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4-Androsten-4-ol-3,17-dione

HCID 3408
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
566-48-3
Standard SMILES
CC12CCC3C(CCC4=C(O)C(=O)CCC43C)C1CCC2=O
InChIKey
OSVMTWJCGUFAOD-UHFFFAOYSA-N
Molecular formula
C19H26O3
Average molar mass
302.4 g/mol
Monoisotopic mass
302.18819469

Names & identifiers

Preferred name
4-Androsten-4-ol-3,17-dione
IUPAC
4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
English name
Formestane
Molecular formula
C19H26O3
Molecular weight
302.41

Names & synonyms

4-Androsten-4-ol-3,17-dioneRefChem:518327625-331-3NCGC00015070-04Lopac0_000068orb342005CHEMBL314699SCHEMBL13838287HMS5080K18CCG-204163LP00068SDCCGSBI-0050056.P002
Show more names
4-OHACYPXIXLENTARONCGP-32349P-450AROMFORMESTANEFROMESTANENSC 282175Stan FuMeiFORMESTAQNE
SMP2_000343NCGC00015070-02NCGC00015070-03NCGC00093579-01NCGC00093579-024-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dioneDB-052952EU-0100068

Database identifiers

CAS
566-48-3
PubChem CID
3408
ChEMBL
CHEMBL314699
EC Number
625-331-3

Properties

Computed structural propertiesFilling in

XLogP
2.6
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
22
Formal charge
0
Complexity
589

Physicochemical properties

Melting point
199 · 199-202°C
alpha
20 · D20 +181° (c = 7.7 in chloroform)
Boiling point
383.44 °C · 383.44°C (rough estimate)
Density
1.1189 · 1.1189 (rough estimate)
refractive index
1.42 · 1.4200 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)
form
solid
pka
9.31 · 9.31±0.60(Predicted)
color
White to Off-White
biological source
rabbit
InChI
InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
InChIKey
OSVMTWJCGUFAOD-KZQROQTASA-N
SMILES
C1(=O)C(O)=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)CC3)CC2

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
BV8152500
risk_code
60
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
T
safety_code
53-36/37/39-45
Storage Class
10 - Combustible liquids
Hazard statements
H360
Precautionary statements
P201-P308+P313

Chemistry & industry

Applications · 6 items

Usesaromatase inhibitors ,it is used for progressive breast cancer. male hormones, assimilating protein class.

DescriptionFormestane is a potent aromatase inhibitor launched in the UK as a second-line endocrine treatment for breast cancer. As a synthetic derivative of androstanedione, the natural substrate for the biosynthesis of estrogen by the enzyme aromatase, formastane selectively inhibits aromatase and binds to its steroid receptor site to cause a rapid and sustained fall in circulating estrogen level and, therefore, inhibits tumor growth. In patients with existing bulky primary tumors, formestane effectively reduces the size of the tumors. Formastane has apparent tolerability advantages and less side effects than other agents such as aminoglutethimide.

Description4-hydroxy Androstenedione (4-HAD) is a steroidal inhibitor of aromatase (also known as cytochrome P450 19A1; Ki = 27 nM). As aromatase catalyzes the conversion of androgens to estrogens, aromatase inhibitors, including 4-HAD, are used against hormone-sensitive breast cancer in menopausal women. They are also abused in combination with anabolic steroids in racehorses and athletes. This product is intended for forensic and research applications.

HistoryFormestane is a second-generation steroidal aromatase inhibitor, and the first one to reach clinical use during the early 1990s[1].

UsesAn antitumor drug. An aromatase inhibitor.

Usesantineoplastic, aromatase inhibitor

Upstream & downstream products

Upstream raw materials

Osmium tetroxidePotassium hydroxideSodium sulfatetert-ButanolAcetylacetoneSodium bisulfite solution

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS DataBase Reference
566 · 566-48-3(CAS DataBase Reference)
FDA UNII
9 T8T355 · PUB9T8T355
NCI Drug Dictionary
formestane
ATC code
2 BG02 · L02BG02
UNSPSC Code
12352203 · 12352203
NACRES
41 · NA.41
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
360 · H360
Precautionary statements
201 · P201-P308+P313
Hazard Codes
T
Risk Statements
60 · 60
Safety Statements
53 · 53-36/37/39-45
WGK Germany
3 · 3
RTECS
8152500 · BV8152500
Storage Class
10 · 10 - Combustible liquids
Ethyl acetate
Dichloromethane
Sodium carbonate
Androst-4-ene-3,17-dione, 2-hydroxy-, (2α)-
Androstan-17-one, 3,4-dihydroxy-, (3α,4β,5α)-
Androstane-3,17-dione, 4,5-dihydroxy- (6CI,9CI)
4-Androsten-4-ol-3,17-dione 4-methylethe R
Androst-3-en-17-one,(5)
Androstenedione

Suppliers100 total

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
Hebei shuoxi biotechnology co. LTD+8613081092107
南京林叶化学试剂有限公司13376084917 13376082704 · [email protected]
Hebei Henghe Import and Export Trading Co. LTD+8618032935937 18032916000 · [email protected]
郑州鸿晟医药科技有限公司0371-55695890 15637198702 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
武汉绿景丰华生物科技有限公司19972070065 · [email protected]
陕西林奈生物化工有限公司15327269642 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
湖南瑞威尔生物科技有限公司18627957289 18173226957 · [email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
西安泽邦生物科技有限公司[email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
杭州东帆化学有限公司86-0571-85151182
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
上海思域化工科技有限公司86-21-34053660 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海诺宝化工有限公司+86(0)21 60484900
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
天成化工(江苏)有限公司0512-66387919 18662433356 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
天津安浩生物科技有限公司[email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Wuhan Biocar Bio-Pharm Co., Ltd.86 15387057351 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466205 15377579727 · [email protected]
武汉鑫儒化工有限公司15927387915 15337108568 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
Shijiazhuang Erche Biotechnology Co., Ltd8613343119830 13343119830 · [email protected]
上海珈得尔化学技术有限公司13564435016 13564435016 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
Additional notes · 1 item

DefinitionChEBI: A 17-oxo steroid that is androst-4-ene-3,17-dione in which the hydrogen at position 4 is replaced by a hydroxy group. Formestane was the first selective, type I steroidal aromatase inhibitor, suppressing oestrogen production from anabolic steroids or proho mones. It was formerly used in the treatment of oestrogen-receptor positive breast cancer in post-meopausal women. As it has poor oral bioavailability, it had to be administered by (fortnightly) intramuscular injection. It fell out of use with the subseque t development of cheaper, orally active aromatase inhibitors. Formestane is listed by the World Anti-Doping Agency as a substance prohibited from use by athletes.