Metallibure

Metallibure (INNTooltip International Nonproprietary Name) (brand names Aimax, Suisynchron, Turisynchron; former developmental code names ICI-33828, AY-61122, NSC-69536), also known as methallibure (USANTooltip United States Adopted Name, BANTooltip British Approved Name) 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a medication which was introduced in 1973 and has been used in veterinary medicine to synchronize estrus.^[1][2] It was withdrawn in the United States and Europe due to teratogenicity and has been replaced with altrenogest (Regumate, Matrix), a progestin.^[2][3]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 names	Aimax, Suisynchron, Turisynchron
Other names	Methallibure; Methallibur; 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
UNII	MBU5XJ97C4
CompTox Dashboard (EPA)	DTXSID70862475
ECHA InfoCard	100.011.952
Chemical and physical data
Formula	C7H14N4S2
Molar mass	218.34 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

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

• Bifluranol
• Paroxypropione
• Quadrosilan