Anastrozol

Katalognummer: B1683761

CAS-Nummer: 120511-73-1

Molekulargewicht: 293.4 g/mol

InChI-Schlüssel: YBBLVLTVTVSKRW-UHFFFAOYSA-N

Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.

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Übersicht

1. Beschreibung

8. Eigenschaften

2. Wirkmechanismus

9. Synthesis routes and methods I

3. Wissenschaftliche Forschungsanwendungen

10. Synthesis routes and methods II

4. Biochemische Analyse

11. Synthesis routes and methods III

5. Vorbereitungsmethoden

12. Retrosynthesis analysis

6. Analyse chemischer Reaktionen

13. Haftungsausschluss

7. Vergleich mit ähnlichen Verbindungen

Beschreibung

Anastrozol: ist ein antiöstrogenes Medikament, das zur Klasse der Aromatasehemmer gehört. Es wird üblicherweise unter dem Markennamen verkauft und wird zusammen mit anderen Behandlungen bei Brustkrebs eingesetzt.

Insbesondere ist es bei der Behandlung von hormonrezeptor-positivem Brustkrebs wirksam. Darüber hinaus wurde es als präventive Maßnahme für Personen mit hohem Brustkrebsrisiko eingesetzt .

Herstellungsmethoden

Synthesewege: this compound wird in einem mehrstufigen Prozess synthetisiert. Der Schlüsselschritt beinhaltet die Kupplung von 1,2,4-Triazol mit einer Phenylmethylgruppe, gefolgt von Nitriladition. Die gesamte Reaktionssequenz führt zur Bildung der Verbindung.

Industrielle Produktion: this compound wird industriell unter Verwendung effizienter Synthesewege hergestellt.

Wirkmechanismus

Wissenschaftliche Forschungsanwendungen

Chemie: Anastrozol ist ein wertvolles Werkzeug in der medizinischen Chemie, insbesondere im Bereich der Krebsforschung.

Biologie: Forscher untersuchen seine Auswirkungen auf den Östrogenstoffwechsel und seine Auswirkungen auf hormonabhängige Krebsarten.

Medizin: Über die Behandlung von Brustkrebs hinaus wird this compound für andere hormonbedingte Erkrankungen untersucht.

Industrie: Seine industriellen Anwendungen erstrecken sich auf die pharmazeutische Herstellung und Arzneimittelentwicklung.

Wirkmechanismus

Östrogenunterdrückung: this compound hemmt das Enzym Aromatase, das Androgene in Östrogene umwandelt. Durch die Blockierung dieses Prozesses reduziert es den Östrogenspiegel im Körper.

Molekulare Ziele: Aromatase selbst ist das primäre molekulare Ziel. Durch seine Hemmung stört this compound die Östrogensynthese.

Beteiligte Wege: Die Verbindung wirkt sich auf östrogenabhängige Wege aus und beeinflusst das Zellwachstum und die Zellproliferation in hormonrezeptor-positiven Brustkrebszellen.

Biochemische Analyse

Biochemical Properties

Anastrozole works by inhibiting the enzyme aromatase, which is responsible for the conversion of androgens to estrogens in peripheral tissues . This inhibition prevents the synthesis of estrogen from adrenal androgens, primarily androstenedione and testosterone . By reducing the amount of estrogen in the body, Anastrozole slows the growth of tumors that require estrogen to grow .

Cellular Effects

Anastrozole has a significant impact on various types of cells and cellular processes. It reduces the risk of early breast cancer recurrence and controls breast cancer that has come back or spread to other parts of the body . Anastrozole can also reduce the risk of breast cancer development if a person’s family history or a genetic test shows they have a higher risk of breast cancer .

Molecular Mechanism

Anastrozole exerts its effects at the molecular level by blocking the production of estrogens in the body, hence having antiestrogenic effects . It does this by reversibly binding to the aromatase enzyme, and through competitive inhibition, blocks the conversion of androgens to estrogens in peripheral (extragonadal) tissues .

Temporal Effects in Laboratory Settings

Anastrozole is generally safe to take for a long time . It can make bones weaker and more likely to break (osteoporosis). Bone density (DEXA) scans may be conducted to check the strength of the bones before starting Anastrozole treatment, 1 or 2 years into treatment, and again after the treatment finishes .

Dosage Effects in Animal Models

Based on findings from animal studies and its mechanism of action, Anastrozole can cause fetal harm when administered to a pregnant woman . Anastrozole caused embryo-fetal toxicities in rats at maternal exposure that were 9 times the human clinical exposure, based on area under the curve (AUC).

Metabolic Pathways

Anastrozole is primarily metabolized in the liver via oxidation and glucuronidation to a number of inactive metabolites, including hydroxyanastrozole (both free and glucuronidated) and anastrozole glucuronide . Oxidation to hydroxyanastrozole is catalyzed predominantly by CYP3A4 (as well as CYP3A5 and CYP2C8, to a lesser extent) and the direct glucuronidation of anastrozole is catalyzed mainly by UGT1A4 .

Transport and Distribution

Anastrozole is rapidly absorbed and T max is typically reached within 2 hours of dosing under fasted conditions . Once absorbed, Anastrozole is widely distributed throughout the body, with about 40% being bound to plasma proteins .

Subcellular Localization

The subcellular localization of Anastrozole is not explicitly mentioned in the literature. Given its mechanism of action, it can be inferred that Anastrozole likely interacts with the aromatase enzyme in the endoplasmic reticulum of cells, where the enzyme is located. This is because aromatase is a membrane-bound enzyme, and its active site is located in the endoplasmic reticulum .

Vorbereitungsmethoden

Synthetic Routes: Anastrozole is synthesized through a multistep process. The key step involves the coupling of 1,2,4-triazole with a phenylmethyl group, followed by nitrile addition. The overall reaction sequence leads to the formation of the compound.

Industrial Production: Anastrozole is produced industrially using efficient synthetic routes.

Analyse Chemischer Reaktionen

Reaktivität: Anastrozol unterliegt aufgrund seiner strukturellen Eigenschaften verschiedenen chemischen Reaktionen. Dazu gehören Oxidations-, Reduktions- und Substitutionsreaktionen.

Häufige Reagenzien und Bedingungen: Spezifische Reagenzien und Bedingungen hängen von der gewünschten Transformation ab. Zum Beispiel

Hauptprodukte: Die aus diesen Reaktionen gebildeten Produkte umfassen modifizierte Derivate von this compound, die veränderte pharmakologische Eigenschaften aufweisen können.

Vergleich Mit ähnlichen Verbindungen

Einzigartigkeit: Die Selektivität und Potenz von Anastrozol unterscheidet es von anderen Aromatasehemmern.

Ähnliche Verbindungen: Andere Aromatasehemmer umfassen und .

Eigenschaften

IUPAC Name	2-[3-(2-cyanopropan-2-yl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	YBBLVLTVTVSKRW-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC(C)(C#N)C1=CC(=CC(=C1)CN2C=NC=N2)C(C)(C)C#N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C17H19N5	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID9022607	Source
Record name	Anastrozole
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID9022607
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	293.4 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Solid	Source
Record name	Anastrozole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015348
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Solubility	Freely soluble in methanol, acetone, ethanol, tetrahydrofuran; very soluble in acetonitrile., In water, 0.5 mg/mL at 25 °C; solubility is dependent of pH in the physiological range., 6.61e-02 g/L	Source
Record name	Anastrozole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01217
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Record name	ANASTROZOLE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7462
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Anastrozole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015348
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action	Anastrazole exerts its anti-estrogenic effects via selective and competitive inhibition of the aromatase enzyme found predominantly in the adrenal glands, liver, and fatty tissues. Many breast cancers are hormone receptor-positive, meaning their growth is stimulated and/or maintained by the presence of hormones such as estrogen or progesterone. In postmenopausal women, estrogen is primarily derived from the conversion of adrenally-produced androgens into estrogens by the aromatase enzyme - by competitively inhibiting the biosynthesis of estrogen at these enzymes, anastrozole effectively suppresses circulating estrogen levels and, subsequently, the growth of hormone receptor-positive tumours., Anastrozole is a nonsteroidal aromatase inhibitor that interferes with estradiol production in peripheral tissues. Adrenally generated androstenedione, the chief source of circulating estrogen in postmenopausal women, is converted by aromatase to estrone, which is further converted to estradiol. Growth of many breast cancer tumors containing estrogen receptors and aromatase can be promoted by estrogen., Anastrozole is a potent and selective non-steroidal aromatase inhibitor. It significantly lowers serum estradiol concentrations and has no detectable effect on formation of adrenal corticosteroids or aldosterone., Because estrogen acts as a growth factor for hormone-dependent breast cancer cells, anastrozole-induced reduction of serum and tumor concentrations of estrogen inhibits tumor growth and delays disease progression. Anastrozole selectively inhibits the conversion of androgens to estrogens. In postmenopausal women, ovarian secretion of estrogen declines and conversion of adrenal androgens (mainly androstenedione and testosterone) to estrone and estradiol in peripheral tissues (adipose, muscle, and liver), catalyzed by the aromatase enzyme, is the principal source of estrogens. Anastrozole inhibits the aromatase enzyme by competitively binding to the heme of the cytochrome P-450 unit of the enzyme; suppression of estrogen biosynthesis in all tissues reduces serum concentrations of circulating estrogens, including estrone, estradiol, and estrone sulfate. Anastrozole selectively inhibits synthesis of estrogens and does not affect synthesis of adrenal corticosteroid, aldosterone, or thyroid hormone. In animals, anastrozole has not been shown to possess direct progestogenic, androgenic, or estrogenic activity, but alterations in the circulating concentrations of progesterone, androgens, and estrogens have been observed.	Source
Record name	Anastrozole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01217
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Record name	ANASTROZOLE
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URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7462
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Color/Form	Crystals from ethyl acetate/cyclohexane, Off-white powder
CAS No.	120511-73-1	Source
Record name	Anastrozole
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=120511-73-1
Description	CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
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Record name	Anastrozole [USAN:USP:INN:BAN]
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Record name	Anastrozole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01217
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Record name	anastrozole
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Record name	anastrozole
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Record name	Anastrozole
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Record name	1,3-Benzenediacetonitrile, α1,α1,α3,α3-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)
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Record name	ANASTROZOLE
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Record name	ANASTROZOLE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7462
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Anastrozole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015348
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	81-82 °C, 130.14 °C	Source
Record name	ANASTROZOLE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7462
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Anastrozole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015348
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Synthesis routes and methods I

Procedure details

4-Amino-1-[3,5-bis-(1-cyano-1-methylethyl)benzyl]-1H-[1,2,4]triazolium bromide (5) (70 g) was dissolved in cone. HCl (280 mL) in a 5 L R.B. flask and cooled to −5° C. A solution of sodium nitrite (15 g) in water (70 mL) was slowly added to the reaction mixture at 0-5° C. in 4 hrs and the reaction mixture was stirred for one hour at 0-5° C. and further at 10-20° C. for next 3 hours. The reaction mixture was quenched by the addition of a solution of urea (4.5 g) in water (15 mL). Toluene (700 mL) was added to the reaction mixture and the heterogeneous solution was further cooled down to 0-5° C. The solution was basified by the addition of liquor ammonia (365 mL) slowly in 4 hours at 5-25° C. Organic layer was separated and further washed with water (200 mL). Aqueous layer was removed and a solution of cone. HCl (140 mL) in water (140 mL) was added to the organic layer slowly in 30 minutes at 25-30° C. and reaction mass was heated at 60-65° C. for 30 minutes. The lower aqueous layer (280-300 mL), containing product was collected in a conical flask maintaining at 50° C. The aqueous part was again washed with toluene (700 mL) at 60-65° C. for 30 minutes. The lower aqueous layer, containing product was charged in a separating funnel and again washed with fresh toluene (700 mL). The aqueous layer, containing product was transferred in a R.B. flask and ethyl acetate (350 mL) was added to it. The heterogeneous solution was cooled to 0-5° C. basified by the slow addition of liquor ammonia (280 mL) in 2-3 hours at 5-25° C. The solution was stirred for one hour at 25-35° C., and the upper organic layer (360-375 mL), containing product was separated and filtered through hyflow super cell bed. Solvent was distilled out below 50° C. under vacuum leaving approximately 100 mL ethyl acetate in the flask. The content of the flask was cooled down to 25-35° C. and cyclohexane (500 mL) was added to the solution slowly in 30 minutes. The precipitated solid product was filtered and washed with fresh cyclohexane (20 mL×2). The product was dried at 45-50° C. to get crude Anastrozole (44 g) with more than 98% HPLC purity contaminated with related substance (6) as 0.36% and with related substance (7) as 0.05%.

Name

4-Amino-1-[3,5-bis-(1-cyano-1-methylethyl)benzyl]-1H-[1,2,4]triazolium bromide

Quantity

70 g

Type

reactant

Reaction Step One

Name

HCl

Quantity

280 mL

Type

reactant

Reaction Step Two

Name

sodium nitrite

Quantity

15 g

Type

reactant

Reaction Step Three

Name

water

Quantity

70 mL

Type

solvent

Reaction Step Three

[Compound]

Name

layer

Quantity

290 (± 10) mL

Type

reactant

Reaction Step Four

Name

cyclohexane

Quantity

500 mL

Type

reactant

Reaction Step Five

Name

Anastrozole

Details

Synthesis routes and methods II

Procedure details

A solution of 2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile), (0.23 g), and 1H-1,2,4-triazole (0.35 g) in acetonitrile (2 ml) was heated under reflux for 18 h, then evaporated to dryness. The residue was partitioned between 1N aqueous potassium hydrogen carbonate solution and ethyl acetate, the organic phase was separated, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography. Elution with methanol:chloroform (1:49 by volume), gave 2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile), identical with the product of Example 1, and further elution with methanol:chloroform (2:23 by volume, gave 2,2'-[5-(4H-1,2,4-triazol-4-ylmethyl)-1,3-phenylene]di(2-methylpropiononit rile), mp. 158°-161°.

Name

2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile)

Quantity

0.23 g

Type

reactant

Reaction Step One

Name

1H-1,2,4-triazole

Quantity

0.35 g

Type

reactant

Reaction Step One

Name

acetonitrile

Quantity

2 mL

Type

solvent

Reaction Step One

Name

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile)

Details

Synthesis routes and methods III

Procedure details

In yet another embodiment of the present invention, the purified bromo compound (formula (III)) is alkylated with 1,2,4-triazole in a suitable solvent using a suitable base in the presence of a phase transfer catalyst such as tetrabutyl ammonium bromide to obtain anastrozole, which is further purified using column chromatography, followed by precipitation/crystallization using ethyl acetate and diisopropyl ether to obtain pure anastrozole in high yield.

Name

bromo

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

1,2,4-triazole

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

tetrabutyl ammonium bromide

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Three

Name

anastrozole

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Anastrozole

Reactant of Route 2

Anastrozole

Reactant of Route 3

Anastrozole

Reactant of Route 4

Anastrozole

Reactant of Route 5

Anastrozole

Reactant of Route 6

Anastrozole

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Anastrozol

Übersicht

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Target of Action

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Biochemical Pathways

Pharmacokinetics

Result of Action

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Wissenschaftliche Forschungsanwendungen

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Vergleich Mit ähnlichen Verbindungen

Eigenschaften

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InChI Key

Canonical SMILES

Molecular Formula

DSSTOX Substance ID

Molecular Weight

Physical Description

Solubility

Mechanism of Action

Color/Form

CAS No.

Melting Point

Synthesis routes and methods I

Procedure details

Synthesis routes and methods II

Procedure details

Synthesis routes and methods III

Procedure details

Retrosynthesis Analysis

Strategy Settings

Feasible Synthetic Routes

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