Metepa

Last updated
Metepa
Metepa.svg
Names
IUPAC name
1-[Bis(2-methyl-1-aziridinyl)phosphoryl]-2-methylaziridine
Preferred IUPAC name
1,1′,1″-Phosphoryltris(2-methylaziridine)
Other names
Methaphoxide
Metapoxide
Methyl aphoxide
METEPA
Trimethylaziridinylphosphine oxide
MAPO
Tris(1,2-propylene)phosphoramide
Tris(2-methyl-1-aziridinyl)phosphine oxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.296 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
Properties [1]
C9H18N3OP
Molar mass 215.237 g·mol−1
AppearanceColorless liquid
Boiling point 90 to 92 °C (194 to 198 °F; 363 to 365 K)(0.15-0.3 mmHg)
Hazards
Lethal dose or concentration (LD, LC):
136 mg/kg (male rat, oral) [1]
213 mg/kg (female rat, oral) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Metepa is a chemosterilant, with the capability to restrict ovarian development. [2] Metepa can also result in carcinogenesis, in particular the formation of teratomas. [3] It is sometimes used as a Rocket propellant. [4]

Related Research Articles

Ovary Female reproductive organ that produces egg cells

The ovary is an organ found in the female reproductive system that produces an ovum. When released, this travels down the fallopian tube into the uterus, where it may become fertilized by a sperm. There is an ovary found on each side of the body. The ovaries also secrete hormones that play a role in the menstrual cycle and fertility. The ovary progresses through many stages beginning in the prenatal period through menopause. It is also an endocrine gland because of the various hormones that it secretes.

Menstrual cycle A type of ovulation cycle where the endometrium is shed if pregnancy does not occur

The menstrual cycle is the regular natural change that occurs in the female reproductive system that makes pregnancy possible. The cycle is required for the production of oocytes, and for the preparation of the uterus for pregnancy. The menstrual cycle occurs due to the rise and fall of estrogen. This cycle results in the thickening of the lining of the uterus, and the growth of an egg,. The egg is released from an ovary around day fourteen in the cycle; the thickened lining of the uterus provides nutrients to an embryo after implantation. If pregnancy does not occur, the lining is released in what is known as menstruation or a "period".

Ovulation

Ovulation is the release of eggs from the ovaries. In women, this event occurs when the ovarian follicles rupture and release the secondary oocyte ovarian cells. After ovulation, during the luteal phase, the egg will be available to be fertilized by sperm. In addition, the uterine lining (endometrium) is thickened to be able to receive a fertilized egg. If no conception occurs, the uterine lining as well as blood will be shed during menstruation.

Teratoma a tumor made up of several different types of tissue, such as hair, muscle, teeth, or bone

A teratoma is a tumor made up of several different types of tissue, such as hair, muscle, teeth, or bone. Teratoma typically form in the ovary, testicle, or coccyx.

Follicle-stimulating hormone

Follicle-stimulating hormone (FSH) is a gonadotropin, a glycoprotein polypeptide hormone. FSH is synthesized and secreted by the gonadotropic cells of the anterior pituitary gland, and regulates the development, growth, pubertal maturation, and reproductive processes of the body. FSH and luteinizing hormone (LH) work together in the reproductive system.

Ovarian cyst Fluid-filled sac in the ovary

An ovarian cyst is a fluid-filled sac within the ovary. Often they cause no symptoms. Occasionally they may produce bloating, lower abdominal pain, or lower back pain. The majority of cysts are harmless. If the cyst either breaks open or causes twisting of the ovary, it may cause severe pain. This may result in vomiting or feeling faint.

Ovarian cancer Cancer originating in or on the ovary

Ovarian cancer is a cancer that forms in or on an ovary. It results in abnormal cells that have the ability to invade or spread to other parts of the body. When this process begins, there may be no or only vague symptoms. Symptoms become more noticeable as the cancer progresses. These symptoms may include bloating, pelvic pain, abdominal swelling, and loss of appetite, among others. Common areas to which the cancer may spread include the lining of the abdomen, lymph nodes, lungs, and liver.

Oogenesis

Oogenesis, ovogenesis, or oögenesis is the differentiation of the ovum into a cell competent to further develop when fertilized. It is developed from the primary oocyte by maturation. Oogenesis is initiated in the embryonic stage.

Ciglitazone

Ciglitazone (INN) is a thiazolidinedione. Developed by Takeda Pharmaceuticals in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class.

Endometrioid tumor

Endometrioid tumors are a class of tumor characterized by a resemblance to endometrium/ endometrial carcinoma, and over a third of cases have focal squamous differentiation.

Anti-Müllerian hormone

Anti-Müllerian hormone (AMH), also known as Müllerian-inhibiting hormone (MIH), is a glycoprotein hormone structurally related to inhibin and activin from the transforming growth factor beta superfamily, whose key roles are in growth differentiation and folliculogenesis. In humans, the gene for AMH is AMH, on chromosome 19p13.3, while the gene AMHR2 codes for its receptor on chromosome 12.

Folliculogenesis

In biology, folliculogenesis is the maturation of the ovarian follicle, a densely packed shell of somatic cells that contains an immature oocyte. Folliculogenesis describes the progression of a number of small primordial follicles into large preovulatory follicles that occurs in part during the menstrual cycle.

Growth differentiation factor-9

Growth/differentiation factor 9 is a protein that in humans is encoded by the GDF9 gene.

Primary ovaries insufficiency (POI) is the partial or total loss of reproductive and hormonal function of the ovaries before age 40 because of folliclular dysfunction or early loss of eggs. POI can be seen as part of a continuum of changes leading to menopause that differ from age-appropriate menopause in the age of onset, degree of symptoms, and sporadic return to normal ovarian function. POI affects approximately 1 in 10,000 women under age 20, 1 in 1,000 women under age 30, and 1 in 100 of those under age 40. A medical triad for the diagnosis is amenorrhea, hypergonadotropism, and hypoestrogenism.

Gonadal dysgenesis is classified as any congenital developmental disorder of the reproductive system in the male or female. It is the atypical development of the gonads in an embryo, with reproductive tissue replaced with functionless, fibrous tissue, termed streak gonads. Streak gonads are a form of aplasia, resulting in hormonal failure that manifests as sexual infantism and infertility, with no initiation of puberty and secondary sex characteristics.

Anti-Müllerian hormone receptor

Anti-Müllerian hormone receptor is a receptor for anti-Müllerian hormone. Anti-Mullerian hormone receptor type 2 is a protein that in humans is encoded by the AMHR2 gene.

FOXL2 Transcription factor gene of the FOX family

Forkhead box protein L2 is a protein that in humans is encoded by the FOXL2 gene.

EIF5A2

Eukaryotic translation initiation factor 5A-2 is a protein that in humans is encoded by the EIF5A2 gene.

Ovarian torsion

Ovarian torsion (OT) is when an ovary twists on its attachment to other structures, such that blood flow is decreased. Symptoms typically include pelvic pain on one side. While classically the pain is sudden in onset, this is not always the case. Other symptoms may include nausea. Complications may include infection, bleeding, or infertility.

NOBOX

Homeobox protein NOBOX, also known as newborn ovary homeobox protein, is a protein that in humans is encoded by the NOBOX gene. The official symbol (NOBOX) and the official full name are maintained by the HGNC. The NOBOX gene is conserved in chimpanzee, Rhesus monkey, cow, mouse, and rat. There are 175 organisms that have orthologs with human gene NOBOX. It is capable of regulating other genes that are important in the development of follicles. Follicles do not develop and oocytes decrease in its absence which lead to infertility.

References

  1. 1 2 3 Merck Index , 12th Edition, 5998
  2. Morgan, Philip B; Labrecque, G. C (1964). "Effect of Tepa and Metepa on Ovarian Development of House Flies". Journal of Economic Entomology. 57 (6): 896–899. doi:10.1093/jee/57.6.896.
  3. Gaines, T. B; Kimbrough, R. D (1966). "The sterilizing, carcinogenic and teratogenic effects of metepa in rats". Bulletin of the World Health Organization. 34 (2): 317–20. PMC   2475925 . PMID   5296141.
  4. "Ababil-100/Al Fat'h". GlobalSecurity.org. Archived from the original on 15 April 2019.