methallibure

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Description

Methallibure: A dithiobiurea compound with anti-gonadotropic activity. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	3003791
CHEMBL ID	2106852
SCHEMBL ID	393014
MeSH ID	M0013548

Synonyms (74)

Synonym
compound 33,828
ai3-51056
ay 61122
metalliburum [latin]
biurea, 2,5-dithio-1-methyl-6-(1-methyl-2-propenyl)-
i.c.i. compound 33828
i.c.i. 33,828
nsc 69536
ici 33,828
1alpha-methylallylthiocarbamoyl-2-methylthiocarbamoylhydrazine
biurea, 1-methyl-6-(1-methylallyl)-2,5-dithio-
einecs 213-146-7
1-alpha-methylallylthiocarbamoyl-2-methylthiocarbamoylhydrazine
metalibura [inn-spanish]
n-((1-methylallyl)thiocarbamoyl)-n'-(methylthiocarbamoyl)hydrazine
metallibur
metalliburum [inn-latin]
1,2-hydrazinedicarbothioamide, n-methyl-n'-(1-methyl-2-propenyl)-
metalibura [spanish]
brn 1212512
wln: suym1&mmyus&my1u1
1-methyl-6-(1-methylallyl)dithiobiurea
metallibure
ay-61122
1-[(.alpha.-methylallyl)thiocarbamoyl]-2-(methylthiocarbamoyl)hydrazine
n-[(1-methylallyl)thiocarbamoyl]-n'-(methylthiocarbamoyl)hydrazine
turisynchron
926-93-2
aimax
2,5-dithio-1-methyl-6-(1-methyl-2-propenyl)biurea
ici 33828
methallibure
1, n-methyl-n'-(1-methyl-2-propenyl)-
suisynchron
ici-33,828
nsc-69536
1-methyl-6-(1-methylallyl)-2,5-dithiobiurea
match
almax
biurea,5-dithio-1-methyl-6-(1-methyl-2-propenyl)-
nsc69536
1, 2-hydrazinedicarbothioamide, n-methyl-n'-(1-methyl-2-propenyl)-
1-methyl-3-(1-methylallylcarbamothioylamino)thiourea
.meta.llibure
{n-[(1-methylallyl)thiocarbamoyl]-n'-(methylthiocarbamoyl)hydrazine}
biurea, 1-methyl-6-(1-methylallyl)-2, 5-dithio-
biurea, 2, 5-dithio-1-methyl-6-(1-methyl-2-propenyl)-
{1-[(.alpha.-methylallyl)thiocarbamoyl]-2-(methylthiocarbamoyl)hydr} azine
n~1~-methyl-n~2~-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide
methallibure (usan/inn)
D04975
NCIOPEN2_003498
1-but-3-en-2-yl-3-(methylcarbamothioylamino)thiourea
metalliburum
metallibure [inn]
mbu5xj97c4 ,
unii-mbu5xj97c4
metalibura
methallibure [usan]
CHEMBL2106852
ici-33828
methallibure [mi]
metallibure [mart.]
SCHEMBL393014
AKOS024403844
CGFFKDRVHZIQHL-UHFFFAOYSA-N
Z1269236938
aimax; ici 33828; methallibure
Q27283830
3-(but-3-en-2-yl)-1-[(methylcarbamothioyl)amino]thiourea
DTXSID70862475
CS-0026371
n-methyl-n'-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide
EN300-1268098

Research Excerpts

Treatment

Methallibure treatment is as effective as hypophysectomy in reducing thyroid activity in H. Cyprinus carpio causes a marked reduction in the steroidogenesis, as indicated by the fall in 3beta-HSD activity in the gonads.

Excerpt	Reference	Relevance
"Methallibure treatment may exert marked inhibitory influence on vitellogenesis in the fish and cause atresia of vitellogenic follicles, the oogonial proliferation is stepped up."	( The effect of methallibure (I.C.I., 33828) on the ovary of the carp, Cyprinus carpio. Kapur, K, 1980)	1.34
"Methallibure treatment is as effective as hypophysectomy in reducing thyroid activity in H. "	( Thyroid activity in response to some gonadal steroids in methallibure-treated Heteropneustes fossilis (Bloch). Raizada, RB; Singh, TP, 1979)	1.95
"Methallibure treatment of mature Cyprinus carpio causes a marked reduction in the steroidogenesis, as indicated by the fall in 3beta-HSD activity in the gonads. "	( The effect of methallibure (I.C.I. 33,828) on the steriodogenesis in the ovary and testis of a fresh water teleost, Cyprinus carpio. Kapur, K; Toor, HS, 1978)	2.06
"Methallibure treatment (1 mg fed on alternate days to a female and a male kept in 1 liter of 25% seawater) started from 1 or 7 days postpartum (early gestation) inhibited gestation in the wild guppy, Poecilia reticulata. "	( Effect of methallibure on gestation in the guppy, Poecilia reticulata. Lam, TJ; Ng, KL; Pavri, C, 1985)	2.11

Dosage Studied

Excerpt	Relevance	Reference
" Clinical inspection, weight gain, haematological findings, blood sugar, serum transaminases, properties of urine and faeces, carcass examination and histological study (internal organs, endocrine glands, skeletal muscle) showed that the 1 mg/kg dosage had no toxic effect."	( [Effect of long-term application of SUISYNCHRON-premix on swine]. Chemnitius, KH; Oettel, M; Schimke, E; Zieger, M, 1974)	0.25
"Twelve groups of German Edelschwein were given the recommended dosage of metallibure zinc complex (SUISYNCHRON) or 5 and 10 times this dosage."	( [Pharmacologic-endocrinological findings in animal experiments with TURISYNCHRON and SUISYNCHRON. 4. Analysis of residuals in pig carcasses]. Chemnitius, KH; Claussen, C; Grass, M; Räche, K; Steiner, G, 1974)	0.25

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (71)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	66 (92.96)	18.7374
1990's	4 (5.63)	18.2507
2000's	1 (1.41)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 15.15

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	15.15 (24.57)
Research Supply Index	4.30 (2.92)
Research Growth Index	4.27 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (15.15)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (2.74%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	71 (97.26%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	1.95	1	diatomic iodine	nutrient
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.94	1	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	1.95	1	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.06	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
meclofenamic acid Meclofenamic Acid: A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.. meclofenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoea (painful periods), osteoarthritis and rheumatoid arthritis.	3.06	1	aminobenzoic acid; organochlorine compound; secondary amino compound	analgesic; anticonvulsant; antineoplastic agent; antipyretic; antirheumatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	1.95	1	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	1.95	1	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
niridazole Niridazole: An antischistosomal agent that has become obsolete.	6.95	1	1,3-thiazoles; C-nitro compound
alpha-chlorohydrin alpha-Chlorohydrin: A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.. 3-chloropropane-1,2-diol : A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.	6.95	1	chloropropane-1,2-diol
estradiol dipropionate estradiol dipropionate: RN given refers to (17beta)-isomer; RN for cpd without isomeric designation not in Chemline 7/83	1.96	1	steroid ester
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.98	1	dithiocarbamic acids	chelator; copper chelator
hydrazine diamine : Any polyamine that contains two amino groups.	2.35	2	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
danazol Danazol: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.	6.95	1	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	1.95	1	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
trenbolone acetate Trenbolone Acetate: An anabolic steroid used mainly as an anabolic agent in veterinary practice.	3.06	1	steroid ester
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	1.95	1	1,2,3-triazole
carazolol carazolol: RN given refers to parent cpd without isomeric designation; structure	3.06	1	carbazoles
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	1.95	1
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.36	2
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	3.46	2	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	5.19	50	one-carbon compound; thioureas; ureas	antioxidant; chromophore
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	3.06	1	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	1.96	1	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
cloprostenol Cloprostenol: A synthetic prostaglandin F2alpha analog. The compound has luteolytic effects and is used for the synchronization of estrus in cattle.	1.97	1	prostanoid
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	1.95	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
24,25-dihydroxyvitamin d 3 24,25-Dihydroxyvitamin D 3: A physiologically active metabolite of VITAMIN D. The compound is involved in the regulation of calcium metabolism, alkaline phosphatase activity, and enhancing the calcemic effect of CALCITRIOL.	1.96	1
altrenogest altrenogest: a synthetic PROGESTERONE agonist; used in estrus synchronization	3.06	1	3-hydroxy steroid
alfaprostol alfaprostol: RN given refers to 1R-(1alpha(Z),2beta(S*), 3alpha,5alpha)-isomer; structure in first source	3.06	1

Condition	Relationship Strength	Studies
Breast Cancer [description not available]	1.94	1
Animal Mammary Carcinoma [description not available]	1.94	1
Experimental Mammary Neoplasms [description not available]	1.94	1
Breast Neoplasms Tumors or cancer of the human BREAST.	1.94	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	5.59	18
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	3.28	2
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	1.96	1
Abnormalities, Autosome [description not available]	2.36	2
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.36	2
Weight Gain Increase in BODY WEIGHT over existing weight.	1.98	1
Goiter Enlargement of the THYROID GLAND that may increase from about 20 grams to hundreds of grams in human adults. Goiter is observed in individuals with normal thyroid function (euthyroidism), thyroid deficiency (HYPOTHYROIDISM), or hormone overproduction (HYPERTHYROIDISM). Goiter may be congenital or acquired, sporadic or endemic (GOITER, ENDEMIC).	1.95	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	1.95	1
Experimental Neoplasms [description not available]	1.95	1
Cancer of Ovary [description not available]	2.35	2
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.35	2
Adipocere [description not available]	1.95	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.05	5
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	1.95	1
Cancer of Testis [description not available]	1.95	1
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	1.95	1
Testicular Neoplasms Tumors or cancer of the TESTIS. Germ cell tumors (GERMINOMA) of the testis constitute 95% of all testicular neoplasms.	1.95	1
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	1.95	1
Chronic Illness [description not available]	1.95	1
Gastroduodenal Ulcer [description not available]	1.95	1
Duodenal Diseases Pathological conditions in the DUODENUM region of the small intestine (INTESTINE, SMALL).	1.95	1
Acute Disease Disease having a short and relatively severe course.	1.95	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	1.95	1
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	1.95	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	1.95	1
Alloxan Diabetes [description not available]	1.95	1
E coli Infections [description not available]	1.95	1
Erysipelothrix Infections Infections with bacteria of the genus ERYSIPELOTHRIX.	1.95	1
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	1.95	1

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