Trilostane

Trilostane
Clinical data
Trade names	Vetoryl, others
Other names	WIN-24,540; 4α,5-Epoxy-3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile
Routes of; administration	By mouth
ATC code	H02CA01 (WHO) QH02CA01 (WHO);
Legal status
Legal status	CA: ℞-only; US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Metabolism	Liver
Metabolites	17-Ketotrilostane
Elimination half-life	Trilostane: 1.2 hours; 17-Ketotrilostane: 1.2 hours
Identifiers
	IUPAC name (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile;
CAS Number	13647-35-3 ;
PubChem CID	656583;
IUPHAR/BPS	6850;
DrugBank	DB01108 ;
ChemSpider	570949 ;
UNII	L0FPV48Q5R;
KEGG	D01180 ;
ChEBI	CHEBI:32260 ;
ChEMBL	ChEMBL1200907 ;
CompTox Dashboard (EPA)	DTXSID9023706 ;
ECHA InfoCard	100.033.743
Chemical and physical data
Formula	C20H27NO3
Molar mass	329.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#C\C4=C(/O)[C@H]5O[C@]35[C@]([C@@H]2[C@H]([C@H]1[C@]([C@@H](O)CC1)(C)CC2)CC3)(C)C4;
	InChI InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1 ; Key:KVJXBPDAXMEYOA-CXANFOAXSA-N ;
	(verify)

Trilostane, sold under the brand name Vetoryl among others, is a medication which has been used in the treatment of Cushing's syndrome, Conn's syndrome, and postmenopausal breast cancer in humans.^[4]^[5]^[6]^[7]^[1] It was withdrawn for use in humans in the United States in the 1990s^[8] but was subsequently approved for use in veterinary medicine in the 2000s to treat Cushing's syndrome in dogs.^[9] It is taken by mouth.^[1]

^ ^a ^b ^c ^d ^e ^f Puddefoot JR, Barker S, Vinson GP (December 2006). "Trilostane in advanced breast cancer". Expert Opinion on Pharmacotherapy. 7 (17): 2413–2419. doi:10.1517/14656566.7.17.2413. PMID 17109615. S2CID 23940491.
^ Cite error: The named reference Trilocur EPAR was invoked but never defined (see the help page).
^ Cite error: The named reference Trilorale EPAR was invoked but never defined (see the help page).
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1245–. ISBN 978-1-4757-2085-3.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 281–. ISBN 978-94-011-4439-1.
^ Negwer M (1987). Organic-chemical Drugs and Their Synonyms: (an International Survey). VCH Publishers. ISBN 978-0-89573-552-2. 5870 (6516) C20H2:NOs 13647-35-3 42,5-Epoxy-173-hydroxy-3-oxo-50-androstane-22carbonitrile = (22,42,52,173)-4,5-Epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile (e) S Desopan, Modrastane, Modrenal, Trilostane", Trilox, Win 24 540, Winstan U Adrenocortical suppressant (steroid biosynthesis inhibitor)
^ Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 34–. ISBN 978-1-351-78989-9.
^ Tung D, Ciallella J, Hain H, Cheung PH, Saha S (December 2013). "Possible therapeutic effect of trilostane in rodent models of inflammation and nociception". Current Therapeutic Research, Clinical and Experimental. 75: 71–76. doi:10.1016/j.curtheres.2013.09.004. PMC 3898193. PMID 24465047.
^ "Cushing's Disease in Dogs Part 3: Current & Investigative Options for Therapy". Today's Veterinary Practice. 24 February 2016. Retrieved 4 January 2021.

[pmid17109615-1] ^ ^a ^b ^c ^d ^e ^f Puddefoot JR, Barker S, Vinson GP (December 2006). "Trilostane in advanced breast cancer". Expert Opinion on Pharmacotherapy. 7 (17): 2413–2419. doi:10.1517/14656566.7.17.2413. PMID 17109615. S2CID 23940491.

[Trilocur_EPAR-2] Cite error: The named reference Trilocur EPAR was invoked but never defined (see the help page).

[Trilorale_EPAR-3] Cite error: The named reference Trilorale EPAR was invoked but never defined (see the help page).

[Elks2014-4] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1245–. ISBN 978-1-4757-2085-3.

[MortonHall2012-5] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 281–. ISBN 978-94-011-4439-1.

[Negwer1987-6] Negwer M (1987). Organic-chemical Drugs and Their Synonyms: (an International Survey). VCH Publishers. ISBN 978-0-89573-552-2. 5870 (6516) C20H2:NOs 13647-35-3 42,5-Epoxy-173-hydroxy-3-oxo-50-androstane-22carbonitrile = (22,42,52,173)-4,5-Epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile (e) S Desopan, Modrastane, Modrenal, Trilostane", Trilox, Win 24 540, Winstan U Adrenocortical suppressant (steroid biosynthesis inhibitor)

[Milne2018-7] Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 34–. ISBN 978-1-351-78989-9.

[pmid24465047-8] Tung D, Ciallella J, Hain H, Cheung PH, Saha S (December 2013). "Possible therapeutic effect of trilostane in rodent models of inflammation and nociception". Current Therapeutic Research, Clinical and Experimental. 75: 71–76. doi:10.1016/j.curtheres.2013.09.004. PMC 3898193. PMID 24465047.

[9] "Cushing's Disease in Dogs Part 3: Current & Investigative Options for Therapy". Today's Veterinary Practice. 24 February 2016. Retrieved 4 January 2021.

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Trilostane

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