(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-ol

• ChemBase ID: 189
• Molecular Formular: C22H30O
• Molecular Mass: 310.473
• Monoisotopic Mass: 310.22966558
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@H]4C(=CCCC4)CC3)C(=C)C2)CC1)CC)C#C
• Canonical SMILES: CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@@]2(O)C#C)CCC1=CCCC[C@H]31
• InChI: InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
• InChIKey: RPLCPCMSCLEKRS-BPIQYHPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-ol; (1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
• IUPAC Traditional name: mircette; desogestrel
• Brand Name: Cerazette; Cyclessa; Desogen; Kariva; Mircette
• Synonyms: 13-Ethyl-11-methylene-18,19-dinor-17α-4-pregnen-20-yn-17-ol; Desogestrel; Desogestrelum [INN-Latin]; Desogestrel; (17α)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol; Cerazette; Cyclosa; Dicromil; Marvelon 150/320; Org 2969; 13-乙基-11-亚甲基-18,19-双失碳孕甾-4-烯-20-炔基-17-醇; 去氧孕烯

Database IDs

• CAS Number: 54024-22-5
• EC Number: 258-929-4
• MDL Number: MFCD00869346
• PubChem SID: 46505739; 160963652
• PubChem CID: 40973

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.993504
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.4206424
• LogD (pH = 7.4): 4.4206424
• Log P: 4.4206424
• Molar Refractivity: 95.7335 cm^3
• Polarizability: 37.4065 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.3
• LOG S: -5.01
• Solubility (Water): 3.01e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 109-110°C
• Hydrophobicity(logP): 4

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C22H30O

DETAILS

DrugBank - DB00304

• Drug Groups: approved
• Description: A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem]
• Indication: For the prevention of pregnancy in women who elect to use this product as a method of contraception.
• Pharmacology: Desogestrel is used as a female contraceptive. Desogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Desogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
• Toxicity: Symptoms of overdose include nausea and vaginal bleeding.
• Affected Organisms: Humans and other mammals
• Biotransformation: Desogestrel is rapidly and completely metabolized by hydroxylation in the intestinal mucosa and on first pass through the liver. It is primarily metabolized to 3α-hydroxydesogestrel with small amounts of 3β-hydroxydesogestrel being formed. Both of these metabolites are then rapidly oxidized to its active metabolite, etonogestrel (3-ketodesogestrel). Other metabolites (e.g. 2-hydroxydesogestrel) with no pharmacologic action have also been identified. Desogestrel and some of its metabolites (e.g. 3β-hydroxydesogestrel, 15β-hydroxydesogestrel) may also undergo glucuronide and sulfate conjugation. Early in vitro studies demonstrated that CYP2C9 and possibly CYP2C19 were involved in the conversion of desogestrel to 3α-hydroxydesogestrel and 3β-hydroxydesogestrel (PMID 9864282); however, later clinical studies conducted in humans refuted this result (PMID 15963096). The latter study indicates that CYP3A4 plays an important role in metabolizing etonogestrel. Thus, strong CYP3A4 inhibitors or inducers could result in increased side effects or therapeutic failure, respectively.
• Absorption: Following oral administration, the relative bioavailability of desogestrel, as measured by serum levels of etonogestrel, is approximately 84%. The absolute oral bioavailability is about 76%.
• Half Life: 27.8±7.2 hours
• Protein Binding: 98.3%
• References: Korhonen T, Tolonen A, Uusitalo J, Lundgren S, Jalonen J, Laine K: The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75. [Pubmed] ; Gentile DM, Verhoeven CH, Shimada T, Back DJ: The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82. [Pubmed]
• External Links: Wikipedia; RxList

Sigma Aldrich - 32809

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - D296875

A progestogen with low androgenic potency.

REFERENCES

• Korhonen T, Tolonen A, Uusitalo J, Lundgren S, Jalonen J, Laine K: The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75. Pubmed
• Gentile DM, Verhoeven CH, Shimada T, Back DJ: The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82. Pubmed
• Viinikka, L., et al.: Eur. J. Clin. Pharmacol., 15, 349 (1979)
• Bergink, E.W., et al.: J. Steroid Biochem., 14, 175 (1981)