Trengestone

Trengestone
Clinical data
Trade names	Reteroid, Retroid, Retrone
Other names	Ro 4-8347; Triengestone; 1,6-Didehydro-6-chlororetroprogesterone; 6-Chloro-9β-10α-pregna-1,4,6-triene-3,20-dione
Routes of; administration	By mouth
Drug class	Progestogen; Progestin
ATC code	None;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	≥41–46% (based on urinary excretion)
Metabolism	Liver
Metabolites	• 20α-Dihydrotrengestone
Elimination half-life	• Trengestone: very short; • 20α-DHTG: 8–14 hours
Excretion	Urine: 41–46%; Feces: 30% (unchanged)
Identifiers
	IUPAC name (8S,9S,10R,13S,14S,17S)-17-acetyl-6-chloro-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one;
CAS Number	5192-84-7;
PubChem CID	56840930;
ChemSpider	28475379;
UNII	VY6S496SVX;
ChEBI	CHEBI:135458;
ChEMBL	ChEMBL2107518;
CompTox Dashboard (EPA)	DTXSID101023713 ;
ECHA InfoCard	100.023.617
Chemical and physical data
Formula	C21H25ClO2
Molar mass	344.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)C=C[C@]34C)Cl)C;
	InChI InChI=1S/C21H25ClO2/c1-12(23)15-4-5-16-14-11-19(22)18-10-13(24)6-8-21(18,3)17(14)7-9-20(15,16)2/h6,8,10-11,14-17H,4-5,7,9H2,1-3H3/t14-,15+,16-,17-,20+,21+/m0/s1; Key:USXVMPAWZOOYDE-HGUQNLGYSA-N;

Trengestone, sold under the brand names Reteroid, Retroid, and Retrone, is a progestin medication which was formerly used to treat menstrual disorders but is now no longer marketed.^[4]^[5]^[6]^[7]^[8] It is taken by mouth.^[9]

Side effects of trengestone include headache, fatigue, and breast tenderness among others.^[7] Trengestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[7] It is not androgenic or estrogenic.^[7]

Trengestone was introduced for medical use in 1974.^[5] It is no longer available.^[8]

^ ^a ^b ^c ^d ^e ^f Cite error: The named reference pmid1116370 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid5510163 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid5510160 was invoked but never defined (see the help page).
^ Elks J (14 November 2014). "6-Chloro-9β-10α-pregna-1,4,6-triene-3,20-dione". The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 259–. ISBN 978-1-4757-2085-3. C-00276.
^ ^a ^b Brudon P, Brudon-Jakobowicz P (1983). Médicaments pour tous en l'an 2000?: les multinationales pharmaceutiques suisses face au tiers monde : l'exemple du Mexique. Editions d'en bas. pp. 93–. ISBN 978-2-8290-0039-3.
^ Morton I, Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 279–. ISBN 978-0-7514-0499-9.
^ ^a ^b ^c ^d Horsky J (6 December 2012). "Therapy of Anovulation". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 329–. ISBN 978-94-009-8195-9.
^ ^a ^b "Micromedex". Merative US L.P.
^ Popper TL, Watnick AS (1971). "Chapter 17. Steroids and Biologically Related Compounds". Annual Reports in Medicinal Chemistry. Vol. 6. Academic Press. pp. 162–181. doi:10.1016/S0065-7743(08)60972-0. ISBN 9780120405060. ISSN 0065-7743. Ro 4-8347 (21), a potent orally active progestagen, when given at the dose of 4 mg/day in the second half of the cycle, was found clinically useful in anovulatory women with decreased ovarian function.109

[pmid1116370-1] ^ ^a ^b ^c ^d ^e ^f Cite error: The named reference pmid1116370 was invoked but never defined (see the help page).

[pmid5510163-2] Cite error: The named reference pmid5510163 was invoked but never defined (see the help page).

[pmid5510160-3] Cite error: The named reference pmid5510160 was invoked but never defined (see the help page).

[Elks2014-4] Elks J (14 November 2014). "6-Chloro-9β-10α-pregna-1,4,6-triene-3,20-dione". The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 259–. ISBN 978-1-4757-2085-3. C-00276.

[Brudon1983-5] Brudon P, Brudon-Jakobowicz P (1983). Médicaments pour tous en l'an 2000?: les multinationales pharmaceutiques suisses face au tiers monde : l'exemple du Mexique. Editions d'en bas. pp. 93–. ISBN 978-2-8290-0039-3.

[MortonHall1999-6] Morton I, Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 279–. ISBN 978-0-7514-0499-9.

[HorskyPresl2012-7] Horsky J (6 December 2012). "Therapy of Anovulation". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 329–. ISBN 978-94-009-8195-9.

[Micromedex-8] "Micromedex". Merative US L.P.

[PopperWatnick1971-9] Popper TL, Watnick AS (1971). "Chapter 17. Steroids and Biologically Related Compounds". Annual Reports in Medicinal Chemistry. Vol. 6. Academic Press. pp. 162–181. doi:10.1016/S0065-7743(08)60972-0. ISBN 9780120405060. ISSN 0065-7743. Ro 4-8347 (21), a potent orally active progestagen, when given at the dose of 4 mg/day in the second half of the cycle, was found clinically useful in anovulatory women with decreased ovarian function.109

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]