Metallibure

Metallibure (INN) (brand names Aimax, Suisynchron, Turisynchron; former developmental code names ICI-33828, AY-61122, NSC-69536), also known as methallibure (USAN, BAN) or methallibur (German), is a medication which was introduced in 1973 and has been used in veterinary medicine to synchronize estrus.[1][2] It was withdrawn in the United States and Europe due to teratogenicity and has been replaced with altrenogest (Regumate, Matrix), a progestin.[2][3]

Metallibure
Clinical data
Trade namesAimax, Suisynchron, Turisynchron
Other namesMethallibure; Methallibur; ICI-33828; AY-61122; NSC-69536
Drug classAntigonadotropin
Identifiers
IUPAC name
  • 1-but-3-en-2-yl-3-(methylcarbamothioylamino)thiourea
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.011.952
Chemical and physical data
FormulaC7H14N4S2
Molar mass218.34 g·mol−1
3D model (JSmol)
SMILES
  • CC(C=C)NC(=S)NNC(=S)NC
InChI
  • InChI=1S/C7H14N4S2/c1-4-5(2)9-7(13)11-10-6(12)8-3/h4-5H,1H2,2-3H3,(H2,8,10,12)(H2,9,11,13)
  • Key:CGFFKDRVHZIQHL-UHFFFAOYSA-N

The precise mechanism of action of metallibure is unknown.[2] It has been described as a "nonsteroidal antigonadotropin" and it appears to act directly on the pituitary gland and/or hypothalamus to suppress gonadotropin secretion.[2] However, metallibure has also been reported to be an antiprogestogen and to act specifically via inhibition of the biosynthesis or secretion of progesterone.[4]

Metallibure has similar endocrinological effects in women.[5] It is associated with several unpleasant side effects including appetite loss, nausea, occasional vomiting, lethargy, and drowsiness.[5] Animal toxicity studies revealed that the medication induced the development of cataracts, and this resulted in the termination of its clinical development.[5]

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 781–. ISBN 978-1-4757-2085-3.
  2. I. Gordon (22 October 2013). Controlled Breeding in Farm Animals. Elsevier. pp. 313–. ISBN 978-1-4832-8569-6.
  3. Brüssow KP, Schneider F, Kanitz W, Rátky J, Kauffold J, Wähner M (2009). "Studies on fixed-time ovulation induction in the pig". Soc Reprod Fertil Suppl. 66: 187–95. PMID 19848281.
  4. A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 523–. ISBN 978-3-642-96158-8.
  5. JUCKER (21 December 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 102–. ISBN 978-3-0348-7065-8.



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