968-93-4 Usage
Description
Testolactone is a non-selective steroidal aromatase inhibitor that prevents the conversion of androgen to estrogen. It is an effective anti-tumor agent and is used in the treatment of familial male precocious puberty.
Uses
Used in Antineoplastic Applications:
Testolactone is used as an antineoplastic agent, particularly in the treatment of familial male precocious puberty. It inhibits the conversion of androgen to estrogen, which helps in controlling the growth and development of tumors.
Used in Breast Cancer Treatment:
Testolactone USP (Teslac) is used as a breast cancer treatment. It acts as a non-selective steroidal aromatase inhibitor, preventing the conversion of androgen to estrogen, which helps in controlling the growth and progression of breast cancer.
Used in Pharmaceutical Industry:
Testolactone is used as a pharmaceutical agent for the development of drugs targeting various types of cancer. Its ability to inhibit the conversion of androgen to estrogen makes it a promising candidate for the treatment of hormone-sensitive cancers.
Originator
Fludestrin,Heyden,W. Germany,1968
Manufacturing Process
(a) Fermentation: A medium of the following composition is prepared: 3.0
grams cornsteep liquor solids; 3.0 grams NH4H2PO4; 2.5 grams CaCO3; 2.2
grams soybean oil; 0.5 gram progesterone and distilled water to make 1 liter.
The medium is adjusted to pH 7.00.1. Then, 100 ml portions of the medium
are distributed in 500 ml Erlenmeyer flasks and the flasks plugged with cotton
and sterilized in the usual manner (i.e., by autoclaving for 30 minutes at
120°C). When cool, each of the flasks is inoculated with 5 to 10% of a
vegetative inoculum of Cylindrocarpon radicola [the vegetative inoculum being
grown from stock cultures (lyophilized vial or agar slant) for 48 to 72 hours in
a medium of the following composition: 15 grams cornsteep liquor; 10 grams
brown sugar; 6 grams NaNO3; 0.001 gram ZnSO4; 1.5 grams KH2PO4;0.5
gram MgSO47H2O; 5 grams CaCO3; 2 grams lard oil; and distilled water to
make 1 liter].The flasks are then placed on a reciprocating shaker (120 one and one-half
inch cycles per minute) and mechanically shaken at 25°C for 3 days. The
contents of the flasks are then pooled and, after the pH of the culture is
adjusted to about 40.2 with sulfuric acid, filtered through Seitz filter pads to
separate the mycelium from the fermented medium.(b) Extraction: 40 liters of the culture filtrate obtained in (a) is extracted with
40 liters chloroform in an extractor (e.g., Podbelniak, US Patent 2,530,886, or
improvements thereon) and the filtered chloroform extract is evaporated to
dryness in vacuo. The residue (11.1 grams) is taken up in 200 ml of 80%
aqueous methanol, and the resulting solution is extracted four times with 100
ml portions of hexane. The 80% aqueous methanol solution is then
concentrated in vacuo until crystals appear; and, after cooling at 0°C for
several (usually about 3 to 4) hours, the crystals formed are recovered by
filtration. About 2.9 grams 1-dehydrotestololactone (MP 217° to 217.5°C) are
thus obtained. Concentration of the mother liquors yields additionally about
6.0 grams of the lactone. Recrystallization from acetone yields a purified 1-dehydrotestololactone having a melting point of 218° to 219°C.
Check Digit Verification of cas no
The CAS Registry Mumber 968-93-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,6 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 968-93:
(5*9)+(4*6)+(3*8)+(2*9)+(1*3)=114
114 % 10 = 4
So 968-93-4 is a valid CAS Registry Number.
InChI:InChI=1/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14?,15-,16-,18?,19?/m0/s1
968-93-4Relevant articles and documents
Effective multi-step functional biotransformations of steroids by a newly isolated Fusarium oxysporum SC1301
Zhang, Hongliu,Ren, Jie,Wang, Yu,Sheng, Cuo,Wu, Qiaqing,Diao, Aipo,Zhu, Dunming
, p. 184 - 189 (2013)
A fungus Fusarium oxysporum SC1301 was isolated from soil samples, which could transform androst-4-ene-3,17-dione, androst-1,4-diene-3,17-dione, dehydroepiandrosterone, progesterone, testosterone, and pregnenolone to give testolactone in 76-98% yields. Especially, for progesterone and pregnenolone, multi-step functional transformations, including oxygenative esterification of 20-ketosteroids, hydrolysis of ester, oxidation of C-17 OH group, oxygenative lactonization of 17-ketosteroids, 1-dehydrogenation, oxidation of C-3 OH group and Δ5→4 CC bond migration, could proceed effectively to yield testolactone as a single product. This is the first example that a F. oxysporum species shows catalytic capability of ring-D lactonization. The results are remarkably distinguished from those previously reported for the closely-related fungus F. oxysporum var. cubense, which predominantly mediates the hydroxylations at different positions of steroids. In addition, F. oxysporum SC1301 may serve as a valuable biocatalyst for the production of testolactone.
Steroids' transformations in Penicillium notatum culture
Bartmanska, Agnieszka,Dmochowska-Gladysz, Jadwiga,Huszcza, Ewa
, p. 193 - 198 (2007/10/03)
The application of Penicillium notatum genus for biotransformations of steroids has been investigated. The reactions observed include insertion of an oxygen atom into D-ring of steroids, 15α-hydroxylation of 17α-methyl testosterone derivatives, ester bond hydrolysis, and degradation of a testosterone derivatives side chain. Microbial production of testolactones, the biologically active compounds, was also achieved using this strain in up to 98% yield.
Microbiological oxidation of progesterone by Fusarium Solani.
NISHIKAWA,NOGUCHI,HASEGAWA
, p. 322 - 323 (2007/11/03)
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