Trengestone

Trengestone
Clinical data
Trade namesReteroid, Retroid, Retrone
Other namesRo 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 classProgestogen; Progestin
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability≥41–46% (based on urinary excretion)[1]
MetabolismLiver[2][3]
Metabolites• 20α-Dihydrotrengestone[1]
Elimination half-life• Trengestone: very short[1]
• 20α-DHTG: 8–14 hours[1]
ExcretionUrine: 41–46%[1]
Feces: 30% (unchanged)[1]
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.023.617 Edit this at Wikidata
Chemical and physical data
FormulaC21H25ClO2
Molar mass344.88 g·mol−1
3D model (JSmol)
  • 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=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]

  1. ^ a b c d e f Cite error: The named reference pmid1116370 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference pmid5510163 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference pmid5510160 was invoked but never defined (see the help page).
  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.
  5. ^ 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.
  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.
  7. ^ 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.
  8. ^ a b "Micromedex". Merative US L.P.
  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