Aminoglutethimide (BA-16038)

Alias: BA-16038; NSC-330915;BA16038; NSC330915;BA 16038; NSC 330915;Ainoglutethimide; Cytadren; Orimeten; Elipten; Aminoglutetimida; Aminoglutethimidum; Ba16038; Cytadren; Prestwick243; CCRIS 7562; CHEBI:2654; Aminoglutethimidum
Cat No.:V1802 Purity: ≥98%
Aminoglutethimide (also known as BA-16038, NSC-330915)is anananticancer drug that acts as a nonsteroidal aromatase inhibitor with IC50 of 10 μM.
Aminoglutethimide (BA-16038) Chemical Structure CAS No.: 125-84-8
Product category: Aromatase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Aminoglutethimide (also known as BA-16038, NSC-330915) is an an anticancer drug that acts as a nonsteroidal aromatase inhibitor with IC50 of 10 μM. Aminoglutethimide decreases the production of sex hormones such as estrogen in women or testosterone in men, and suppresses the growth of tumors that need sex hormones to grow. Aminoglutethimide blocks the production of steroids derived from cholesterol and is clinically used in the treatment of Cushing's syndrome and metastatic breast cancer.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Aminoglutethimide displays aromatase inhibition in vitro assay with human placental aromatase, which is an enzyme involved in the conversion of androgens into estrogens, and an important target for the endocrine treatment of breast cancer. Aminoglutethimide inhibits ACTH receptor (ACTH-R) mRNA expression in ovine adrenocortical cells in a time-dependent fashion. Aminoglutethimide significantly suppresses steroid secretion and the baseline ACTH-R mRNA expression in a dose-dependent fashion (300 μM AG, 5±1%; 30 μM AG, 64±1%; 3 μM AG, 108±19% compared with control cells, 100±11%) by affecting the gene expression or by decreasing transcript accumulation via an effect on RNA stability, in the human NCI-h295 adrenocortical carcinoma cell line, which expresses functional ACTH receptors and produces steroids of the glucocorticoid, mineralocorticoid and androgen pathway. Aminoglutethimide inhibits aromatase in a dose-dependent fashion with IC50 of 13 μM in 6 breast tumor homogenates, placental aromatase with IC50 of 6 μM and hypothalamic aromatase with IC50 of 8 μM.


Kinase Assay: The microsomal protein (30 μg), [1β-3H]androstenedione (6.6 × 105 dpm) and NADPH (270 μM) are used for the concentration–response experiment with an incubation time of 20 minutes. The Aminoglutethimide is initially tested at 10 μM and 100 μM concentrations, followed by a full concentration–response study with at least 8 concentrations ranging from 0.01 μM to 160 μM. For the initial velocity study the concentration of [1β-3H]androstenedione is varied from 7.5 to 100 nM and the incubation time is set to 5 minutes. The tritiated water formed during the conversion of the tritiated substrate, [1β-3H]androstenedione, to estrone is quantified by liquid scintillation counting. Each assay is performed three times in duplicate and the results are treated by nonlinear regression analysis allowing the determination of the half-maximal inhibitory concentration (IC50).


Cell Assay: The NCI-h295 tumor cell line is maintained in RPMI 1640 medium supplemented with transferrin (0.1 mg/mL), insulin (5 μg/mL), selenium (5.2 μg/mL) and 2% FCS. The cells are incubated for 48 hours with Aminoglutethimide (3, 30, 300 μM). Then cells are examined by trypan blue staining for cell viability, counted with a coulter counter. For the assessment of ACTH-R mRNA, cells are harvested, and total RNA is extracted, electrophoresed, blotted and hybridized with a human ACTH-R cDNA probe.

ln Vivo
Aminoglutethimide accelerates its own metabolism from a basal value of 2.6±0.3 (S.E.) liters/24 hours to 5.3±1.4 liters/24 hours after 1 to 2 weeks of Aminoglutethimide administration, and markedly accelerates the metabolism of the synthetic glucocorticoid and dexamethasone, from basal values of 145±26.6 liters/24 hours to 568±127 liters/24 hours (p < 0.02) after 2 weeks of Aminoglutethimide administration. Aminoglutethimide (150 mg/kg) abolishes the induction of ornithine decarboxylase (ODC) and almost depletes the gonads and plasma of progesterone or testosterone elicited by human chorionic gonadotropin (hCG) in the ovary of adult female mice and the testis of immature male mice, which is related to an inhibition of cAMP-dependent protein kinase (IC50 287 μM) rather than blockade of the steroidogenic pathway.
Animal Protocol
Dissolved in DMSO and diluted in saline; 150 mg/kg; i.p. injection
Swiss CD1 male and female mice
References
Eur J Med Chem.2009 Oct;44(10):4121-7;Cancer Res.1982 Aug;42(8 Suppl):3353s-3359s.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H16N2O2
Molecular Weight
232.28
CAS #
125-84-8
Related CAS #
125-84-8
SMILES
CCC1(C2=CC=C(N)C=C2)CCC(NC1=O)=O
Synonyms
BA-16038; NSC-330915;BA16038; NSC330915;BA 16038; NSC 330915;Ainoglutethimide; Cytadren; Orimeten; Elipten; Aminoglutetimida; Aminoglutethimidum; Ba16038; Cytadren; Prestwick243; CCRIS 7562; CHEBI:2654; Aminoglutethimidum
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 20 mg/mL (86.1 mM)
Water:<1 mg/mL
Ethanol: 7 mg/mL (30.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.76 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 1% DMSO +30% polyethylene glycol+1% Tween 80 : 8 mg/mL

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3051 mL 21.5257 mL 43.0515 mL
5 mM 0.8610 mL 4.3051 mL 8.6103 mL
10 mM 0.4305 mL 2.1526 mL 4.3051 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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