Metallibure

Metallibure
Clinical data
Trade names	Aimax, Suisynchron, Turisynchron
Other names	Methallibure; ICI-33828; AY-61122; NSC-69536
Drug class	Antigonadotropin
Identifiers
	IUPAC name 1-but-3-en-2-yl-3-(methylcarbamothioylamino)thiourea;
CAS Number	926-93-2;
PubChem CID	3003791;
ChemSpider	2274191;
CompTox Dashboard (EPA)	DTXSID70862475 ;
ECHA InfoCard	100.011.952
Chemical and physical data
Formula	C7H14N4S2
Molar mass	218.337 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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;

Metallibure (INNTooltip International Nonproprietary Name) (brand names Aimax, Suisynchron, Turisynchron; former developmental code names ICI-33828, AY-61122, NSC-69536), or methallibure (USANTooltip United States Adopted Name, BANTooltip British Approved Name) is a nonsteroidal antigonadotropin that was introduced in 1973 and has been used in veterinary medicine to synchronize estrus.^[1]^[2] It was withdrawn in the United States and Europe due to teratogenicity and has been replaced with altrenogest.^[2]^[3] The precise mechanism of action of metallibure is unknown.^[2] However, it appears to act directly on the pituitary gland and/or hypothalamus to suppress gonadotropin secretion.^[2]

Metallibure is similarly effective as an antigonadotropin in women.^[4] It is associated with several unpleasant side effects including appetite loss, nausea, occasional vomiting, lethargy, and drowsiness.^[4] Animal toxicity studies revealed that the drug induced the development of cataracts, and this resulted in the termination of its clinical development.^[4]

References

^ 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.
^ ^a ^b ^c ^d I. Gordon (22 October 2013). Controlled Breeding in Farm Animals. Elsevier. pp. 313–. ISBN 978-1-4832-8569-6.
^ 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.
^ ^a ^b ^c 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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