of CALUSTERONE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
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