Progesterone
Title: Progesterone
CAS Registry Number: 57-83-0
CAS Name: Pregn-4-ene-3,20-dione
Additional Names: D4-pregnene-3,20-dione; corpus luteum hormone; luteohormone
Trademarks: Crinone (Serono); Cyclogest (Alpharma); Estima (EFFIK); Gestone (Nordic); Menaelle (Thžamex); Progestasert (Alza); Progestogel (Besins-Iscovesco); Progeston (Fuji); Proluton (Schering AG); Utrogestan (Besins-Iscovesco)
Molecular Formula: C21H30O2
Molecular Weight: 314.46
Percent Composition: C 80.21%, H 9.62%, O 10.18%
Literature References: Active principle of the corpus luteum, secreted during the latter half of the menstrual cycle. If pregnancy ensues, secretion continues. Exerts an antiovulatory effect when administered during days 5 to 25 of the normal menstrual cycle. Isoln from corpus luteum of pregnant sows: Butenandt, Westphal, Ber. 67, 1440 (1934); Wintersteiner, Allen, J. Biol. Chem. 107, 321 (1934). Structure: Butenandt et al., Ber. 67, 1611 (1934). Synthesis of DL-form: Johnson et al., J. Am. Chem. Soc. 93, 4332 (1971). Prepn from other steroids in review by W. H. Strain in Gilman's Organic Chemistry vol. II (Wiley, New York, 2nd ed., 1943) pp 1487-1489. Numerous patents, e.g., US 2379832; US 2232438; US 2314185. Anesthetic effect and toxicity: H. Selye, Proc. Soc. Exp. Biol. Med. 46, 116 (1941). Review of physiology: Csapo, Sci. Am. 198, 40-46 (April, 1958); Rothchild, Vitam. Horm. 23, 209-327 (1965). Book: Progesterone and Progestins, C. W. Bardin et al., Eds. (Raven Press, New York, 1982) 462 pp.
Properties: Exists in two cryst forms of equal physiologic activity and which are readily interconverted. The a-form is orthorhombic (prisms from dil alc) with a:b:c = 0.750:1:0.905. Crystals show (011), (110), (010). Poor (011) cleavage. d23 1.166. mp 127-131°. The b-form is orthorhombic (needles) with a:b:c = 0.563:1:0.275. Crystals acicular with parallel extinction and negative elongation. Cleavage on (001) and (110). d20 1.171. mp 121°. [a]D20 +172 to +182° (c = 2 in dioxane). uv max: 240 nm. Insol in water. Sol in alcohol, acetone, dioxane, concd H2SO4. Sparingly sol in vegetable oils. 1 mg = 1 I.U.
Melting point: mp 127-131°; mp 121°
Optical Rotation: [a]D20 +172 to +182° (c = 2 in dioxane)
Absorption maximum: uv max: 240 nm
Density: d23 1.166; d20 1.171
CAUTION: This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-223.
Therap-Cat: Progestogen.
Therap-Cat-Vet: Progestogen. Has been used to control habitual abortion, to suppress or synchronize estrus.
Keywords: Progestogen.

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