D(minus)-norgestrel (CAS 797-63-7) — formula C21H28O2, molecular weight 312.4.
| CAS Number | 797-63-7 |
|---|---|
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4 |
| Melting Point | 232-239 |
| Boiling Point | 459.1 |
| LogP | 3.8 |
| Applications | Uses: MEDICATION, Used as a combined oral contraceptive with ethinylestradiol in monophasic, biphasic, and triphasic regimens. It is also used as a 'progestin-only' contraceptive pill and subdermal implant., MEDICATION, Use (kg, approx.) in Germany (2009): >50, Consumption (g per capita, approx.) in Germany (2009): 0.000611, Calculated removal (%): 24.5, For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive., Use Classification: Pharmaceuticals, Methods of Manufacturing: In a representative chemical synthesis, 6-methoxy-alpha-tetralone is reacted with vinylmagnesium bromide, and the resulting 1, 2, 3, 4-tetrahydro-6-methoxy-1-vinyl-1-naphthol is condensed with 2-ethyl-1, 3-cyclopentanedione to form initially a tricyclic intermediate (secosteroid) containing all of the gonane skeleton carbon atoms. Cyclization of the secosteroid via dehydration yields a 13-ethylgona-1, 5(10)-8, 14-pentaene structure which is then successively reduced and ethynylated., Prepn: H. Smith, Belg. pat. 623, 844 (1963), C.A. 61, 4427c (1964), G.A. Hughes, H. Smith, U.S. pat. 3, 959, 322 (1976 to Herchel Smith), The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel. Synthesis of the levorotatory form involves meta-cresol methyl ether, dimethyl malonate and trans-1, 4-dibromo-2-butene as starting materials. The steroid skeleton was constructed by using an intramolecular Diels-Alder reaction of an ortho-quinodimethane derivative, preceded by photo-enolization of an appropriate methyl-substituted acetophenone derivative. Chirality was introduced at an early stage during a nucleophilic substitution reaction. It is not known if this synthesis is used commercially., Impurities: Reported impurities include: 13-ethyl-3, 4-diethynyl-18, 19-dinor-17alpha-pregn-5-en-20- yn-3beta, 4alpha, 17-triol, 13-ethyl-3, 19-dinor-17alpha-pregn-5-en-20-yn-3alpha, 17- triol 13-ethyl-18, 19-dinor-17alpha-pregn-4-en-20-yn-17-ol, 13-ethyl-3-ethynyl-18, 19-dinor-17alpha-pregna-3, 5-dien-20-yn-17-ol, 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregna-4, 8(14)- dien-20-yn-3-one and 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregn-5(10)-en-20-yn-3-one., Formulations, Preparations: Mixture of levonorgestrel with ethinyl estradiol. Levlen, Logynon, Microgynon, Nordette, Ovran, Ovranette, Tetre-gynon, Tri-Levlen, Trinordiol, Triphasil. Clinical trial in acne treatment., Mixture with ethinyl estradiol. Lo, Ovral, Stediril. Clinical efficiacy as oral contraceptive., Norgestrel is available commercially as a single-ingredient tablet and as a component of combination tablets with ethinylestradiol, estradiol valerate or as combined injectable solution with ethinylestradiol., Oral: Tablets: Norgestrel and Ethinyl Estradiol 0.3 mg, 0.03 mg, Low-ogestrel (Watson Pharma)., Oral: Tablets: 2 mg estradiol valerate (white tablets taken day 1-11), 500 ug norgestrel + 2 mg estradiol valerate (pale brown tablets taken day 12-21), Cyclo-Progynova (Meda Pharmaceuticals)., Levonorgestrel is available commercially as a single-ingredient tablet and in combined tablets with estradiol, estradiol valerate, estriol and ethinylestradiol ... It is also available as an intrauterine system and as a flexible, closed-capsule implant made of silicone rubber tubing., Plan B (levonorgestrel) tablets, 0.75 mg, are available for a single course of treatment in PVC, aluminum foil blister packages of two tablets each., General Manufacturing Information: A synthetic steroid hormone used as an ingredient of oral contraceptives, The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel., ...was manufactured or formulated in Augentina, Australia, Austria, Belgium, Brazil, Canada, Finland, France, German, India, Mexico, the Netherlands, New Zealand, Portugal, South Africa, Spain, Switzerland, the United Kingdom and the U.S. |
Documented applications: Uses: MEDICATION, Used as a combined oral contraceptive with ethinylestradiol in monophasic, biphasic, and triphasic regimens. It is also used as a 'progestin-only' contraceptive pill and subdermal implant., MEDICATION, Use (kg, approx.) in Germany (2009): >50, Consumption (g per capita, approx.) in Germany (2009): 0.000611, Calculated removal (%): 24.5, For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive., Use Classification: Pharmaceuticals, Methods of Manufacturing: In a representative chemical synthesis, 6-methoxy-alpha-tetralone is reacted with vinylmagnesium bromide, and the resulting 1, 2, 3, 4-tetrahydro-6-methoxy-1-vinyl-1-naphthol is condensed with 2-ethyl-1, 3-cyclopentanedione to form initially a tricyclic intermediate (secosteroid) containing all of the gonane skeleton carbon atoms. Cyclization of the secosteroid via dehydration yields a 13-ethylgona-1, 5(10)-8, 14-pentaene structure which is then successively reduced and ethynylated., Prepn: H. Smith, Belg. pat. 623, 844 (1963), C.A. 61, 4427c (1964), G.A. Hughes, H. Smith, U.S. pat. 3, 959, 322 (1976 to Herchel Smith), The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel. Synthesis of the levorotatory form involves meta-cresol methyl ether, dimethyl malonate and trans-1, 4-dibromo-2-butene as starting materials. The steroid skeleton was constructed by using an intramolecular Diels-Alder reaction of an ortho-quinodimethane derivative, preceded by photo-enolization of an appropriate methyl-substituted acetophenone derivative. Chirality was introduced at an early stage during a nucleophilic substitution reaction. It is not known if this synthesis is used commercially., Impurities: Reported impurities include: 13-ethyl-3, 4-diethynyl-18, 19-dinor-17alpha-pregn-5-en-20- yn-3beta, 4alpha, 17-triol, 13-ethyl-3, 19-dinor-17alpha-pregn-5-en-20-yn-3alpha, 17- triol 13-ethyl-18, 19-dinor-17alpha-pregn-4-en-20-yn-17-ol, 13-ethyl-3-ethynyl-18, 19-dinor-17alpha-pregna-3, 5-dien-20-yn-17-ol, 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregna-4, 8(14)- dien-20-yn-3-one and 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregn-5(10)-en-20-yn-3-one., Formulations, Preparations: Mixture of levonorgestrel with ethinyl estradiol. Levlen, Logynon, Microgynon, Nordette, Ovran, Ovranette, Tetre-gynon, Tri-Levlen, Trinordiol, Triphasil. Clinical trial in acne treatment., Mixture with ethinyl estradiol. Lo, Ovral, Stediril. Clinical efficiacy as oral contraceptive., Norgestrel is available commercially as a single-ingredient tablet and as a component of combination tablets with ethinylestradiol, estradiol valerate or as combined injectable solution with ethinylestradiol., Oral: Tablets: Norgestrel and Ethinyl Estradiol 0.3 mg, 0.03 mg, Low-ogestrel (Watson Pharma)., Oral: Tablets: 2 mg estradiol valerate (white tablets taken day 1-11), 500 ug norgestrel + 2 mg estradiol valerate (pale brown tablets taken day 12-21), Cyclo-Progynova (Meda Pharmaceuticals)., Levonorgestrel is available commercially as a single-ingredient tablet and in combined tablets with estradiol, estradiol valerate, estriol and ethinylestradiol ... It is also available as an intrauterine system and as a flexible, closed-capsule implant made of silicone rubber tubing., Plan B (levonorgestrel) tablets, 0.75 mg, are available for a single course of treatment in PVC, aluminum foil blister packages of two tablets each., General Manufacturing Information: A synthetic steroid hormone used as an ingredient of oral contraceptives, The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel., ...was manufactured or formulated in Augentina, Australia, Austria, Belgium, Brazil, Canada, Finland, France, German, India, Mexico, the Netherlands, New Zealand, Portugal, South Africa, Spain, Switzerland, the United Kingdom and the U.S..
D(minus)-norgestrel is a chemical compound with CAS registry number 797-63-7 and molecular formula C21H28O2 (molecular weight 312.4).
CAS number: 797-63-7
Its molecular formula C21H28O2 comprises 21 C, 28 H, 2 O atoms.
Also known as: D(minus)-norgestrel · D(减)-炔诺孕酮 · Levonorgestrel
The CAS registry number of D(minus)-norgestrel is 797-63-7.
Molecular formula C21H28O2, molecular weight 312.4.
It is also registered under: D(minus)-norgestrel, D(减)-炔诺孕酮, Levonorgestrel.
Recorded applications: Uses: MEDICATION, Used as a combined oral contraceptive with ethinylestradiol in monophasic, biphasic, and triphasic regimens. It is also used as a 'progestin-only' contraceptive pill and subdermal implant., MEDICATION, Use (kg, approx.) in Germany (2009): >50, Consumption (g per capita, approx.) in Germany (2009): 0.000611, Calculated removal (%): 24.5, For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive., Use Classification: Pharmaceuticals, Methods of Manufacturing: In a representative chemical synthesis, 6-methoxy-alpha-tetralone is reacted with vinylmagnesium bromide, and the resulting 1, 2, 3, 4-tetrahydro-6-methoxy-1-vinyl-1-naphthol is condensed with 2-ethyl-1, 3-cyclopentanedione to form initially a tricyclic intermediate (secosteroid) containing all of the gonane skeleton carbon atoms. Cyclization of the secosteroid via dehydration yields a 13-ethylgona-1, 5(10)-8, 14-pentaene structure which is then successively reduced and ethynylated., Prepn: H. Smith, Belg. pat. 623, 844 (1963), C.A. 61, 4427c (1964), G.A. Hughes, H. Smith, U.S. pat. 3, 959, 322 (1976 to Herchel Smith), The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel. Synthesis of the levorotatory form involves meta-cresol methyl ether, dimethyl malonate and trans-1, 4-dibromo-2-butene as starting materials. The steroid skeleton was constructed by using an intramolecular Diels-Alder reaction of an ortho-quinodimethane derivative, preceded by photo-enolization of an appropriate methyl-substituted acetophenone derivative. Chirality was introduced at an early stage during a nucleophilic substitution reaction. It is not known if this synthesis is used commercially., Impurities: Reported impurities include: 13-ethyl-3, 4-diethynyl-18, 19-dinor-17alpha-pregn-5-en-20- yn-3beta, 4alpha, 17-triol, 13-ethyl-3, 19-dinor-17alpha-pregn-5-en-20-yn-3alpha, 17- triol 13-ethyl-18, 19-dinor-17alpha-pregn-4-en-20-yn-17-ol, 13-ethyl-3-ethynyl-18, 19-dinor-17alpha-pregna-3, 5-dien-20-yn-17-ol, 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregna-4, 8(14)- dien-20-yn-3-one and 13-ethyl-17-hydroxy-18, 19-dinor-17alpha-pregn-5(10)-en-20-yn-3-one., Formulations, Preparations: Mixture of levonorgestrel with ethinyl estradiol. Levlen, Logynon, Microgynon, Nordette, Ovran, Ovranette, Tetre-gynon, Tri-Levlen, Trinordiol, Triphasil. Clinical trial in acne treatment., Mixture with ethinyl estradiol. Lo, Ovral, Stediril. Clinical efficiacy as oral contraceptive., Norgestrel is available commercially as a single-ingredient tablet and as a component of combination tablets with ethinylestradiol, estradiol valerate or as combined injectable solution with ethinylestradiol., Oral: Tablets: Norgestrel and Ethinyl Estradiol 0.3 mg, 0.03 mg, Low-ogestrel (Watson Pharma)., Oral: Tablets: 2 mg estradiol valerate (white tablets taken day 1-11), 500 ug norgestrel + 2 mg estradiol valerate (pale brown tablets taken day 12-21), Cyclo-Progynova (Meda Pharmaceuticals)., Levonorgestrel is available commercially as a single-ingredient tablet and in combined tablets with estradiol, estradiol valerate, estriol and ethinylestradiol ... It is also available as an intrauterine system and as a flexible, closed-capsule implant made of silicone rubber tubing., Plan B (levonorgestrel) tablets, 0.75 mg, are available for a single course of treatment in PVC, aluminum foil blister packages of two tablets each., General Manufacturing Information: A synthetic steroid hormone used as an ingredient of oral contraceptives, The activity of norgestrel is found in the levorotatory form D-l-norgestrel or levonorgestrel., ...was manufactured or formulated in Augentina, Australia, Austria, Belgium, Brazil, Canada, Finland, France, German, India, Mexico, the Netherlands, New Zealand, Portugal, South Africa, Spain, Switzerland, the United Kingdom and the U.S..
Independent reference data for D(minus)-norgestrel (CAS 797-63-7), compiled from public chemistry databases.
| CAS Registry Number | 797-63-7 |
|---|---|
| PubChem CID | 13109 |
| Molecular formula | C21H28O2 |
| IUPAC name | (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one |
| UNII (FDA) | 3J8Q1747Z2 |
| Molecular Weight | 312.4 |
|---|---|
| XLogP3 | 3.3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Exact Mass | 312.208930132 |
| Monoisotopic Mass | 312.208930132 |
| Topological Polar Surface Area | 37.3 |
| Heavy Atom Count | 23 |
| Boiling Point | 459.1 |
|---|---|
| Melting Point | 232-239 |
| Melting Point | 205-207 °C |
| Melting Point | 206 °C |
| Melting Point | 240 °C |
| Solubility | 2.05 |
| Solubility | 5.83e-03 g/L |
| LogP | 3.8 |
| LogP | 3.62 |
| Dissociation Constants | 17.91,-1.5 |
Levonorgestrel; 797-63-7; D-Norgestrel; Mirena; Microval; NORPLANT; Plan B; (-)-Norgestrel; D-(-)-Norgestrel; Levonova; Jadelle; d(-)-Norgestrel; Microlut; Levonorgestrelum; 18-Methylnorethisterone; Norplant II
| Reported hazard statements | H302 (20.2%), H312 (61.8%), H332 (61.8%), H351 (97.8%), H360 (94.4%), H362 (31.5%), H315 (11.1%), H319 (11.1%) |
|---|
H302 (20.2%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (61.8%): Harmful in contact with skin [Warning Acute toxicity, dermal]
Levonorgestrel · CAS 797-63-7 · C21H28O2. UNII 3J8Q1747Z2. Boiling Point: 459.1; Melting Point: 232-239; Melting Point: 205-207 °C.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: D(减)-炔诺孕酮